76231-76-0

Basic information

• Product Name: ALPHA+BETA-THUJONE
• Synonyms: THUJONE, (alpha, beta)-(SG);alpha,beta-Thujone technical, ~70% alpha-thujone basis, ~10% beta-thujone basis
• CAS NO: 76231-76-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• Mol File: 76231-76-0.mol

Chemical Properties

• Boiling Point: 84-86 °C/17 mmHg(lit.)
• Flash Point: 64 °C
• 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
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly), Methanol (Sl
• CAS DataBase Reference: ALPHA+BETA-THUJONE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA+BETA-THUJONE(76231-76-0)
• EPA Substance Registry System: ALPHA+BETA-THUJONE(76231-76-0)

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: 76231-76-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
ALPHA+BETA-THUJONE is used as a reactant in organic synthesis for various chemical reactions. Its unique structure allows it to participate in a range of reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Aromatherapy:
ALPHA+BETA-THUJONE is used in aromatherapy as a component of essential oils. Its aromatic properties can provide a range of therapeutic benefits, such as promoting relaxation, reducing stress, and improving mood.
Used in Flavor and Fragrance Industry:
ALPHA+BETA-THUJONE is used as a flavoring agent and fragrance component in the food and cosmetics industries. Its distinct scent and taste can enhance the sensory experience of various products.
Used in Pharmaceutical Industry:
ALPHA+BETA-THUJONE has potential applications in the pharmaceutical industry as a starting material for the synthesis of various drugs. Its unique chemical properties make it a promising candidate for the development of new therapeutic agents.
Used in Pest Control:
ALPHA+BETA-THUJONE has been found to have insecticidal properties, making it a potential component in pest control products. Its ability to repel or kill insects can be utilized in the development of eco-friendly and effective pest control solutions.

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+/m1/s1

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 74-88-4 methyl iodide 
• 2175-91-9 6,6'-dimethyl fulvene 

Downstream Products

• 5523-90-0 (1R)-2c-Methyl-5c-isopropyl-(1rH)-bicyclo<3.1.0>hexan, (-)-Thujan B, (-)-cis-Thujan 
• 69297-61-6 α-Thujaketocarbonsaeuremethylester 
• 81489-44-3 α-Thujaoximinocarbonsaeuremethylester 
• 74418-34-1 4β-(Hydroxymethyl)-thujan-3-one 
• 178686-04-9 (1R-(1α,2α/β,6α))-2-methyl-6-(1-methylethyl)bicyclo-[4.1.0]heptan-3-one 
• 74418-36-3 Thujone-4β-carboxylic Acid 
• 69460-05-5 ((1S)-2c-acetyl-1-isopropyl-cycloprop-r-yl)-acetic 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.