BISABOLENE

Base Information

• Chemical Name: BISABOLENE
• CAS No.: 495-62-5
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• European Community (EC) Number: 207-805-8
• DSSTox Substance ID: DTXSID9052131
• Wikipedia: Bisabolene
• Wikidata: Q27121553
• Mol file: 495-62-5.mol

Synonyms:BISABOLENE;2,6,10-Bisabolatriene;FEMA 3331;limene;(Z)-gamma-bisabolene;Bisabolene,mixture of isomers;cis-bisabolene;

Chemical Property of BISABOLENE

Chemical Property:

• Refractive Index: 1.4940
• Boiling Point: 155-157 °C
• PSA: 0.00000
• Density: 0.89
• LogP: 5.11530
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Sensitive.: Air Sensitive
• Solubility.: Benzene (Slightly), Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slig
• Water Solubility.: Soluble in alcohol, water, (0.008994 mg/L @ 25°C (est)).
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 296

Purity/Quality:

98%,99%, ^*data from raw suppliers

γ-Bisabolene(MixtureofIsomers)(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(=C(C)CCC=C(C)C)CC1
• Uses: It finds use in artificial oil of bergamot, myrrh and lemon, and is an excellent fixative for neroli bases. γ-Bisabolene (Mixture of Isomers), is a sesquiterpene and can be extracted from?oregano and other aromatic plants. It may be a potential anticancer agent that can induce apoptosis in A549 cancer cell line.

Technology Process of BISABOLENE

There total 63 articles about BISABOLENE 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: 82.0%

(2Z,6E)-3,7,11-Trimethyl-6-trimethylsilanyl-dodeca-2,6,10-trien-1-ol → (Z)-γ-bisabolene (495-62-5,5957-36-8,13062-00-5,53585-13-0,90458-95-0) + [E]-γ-bisabolene (53585-13-0)

Guidance literature:

With titanium tetrachloride; N-methylaniline; In dichloromethane; for 1h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)84133-7

Reference yield: 64.0%

(2Z)-5-allyl-2,6,10-trimethyl-1,5,9-undecatriene (370565-24-5) → (Z)-γ-bisabolene (495-62-5,5957-36-8,13062-00-5,53585-13-0,90458-95-0)

Guidance literature:

With Grubbs catalyst first generation; In benzene; for 24h;

DOI:10.1002/1099-0690(200108)2001:16<3039::AID-EJOC3039>3.0.CO;2-V

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (E)-β-farnesene (18794-84-8) + sesquisabinene A + (Z)-γ-bisabolene (495-62-5,5957-36-8,13062-00-5,53585-13-0,90458-95-0) + (Z)-α-bisabolene (29837-07-8) + 10-epi-β-acoradiene (28477-64-7) + β-sesquiphellandrene (19888-22-3,20307-83-9,20489-36-5,26882-41-7,27461-50-3,32182-04-0,73744-93-1,109278-27-5)

Guidance literature:

With Streptomyces coelicolor A₃⁽²⁾ epi-isozizaene synthase, F₁₉₈A mutant; In n-pentane; at 30 ℃; for 18h; pH=6.5; aq. buffer; Enzymatic reaction;

DOI:10.1021/bi902088z

upstream raw materials:

4-methyl-1-(1'-propanalethylidene)-3-cyclohexene

isopropyltriphenylphosphonium iodide

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

catechol (Z,Z)-monofarnesyl ether

Downstream raw materials:

succinic acid

levulinic acid

acetone

terephthalic acid

Refernces

• 1、 -. "Synthesis method of bisabolene". . . Retrieved 2019/04/02.
• 2、 -. "METHOD FOR THE PRODUCTION OF ALPHA-BISABOLOL FROM NEROLIDOL". Page/Page column 9. . Retrieved 2008/06/13.