118-65-0

Basic information

• Product Name: (-)-ISOCARYOPHYLLENE
• Synonyms: ,9s)]-;4,11,11-trimethyl-8-methylene-,[1R-(1R*,4Z,9S*)]-Bicyclo[7.2.0]undec-4-ene;Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-,[1R-(1R*,4Z,9S*)]-;bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-,[1theta-(1theta,4z;(-)-ISOCARYOPHYLLENE;ISOCARYOPHYLLENE, (-)-;BETA-CARYOPHYLLENE;(1R,9S)-8-METHYLEN-4,11,11-TRIMETHYL-BICYCLO[7.2.0]UNDEC-4-ENE
• CAS NO: 118-65-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 204-267-6
• Product Categories: pharmacetical
• Mol File: 118-65-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 271-273 °C(lit.)
• Flash Point: 215 °F
• Appearance: /
• Density: 0.893 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0128mmHg at 25°C
• Refractive Index: n20/D 1.496
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (-)-ISOCARYOPHYLLENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ISOCARYOPHYLLENE(118-65-0)
• EPA Substance Registry System: (-)-ISOCARYOPHYLLENE(118-65-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 118-65-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 118-65-0 differently. You can refer to the following data:
1. In perfumery.
2. Isocaryophyllene is an Z- isomer of β-Caryophyllene (C184725). β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.

Purification Methods

Purify it by vacuum distillation or GLC using a nitrile-silicone column [Corey et al. J Am Chem Soc 86 485 1964, Ramage & Simonsen J Chem Soc 741 1936, Kumar et al.Synthesis 461 1976]. [Beilstein 5 III 1085.]

InChI:InChI=1/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1

Upstream product

• 60594-22-1 caryophyllene oxide 
• 61824-50-8 (Z)-(1R,9S)-4,11,11-Trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-one 
• 87-44-5 β-caryophyllene 
• 60362-45-0 8-Oxo-4,11,11-trimethylbicyclo<7.2.0>undec-4-en 

Downstream Products

• 57082-24-3 caryophyllene acetate 
• 469-92-1 (-)-Clovene 
• 58404-89-0 β-caryolanol 
• 1217184-42-3 (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0(2,5)]dodecanyl acetate 
• 10306-22-6 kobusone 
• 597-43-3 2,2-dimethylsuccinic acid 
• 88514-14-1 (1R,6R,10S)-5,12,12-Trimethyl-9-methylene-4-oxa-tricyclo[8.2.0.0^3,5]dodecan-6-ol 
• 19431-76-6 caryophyllenol-II 
• 1139-30-6 caryophyllene epoxide 
• 18755-93-6 Photocaryophyllen D 
• 19431-79-9 (1S,5S,9R)-10,10-Dimethyl-2,6-dimethylene-bicyclo[7.2.0]undecan-5-ol 
• 19431-76-6 caryophyllenol-I 
• 32214-91-8 Acetic acid (Z)-(1R,5R,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-yl ester 
• 496-99-1 (+)-trans-Norcaryophyllensaeure 

Relevant articles and documents

Electron transfer-initiated epoxidation and isomerization chain reactions of β-caryophyllene

The abundant sesquiterpene b-caryophyllene can be epoxidized by molecular oxygen in the absence of any catalyst. In polar aprotic solvents, the reaction proceeds smoothly with epoxide selectivities exceeding 70%. A mechanistic study has been performed and the possible involvement of free radical, spin inversion, and electron transfer mechanisms is evaluated using experimental and computational methods. The experimental data-including a detailed reaction product analysis, studies on reaction parameters, solvent effects, additives and an electrochemical investigation-all support that the spontaneous epoxidation of b-caryophyllene constitutes a rare case of unsensitized electron transfer from an olefin to triplet oxygen under mild conditions (80 8C, 1 bar O2). As initiation of the oxygenation reaction, the formation of a caryophyllene-derived radical cation via electron transfer is proposed. This radical cation reacts with triplet oxygen to a dioxetane via a chain mechanism with chain lengths exceeding 100 under optimized conditions. The dioxetane then acts as an in situ-formed epoxidizing agent. Under nitrogen atmosphere, the presence of a one-electron acceptor leads to the selective isomerization of b -caryophyllene to isocaryophyllene. Observations indicate that this isomerization reaction is a novel and elegant synthetic pathway to isocaryophyllene.

Betulenols from Betula species

The essential oils from buds of five Betula species growing in Turkey were investigated by GC-MS. A major component in the essential oils was shown to be 14-hydroxy-β-caryophyllene (6). The structure of β-betulenal (12) which was isolated from Betula essential oils was also confirmed by synthesis. Chemical reactions yielded 14-acetoxy-β-aryophyllene (15), 14- hydroxy-isocaryophyllene (10) and its acetate (14), giving evidence to the natural occurrence in Betula species of the formerly known α-betulenol acetate (3), β-betulenol (2) and β-betulenol acetate (4), respectively. Compounds 6, 9, 10, 12, and 15 were evaluated for antimicrobial activity.