Honokiol supplier | CasNO.35354-74-6

Name
Honokiol
EINECS 609-119-8
CAS No. 35354-74-6
Article Data19
CAS DataBase
Density 1.107 g/cm³
Solubility DMSO: 36 mg/mL
Melting Point 87.5ºC
Formula C₁₈H₁₈O₂
Boiling Point 400.1 °C at 760 mmHg
Molecular Weight 266.34
Flash Point 184 °C
Transport Information UN 3077 9/PG 3
Appearance Dark brown to white fine powder with pleasant odor, spicy and slightly bitter taste.
Safety 26-39-61
Risk Codes 41-51/53
Molecular Structure
Hazard Symbols Xi,N
Synonyms [1,1'-Biphenyl]-2,4'-diol,3',5-di-2-propenyl- (9CI);3',5-Diallyl-2,4'-biphenyldiol;NSC 293100;Honokiol,(S);
PSA 40.46000
LogP 4.22180

Synthetic route

: 68592-18-7
Dimethylhonokiol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
With aluminum (III) chloride at -5 - 0℃; for 0.333333h;	97%
With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane at 65℃; for 15h; Reagent/catalyst; Temperature; Inert atmosphere;	95%
Stage #1: Dimethylhonokiol With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #3: With water In tetrahydrofuran	57.8%

: 68592-19-8
3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
With boron trichloride - methyl sulfide complex In dichloromethane; 1,2-dichloro-ethane for 18h; Reflux;	91%
With boron tribromide In dichloromethane at 20℃; for 0.416667h; Inert atmosphere;	90%
With boron tribromide at -15 - 20℃;
With boron tribromide In dichloromethane at 20℃; for 0.416667h; Inert atmosphere;	430 mg

: 108886-93-7
5-allyl-4'-(allyloxy)-[1,1'-biphenyl]-2-ol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
With N,N-diethylaniline at 200℃; for 24h; Claisen Rearrangement; Sealed tube; Schlenk technique; Inert atmosphere;	90%
With boron trichloride In chlorobenzene at -15℃; for 1h;	80%

: 711012-14-5
5,3'-diallyl-2,4'-bis-methoxymethoxy-biphenyl

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 44h;	89%

: 3,5'-diallyl-2'-(methoxymethoxy)-[1,1'-biphenyl]-4-ol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
With methanol; chloro-trimethyl-silane at 0 - 20℃; for 6h;	85%

: 911812-86-7
2,4'-bis-O-allylbiphenyl

A: 3,3'-diallyl biphenyl-2,4'-diol

B: 35354-74-6
Honokiol

Conditions

Conditions	Yield
for 1.33333h; Claisen Rearrangement; Microwave irradiation; Heating; Sealed tube;	A 40% B 60%
at 180℃; for 1.33333h; Claisen Rearrangement; Microwave irradiation;	A 40% B 60%
at 190℃; for 12h; Claisen Rearrangement; Sealed tube;	A 55% B 40%
at 190℃; for 12h; Claisen Rearrangement; Sealed tube;	A 55% B 40%

: 1133087-04-3
5-allyl-4'-(allyloxy)-2-methoxybiphenyl

A: 35354-74-6
Honokiol

B: 1253950-18-3
5-allyl-[1,1'-biphenyl]-2,4'-diol

Conditions

Conditions	Yield
With boron trichloride - methyl sulfide complex In dichloromethane; 1,2-dichloro-ethane for 18h; Claisen rearrangement; Reflux;	A 47% B 49%

: 126654-55-5
eudeshonokiol A

A: 35354-74-6
Honokiol

B: 60132-35-6, 92857-25-5, 108006-39-9, 122674-21-9, 143004-65-3, 4666-84-6
cryptomeridiol

Conditions

Conditions	Yield
With trifluoroacetic acid In benzene

: 126654-55-5
eudeshonokiol A

A: 35354-74-6
Honokiol

B: 13902-07-3, 15051-81-7, 72173-98-9, 98683-12-6, 117066-77-0, 1209-71-8
eudesm-4-en-11-ol

Conditions

Conditions	Yield
With trifluoroacetic acid In benzene for 10h; Ambient temperature;	A 7 mg B 3 mg

