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

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

Used in Pharmaceutical Industry:
(1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane is used as an active constituent for investigating the toll-like receptor 4 signaling pathway and the inhibition of TNF-α, IL-1β, IL-6, and IL-12 expressions. Its anti-inflammatory properties make it a promising candidate for the development of new drugs targeting inflammatory diseases.
Used in Chemical Research:
(1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane is used as a research compound for studying the synthesis and properties of complex organic molecules. Its unique structure allows chemists to explore new methods for the construction of cyclohexane derivatives and their potential applications in various fields.
Used in Material Science:
(1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane is used as a precursor in the synthesis of novel polymers and materials with specific properties. Its ability to form stable structures and interact with other molecules makes it a valuable component in the development of advanced materials for various applications, such as coatings, adhesives, and composites.

Anticancer Research

For (1alpha,2beta,4beta)-1-methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane, 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

• 21499-60-5 ethyl 2-methyl-5-isopropenyl-8,8-ethylenedioxy-trans-2-nonenoate 
• 21499-61-6 ethyl (5R*,E)-2-methyl-8-oxo-5-(prop-1-en-2-yl)non-2-enoate 
• 21499-63-8 (2E,8Ξ)-5-isopropenyl-2,8-dimethyl-deca-2,8-diene-1,10-diol 
• 88682-28-4 (5R*)-5-(2-hydroxyethyl)-6-methylhept-6-en-2-one 
• 7086-79-5 (3R*)-6-oxo-3-(prop-1-en-2-yl)heptanal 
• 138-86-3 limonene. 
• 1779-49-3 Methyltriphenylphosphonium bromide 

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.

Isogermacrene A, a proposed intermediate in sesquiterpene biosynthesis

A sesquiterpene hydrocarbon, isogermacrene A (5), which is structurally related to the gorgonanes and zieranes, was isolated from the essential oil of Saccogyna viticulosa (Hepaticae). This monocyclic compound is proposed as the biogenetic intermediate of some rare sequiterpene skeletons. In the essential oil of the liverwort Saccogyna viticulosa, collected on the island of Madeira, the new sesquiterpene hydrocarbons isogermacrene A (5) and its Cope rearrangement product iso-β-elemene (6) were identified. 5 is proposed to act as the biogenetic precursor of several new sesquiterpenes identified in the volatiles of S. viticulosa. These include iso-α-humulene, α-gorgonene, gorgona-1,4(15),11-triene and gorgon-11-en-4-ol. In addition, the Cope product of zierene, isozierene, allo-aromadendra-4(15),10(14)-diene, aromadendra-4(15),10(14)-dien-1-ol and a prenylguaiane diterpene alcohol, named viticulol, were identified as new natural products.

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.

Enantioselective total synthesis of β-elemene and fuscol based on enantiocontrolled Ireland-Claisen rearrangement

The potent antiinflammatory agent precursor (+)-fuscol (2) has been synthesized using the chiral reagent 1 to effect the key step, the completely enantioselective Ireland-Claisen rearrangement of ester 3 to acid 4a. Conversion of 4a to the corresponding aldehyde 4c, cation-olefin cyclization to 5a, and deoxygenation produced (+)-β-elemene (6). (+)-Fuscol (2) was synthesized from 6 via intermediates 7 and 8.

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.