Isopulegone

Base Information

• Chemical Name: Isopulegone
• CAS No.: 529-00-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• European Community (EC) Number: 249-725-6
• DSSTox Substance ID: DTXSID40865498
• Nikkaji Number: J2.365.190D
• Wikidata: Q27117020
• Mol file: 529-00-0.mol

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

Chemical Property of Isopulegone

Chemical Property:

• Refractive Index: 1.4675 (estimate)
• Boiling Point: 234.73°C (rough estimate)
• PSA: 17.07000
• Density: 0.9198
• 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:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(=O)C1)C(=C)C
• Uses: 5-Methyl-2-(prop-1-en-2-yl)cyclohexanone is an intermediate in the synthesis of Δ6a,10a-Tetrahydrocannabinol (T298635), a synthetic cannabinoid with psychoactive properties.

Technology Process of Isopulegone

There total 6 articles about Isopulegone 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: 85.0%

(S)-2-Isopropenyl-5-methyl-cyclohexanol (89-79-2,7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8) → (S)-isopulegone (529-00-0,3391-89-7,6090-04-6,17882-43-8,29606-79-9,52152-10-0,57129-09-6,122517-59-3)

Guidance literature:

With aluminum oxide; pyridinium chlorochromate; In hexane; for 14h; Ambient temperature;

DOI:10.1055/s-1988-27724

Reference yield:

pulegone (89-82-7,90449-51-7) → (+)-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:

under 140 Torr; Erhitzen unter Argon auf Siedetemperatur;

upstream raw materials:

pulegone

(-)-(4R)-isopiperitenone

(S)-2-Isopropenyl-5-methyl-cyclohexanol

(S)-3,7-dimethyl-6-octen-1-ol

Downstream raw materials:

<1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol

(+)-isoisopulegone semicarbazone

isopulegol

pulegone