p-MENTH-8-EN-3-ONE, trans-

Base Information

• Chemical Name: p-MENTH-8-EN-3-ONE, trans-
• CAS No.: 29606-79-9
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2914299000
• European Community (EC) Number: 249-725-6
• UNII: ERN62726IX,681XD66YSR
• DSSTox Substance ID: DTXSID601233729
• Nikkaji Number: J221.483K
• Wikidata: Q67880130
• Mol file: 29606-79-9.mol

Synonyms:cis-isopulegone;isopulegone;pulegone;pulegone, (R)-isomer;pulegone, (S)-isomer

Chemical Property of p-MENTH-8-EN-3-ONE, trans-

Chemical Property:

• Vapor Pressure: 0.14mmHg at 25°C
• Refractive Index: 1.4675 (estimate)
• Boiling Point: 216.4°Cat760mmHg
• Flash Point: 79.5°C
• PSA: 17.07000
• Density: 0.903g/cm³
• LogP: 2.56780
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

TRANS-5-METHYL-2-(1-METHYLVINYL)CYCLOHEXAN-1-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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: The structure of isopulegone was defined by Tiemann and Schmidt as well as by Hugh, Kon, and Linstead; usually prepared from isopulegol.

Technology Process of p-MENTH-8-EN-3-ONE, trans-

There total 35 articles about p-MENTH-8-EN-3-ONE, trans- 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%

(-)-(4R)-isopiperitenone (80995-97-7) → (+)-cis-isopulegone (529-00-0,6090-04-6,17882-43-8,29606-79-9,52152-10-0,57129-09-6,122517-59-3,3391-89-7)

Guidance literature:

With glucose dehydrogenase; D-glucose; (?)-isopiperitenone reductase; nicotinamide adenine dinucleotide phosphate; D,L-dithiothreitol; In aq. phosphate buffer; ethanol; at 25 ℃; for 4h; pH=6.4; Sealed tube; Enzymatic reaction;

DOI:10.1021/acs.jnatprod.7b01026

Reference yield: 81.0%

Isopulegol (89-79-2) → isopulegone (29606-79-9)

Guidance literature:

With aluminum oxide; pyridinium chlorochromate; In hexane; for 6h; Ambient temperature;

DOI:10.1055/s-1980-28975

Reference yield: 80.0%

pulegone (89-82-7,3285-04-9,3391-90-0,15932-80-6,90449-51-7) → isopulegone (29606-79-9)

Guidance literature:

With potassium hydroxide; sodium hydrogencarbonate; acetic acid; In 1,2-dimethoxyethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91490-5

upstream raw materials:

(R)-Citronellal

8-bromo-p-menthan-3-one

pulegone

Isopulegol

Downstream raw materials:

(S)-(-)-pulegone

pulegone

(2R,5S)-menthone

(1R,4R)-(+)-isomenthone

Refernces

• 1、 -. "Method of preparing L-menthone from R-citronellal". Paragraph 0093-0094. . Retrieved 2020/04/06.
• 2、 Cheallaigh, Aisling Ní,Mansell, David J.,Toogood, Helen S.,Tait, Shirley,Lygidakis, Antonios,Scrutton, Nigel S.,Gardiner, John M.. "Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway". . p. 1546 - 1552. Retrieved 2018/08/04.