2867-05-2

Basic information

• Product Name: THUJONE, (A + B)(SG)
• Synonyms: 3-Thujene;alpha-thuiene;alpha-Thujene;Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)-;Origanene;THUJONE, (A + B)(SG);5-isopropyl-2-methylbicyclo[3.1.0]hex-2-ene;α-thujene,2-methyl-5-(1-methylethyl)-bicyclo[3.1.0]hex-2-ene,3-thujene,origanene
• CAS NO: 2867-05-2
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23404
• EINECS: 220-686-7
• Mol File: 2867-05-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 152°C
• Flash Point: 36°C
• Appearance: /
• Density: 0.8301
• Vapor Pressure: 4.77mmHg at 25°C
• Refractive Index: 1.4515
• CAS DataBase Reference: THUJONE, (A + B)(SG)(CAS DataBase Reference)
• NIST Chemistry Reference: THUJONE, (A + B)(SG)(2867-05-2)
• EPA Substance Registry System: THUJONE, (A + B)(SG)(2867-05-2)

Safety Data

• Hazardous Substances Data: 2867-05-2(Hazardous Substances Data)

Usage

General Description

THUJONE, (A + B)(SG) is a chemical compound that is a mixture of two isomeric forms of thujone, known as alpha-thujone (A) and beta-thujone (B), with a specific gravity (SG) value. Thujone is a naturally occurring monoterpene ketone found in several plants, including the common sage and wormwood. It is known for its psychoactive effects and has been used traditionally for its medicinal and insecticidal properties. However, there are also concerns about its potential toxicity and its impact on the central nervous system. The specific gravity value is a measure of the density of the compound compared to water, which can be useful in various analytical and industrial applications.

InChI:InChI=1/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3

Upstream product

• 33741-33-2 (+)-isothujone p-tosylhydrazone 
• 21653-20-3 (-)-3-thujol 
• 471-15-8 (+)-isothujone 
• 18791-12-3 (-)-thujone p-tosylhydrazone 
• 177324-96-8 Methanesulfonic acid (1S,3S,4R,5R)-1-isopropyl-4-methyl-bicyclo[3.1.0]hex-3-yl ester 
• 2009-00-9 sabinene 
• 53833-85-5 trans-sabinyl acetate 
• 1125-12-8 (-)-α-thujone 
• 21653-18-9 (-)-neothujol 
• 54825-97-7 dithiocarbonic acid S-methyl ester-O-thujan-3-yl ester 
• 471-16-9 sabinol 
• 763-10-0 geranyl diphosphate 

Downstream Products

• 99-87-6 4-methylisopropylbenzene 
• 1197-15-5 p-mentha-1,3-dien-7-al 
• 489-20-3 1,2-dimethyl-3-(1-methylethyl)cyclopentane 
• 471-12-5 thujane 
• 562-74-3 TERPINEN-4-OL 
• 99-83-2 p-mentha-1,5-diene 
• 174512-63-1 α-thujene epoxide 
• 7766-03-2 trans-2-hydroxy-3-thujene 

Relevant articles and documents

CIDNP study and ab-initio calculations of rigid vinylcyclopropane systems: Evidence for delocalized 'ring-closed' radical cations

The radical cations of three terpenes, sabinene, 1, and α-, 2, and β-thujene, 3, containing vinylcyclopropane functions held rigidly in either an anti- or syn-orientation, have been elucidated by CIDNP studies. The structures assigned to these species are discussed in view of their reactivities and compared with three simplified radical cations, 2-methylenebicyclo[3.1.0]hexane, 4, bicyclo[3.1.0]hex-2-ene, 5, and 5-methylbicyclo[3.1.0]hex-2-ene, 6, calculated by ab initio molecular orbital methods.

Kinetics of thermal rearrangements in the Δ2-thujene system: A full quadrisection of a perturbed bicyclo[3.1.0]hex-2-ene

Further insight into the behavior of suppositional diradicals in a caldera is sought in the thermal rearrangements among the four "Δ 2-thujenes", two 1-isopropyl-4-methylbicyclo[3.1.0]hex-2-enes [(-)-cis-1 and (+)-trans-2] and two isomers, exo- and endo-3-isopropyl-6- methylbicyclo[3.1.0]hex-2-ene [(+)-exo-3 and (-)-endo-4]. Optically pure trans-3-isopropyl-5-vinylcyclopentene (5) is the final, strongly thermochemically favored product, the result of an intramolecular homodienyl shift of a methyl hydrogen atom in (-)-endo-4. The set of twelve specific rate constants, four sets of three each, that define the interrelations among the four isomers has been extracted from data acquired starting from each isomer. An attractive mechanistic hypothesis involving an, intermediate diradical of iso conformation, common, for example, to both (-)-cis-1 and (+)-exo-3 (as educts), that proceeds to an anticonformer common to both (+)-trans-2 and (-)-endo-4 does not lead to a satisfactory rationalization of the product distribution. Addition of a second mechanistic conceptual scheme, that of a diradical-in-transit behaving as if there were a measure of continuous bonding (for example, (+)-trans-2 proceeding directly to (-)-cis-1), improves agreement with experiment. Over a 30 °C range of temperature, there is no credible change in product distribution.

ENANTIOMERIC COMPOSITION OF MONOTERPENE HYDROCARBONS FROM THE LIVERWORT CONOCEPHALUM CONICUM

Volatiles from the essential oil of the liverwort Conocephalum conicum were analysed.The chirality of the monoterpene hydrocarbons was studied by two-dimensional gas chromatography.All compounds except β-phellandrene showed high optical purity.For the identification of enantiomers, (+)-β-phellandrene and (-)-α-thujene were prepared from (+)-limonene and (+)-sabinene, respectively.Key Word Index: Conocephalum conicum; Hepaticae; liverwort; monoterpene hydrocarbons; (+)-β-phellandrene; (-)-α-thujene; chiral composition