Pulegone

Base Information

• Chemical Name: Pulegone
• CAS No.: 89-82-7
• Deprecated CAS: 90449-51-7
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2914 29 00
• European Community (EC) Number: 201-943-2
• UNII: 4LF2673R3G
• DSSTox Substance ID: DTXSID2025975
• Nikkaji Number: J3.216F
• Wikipedia: Pulegone
• Wikidata: Q413816
• RXCUI: 2393774
• Metabolomics Workbench ID: 28113
• ChEMBL ID: CHEMBL2924219
• Mol file: 89-82-7.mol

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

Chemical Property of Pulegone

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 138 mm Hg ( 25 °C)
• Melting Point: <=25°C
• Refractive Index: n20/D 1.488
• Boiling Point: 224°C(lit.)
• Flash Point: 185°F
• PSA: 17.07000
• Density: 0.937g/mLat 25°C(lit.)
• LogP: 2.71190
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

≥98% ^*data from raw suppliers

(R)-Pulegone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1CCC(=C(C)C)C(=O)C1
• Isomeric SMILES: C[C@@H]1CCC(=C(C)C)C(=O)C1
• Uses: (R)-(+)-Pulegone may be used as a starting material to synthesize:(2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane, a spiroketal(R)-(+)-citronellic acid, an intermediate to prepare leucine-d3(+)-fawcettidine, a lycopodium alkaloid A monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).

Technology Process of Pulegone

There total 72 articles about Pulegone 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%

(+)-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) → pulegone (89-82-7,90449-51-7)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1021/acs.jnatprod.7b01026

Reference yield: 93.0%

(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one (308358-04-5,5730-01-8) → pulegone (89-82-7,90449-51-7)

Guidance literature:

With molybdenum hexacarbonyl; In benzene; for 1h; Heating;

DOI:10.1016/S0040-4039(03)00231-4

Reference yield: 90.0%

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) → pulegone (89-82-7,90449-51-7)

Guidance literature:

With hydrogen; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; [Rh(cyclooctadiene)2](PF₆); [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide; In ethyl acetate; at 50 ℃; for 20h; under 22502.3 Torr; Product distribution / selectivity;

upstream raw materials:

p-menth-8-en-3-one semicarbazone

oxalic acid

Citronellol

3,7-dimethyl-6-octenoyl chloride

Downstream raw materials:

1-butyl-2-isopropylidene-5-methyl-cyclohexanol

methylisopulegene

(+)-trans-Caran

1-methyl-3-methylene-cyclohexane

Refernces

A spontaneous bicyclization facilitates a synthesis of (-)-hispidospermidin

10.1016/S0040-4020(03)00936-0

The study presents an enantiospecific synthesis of the phospholipase C inhibitor (2)-hispidospermidin, a natural product with potential cell growth inhibitory properties. The synthesis approximates the architecture of a reactive intermediate that may be involved in the biosynthetic pathway of the natural product. Key chemicals used include (R)-(t)-pulegone as a starting material, farnesyl pyrophosphate as a proposed biosynthetic precursor, and a variety of reagents and intermediates such as spiro[4.5]deca-1,7-diene, cyanohydrin, and enal derivatives. These chemicals serve to construct the complex tetracyclic framework of (2)-hispidospermidin through a series of reactions, including carbonyl addition, bicyclization, and reduction steps. The purpose of these chemicals is to facilitate the formation of the target molecule's core structure and its side chain, ultimately leading to the synthesis of (2)-hispidospermidin with high stereochemical control.

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