495-61-4

Basic information

• Product Name: (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene
• Synonyms: (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene;Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexenyl)-, (4S)-;Cyclohexene,1-methyl-4-(5-;B-Bisabolene;6-methyl-2-[(1R)-4-methyl-1-cyclohex-3-enyl]hepta-1,5-diene;[S,(-)]-1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene;1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)-cyclohex-1-ene;(S)-beta-bisabolene
• CAS NO: 495-61-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• EINECS: 310-198-3
• Mol File: 495-61-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 277.87°C (rough estimate)
• Flash Point: 109.8°C
• Appearance: /
• Density: 0.8673
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.4880
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene(495-61-4)
• EPA Substance Registry System: (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene(495-61-4)

Safety Data

• Hazardous Substances Data: 495-61-4(Hazardous Substances Data)

Usage

Description

(-)-β-bisabolene, also known as β-bisabolene or 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene, is a naturally occurring sesquiterpene with the (1S)-configuration. It can be extracted from aromatic plants such as oregano and has potential applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
(-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene is used as a potential anticancer agent for its ability to induce apoptosis in the A549 cancer cell line. This suggests that it may play a role in the development of new cancer treatments or therapies.
Used in Aromatherapy and Perfumery:
(-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene is used as a fragrance ingredient in the aromatherapy and perfumery industries. Its pleasant aroma and natural origin make it a desirable component in creating various scent profiles.
Used in Cosmetics Industry:
In the cosmetics industry, (-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene is used as an ingredient in skincare and hair care products. Its potential anti-inflammatory and soothing properties can contribute to the effectiveness of these products in addressing various skin and hair concerns.
Used in Flavor and Food Industry:
(-)-β-bisabolene,β-bisabolene,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene may also be used in the flavor and food industry as a natural additive to enhance the taste and aroma of various products. Its unique scent can provide a distinct flavor profile to food and beverages.

Anticancer Research

The first study seemed that β-bisabolene had promising activities against 4T1 mammarytumor cells in vitro and transplanted in mice (Krifa et al. 2016).

InChI:InChI=1/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1

Upstream product

• 372-97-4 farnesyl pyrophosphate 
• 16106-95-9 (2Z,6Z)-farnesol 
• 24163-93-7 (Z,Z)-farnesyl bromide 
• 170080-85-0 (S)-4-methyl-3-cyclohexene-1-carbonyl chloride 
• 102096-63-9 (R)-2-<(S)-4-methyl-3-cyclohexene-1-carboxy>-3,3-dimethyl-γ-butyrolactone 
• 102208-60-6 (S)-4-methyl-3-cyclohexene-1-carboxylic acid 
• 170080-86-1 (S)-2-methyl-6-keto-(4-methyl-3-cyclohexen-1-yl)-2-hexene 
• 74-95-3 1,1-dibromomethane 
• 86803-80-7 (R)-(+)-1,1'-bi-2-naphthol (Z,E)-monofarnesyl ether 
• 86803-80-7 (R)-(+)-1,1'-bi-2-naphthol (Z,Z)-monofarnesyl ether 
• 5989-27-5 D-limonene 
• 870-63-3 prenyl bromide 

Downstream Products

• 110160-83-3 2,6-dichloro-2-(4-chloro-4-methyl-cyclohexyl)-6-methyl-heptane 

Relevant articles and documents

Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays

Multiproduct terpene synthases TPS4-B73 and TPS5-Delprim from Zea mays exhibit isotopically sensitive branching in the formation of mono- and sesquiterpene volatiles. The impact of the kinetic isotope effects and the stabilization of the reactive intermediates by hyperconjugation along with the shift of products from alkenes to alcohols are discussed.

CHIRAL LEAVING GROUP: ASYMMETRIC SYNTHESIS OF LIMONENE AND BISABOLENE

The biogenetic-type asymmetric synthesis of limonene and bisabolenes is described.As model studies for the present asymmetric synthesis, the cyclization of catechol, biphenol and binaphthol mononeryl ethers 1, 4, and 5, with organoaluminium reagents are executed to furnish limonene as a major product.Since the reaction of 1, 4, and 5 has proved to proceed much faster than that of neryl phenyl ether under the similar conditions, the rate acceleration is attributed to the novel metal-anchimeric assistance of the aluminium reagents bound with the neighboring hydroxyl group for effecting the generation of the allyl cathion.This anchimeric effect is utilized for the enantioselective cyclization of (R)-(+)-1,1'-bi-2-naphthol mononeryl ether (8) upon treatment with modified aluminium reagent 9 to produce limonene with high optical purity (77percent ee).In a similar fashion, (R)-(+)-binaphtol (Z,Z)-monofarnesyl ether 16a undergoes the enantioselective cyclization to give β-bisabolene in 76percent ee.