33880-83-0

Basic information

• Product Name: (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane
• Synonyms: (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane;β-elemene,(1alpha,2beta,4beta)-1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane,β-elemene;(1R,2R,4S)-1-Methyl-1-vinyl-2,4-diisopropenylcyclohexane;[1R,(+)]-1-Methyl-2β,4β-diisopropenyl-1-vinylcyclohexane;1α-Ethenyl-1-methyl-2β,4β-bis(1-methylethenyl)cyclohexane;Elemene;1-Ethenyl-1-methyl-2,4-di(prop-1-en-2-yl)cyclohexane;beta-Elemene
• CAS NO: 33880-83-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• EINECS: 251-713-0
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 33880-83-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 277.87°C (rough estimate)
• Flash Point: 98.341 °C
• Appearance: /
• Density: 0.8749
• Vapor Pressure: 0.031mmHg at 25°C
• Refractive Index: 1.4935
• CAS DataBase Reference: (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane(33880-83-0)
• EPA Substance Registry System: (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane(33880-83-0)

Safety Data

• Hazardous Substances Data: 33880-83-0(Hazardous Substances Data)

Usage

Uses

β-Elemene is an active constituent of Delonix regia and an anti-inflammatory agent. β-Elemene is a useful compound for investigating the toll-like receptor 4 signaling pathway and the inhibition of TNF-?a, IL-?1b, IL-?6 and IL-?12 expressions.

Anticancer Research

For this compound, a reduction of tumoral cell proliferation in human and murinemodels was reported (Misharina et al. 2013).

InChI:InChI=1/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m0/s1

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 138-86-3 limonene. 
• 7086-79-5 (3R*)-6-oxo-3-(prop-1-en-2-yl)heptanal 
• 88682-28-4 (5R*)-5-(2-hydroxyethyl)-6-methylhept-6-en-2-one 
• 100693-09-2 (5E,9E)-6,10-Dimethyl-11-vinyloxy-undeca-5,9-dien-2-one 
• 93525-18-9 (5E,9E)-11-hydroxy-6,10-dimethyl-5,9-undecadien-2-one 
• 3796-70-1 trans geranyl acetone 

Downstream Products

• 1460-98-6 1,3-di-isopropyl-4-methylbenzene 

Relevant articles and documents

Synthesis of trans-β-Elemene

Highly efficient syntheses of the anti-cancer agent trans-β-elemene have been achieved by using the readily available (±)-limonene as starting material. The syntheses were achieved in only nine to eleven steps with good overall yields. The key step in these reaction sequences is a stereoselective radical cyclization, induced by titanocene chloride.

Stereoselective synthesis of (±)-β-elemene by a doubly diastereodifferentiating internal alkylation: A remarkable difference in the rate of enolization between syn and anti esters

A total synthesis of the sesquiterpene (±)-β-elemene (1) has been achieved starting from a simple acyclic precursor 4. Key transformations include a 'doubly diastereodifferentiating folding and allylic strain-controlled' intramolecular ester enolate alkylation. In the course of the synthesis, we encountered remarkably different reactivity between syn and anti diastereomeric esters in the enolization step.

SYNTHESIS OF HELMINTHOGERMACRENE AND β-ELEMENE

Helminthogermacrene (1) and β-elemene (3) have been synthesized by a short route starting from geranylacetone.Titanium-induced cyclization of 3-isopropenyl-6-methyl-10-oxo-6E-undecenal (7) was used as the key step.