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| CAS No.: | 35354-74-6 |
|---|---|
| Name: | Honokiol |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi, N
|
| Risk Codes: | 41-51/53 |
| Safety: | 26-39-61 |
| Transport Information: | UN 3077 9/PG 3 |
| PSA: | 40.46000 |
| LogP: | 4.22180 |
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- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 68592-18-7
Dimethylhonokiol
- 35354-74-6
Honokiol
| 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 | 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 | 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 | Yield |
|---|---|
| With hydrogenchloride In methanol at 20℃; for 44h; | 89% |
- 35354-74-6
Honokiol
| Conditions | Yield |
|---|---|
| With methanol; chloro-trimethyl-silane at 0 - 20℃; for 6h; | 85% |
| 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 | 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
| 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 | 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 | 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 |
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Chemistry
Molecular Structure of Honokiol (CAS NO.35354-74-6):
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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): 
Xi,
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