Piperitone

Base Information

• Chemical Name: Piperitone
• CAS No.: 89-81-6
• Deprecated CAS: 6091-52-7,1082702-70-2,1082702-70-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 201-942-7
• NSC Number: 176162,251528,1100
• UNII: 1VZ8RG269R
• DSSTox Substance ID: DTXSID7052604
• Nikkaji Number: J4.308G
• Wikipedia: Piperitone
• Wikidata: Q2041498
• Metabolomics Workbench ID: 155895
• ChEMBL ID: CHEMBL2252746
• Mol file: 89-81-6.mol

Synonyms:piperitone

Chemical Property of Piperitone

Chemical Property:

• Appearance/Colour: clear, light yellowish to yellow liquid
• Vapor Pressure: 0.0572mmHg at 25°C
• Melting Point: -29ºC
• Refractive Index: -60 ° (C=4, benzene)
• Boiling Point: 233ºC
• Flash Point: 90.9 ºC
• PSA: 17.07000
• Density: 0,93g/cm³
• LogP: 2.56780
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 189

Purity/Quality:

99.9% ^*data from raw suppliers

Piperitone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(CC1)C(C)C
• Uses: Piperitone is a monoterpene compound that has a fresh minty camphor-like odour, and naturally occurs in extracts of commercial oil of peppermint. Piperitone is also used as a starting material in the synthesis of Thymol (T413000), a phenolic compound that is used for its antibacterial properties.

Technology Process of Piperitone

There total 74 articles about Piperitone 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: 98.0%

1-isopropyl-2-methoxy-4-methylcyclohexa-1,4-diene (94733-48-9) → piperitone (89-81-6,6091-52-7)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 2h;

DOI:10.1007/BF00630244

Reference yield: 92.0%

((1R,6R)-6-Isopropyl-3-methyl-cyclohex-2-enyloxy)-trimethyl-silane → piperitone (89-81-6,6091-52-7)

Guidance literature:

With tripropylammonium fluorochromate (VI); In dichloromethane; at 20 ℃;

DOI:10.1002/jccs.199900089

Reference yield: 86.0%

Se-phenyl 3,7-dimethylocta-2E,6-dienselenoate → piperitone (89-81-6,6091-52-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1.5h; Heating;

DOI:10.1016/0040-4039(95)02147-7

upstream raw materials:

1-isopropyl-2-methoxy-4-methylcyclohexa-1,4-diene

3-(2-isopropyl-5-methyl-phenoxy)-propane-1,2-diol

(+)-p-menth-1-ene

acetic anhydride

Downstream raw materials:

1-isopropyl-2,4-dimethyl-cyclohexa-1,3-diene

isomenthol

2-chloro-1-hydroxy-p-menthan-3-one

(1R*,6S*)-6-isopropyl-3-methylcyclohex-2-en-1-ol

Refernces

• 1、 Chen, Yifeng,Huang, David,Zhao, Yizhou,Newhouse, Timothy R.. "Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization". supporting information. p. 8258 - 8262. Retrieved 2017/06/30.
• 2、 Ohshima, Takashi,Tadaoka, Hiroshi,Hori, Kiyoto,Sayo, Noboru,Mashima, Kazushi. "Highly enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: Alternative synthesis of (-)-menthol". scheme or table. p. 2060 - 2066. Retrieved 2009/04/07.