: 89-55-4
5-bromosalicyclic acid

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 100 percent / aq. H2SO4 / Heating 2: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 3: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 8: 52 percent / CuI / tetrahydrofuran / -26 °C 9: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 100 percent / aq. H2SO4 / Heating
2: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
3: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
8: 52 percent / CuI / tetrahydrofuran / -26 °C
9: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 29415-97-2
methyl 3-bromo-4-hydroxybenzoate

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 2: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 3: 100 percent / imidazole / dimethylformamide / 20 °C 4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 8: 52 percent / CuI / tetrahydrofuran / -26 °C 9: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
2: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
3: 100 percent / imidazole / dimethylformamide / 20 °C
4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
8: 52 percent / CuI / tetrahydrofuran / -26 °C
9: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 4068-76-2
5-bromo-2-hydroxy-benzoic acid methyl ester

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 2: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 7: 52 percent / CuI / tetrahydrofuran / -26 °C 8: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
2: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
7: 52 percent / CuI / tetrahydrofuran / -26 °C
8: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 99-76-3
methyl 4-hydroxylbenzoate

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C 2: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 3: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 4: 100 percent / imidazole / dimethylformamide / 20 °C 5: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 6: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 7: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 8: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 9: 52 percent / CuI / tetrahydrofuran / -26 °C 10: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C
2: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
3: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
4: 100 percent / imidazole / dimethylformamide / 20 °C
5: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
6: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
7: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
8: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
9: 52 percent / CuI / tetrahydrofuran / -26 °C
10: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 162269-91-2
(3-bromo-4-methoxymethoxy-phenyl)-methanol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / imidazole / dimethylformamide / 20 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 100 percent / imidazole / dimethylformamide / 20 °C
2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
6: 52 percent / CuI / tetrahydrofuran / -26 °C
7: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 711012-12-3
5-bromo-2-methoxymethoxy-benzoic acid methyl ester

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C
2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
6: 52 percent / CuI / tetrahydrofuran / -26 °C
7: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 672922-57-5
3-bromo-4-methoxymethoxybenzoic acid methyl ester

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 2: 100 percent / imidazole / dimethylformamide / 20 °C 3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 7: 52 percent / CuI / tetrahydrofuran / -26 °C 8: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
2: 100 percent / imidazole / dimethylformamide / 20 °C
3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
7: 52 percent / CuI / tetrahydrofuran / -26 °C
8: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 711012-11-2
(3-bromo-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 2: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 4: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 5: 52 percent / CuI / tetrahydrofuran / -26 °C 6: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 99-96-7
4-hydroxy-benzoic acid

acid: acid

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 99 percent / aq. H2SO4 / Heating 2: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C 3: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 4: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 5: 100 percent / imidazole / dimethylformamide / 20 °C 6: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 7: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 8: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 9: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 10: 52 percent / CuI / tetrahydrofuran / -26 °C 11: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 99 percent / aq. H2SO4 / Heating
2: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C
3: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C
4: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
5: 100 percent / imidazole / dimethylformamide / 20 °C
6: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C
7: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C
8: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C
9: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2
10: 52 percent / CuI / tetrahydrofuran / -26 °C
11: 89 percent / aq. HCl / methanol / 44 h / 20 °C
View Scheme

: 711012-10-1
2-methoxymethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 2: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 4: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 5: 52 percent / CuI / tetrahydrofuran / -26 °C 6: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 711012-16-7
5,3'-bis-bromomethyl-2,4'-bis-methoxymethoxy-biphenyl

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / CuI / tetrahydrofuran / -26 °C 2: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 711012-13-4
(3'-hydroxymethyl-6,4'-bis-methoxymethoxy-biphenyl-3-yl)-methanol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 2: 52 percent / CuI / tetrahydrofuran / -26 °C 3: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 711012-09-8
5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-carboxylic acid methyl ester

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 2: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 3: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 4: 52 percent / CuI / tetrahydrofuran / -26 °C 5: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 711012-15-6
[5'-(tert-butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-yl]-methanol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 2: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 3: 52 percent / CuI / tetrahydrofuran / -26 °C 4: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

: 501-92-8
4-(prop-2-enyl)phenol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 29.2 percent / acetic acid / 0.25 h / Ambient temperature 2: 1.) methyl iodide, Mg / 1.) ether, reflux, 5 h; 2.) ether, -15 deg C, 30 min 3: 80 percent / BCl3 / chlorobenzene / 1 h / -15 °C View Scheme

