3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one

Base Information

• Chemical Name: 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
• CAS No.: 491-09-8
• Molecular Formula: C10H14 O
• Molecular Weight: 150.221
• European Community (EC) Number: 207-729-5
• NSC Number: 667470
• UNII: IKR841W74D
• DSSTox Substance ID: DTXSID10883402
• Nikkaji Number: J6.050J
• Wikidata: Q27102310
• Metabolomics Workbench ID: 28144
• ChEMBL ID: CHEMBL54161
• Mol file: 491-09-8.mol

Synonyms:Pulespenone(7CI); p-Mentha-1,4(8)-dien-3-one (8CI); 3-Terpinolenone; NSC 667470;Piperitenone

Chemical Property of 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one

Chemical Property:

• Vapor Pressure: 0.04mmHg at 25°C
• Melting Point: 184-184.5 °C
• Refractive Index: 1.5294 (estimate)
• Boiling Point: 239.5°Cat760mmHg
• Flash Point: 93.7°C
• PSA: 17.07000
• Density: 0.962g/cm³
• LogP: 2.63200
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 240

Purity/Quality:

99%, ^*data from raw suppliers

3-Methyl-6-(propan-2-ylidene)cyclohex-2-enone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(=C(C)C)CC1
• Description: Piperitenone is a monoterpene that has been found in various plants, including Cannabis, and has antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell free assay (IC50 = 22.7 μg/ml). Piperitenone also inhibits peroxidation of linoleic acid .

Technology Process of 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one

There total 44 articles about 3-methyl-6-(1-methylethylidene)cyclohex-2-en-1-one 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: 87.0%

3,3-dimethyl acrylaldehyde (107-86-8) → 3-terpinolenone (491-09-8)

Guidance literature:

With formic acid; In pentane;

Reference yield: 81.0%

β-pinene-6-one → 3-terpinolenone (491-09-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; at -60 ℃;

DOI:10.1016/S0040-4039(98)01399-9

Reference yield: 77.8%

4-methyl-pent-3-en-2-one (141-79-7) + methyl vinyl ketone (78-94-4,25038-87-3) → 3-terpinolenone (491-09-8)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; for 1.33333h; Heating;

upstream raw materials:

(E)-geranic acid

sodium acetate

acetic anhydride

(±)-3-hydroxy-3,7-dimethyloct-6-enoic acid

Downstream raw materials:

1-(1-Isopropenyl-4-methyl-2-oxo-cyclohex-3-enyl)-4-phenyl-[1,2,4]triazolidine-3,5-dione

piperitone

pulegone

cis-5-methyl-2-(1-methylethyl)cyclohexanone

Refernces

• 1、 Liu, Chang-Hui,Li, Fei,Tang, Rui-Ren. "Effective aerobic allylic oxidation of β-ionone and series of olefins catalyzed by phosphomolybdic acid". body text. p. 1723 - 1725. Retrieved 2010/10/19.
• 2、 Baptistella, Lucia H. B.,Aleixo, Adriana M.. "α′-hydroxy-α,β-unsaturated tosylhydrazones: Preparation and use as intermediates for carbonyl and enone transpositions". . p. 2937 - 2950. Retrieved 2007/10/03.