alpha-Bisabolol

Base Information

• Chemical Name: alpha-Bisabolol
• CAS No.: 515-69-5
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.371
• Hs Code.: 29061900
• European Community (EC) Number: 208-205-9
• UNII: 37VB7WIC8L
• DSSTox Substance ID: DTXSID301140604
• Nikkaji Number: J291.104C
• Wikipedia: Bisabolol
• Wikidata: Q27256708
• RXCUI: 19461
• Metabolomics Workbench ID: 137717
• ChEMBL ID: CHEMBL477832
• Mol file: 515-69-5.mol

Synonyms:3-Cyclohexene-1-methanol, a,4-dimethyl-a-(4-methyl-3-pentenyl)-, (aR,1R)-rel- (9CI);5-Hepten-2-ol,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)- (6CI,7CI,8CI);Bisabolol;Camilol;Dragosantol;Dragosantol 100;Hydagen B;dl-a-Bisabolol;a-Bisabolol;alpha-Bisabolol;

Chemical Property of alpha-Bisabolol

Chemical Property:

• Appearance/Colour: Colorless or festucine mucous liquid
• Vapor Pressure: 4E-05mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: n20/D 1.496
• Boiling Point: 154-156°C
• PKA: 15.04±0.29(Predicted)
• Flash Point: 135°C
• PSA: 20.23000
• Density: 0.93 g/mL at 20 °C(lit.)
• LogP: 4.23020
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Soluble in alcohol, natural, mineral and synthetic oils. Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

99%, ^*data from raw suppliers

Dragosantol(>80%) ^*data from reagent suppliers

Safty Information:

• Statements: 33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CCC(CC1)C(C)(CCC=C(C)C)O
• Isomeric SMILES: CC1=CC[C@H](CC1)[C@@](C)(CCC=C(C)C)O
• Uses: alpha-Bisabolol is a botanical used for its anti-inflammatory and soothing properties. It is derived from chamomile and/or yarrow. It finds its application as a masking agent, skin conditioning agent and soothing agent in cosmetics industry. The most important effects of Bisabolol for the use in cosmetics are anti-inflammatory, wound-healing, anti-bacterial and anti-mycotic. Bisabolol is therefore perfectly suited for the use in all kinds of skin-care products It can be used as active substance in cosmetic preparations for the protection and care of sensitive skin, preparations for babies and children, sunscreen and after-sun products, aftershaves and preparations for the oral hygiene.

Technology Process of alpha-Bisabolol

There total 65 articles about alpha-Bisabolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

4-methyl-1,3-pentadiene (926-56-7,54363-49-4) + (+-)-4-acetyl-1-methylcyclohexene (6090-09-1) → bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl-formamide; electroreductive coupling;

DOI:10.1021/jo00287a001

Reference yield: 80.0%

3-(4-Methyl-3-pentenyl)-1,3-dimethyl-2-oxabicyclo<2.2.2>octan-6-one (129080-75-7,129171-15-9) → bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5) + sesquicineole (84765-62-8,90131-02-5,135912-01-5,135912-02-6)

Guidance literature:

With potassium carbonate; hydrazine hydrate; In various solvent(s); Heating;

DOI:10.1016/S0040-4020(01)81519-2

Reference yield: 75.0%

2-methyl-6-keto-6-(4-methyl-3-cyclohexen-1-yl)-2-hexene (76280-88-1) + methylmagnesium bromide (75-16-1) → bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5)

Guidance literature:

In diethyl ether; at 35 ℃; for 3h;

DOI:10.1016/S0040-4020(01)88587-2

upstream raw materials:

methanol

(2R,3R,4S,5R,6S)-2-methyl-6-{[(2S)-6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}tetrahydro-2H-pyran-3,4,5-triol

(4S,8R)-8,9-Epoxy-p-menth-1-ene

(S)-4-Isopropenyl-1-methylcyclohexene 7,8-epoxide

Downstream raw materials:

(6R,1'S)-epi-hernandulcin

2,6-dichloro-2-(4-chloro-4-methyl-cyclohexyl)-6-methyl-heptane

6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-6-methoxyheptan-2-ol

(Z)-γ-bisabolene

Refernces

• 1、 De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.. "Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol". . p. 271 - 275. Retrieved 2015/07/07.
• 2、 -. "Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol". Paragraph 0118 - 0122; 0125 - 0137. . Retrieved 2013/11/06.