Isomenthone, (+/-)-

Base Information

• Chemical Name: Isomenthone, (+/-)-
• CAS No.: 491-07-6
• Deprecated CAS: 36977-92-1
• Molecular Formula: C10H18 O
• Molecular Weight: 372.244
• European Community (EC) Number: 253-295-5
• UNII: 9WZ3E2G6CL,11T7AFM2DS
• DSSTox Substance ID: DTXSID501315467
• Nikkaji Number: J100.108F
• Wikidata: Q27116856
• Metabolomics Workbench ID: 46781
• Mol file: 491-07-6.mol

Synonyms:isomenthone

Chemical Property of Isomenthone, (+/-)-

Chemical Property:

• Melting Point: -35 °C
• Refractive Index: 1.4666 (estimate)
• Boiling Point: 205°Cat760mmHg
• Flash Point: 72.8°C
• PSA: 17.07000
• Density: 0.881g/cm³
• LogP: 2.64770
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

99%, ^*data from raw suppliers

(±)-Isomenthone(Contains~20%oftrans-isomer) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(=O)C1)C(C)C
• Isomeric SMILES: C[C@H]1CC[C@H](C(=O)C1)C(C)C
• Description: Synthesis: By hydrogenation of pipertone.
• Uses: (±)-Isomenthone is a constituent of some commercial essential oils with antimicrobial and antioxidant properties.

Technology Process of Isomenthone, (+/-)-

There total 63 articles about Isomenthone, (+/-)- 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: 100.0%

menthol (15356-70-4) → (+/-)-menthone (491-07-6,1074-95-9,1196-31-2,3391-87-5,10458-14-7,14073-97-3,18309-28-9,36977-92-1,117773-78-1,89-80-5,17627-49-5,7786-64-3)

Guidance literature:

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; tetraethylammonium trichloride; In acetonitrile; Ambient temperature;

DOI:10.1002/anie.199723421

Reference yield: 100.0%

DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) → (+/-)-menthone (491-07-6,1074-95-9,1196-31-2,3391-87-5,10458-14-7,14073-97-3,18309-28-9,36977-92-1,117773-78-1,89-80-5,17627-49-5,7786-64-3)

Guidance literature:

With jones reagent; silica gel; In dichloromethane; for 0.0833333h;

DOI:10.1081/SCC-100106049

Reference yield: 98.0%

2-isopropyl-5-methylcyclohexan-1-ol (89-78-1,490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8) → (+/-)-menthone (491-07-6,1074-95-9,1196-31-2,3391-87-5,10458-14-7,14073-97-3,18309-28-9,36977-92-1,117773-78-1,89-80-5,17627-49-5,7786-64-3)

Guidance literature:

With aluminum oxide; ammonium chlorochromate; for 0.0333333h; microwave irradiation;

DOI:10.1515/znb-1999-0618

upstream raw materials:

pulegone

3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen

acetyl chloride

allyl bromide

Downstream raw materials:

(+/-)-Menthon-2,4-DNP

(+/-)-(3R,6R)-3-isopropyl-6-methyl-1-cyclohexene

isomenthone

2-cyclopentylcyclopentanol

Refernces

• 1、 Song, Tao,Ma, Zhiming,Yang, Yong. "Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water". . p. 1313 - 1319. Retrieved 2019/01/25.
• 2、 Ozen, Recep. "3,4-Dihydroisoquinolinium trichloroacetatochromate: A mild and effective new reagent for oxidation of alcohols to carbonyl compounds and arenes to their quinones". . p. 6081 - 6083. Retrieved 2015/02/19.