3-Thujanone

Base Information

• Chemical Name: 3-Thujanone
• CAS No.: 1125-12-8
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 214-405-7,208-912-2
• NSC Number: 407281
• DSSTox Substance ID: DTXSID20859476
• Nikkaji Number: J138.260H
• Wikipedia: Thujone
• Wikidata: Q27121853
• Mol file: 1125-12-8.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 3-Thujanone

Chemical Property:

• Refractive Index: n20/D 1.455(lit.)
• Boiling Point: 200.5°Cat760mmHg
• Flash Point: 64.4°C
• PSA: 17.07000
• Density: 1.009g/cm³
• LogP: 2.25760
• 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% ^*data from raw suppliers

Thujone (α- and β- mixture) >70.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38-42/43
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC2(CC1=O)C(C)C
• Uses: 3-Thujanone is an essential oil component of Folium Artemisiae Argyi.

Technology Process of 3-Thujanone

There total 44 articles about 3-Thujanone 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:

(-)-α-thujone

sabinol

aluminum isopropoxide

dihydroumbellulol

Downstream raw materials:

(-)-α-thujone

carvacrol

(-)-3-thujol

thujone oxime