(-)-Isopulegol

Base Information

• Chemical Name: (-)-Isopulegol
• CAS No.: 89-79-2
• Deprecated CAS: 18674-66-3,59905-53-2
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• Hs Code.: 2906199090
• European Community (EC) Number: 201-940-6,256-557-7
• NSC Number: 1263
• UNII: 3TH92O3BXN,NVG8YK55NL
• DSSTox Substance ID: DTXSID5047116,DTXSID90110001
• Nikkaji Number: J3.215H
• Wikidata: Q2103922
• Pharos Ligand ID: D4F2UF9X552J
• Metabolomics Workbench ID: 47179
• ChEMBL ID: CHEMBL237994
• Mol file: 89-79-2.mol

Synonyms:isopulegol

Chemical Property of (-)-Isopulegol

Chemical Property:

• Vapor Pressure: 0.0993mmHg at 25°C
• Melting Point: 78°C
• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 212 °C(lit.)
• PKA: 15.11±0.60(Predicted)
• Flash Point: 195 °F
• PSA: 20.23000
• Density: 0.912 g/mL at 25 °C(lit.)
• LogP: 2.35960
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 3g/L at 21.9℃
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

99.9% ^*data from raw suppliers

(-)-Isopulegol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(C(C1)O)C(=C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(=C)C
• Description: Synthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal. (–)-Isopulegol is a monoterpene that has been found in the essential oils of several aromatic plants, including Cannabis, with diverse biological activities. It has antibacterial activity against S. aureus, E. faecium, E. coli, and M. smegmatis (MICs = 0.78, 12.5, 0.78, and 1.56 μl/ml, respectively, in an agar diffusion assay) and antifungal activity against C. albicans and A. niger (MIC = 1.56 μl/ml for both in an agar diffusion assay). (–)-Isopulegol inhibits C. albicans morphogenesis, adhesion, and biofilm formation (MICs = 0.125, 4, and 0.25 mg/ml, respectively). In vivo, (–)-isopulegol (50 mg/kg, i.p.) increases immobility time in the forced swim and tail suspension tests and increases the number of head dips in a hole board test and time spent in the open arms of the elevated plus maze in mice, indicating depressant- and anxiolytic-like activity. It reduces the size of ulcerated lesions in the stomach in mouse models of ethanol- and indomethacin-induced gastric lesions when administered at a dose of 100 mg/kg.
• Uses: (?)-Isopulegol can be used as a starting material for the enantioselective preparation of:?????? 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,·???????? Stereoisomers of 5,9-dimethylpentadecane. Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.????? p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation. Perfumery (geranium and rose compounds), flavoring.

Technology Process of (-)-Isopulegol

There total 167 articles about (-)-Isopulegol 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: 99.7%

(R)-Citronellal (2385-77-5) → 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)

Guidance literature:

With 4,4'-methylene-bis-(2,6-diphenylphenol); acetic anhydride; at 0 ℃; for 72h; Reagent/catalyst; Time; enantioselective reaction;

Reference yield: 92.0%

(R)-Citronellal (2385-77-5) → (+)-isopulegol (104870-56-6) + 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)

Guidance literature:

aluminium tris(2,6-diphenylphenoxide); In toluene; at 5 ℃; for 5h;

Reference yield: 71.0%

(R)-Citronellal (2385-77-5) → (+)-neoisopulegol (20549-46-6) + <1R-(1α,2α,5α)>-5-Methyl-2-(1-methylethenyl)cyclohexanol (144541-38-8) + <1S-(1α,2β,5β)>-5-Methyl-2-(1-methylethenyl)cyclohexanol (96612-21-4) + 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)

Guidance literature:

With H-Beta-11; In cyclohexane; at 90 ℃; for 3h; under 7500.6 Torr; Further Variations:; Reagents; Product distribution;

DOI:10.1016/j.jcat.2004.03.043

upstream raw materials:

phenylethynylmagnesium bromide

(R)-Citronellal

formic acid

3,7-dimethyl-oct-6-enal

Downstream raw materials:

isopulegol ether

3-methyladipic acid

thymol

(2R,5S)-menthone

Refernces

Synthesis and organoleptic properties of p-menthane lactones

10.1016/S0040-4020(00)00397-5

The study focuses on the stereoselective synthesis and organoleptic properties of p-menthane lactones (7a-h), a class of compounds with significant interest to the perfume industry due to their exceptional odor intensity and typical coumarin-like note. The research corrects published data concerning these compounds and identifies 7a, 7b, and 7g as trace components in Italo Mitcham black peppermint oil (Mentha piperita). Various chemicals were used in the study, including (-)-isopulegol, (+)-neoisopulegol, m-chloroperbenzoic acid, lithium diisopropylamide (LDA), potassium permanganate, Raney nickel, and several others, serving as starting materials, reagents, and catalysts in the synthesis of the lactones. The purpose of these chemicals was to facilitate the synthesis of the p-menthane lactones, allowing for their characterization and evaluation of their sensory properties, which are crucial for their potential use in the perfume and flavoring industries.

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