Product Name

  • Name

    GOSSYPOL

  • EINECS 636-899-7
  • CAS No. 303-45-7
  • Article Data16
  • CAS DataBase
  • Density 1.403 g/cm3
  • Solubility Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonate, and dilute aqueous solutions of ammonia . Insoluble in water. Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain antitumor, anitviral, and antioxidant properties.
  • Melting Point 181-183 °C
  • Formula C30H30O8
  • Boiling Point 707.888 °C at 760 mmHg
  • Molecular Weight 518.563
  • Flash Point 395.872 °C
  • Transport Information
  • Appearance
  • Safety 22-36-36/37/39-27-26
  • Risk Codes 22-40-36/37/38
  • Molecular Structure Molecular Structure of 303-45-7 (GOSSYPOL)
  • Hazard Symbols IrritantXi, HarmfulXn
  • Synonyms [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- (8CI);1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarboxaldehyde;1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde;2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthyl];2,2'-Bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthyl];BL 193;NSC 56817;NSC 624336;No Fertil;Pogosin;Tash 1;
  • PSA 155.52000
  • LogP 6.38220

Synthetic route

(±)-gossypol acetic acid
5453-04-3, 866541-93-7, 1189561-66-7

(±)-gossypol acetic acid

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With iron(III) chloride In acetone at 60℃;85%
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication;105 mg
2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde
40817-07-0

2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;76.1%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere;52%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique;41%
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer;
apogossypol
784206-41-3

apogossypol

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h;72%
apogossypol
784206-41-3

apogossypol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;37%
4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)
73728-76-4

4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
In water; acetone for 48h;
Gossypol
17273-29-9, 38152-98-6, 125278-11-7

Gossypol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.);
sulfuric acid
7664-93-9

sulfuric acid

dianilogossipol
6952-36-9

dianilogossipol

(rac)-gossypol
303-45-7

(rac)-gossypol

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
C54H54N4O10

C54H54N4O10

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 20 °C / Inert atmosphere; Schlenk technique
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
4.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
2: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
3: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 3 steps
1: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde
50399-96-7

4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one
1256723-09-7

4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-hydroxy-6-isopropyl-3-methyl-benzaldehyde
1665-99-2

2-hydroxy-6-isopropyl-3-methyl-benzaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
carvacrol
499-75-2

carvacrol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C11H13BrO2

C11H13BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H26O5

C24H26O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H19BrO2

C18H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C20H23F3O5

C20H23F3O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C17H19BrO2

C17H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C19H22O3

C19H22O3

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H28O6

C24H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C26H28O6

C26H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H30O5

C24H30O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 °C / Inert atmosphere; Schlenk technique
2.2: 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 32 h / 20 °C / Schlenk technique
4.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
4.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C / Inert atmosphere; Schlenk technique
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
7.1: 2,6-di-tert-butyl-4-methyl-phenol / chlorobenzene / 13 h / 160 °C / Schlenk technique; Inert atmosphere
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
9.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
10.2: 20 °C / Inert atmosphere; Schlenk technique
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
12.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
2.2: 20 °C / Inert atmosphere; Schlenk technique
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
4.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
5.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 4 h / 80 °C
2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
4: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(rac)-gossypol
303-45-7

(rac)-gossypol

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In methanol for 5h; Ambient temperature;100%
(rac)-gossypol
303-45-7

(rac)-gossypol

methyl tryptophanate hydrochloride
5619-09-0, 7524-52-9, 14907-27-8, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8

methyl tryptophanate hydrochloride

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 45℃; for 2h; Resolution of racemate;A 99.4%
B 95%
...Expand
heptane-1,7-diamine
646-19-5

heptane-1,7-diamine

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;98.7%
(rac)-gossypol
303-45-7

(rac)-gossypol

Glycyrrhizin ammonium
53956-04-0

Glycyrrhizin ammonium

C42H62O16*C30H30O8*H3N

C42H62O16*C30H30O8*H3N

Conditions
ConditionsYield
at 20℃;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

(R)-(+)-tryptophan methyl ester hydrochloride
14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8

(R)-(+)-tryptophan methyl ester hydrochloride

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

(S)-tryptophan methyl ester hydrochloride
7524-52-9, 26988-71-6, 5619-09-0, 14907-27-8, 41222-70-2, 67557-19-1, 109492-62-8

(S)-tryptophan methyl ester hydrochloride

C54H54N4O10
132303-09-4

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

(S)-tryptophan methyl ester hydrochloride
7524-52-9, 26988-71-6, 5619-09-0, 14907-27-8, 41222-70-2, 67557-19-1, 109492-62-8

(S)-tryptophan methyl ester hydrochloride

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 0.5h;A 97%
B 94%
...Expand
(rac)-gossypol
303-45-7

(rac)-gossypol

ethylamine
75-04-7

ethylamine

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine
307976-02-9

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
With isopropyl alcohol
(rac)-gossypol
303-45-7

(rac)-gossypol

isopropylamine
75-31-0

isopropylamine

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
Tau
107-35-7

Tau

(rac)-gossypol
303-45-7

(rac)-gossypol

megosin

megosin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; Heating;95.8%
(rac)-gossypol
303-45-7

(rac)-gossypol

5-Aminosalicylic Acid
89-57-6

5-Aminosalicylic Acid

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

Conditions
ConditionsYield
In ethanol for 3h; Heating;95.31%
(rac)-gossypol
303-45-7

