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35354-74-6

Basic Information
CAS No.: 35354-74-6
Name: Honokiol
Article Data: 19
Cas Database
Molecular Structure:
Molecular Structure of 35354-74-6 (Honokiol)
Formula: C18H18O2
Molecular Weight: 266.34
Synonyms: [1,1'-Biphenyl]-2,4'-diol,3',5-di-2-propenyl- (9CI);3',5-Diallyl-2,4'-biphenyldiol;NSC 293100;Honokiol,(S);
EINECS: 609-119-8
Density: 1.107 g/cm3
Melting Point: 87.5ºC
Boiling Point: 400.1 °C at 760 mmHg
Flash Point: 184 °C
Solubility: DMSO: 36 mg/mL
Appearance: Dark brown to white fine powder with pleasant odor, spicy and slightly bitter taste.
Hazard Symbols: IrritantXi,DangerousN
Risk Codes: 41-51/53
Safety: 26-39-61
Transport Information: UN 3077 9/PG 3
PSA: 40.46000
LogP: 4.22180
Synthetic route
68592-18-7

Dimethylhonokiol

35354-74-6

Honokiol

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

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

35354-74-6

Honokiol

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

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

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.

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.
 

Production

Synthesis

Safety Profile

Hazard Codes of Honokiol (CAS NO.35354-74-6): IrritantXi,DangerousN
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