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

Description

[S-(R,S)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene, also known as α-Zingiberene, is a sesquiterpene found in the dried rhizomes of Indonesian ginger, Zingiber officinale. It is characterized by a 2-methylcyclohexa-1,3-diene structure with a hydrogen at the 5 position substituted (R configuration) by a 6-methyl-hept-5-en-2-yl group (S configuration). [S-(R,S)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene is currently being evaluated for its cytotoxicity towards human tumor cell lines.

Uses

Used in Pharmaceutical Industry:
[S-(R,S)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene is used as a potential cytotoxic agent for the development of anticancer drugs. Its application is based on its cytotoxicity towards human tumor cell lines, which makes it a promising candidate for further research and development in the fight against cancer.
Used in Aromatherapy and Perfumery:
As a naturally occurring sesquiterpene, [S-(R,S)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene can be used as a fragrance ingredient in the aromatherapy and perfumery industries. Its unique scent and natural origin make it an attractive option for creating various fragrances and aromatherapy products.
Used in Flavor Industry:
Due to its natural occurrence in ginger, [S-(R,S)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene can also be used as a flavoring agent in the food and beverage industry. Its ginger-like aroma can be utilized to enhance the taste and aroma of various products, providing a natural and unique flavor profile.

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

• 75-16-1 methylmagnesium bromide 
• 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 

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.

Total synthesis and structural revision of biyouyanagin B

Figure Presented An intriguing chase of the newly reported biyouyanagin B leads to its total synthesis and structural revision from 1' to 1.