alpha-Thujone

Base Information

• Chemical Name: alpha-Thujone
• CAS No.: 546-80-5
• Deprecated CAS: 1310340-03-4,2407704-71-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Hs Code.: 2914290090
• European Community (EC) Number: 208-912-2
• UNII: R0SQ9G0DU5
• DSSTox Substance ID: DTXSID3026148
• Nikkaji Number: J6.432G
• Wikipedia: Thujone
• Wikidata: Q421838
• Metabolomics Workbench ID: 28171
• ChEMBL ID: CHEMBL1444078
• Mol file: 546-80-5.mol

Synonyms:(+)-thujone;(-)-thujone;3-isothujone;3-thujanone;alpha, beta-thujone;alpha-thujone;beta-thujone;beta-thujone, (1alpha,4alpha,5alpha)-isomer;beta-thujone, (1S-(1alpha,4alpha,5alpha))-isomer;beta-thujone, 1S-(1alpha,4beta,5alpha)-isomer;cis-thujone;thujone

Chemical Property of alpha-Thujone

Chemical Property:

• Appearance/Colour: Colorless or almost colorless liquid with a menthol- like odor (Albert-Puleo, 1978; Budavari, 1996)
• Melting Point: 181℃
• Refractive Index: n20/D 1.450
• Boiling Point: 84-86 °C17 mm Hg(lit.)
• Flash Point: 148 °F
• PSA: 17.07000
• Density: 0.914 g/mL at 20 °C(lit.)
• LogP: 2.25760
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 207

Purity/Quality:

99.9% ^*data from raw suppliers

α-Thujone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion.
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C2CC2(CC1=O)C(C)C
• Isomeric SMILES: C[C@@H]1[C@H]2C[C@]2(CC1=O)C(C)C
• Uses: α-Thujone is a GABA modulator and a genotoxic compound found in plants used in traditional medicines in developing countries.

Technology Process of alpha-Thujone

There total 29 articles about alpha-Thujone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(-)-3-thujol (21653-20-3) → (-)-α-thujone (1125-12-8,546-80-5)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(01)97203-5

Reference yield: 60.0%

(1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane (191861-60-6) → (-)-α-thujone (1125-12-8,546-80-5)

Guidance literature:

With n-butyllithium; MoO₅*pyridine*HMPA; diisopropylamine; In tetrahydrofuran; at -78 ℃; 1.) 5 min; 2.) 20 min;

DOI:10.1002/hlca.19970800302

Reference yield: 38.0%

(+)-1-isopropylbicyclo[3.1.0]hexan-3-one + methyl iodide (74-88-4) → (-)-α-thujone (1125-12-8,546-80-5)

Guidance literature:

(+)-1-isopropylbicyclo[3.1.0]hexan-3-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

methyl iodide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; toluene; at -78 ℃; for 2h;

DOI:10.1039/c6cc05376a

upstream raw materials:

cyclopenta-1,3-diene

methyl iodide

6,6'-dimethyl fulvene

phthalic anhydride

Downstream raw materials:

(-)-3-thujol

thujone

carvacrol

thujone oxime

Refernces

• 1、 Von E. Doering, William,Zhang, Ting-Hu,Schmidt, Eckhart K. G.. "Kinetics of thermal rearrangements in the Δ2-thujene system: A full quadrisection of a perturbed bicyclo[3.1.0]hex-2-ene". . p. 5688 - 5693. Retrieved 2007/10/03.
• 2、 Lightner, David A.,Pak, Chwang Siek,Crist, B. Vincent,Rodgers, Stephen L.,Givens, John W.. "THE OCTANT RULE. XVI. CONFORMATION AND CIRCULAR DICHROISM OF SYN AND ANTI 2-METHYLBICYCLOHEXAN-3-ONES, THUJONE AND ISOTHUJONE". . p. 4321 - 4330. Retrieved 2007/10/02.