(-)-Isopulegone

Base Information

• Chemical Name: (-)-Isopulegone
• CAS No.: 17882-43-8
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• European Community (EC) Number: 249-725-6
• UNII: AHQ6120987
• DSSTox Substance ID: DTXSID101318152
• Nikkaji Number: J221.484I
• Wikidata: Q27273928
• Mol file: 17882-43-8.mol

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

Chemical Property of (-)-Isopulegone

Chemical Property:

• 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:

GC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(C(=O)C1)C(=C)C
• Isomeric SMILES: C[C@@H]1CC[C@H](C(=O)C1)C(=C)C

Technology Process of (-)-Isopulegone

There total 12 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: 88.2%

isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (?)-trans-isopulegone (17882-43-8)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2003.09.030

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

upstream raw materials:

pulegone

(-)-(4R)-isopiperitenone

isopulegol

(-)-isopulegol

Downstream raw materials:

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

isopulegol

pulegone

(2R,5S)-menthone