495-60-3

Basic information

• Product Name: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
• Synonyms: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene;α-zingiberene,[S-(R,S)]-5-(1,5-dimethyl-4-hexenyl)-2-methyl-1,3-cyclohexadiene,(-)-zingiberene;1,3-Cyclohexadiene, 5-(1,5-dimethyl-4-hexenyl)-2-methyl-, (S-(R*,S*))-;(R)-5-[(S)-1,5-Dimethyl-4-hexenyl]-2-methyl-1,3-cyclohexadiene;(R)-2-Methyl-5-((S)-6-methylhept-5-en-2-yl)-cyclohexa-1,3-diene;(5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene;(5R)-5-[(1S)-1,5-dimethylhex-4-enyl]-2-methyl-cyclohexa-1,3-diene;Zingiberene (7CI)
• CAS NO: 495-60-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• EINECS: 207-804-2
• Mol File: 495-60-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 270.7°Cat760mmHg
• Flash Point: 107.5°C
• Appearance: /
• Density: 0.854g/cm³
• Vapor Pressure: 0.0112mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(495-60-3)
• EPA Substance Registry System: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(495-60-3)

Safety Data

• Hazardous Substances Data: 495-60-3(Hazardous Substances Data)

Usage

Uses

α-Zingiberene is a sesquiterpine found in leaf glandular trichomes that is currently being evaluated for its cytotoxicity towards human tumour cell lines.

Definition

ChEBI: 2-Methylcyclohexa-1,3-diene in which a hydrogen at the 5 position is substituted (R configuration) by a 6-methyl-hept-5-en-2-yl group (S configuration). It is a sesquiterpene found in the dried rhizomes of Indonesian ginge , Zingiber officinale.

InChI:InChI=1/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m0/s1

Upstream product

• 87680-38-4 (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol 
• 87680-39-5 (3S,6R,7S)-1,10-bisaboladien-3-ol 
• 343239-55-4 4-[(1S)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 
• 1242417-59-9 C₂₃H₂₉N₃O₂ 
• 1242417-58-8 C₂₃H₂₉N₃O₂ 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 1242140-82-4 C₃₁H₃₈O₄ 
• 1242140-81-3 C₃₁H₃₈O₄ 
• 1242140-77-7 C₃₁H₃₈O₄ 
• 3649-81-8 (S)-curcumene 
• 1198212-60-0 (+)-biyouyanagin A 
• 244179-42-8 (6S)-2-methyl-6-(4-methyl-cyclohexyl)-heptane 

Relevant articles and documents

Discovery of the aggregation pheromone of the brown marmorated stink bug (Halyomorpha halys) through the creation of stereoisomeric libraries of 1-bisabolen-3-ols

We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.

PLANT VOLATILES BASED ON R-CURCUMENE

The invention provides a method for controlling whiteflies which comprises the steps of: providing a composition comprising or consisting of R-curcumene and optionally further beta-myrcene, para-cymene, gamma-terpinene, alpha-terpinene, alpha-phellandrene zingiberene and/or 7-epi-zingiberene; and adding said composition one or more times to a plurality of crop plants. The method can be combined with the use of attractant compositions comprising beta-phellandrene, limonene and/or 2-carene, and optionally adding said composition one or more times to one or more trap plants and/or trap materials.