1461-03-6

Basic information

• Product Name: himachalene
• Synonyms: himachalene;(R)-2,4a,5,6,7,8-Hexahydro-3,5,5,9-tetramethyl-1H-benzocycloheptene;(R)-beta-himachalene
• CAS NO: 1461-03-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• Mol File: 1461-03-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 275.9°C at 760 mmHg
• Flash Point: 108.6°C
• Appearance: /
• Density: 0.9g/cm³
• Vapor Pressure: 0.00833mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: himachalene(CAS DataBase Reference)
• NIST Chemistry Reference: himachalene(1461-03-6)
• EPA Substance Registry System: himachalene(1461-03-6)

Safety Data

• Hazardous Substances Data: 1461-03-6(Hazardous Substances Data)

Usage

Definition

ChEBI: The (R)-enantiomer of beta-himachalene.

InChI:InChI=1/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h10,14H,5-9H2,1-4H3

Upstream product

• 116538-30-8 humula-4,9-dien-8-ol 
• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 
• 5989-08-2 (+)-α-Longipinene 

Downstream Products

• 19419-67-1 (S)-1,1,5,8-tetramethyl-1,2,3,4,5-pentahydrobenzo[a][7]annulene 
• 18067-37-3 Himachalen-dihydrochlorid 
• 18067-37-3 Himachalen-dihydrochlorid 

Relevant articles and documents

Alternate Cyclization Cascade Initiated by Substrate Isomer in Multiproduct Terpene Synthase from Medicago truncatula

Promiscuity of terpene synthases results in the enormous diversity of terpenes found in nature. Multiproduct sesquiterpene synthase MtTPS5 isolated from Medicago truncatula generates 27 optically pure products from its natural substrate (2E,6E)-farnesyl diphosphate (FDP). In order to study the promiscuity of MtTPS5, (2Z,6E)-FDP, an analogue of presumptive reaction intermediates from natural reaction cascade, was utilized as a substrate. This stereoisomer induced a novel cyclization pathway leading to sesquiterpenes based on humulane, amorphene, and himachalane skeletons. Interestingly, none of these products matched those observed on incubation of MtTPS5 with natural (2E,6E)-FDP. Further determination of the absolute configuration of each product helped rebuild the stereochemical route of the reaction cascade. Interestingly, the presence of only one enantiomer of each product was observed, indicating the highly stereospecific nature of the enzymatic reaction. Substrate promiscuity of terpene synthases provides organism access to novel chemical bouquets of high optical purity by utilizing existing enzymes. The presence of this mechanism was indicated by the presence of these alternate products in natural herbivore-induced volatiles of M. truncatula.

NEW SESQUITERPENOIDS FROM THE OLEORESIN OF Abies alba

The structures of four new sesquiterpenoids from the oleoresin of Abies alba have been studied, On the basis of various spectral characteristics, the structures of (10S, 11S)-himachala-2,4-diene, (10S, 11S)-himachala-3(12),4-diene, humula-4,9-dien-8-ol, and (4S, 5S, 10S)-selina-6-en-4-ol have been proposed for the compounds isolated.The stereochemistry of the assymetric centers was determined by the conversion of these compounds into known sesquiterpenes and also by analysis of PMR spectra with a shift reagent.