15352-77-9

Basic information

• Product Name: β-bisabolol,(1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol,β-bisabolol
• Synonyms: β-bisabolol,(1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol,β-bisabolol;1-(1,5-Dimethyl-4-hexenyl)-4-methyl-3-cyclohexen-1-ol;1-(6-Methylhept-5-en-2-yl)-cyclohex-3-enol
• CAS NO: 15352-77-9
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37
• Mol File: 15352-77-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 305.7°Cat760mmHg
• Flash Point: 130.5°C
• Appearance: /
• Density: 0.921g/cm³
• Vapor Pressure: 7.57E-05mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.87±0.40(Predicted)
• CAS DataBase Reference: β-bisabolol,(1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol,β-bisabolol(CAS DataBase Reference)
• NIST Chemistry Reference: β-bisabolol,(1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol,β-bisabolol(15352-77-9)
• EPA Substance Registry System: β-bisabolol,(1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol,β-bisabolol(15352-77-9)

Safety Data

• Hazardous Substances Data: 15352-77-9(Hazardous Substances Data)

Usage

General Description

β-bisabolol is a natural monocyclic sesquiterpene alcohol found in various plants, including chamomile and the candeia tree. It is known for its anti-inflammatory, anti-irritant, and anti-microbial properties, making it a popular ingredient in skincare and cosmetic products. Its chemical structure, (1S)-1-[(1S)-1,5-dimethyl-4-hexenyl]-4-methyl-3-cyclohexen-1-ol, contributes to its soothing and calming effects on the skin. β-bisabolol is also commonly used as a fragrance ingredient due to its pleasant, floral aroma. Additionally, it has been studied for its potential therapeutic effects in treating certain diseases and conditions, making it a versatile and valuable compound in the field of natural products and pharmaceuticals.

InChI:InChI=1/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3

Synthetic route

[(S)-1-((S)-1,5-Dimethyl-hex-4-enyl)-4-methyl-cyclohex-3-enyloxy]-trimethyl-silane (105987-39-1) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
With hydrogenchloride; water In methanol for 1h;

(-)-(S)-p-mentha-1,8-dien-4-ol (73069-45-1) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 11 steps 1: CO/H2 / RhH(Co)(PPh3)3 / hexane / 6 h / 110 °C / 150012 Torr 2: LiAlH4 / diethyl ether / 2 h / Heating 3: pyridine / 2 h / Ambient temperature 4: hexamethyldisilazane, pyridine / 48 h / Heating 5: LiAlH4 / diethyl ether / 1 h / Heating 6: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 7: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 8: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 9: PDC, NaOAc / CH2Cl2 10: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 11: HCl, H2O / methanol / 1 h View Scheme

(1R,3S,6S)-3-Isopropenyl-6-methyl-7-oxa-bicyclo[4.1.0]heptan-3-ol (106035-80-7) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 12 steps 1: Zn dust, NaOAc, NaI / acetic acid / 25 h 2: CO/H2 / RhH(Co)(PPh3)3 / hexane / 6 h / 110 °C / 150012 Torr 3: LiAlH4 / diethyl ether / 2 h / Heating 4: pyridine / 2 h / Ambient temperature 5: hexamethyldisilazane, pyridine / 48 h / Heating 6: LiAlH4 / diethyl ether / 1 h / Heating 7: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 8: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 9: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 10: PDC, NaOAc / CH2Cl2 11: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 12: HCl, H2O / methanol / 1 h View Scheme

3-((S)-1-Hydroxy-4-methyl-cyclohex-3-enyl)-butyraldehyde → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 10 steps 1: LiAlH4 / diethyl ether / 2 h / Heating 2: pyridine / 2 h / Ambient temperature 3: hexamethyldisilazane, pyridine / 48 h / Heating 4: LiAlH4 / diethyl ether / 1 h / Heating 5: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 6: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 7: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 8: PDC, NaOAc / CH2Cl2 9: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 10: HCl, H2O / methanol / 1 h View Scheme

3-<(1S)-1-hydroxy-4-methylcyclohex-3-enyl>butanol → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 9 steps 1: pyridine / 2 h / Ambient temperature 2: hexamethyldisilazane, pyridine / 48 h / Heating 3: LiAlH4 / diethyl ether / 1 h / Heating 4: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 5: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 6: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 7: PDC, NaOAc / CH2Cl2 8: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 9: HCl, H2O / methanol / 1 h View Scheme