: 108886-90-4
1-allyl-4-oxocyclohexa-2,5-dienylethanoate

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) methyl iodide, Mg / 1.) ether, reflux, 5 h; 2.) ether, -15 deg C, 30 min 2: 80 percent / BCl3 / chlorobenzene / 1 h / -15 °C View Scheme

: 68592-15-4
methylhonokiol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Stage #1: methylhonokiol With boron tribromide In dichloromethane at -78℃; Stage #2: With water
Grignard reaction;

: 1133087-04-3
5-allyl-4'-(allyloxy)-2-methoxybiphenyl

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme

: 87688-94-6
4-allyl-2-bromo-1-methoxybenzene

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice 3.2: 2.08 h / 20 °C / Inert atmosphere 3.3: 18 h / 140 °C / Inert atmosphere 4.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere 5.1: potassium carbonate / acetone / 20 °C / Inert atmosphere 6.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 7.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere 2.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling 3.2: 2 h / 20 °C / Inert atmosphere; Cooling 3.3: 18 h / 140 °C / Inert atmosphere 4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere 5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice
3.2: 2.08 h / 20 °C / Inert atmosphere
3.3: 18 h / 140 °C / Inert atmosphere
4.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere
5.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
6.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
7.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme

Multi-step reaction with 6 steps
1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere
2.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling
3.2: 2 h / 20 °C / Inert atmosphere; Cooling
3.3: 18 h / 140 °C / Inert atmosphere
4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme

: 1133087-02-1
5'-allyl-2'-methoxy-biphenyl-4-ol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 20 °C / Inert atmosphere 2: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 3: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 20 °C / Inert atmosphere 2: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 3: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme

: 1355483-89-4
3-(3-bromo-4-methoxy-phenyl)-propane-1,2-diol

: 35354-74-6
Honokiol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice 2.2: 2.08 h / 20 °C / Inert atmosphere 2.3: 18 h / 140 °C / Inert atmosphere 3.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere 4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere 5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling 2.2: 2 h / 20 °C / Inert atmosphere; Cooling 2.3: 18 h / 140 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 20 °C / Inert atmosphere 4.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere 5.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice
2.2: 2.08 h / 20 °C / Inert atmosphere
2.3: 18 h / 140 °C / Inert atmosphere
3.1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere
4.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
5.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
6.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme

Multi-step reaction with 5 steps
1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 18 h / 80 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling
2.2: 2 h / 20 °C / Inert atmosphere; Cooling
2.3: 18 h / 140 °C / Inert atmosphere
3.1: potassium carbonate / acetone / 20 °C / Inert atmosphere
4.1: diethylaluminium chloride / hexane / 2 h / 20 °C / Inert atmosphere
5.1: boron tribromide / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
View Scheme

: 35354-74-6
Honokiol

: 98-88-4
benzoyl chloride

: 3',5-diallyl-2,4'-diphenylformyloxybiphenyl

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice;	98.4%

: 35354-74-6
Honokiol

: 106-95-6
allyl bromide

: 3',5-diallyl-2,4'-bis(allyloxy)-1,1'-biphenyl

Conditions

Conditions	Yield
With potassium carbonate In acetone at 56℃; for 12h;	97%

: 50-00-0
formaldehyd

: 35354-74-6
Honokiol

: 75-04-7
ethylamine

: C26H32N2O2

Conditions

Conditions	Yield
In 1,4-dioxane; toluene at 120℃; for 24h;	95.5%

...Expand

: 50-00-0
formaldehyd

: 111-26-2
hexan-1-amine

: 35354-74-6
Honokiol

: C34H48N2O2

Conditions

Conditions	Yield
In 1,4-dioxane; toluene at 110℃; for 43h;	95.5%

...Expand

: 35354-74-6
Honokiol

: 108-24-7
acetic anhydride

: 35347-50-3
2,4'-diacetoxy-5,3'-di(2-propenyl)biphenyl

Conditions

Conditions	Yield
With pyridine	95%
With potassium carbonate at 20℃; for 0.5h;	56%
With pyridine at 25℃; for 18h;
With sodium hydrogencarbonate In ethyl acetate for 48h;

