Product Name

  • Name

    Costunolide

  • EINECS
  • CAS No. 553-21-9
  • Article Data4
  • CAS DataBase
  • Density 1.03 g/cm3
  • Solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
  • Melting Point 106-109oC
  • Formula C15H20O2
  • Boiling Point 385.4 °C at 760 mmHg
  • Molecular Weight 232.323
  • Flash Point 162 °C
  • Transport Information
  • Appearance
  • Safety 26-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 553-21-9 (Costunolide)
  • Hazard Symbols Xi
  • Synonyms (1S,4E,8E,10S)-4,8-dimethyl-13-methylidene-11-oxabicyclo[8.3.0]trideca-4,8-dien-12-one;Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11ahexahydro- 6,10-dimethyl-3-methylene-,(3aS,6E,10E,11aR)-;Costunolid;(1S,10S)-4,8-dimethyl-13-methylidene-11-oxabicyclo[8.3.0]trideca-4,8-dien-12-one;Costus lactone;(E,E)-6-alpha-Hydroxygermacra-1(10),4,11(13)-trien-12-oic acid gamma-lactone;
  • PSA 26.30000
  • LogP 3.55080

Synthetic route

saussureamine A

saussureamine A

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%
(R)-2-Amino-3-((6E,10E)-(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethylsulfanyl)-propionic acid

(R)-2-Amino-3-((6E,10E)-(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethylsulfanyl)-propionic acid

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%
(S)-2-[((6E,10E)-(3R,3aS,11aS)-6,10-Dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid

(S)-2-[((6E,10E)-(3R,3aS,11aS)-6,10-Dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%
1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol
97317-60-7, 104486-16-0

1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Inert atmosphere;82%
With manganese(IV) oxide In dichloromethane at 20℃; for 12h;78%
(2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-ol

(2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-ol

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
3: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
4: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
5: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
2: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
4: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
5: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(4R,5S)-4-((1E,5E)-7-bromo-2,6-dimethylhepta-1,5-dien-1-yl)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepane

(4R,5S)-4-((1E,5E)-7-bromo-2,6-dimethylhepta-1,5-dien-1-yl)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepane

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
2: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
3: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
4: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-6-(phenylsulfonyl)-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-6-(phenylsulfonyl)-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
2: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
3: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
2: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(E)-4-((tert-butyldimethylsilyl)oxy)-3-methylbut-2-enoic acid

(E)-4-((tert-butyldimethylsilyl)oxy)-3-methylbut-2-enoic acid

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0 - 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
3.2: 0.08 h / -78 °C / Inert atmosphere
4.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
9.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
11.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
12.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
13.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0 - 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
3.2: 0.08 h / -78 °C / Inert atmosphere
4.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
9.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
11.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
12.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
13.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(E)-4-((tert-butyldimethylsilyl)oxy)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-methylbut-2-en-1-one

(E)-4-((tert-butyldimethylsilyl)oxy)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-methylbut-2-en-1-one

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
1.2: 0.08 h / -78 °C / Inert atmosphere
2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
7.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
1.2: 0.08 h / -78 °C / Inert atmosphere
2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
7.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
C11H21ClO2Si

C11H21ClO2Si

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
2.2: 0.08 h / -78 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
10.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
12.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
2.2: 0.08 h / -78 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
10.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
12.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(2E,6E)-8-((tert-butyldiphenylsilyl)oxy)-3,7-dimethylocta-2,6-dienal

(2E,6E)-8-((tert-butyldiphenylsilyl)oxy)-3,7-dimethylocta-2,6-dienal

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
1.2: 0.08 h / -78 °C / Inert atmosphere
2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
7.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
1.2: 0.08 h / -78 °C / Inert atmosphere
2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
7.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(2E,6E)-8-((tert-butyldiphenylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-ol
127969-90-8

(2E,6E)-8-((tert-butyldiphenylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-ol

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: manganese(IV) oxide / dichloromethane / 6 h / Reflux; Inert atmosphere
1.2: Inert atmosphere
2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
2.2: 0.08 h / -78 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
10.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
12.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: manganese(IV) oxide / dichloromethane / 6 h / Reflux; Inert atmosphere
1.2: Inert atmosphere
2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere
2.2: 0.08 h / -78 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
10.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
12.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
C41H57NO6SSi