3-<(1S)-4-methyl-1-(trimethylsilyloxy)cyclohex-3-enyl>butyl acetate → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 1 h / Heating 2: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 3: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 4: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 5: PDC, NaOAc / CH2Cl2 6: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 7: HCl, H2O / methanol / 1 h View Scheme

(S)-3-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-butan-1-ol (105987-22-2) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 2: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 3: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 4: PDC, NaOAc / CH2Cl2 5: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 6: HCl, H2O / methanol / 1 h View Scheme

Acetic acid 3-((S)-1-hydroxy-4-methyl-cyclohex-3-enyl)-butyl ester → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: hexamethyldisilazane, pyridine / 48 h / Heating 2: LiAlH4 / diethyl ether / 1 h / Heating 3: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 4: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 5: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 6: PDC, NaOAc / CH2Cl2 7: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 8: HCl, H2O / methanol / 1 h View Scheme

Trimethyl-[(S)-4-methyl-1-((S)-1-methyl-but-3-enyl)-cyclohex-3-enyloxy]-silane (105987-36-8) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 2: PDC, NaOAc / CH2Cl2 3: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 4: HCl, H2O / methanol / 1 h View Scheme

(S)-4-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-pentan-1-ol (105987-37-9) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: PDC, NaOAc / CH2Cl2 2: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 3: HCl, H2O / methanol / 1 h View Scheme

(S)-4-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-pentanal (105987-38-0) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 2: HCl, H2O / methanol / 1 h View Scheme

(S)-3-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-butyraldehyde (105987-35-7) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 2: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 3: PDC, NaOAc / CH2Cl2 4: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 5: HCl, H2O / methanol / 1 h View Scheme

(1S,2R,4R)-limonene-1,2-epoxide (6909-30-4) → (+)-(4S,8S)-β-bisabolol (15352-77-9)

Conditions

Yield

Multi-step reaction with 13 steps 1: t-BuOOH, SeO2 / CH2Cl2 / 240 h / 25 °C 2: Zn dust, NaOAc, NaI / acetic acid / 25 h 3: CO/H2 / RhH(Co)(PPh3)3 / hexane / 6 h / 110 °C / 150012 Torr 4: LiAlH4 / diethyl ether / 2 h / Heating 5: pyridine / 2 h / Ambient temperature 6: hexamethyldisilazane, pyridine / 48 h / Heating 7: LiAlH4 / diethyl ether / 1 h / Heating 8: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature 9: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h 10: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h 11: PDC, NaOAc / CH2Cl2 12: 1.) BuLi / diethyl ether; hexane / 1 h / Heating 13: HCl, H2O / methanol / 1 h View Scheme

Upstream product

• 6909-30-4 (1S,2R,4R)-limonene-1,2-epoxide 
• 105987-35-7 (S)-3-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-butyraldehyde 
• 105987-38-0 (S)-4-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-pentanal 
• 105987-37-9 (S)-4-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-pentan-1-ol 
• 105987-36-8 Trimethyl-[(S)-4-methyl-1-((S)-1-methyl-but-3-enyl)-cyclohex-3-enyloxy]-silane 
• 105987-22-2 (S)-3-((S)-4-Methyl-1-trimethylsilanyloxy-cyclohex-3-enyl)-butan-1-ol 
• 106035-80-7 (1R,3S,6S)-3-Isopropenyl-6-methyl-7-oxa-bicyclo[4.1.0]heptan-3-ol 
• 73069-45-1 (-)-(S)-p-mentha-1,8-dien-4-ol 
• 105987-39-1 [(S)-1-((S)-1,5-Dimethyl-hex-4-enyl)-4-methyl-cyclohex-3-enyloxy]-trimethyl-silane 

Relevant articles and documents

The Absolute Configuration of β-Bisabolol

From bergamot oil (Citrus bergamia RISSO), (-)-(4S,8R)-8-epi-α-bisabolol (2) and (-)-(4R,8S)-4-epi-β-bisabolol (3) were isolated.The absolute configuration of their stereoisomers 4 and 5 was established by an enantioselective synthesis starting from (-)-(S)-p-mentha-1,8-dien-4-ol.