: 35354-74-6
Honokiol

: 35406-31-6
Tetrahydrohonokiol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 5h; Reflux;	94%
With sodium tetrahydroborate; nickel dichloride	70%
With hydrogen; palladium on activated charcoal
With palladium on activated charcoal; hydrogen
With Lindlar's catalyst; hydrogen In ethanol at 20℃; under 760.051 Torr; for 24h;

: 50-00-0
formaldehyd

: 35354-74-6
Honokiol

: 62-53-3
aniline

: C34H32N2O2

Conditions

Conditions	Yield
In 1,4-dioxane; toluene at 100℃; for 58h;	93.6%

...Expand

: 50-00-0
formaldehyd

: 617-89-0
furan-2-ylmethanamine

: 35354-74-6
Honokiol

: C32H32N2O4

Conditions

Conditions	Yield
In 1,4-dioxane; toluene at 100℃; for 52h;	90.8%

...Expand

: 31643-49-9
4-Nitrophthalonitrile

: 35354-74-6
Honokiol

: C34H22N4O2

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 40℃; for 48h; Inert atmosphere;	90%

: 35354-74-6
Honokiol

: 105-36-2
ethyl bromoacetate

: 1333391-01-7
diethyl 2,2'-((3',5-diallyl-[1,1'-biphenyl]-2,4'-diyl)bis(oxy))diacetate

Conditions

Conditions	Yield
Stage #1: Honokiol With potassium carbonate In N,N-dimethyl-formamide at 20 - 25℃; Williamson synthesis; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 30℃; for 6h; Williamson synthesis;	89.3%

: 35354-74-6
Honokiol

: 1416567-14-0
4-allyl-2-(2-methyl-benzofuran-5-yl)phenol

Conditions

Conditions	Yield
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6080.41 Torr; for 16h; Autoclave;	86%
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6080.41 Torr; for 16h; Autoclave;	86%
With oxygen; sodium acetate; palladium dichloride In N,N-dimethyl acetamide; water at 60℃; under 6000.6 Torr; for 16h; Wacker Oxidation;	86%

: 50-00-0
formaldehyd

: 35354-74-6
Honokiol

: 124-40-3
dimethyl amine

: 3',5-diallyl-3,5'-bis((dimethylamino)methyl)-[1,1'-biphenyl]-2,4'-diol

Conditions

Conditions	Yield
In methanol; water at 20℃; for 16h;	86%
Stage #1: formaldehyd; dimethyl amine With hydrogenchloride In methanol; water at 2 - 35℃; for 1h; Stage #2: Honokiol In methanol; water at 75℃; for 6h;	60%

...Expand

: 35354-74-6
Honokiol

: 74-88-4
methyl iodide

: 68592-18-7
Dimethylhonokiol

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	84%
With sodium hydride In water; dimethyl sulfoxide at 0℃;	38%

: 35354-74-6
Honokiol

: 3',5-diallyl-3,5'-dinitroso-1,1'-biphenyl-2,4'-diphenol

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water; acetonitrile at 20℃; for 1.5h; Cooling with ice;	79%
With hydrogenchloride; sodium nitrite In water; acetonitrile at 20℃; for 1.5h;	79.3%

: 35354-74-6
Honokiol

: 4392-24-9
3-bromo-1-phenyl-1-propenyl bromide

: 3',5-diallyl-2E,4'E-bis(cinnamyloxy)-1,1'-biphenyl

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃;	78%

: 35354-74-6
Honokiol

: 67-68-5
dimethyl sulfoxide

: 4-allyl-2-(2-((methylthio)methyl)-2,3-dihydrobenzofuran-5-yl)phenol

Conditions

Conditions	Yield
With ammonium iodide at 130℃; for 18h; Schlenk technique;	76%

: 50-00-0
formaldehyd

: 35354-74-6
Honokiol

: 124-40-3
dimethyl amine

: C21H25NO2

Conditions

Conditions	Yield
Stage #1: formaldehyd; dimethyl amine In water at 55℃; for 0.666667h; Mannich Aminomethylation; Stage #2: Honokiol In water	76%

...Expand

: 35354-74-6
Honokiol

: 264882-00-0
methyl 2-(2-chlorophenyl)-2-diazoacetate

: methyl 2-(2-chlorophenyl)-2-((5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl)oxy)acetate

