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

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

Uses

Used in Pharmaceutical Industry:
THUJONE, (A + B)(SG) is used as a medicinal compound for its traditional healing properties, including its psychoactive effects and potential applications in treating various health conditions.
Used in Insecticidal Applications:
THUJONE, (A + B)(SG) is used as an insecticide due to its natural ability to repel or kill insects, making it a component in certain pest control products.
Used in Analytical Chemistry:
THUJONE, (A + B)(SG) is used as a reference or standard in analytical chemistry for its specific gravity (SG) value, aiding in the determination of densities of other compounds in research and quality control processes.
Used in Flavor and Fragrance Industry:
THUJONE, (A + B)(SG) is used as a component in the creation of flavors and fragrances, capitalizing on its distinctive aromatic properties derived from natural plant sources.

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

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

Downstream Products

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

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.

Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays

Multiproduct terpene synthases TPS4-B73 and TPS5-Delprim from Zea mays exhibit isotopically sensitive branching in the formation of mono- and sesquiterpene volatiles. The impact of the kinetic isotope effects and the stabilization of the reactive intermediates by hyperconjugation along with the shift of products from alkenes to alcohols are discussed.

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.

A convenient synthesis of trans-sabinene hydrate from (-)-3-thujol via a highly selective ene reaction of singlet oxygen

trans-Sabinene hydrate (1), was synthesized from (-)-3-thujol (2) in four steps. The key step was the selective formation of trans-2-hydroxy-3-thujene (6) by photooxygenation of a 3:1 mixture of 2- and 3-thujenes (4 and 5) obtained from (-)-3-thujol mesylate (3). Hydrogenation of 6 gave compound 1 in 46% overall yield.

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