471-15-8

Basic information

• Product Name: THUJONE
• Synonyms: (E)-Thujone;(Z)-thujone;3-Thujanone, (1S,4S,5R)-(+)-;Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1alpha,4beta,5alpha)]-;cis-Thujone;D-beta-Thujone;D-isothujone;Thujone cis
• CAS NO: 471-15-8
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 304.47
• Mol File: 471-15-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 84-86 °C17 mm Hg(lit.)
• Flash Point: 148 °F
• Appearance: /
• Density: 0.925 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.323mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: THUJONE(CAS DataBase Reference)
• NIST Chemistry Reference: THUJONE(471-15-8)
• EPA Substance Registry System: THUJONE(471-15-8)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38-42/43
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 471-15-8(Hazardous Substances Data)

Usage

Uses

β-Thujone is a component of the essential oil of Pistacia vera L. It is also used as as a reactant in organic synthesis.

InChI:InChI=1/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m0/s1

Upstream product

• 85-44-9 phthalic anhydride 
• 4584-08-1 (1S,4R)-thujan-3-one semicarbazone 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 2175-91-9 6,6'-dimethyl fulvene 
• 74-88-4 methyl iodide 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 342614-13-5 (2R)-2-hydroxy-β-thujone 
• 499-71-8 carvotanacetone 
• 7712-79-0 isothujol 
• 21653-20-3 (-)-3-thujol 
• 21653-19-0 1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol 
• 21653-18-9 (-)-neothujol 
• 86682-70-4 <(-)-Thujyliden>-phenylethylamin 
• 69460-05-5 ((1S)-2c-acetyl-1-isopropyl-cycloprop-r-yl)-acetic acid 
• 74418-34-1 4β-(Hydroxymethyl)-thujan-3-one 
• 43205-82-9 carvotanacetone 
• 498-51-1 5-isopropyl-hex-5-en-2-one 
• 2553-61-9 (1S,4S)-thujan-3-one-(2,4-dinitro-phenylhydrazone); (+)-isothujone-(2,4-dinitro-phenylhydrazone) 
• 40267-59-2 (+)-isothujone oxime 
• 74418-36-3 Thujone-4β-carboxylic Acid 

Relevant articles and documents

A six-step total synthesis of α-thujone and: D 6-α-thujone, enabling facile access to isotopically labelled metabolites

The short synthesis of α-thujone relies on the functionalization of the readily available dimethylfulvene. Furthermore, the three main metabolites of the natural product were also synthesized. Since d6-acetone can be used as a starting material, the route developed allows for the facile incorporation of isotopic labels which are required for detecting and quantifying trace amounts via GC/MS analysis.

(-) 3 Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice

(-) 3 isothujone and (+) 3 thujone were examined for antinociceptive activity using the hot plate and Nilsen tests. In the hot plate test (-) 3 isothujone (ED50 = 6.5 mg/kg) was found to be codeine like and equipotent with (-) Δ9 tetrahydrocannabinol while the racemic material was essentially half as potent as the levorotatory isomer. (+) 3 Thyjone was inactive in both antinociceptive tests as were several structural analogues of the 3 thujones. As with the THC's less antinociceptive activity was observed in the Nilsen test than in the hot plate assay. Acute toxicities for the 3 thujones were determined and vastly improved synthetic procedures have been developed for two long known but difficultly accessible 3 thujanols.