Conditions

Conditions	Yield
With sewage sludge-derived carbon material treated with perchloric acid In 1,2-dichloro-ethane at 70℃; for 24h;	72%

: 35354-74-6
Honokiol

: 77-78-1
dimethyl sulfate

: 68592-18-7
Dimethylhonokiol

Conditions

Conditions	Yield
With sodium In ethanol for 5h; Inert atmosphere; Reflux;	70%

: 35354-74-6
Honokiol

: 3,3'-(4,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(propane-1,2-diol)

Conditions

Conditions	Yield
Stage #1: Honokiol With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h; Stage #2: With sodium hydroxide In tetrahydrofuran for 1h; Reflux;	66%
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 1 h / Reflux View Scheme

: 35354-74-6
Honokiol

: C18H17IO2

Conditions

Conditions	Yield
With iodine In ethanol; water at 50℃; for 12h;	65.87%

: 50-00-0
formaldehyd

: 35354-74-6
Honokiol

: 1333391-05-1
3',5-diallyl-3,5'-bis(hydroxymethyl)biphenyl-2,4'-diol

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 24h;	63.15%

: 35354-74-6
Honokiol

: 3',5-aiallyl-3,5'-dinitro-[1,1'-biphenyl]-2,4'-diol

Conditions

Conditions	Yield
Stage #1: Honokiol With acetic acid In dichloromethane for 0.0833333h; Cooling with ice; Stage #2: With nitric acid In dichloromethane at 0℃; for 6h;	61.3%
With nitric acid; acetic acid In dichloromethane at 10 - 20℃; for 1h;	52%

: 35354-74-6
Honokiol

: 590-17-0
cyanomethyl bromide

: C22H20N2O2

Conditions

Conditions	Yield
With caesium carbonate; potassium iodide In acetone at 20℃; for 24h;	61%

Honokiol Chemical Properties

Molecular Structure of Honokiol (CAS NO.35354-74-6):

Molecular Formula: C₁₈H₁₈O₂
Molecular Weight: 266.3343
IUPAC Name: 2-(4-Hydroxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
Synonyms of Honokiol (CAS NO.35354-74-6): NSC 293100 ; 3,5'-Diallyl-4,2'-dihydroxybiphenyl
CAS NO: 35354-74-6
Classification Code: Anti-allergic agents ; Anti-anxiety agents ; Anti-arrhythmia agents ; Anti-infective agents ; Antineoplastic Agents ; Antineoplastic agents, phytogenic ; Cardiovascular Agents ; Central Nervous System Agents ; Central nervous system depressants ; Enzyme Inhibitors ; Gastrointestinal agents ; Psychotropic Drugs ; Tranquilizing Agents
Polar Surface Area: 18.46 Å²
Index of Refraction: 1.601
Molar Refractivity: 82.42 cm³
Molar Volume: 240.4 cm³
Surface Tension: 44.6 dyne/cm
Density of Honokiol (CAS NO.35354-74-6): 1.107 g/cm³
Flash Point: 184 °C
Enthalpy of Vaporization: 67.63 kJ/mol
Boiling Point: 400.1 °C at 760 mmHg
Vapour Pressure: 5.65E-07 mmHg at 25°C

Honokiol History

In the late 1990s, honokiol(35354-74-6) saw a revival in western countries as a potent and highly tolerable anti-tumorigenic and neurotrophic compound.

Honokiol Uses

Honokiol (CAS NO.35354-74-6) has been used in the traditional Japanese medicine Saiboku-to as an anxiolytic, antithrombotic, anti-depressant, anti-emetic, and anti-bacterial. In the late 1990s, It saw a revival in western countries as a potent and highly tolerable anti-tumorigenic and neurotrophic compound.

Honokiol Production

Synthesis

Honokiol Safety Profile

Hazard Codes of Honokiol (CAS NO.35354-74-6): Irritant Xi, Dangerous N
Risk Statements: 41-51/53
R41: Risk of serious damage to the eyes.
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-39-61
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39: Wear eye / face protection.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3

Product Name

Honokiol

Synthetic route

Honokiol Chemical Properties

Honokiol History

Honokiol Uses

Honokiol Production

Honokiol Safety Profile

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