C41H57NO6SSi

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
5.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
6.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
7.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
8.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
9.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
5.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
7.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
8.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
9.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
C47H71NO6SSi2

C47H71NO6SSi2

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
6.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
8.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
10.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
6.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
10.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
((4R,5S)-4-((1E,5E)-7-((tert-butyldiphenylsilyl)oxy)-2,6-dimethylhepta-1,5-dien-1-yl)-2,2-dimethyl-6-methylene-1,3-dioxepan-5-yl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

((4R,5S)-4-((1E,5E)-7-((tert-butyldiphenylsilyl)oxy)-2,6-dimethylhepta-1,5-dien-1-yl)-2,2-dimethyl-6-methylene-1,3-dioxepan-5-yl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
6.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
7.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
8.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
6.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
7.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
8.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
C24H33IO4S

C24H33IO4S

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
3: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
4: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
tert-butyl(((2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylthio)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-yl)oxy)diphenylsilane

tert-butyl(((2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylthio)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-yl)oxy)diphenylsilane

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
3: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
5: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
6: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
7: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
3: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
4: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
6: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
7: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
tert-butyl(((2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-yl)oxy)diphenylsilane

tert-butyl(((2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-yl)oxy)diphenylsilane

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
4: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
5: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
6: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere
3: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
4: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere
5: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere
6: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
(((1R,2E,6E,10S)-3,7-dimethyl-10-(prop-1-en-2-yl)cyclodeca-2,6-dien-1-yl)oxy)triisopropylsilane

(((1R,2E,6E,10S)-3,7-dimethyl-10-(prop-1-en-2-yl)cyclodeca-2,6-dien-1-yl)oxy)triisopropylsilane

costunolide
553-21-9

costunolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tert.-butyl lithium; N,N,N,N,-tetramethylethylenediamine / hexane; pentane / 36 h / 20 °C / Inert atmosphere
1.2: 3 h / -78 - -30 °C
2.1: manganese(IV) oxide / dichloromethane / 12 h / 20 °C
View Scheme

Costunolide Chemical Properties

Molecular Structure of Costunolide (CAS NO.553-21-9):


IUPAC: (3AS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[d]furan-2-one
Molecular Formula:C15H20O2
Molecular Weight:232.32
Product Categories:Miscellaneous Natural Products;chiral
Density:1.03 g/cm3
Flash Point:162oC
Boiling Point:385.4oC at 760 mmHg
SMILES:O=C/1O[C@@H]2/C=C(/CC/C=C(/CC[C@H]2C\1=C)C)C 
InChI:InChI=1/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1 
InChIKey:HRYLQFBHBWLLLL-AHNJNIBGBA 
Index of Refraction:1.519 
Molar Volume:224.4 cm3
Surface Tension:35.1 dyne/cm
Molar Refractivity:68.12 cm3
Enthalpy of Vaporization:63.42 kJ/mol
Vapour Pressure:3.8E-06 mmHg at 25oC

Costunolide Production

 Costunolide with cas registry number of 553-21-9 can be obtained from tree eremanthus elaegnus .

Costunolide Specification

 Costunolide with cas registry number of 553-21-9 is also known as (3AS,6E,10E,11AR)-3A,4,5,8,9,11A-hexahydro-6,10-dimethyl-3-methylene-cyclodeca[B]furan-2(3H)-one ; Costunolide ; (E,E)-6-alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oicacidgamma-lactone ; Costunolid ; Germacra-1(10),4,11(13)-trien-12-oicacid,6-alpha-hydroxy-,gamma-lactone,(e, ; Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3- methylene-,[3aS-(3aR*,6E,10E,11aS*)]- ; Custunolide ; (3AS,6E,10E,11aR)-6,10-Dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[d]furan-2-one . Costunolide is an active sesquiterpene lactone of medicinal herbs with anti-inflammatory and potential anti-cancer activity. It affects nuclear organization and reorganized microtubule architecture. Costunolide demonstrates polymerizing ability, by inducing the formation of well organized microtubule polymers. It also used as chemoprophylactic agent in schistosomiasis.

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