(rac)-gossypol

apogossypol
784206-41-3

apogossypol

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With sodium hydroxide; acetic acid In water at 90℃; for 3.5h; darkness;
Stage #2: With sulfuric acid In water at 0℃;		95%
Stage #1: (rac)-gossypol With water; sodium hydroxide at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water Cooling with ice;		95%
Stage #1: (rac)-gossypol With sodium hydroxide In water at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water		95%
(rac)-gossypol
303-45-7

(rac)-gossypol

methylamine
74-89-5

methylamine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In N,N-dimethyl-formamide Condensation;95%
(rac)-gossypol
303-45-7

(rac)-gossypol

4-hydroxynon-2-enal
850480-50-1

4-hydroxynon-2-enal

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

Conditions
ConditionsYield
With zinc(II) chloride In acetonitrile at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature;93.5%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
Stage #1: 1.3-propanedithiol; (rac)-gossypol In chloroform at 20℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In chloroform at 20℃; for 15h;		93%
glucosamine
14257-69-3

glucosamine

(rac)-gossypol
303-45-7

(rac)-gossypol

C36H41NO12

C36H41NO12

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.9%
(rac)-gossypol
303-45-7

(rac)-gossypol

tetra-acetyl glucosamine
17460-45-6, 23707-23-5, 23739-93-7, 23743-51-3, 26108-75-8, 59042-16-9, 124516-07-0, 124580-56-9

tetra-acetyl glucosamine

C44H49NO16

C44H49NO16

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.6%
p-Aminohippuric acid
61-78-9

p-Aminohippuric acid

(rac)-gossypol
303-45-7

(rac)-gossypol

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;92.3%
propylamine
107-10-8

propylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
2-phenylpropylamine
582-22-9

2-phenylpropylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
(rac)-gossypol
303-45-7

(rac)-gossypol

pentafluorophenyl hydrazine
828-73-9

pentafluorophenyl hydrazine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol for 3h; Heating;91.9%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-Aminoanabasine
86133-36-0

N-Aminoanabasine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
86133-35-9

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol Heating;91%
n-Dodecylamine
124-22-1

n-Dodecylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine
5463-57-0

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;91%
(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolone
4547-72-2

gossypolone

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With iron(III) chloride; acetic acid In water; acetone at 100℃; for 2h;
Stage #2: With sulfuric acid In diethyl ether; water		91%
With iron(III) chloride In acetic acid; acetone at 60 - 70℃; Oxidation;49%
With iron(III) chloride; acetic acid In acetone at 70℃; for 0.75h;
(rac)-gossypol
303-45-7

(rac)-gossypol

C7H10N2O5(2-)*2Na(1+)

C7H10N2O5(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 3h; pH=7.4; Inert atmosphere;90.8%
4-aminophthalimide
3676-85-5

4-aminophthalimide

(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolydenebis-N-(3-iminophthalimide)

gossypolydenebis-N-(3-iminophthalimide)

Conditions
ConditionsYield
In ethanol for 3h; Heating;90.17%
4'-aminobenzo-15-crown-5-ether
60835-71-4

4'-aminobenzo-15-crown-5-ether

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
In ethanol for 6h; Heating;90.1%
4-(3-Aminopropyl)morpholine
123-00-2

4-(3-Aminopropyl)morpholine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
104757-46-2

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In isopropyl alcohol Heating;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

isobutylamine
78-81-9

isobutylamine

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-butylamine
109-73-9

N-butylamine

GSBN

GSBN

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%

Gossypol Consensus Reports

EPA Genetic Toxicology Program.

Gossypol Specification

The Gossypol, with the CAS registry number 303-45-7, is also known as 2,2'-Bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene). It belongs to the product categories of Aromatic Phenols; Antitumour. This chemical's molecular formula is C30H30O8 and molecular weight is 518.55. What's more, its IUPAC name is called 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde. Gossypol is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. And this chemical should be kept in a cold, dry place.

Physical properties about Gossypol are: (1)ACD/LogP: 5.42; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5.405; (4)ACD/LogD (pH 7.4): 4.795; (5)ACD/BCF (pH 5.5): 7488.263; (6)ACD/BCF (pH 7.4): 1838.539; (7)ACD/KOC (pH 5.5): 20462.531; (8)ACD/KOC (pH 7.4): 5024.019; (9)#H bond acceptors: 8; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 155.52 Å2; (13)Index of Refraction: 1.742; (14)Molar Refractivity: 149.345 cm3; (15)Molar Volume: 369.555 cm3; (16)Surface Tension: 71.297 dyne/cm; (17)Density: 1.403 g/cm3; (18)Flash Point: 395.872 °C; (19)Enthalpy of Vaporization: 107.239 kJ/mol; (20)Boiling Point: 707.888 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Gossypol: it is a polyphenol derived from the cotton plant (genus Gossypium, family Malvaceae). It is formed metabolically through acetate via the isopernoid pathway.

 Gossypol is formed metabolically through acetate via the isopernoid pathway.

Uses of Gossypol: it is used to produce other chemicals. For example, it can react with Ethylamine to get 1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine. The reaction occurs with solvents diethyl ether, propan-2-ol at temperature of 20-45 °C. The yield is 96 %.

Gossypol can react with Ethylamine to get 1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. It may cause damage to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And you must take off immediately all contaminated clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Cc1cc2c(c(c(c(c2C(C)C)O)O)C=O)c(c1c3c(cc4c(c3O)c(c(c(c4C(C)C)O)O)C=O)C)O
(2) InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
(3) InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
pig LD50 oral 550mg/kg (550mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Journal of the American Oil Chemists' Society. Vol. 40, Pg. 571, 1963.
rat LD50 oral 2315mg/kg (2315mg/kg)   Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960.

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