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| | ISOPULEGOL Basic information |
| Product Name: | ISOPULEGOL | | Synonyms: | 5-methyl-2-(1-methylethenyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol;(-)-Isopulegol 99%;Isopulegol solution;(-)-ISOPULEGOL, TERPENE STANDARD;(-)-ISOPULEGOL 95+%;ISOPULEGOL 99+%;(-)-ISOPULEGOL;ISOPULEGOL | | CAS: | 89-79-2 | | MF: | C10H18O | | MW: | 154.25 | | EINECS: | 201-940-6 | | Product Categories: | | | Mol File: | 89-79-2.mol |  |
| | ISOPULEGOL Chemical Properties |
| Melting point | 78°C | | Boiling point | 212 °C(lit.) | | density | 0.912 g/mL at 25 °C(lit.) | | vapor pressure | 13.97Pa at 20℃ | | refractive index | n20/D 1.471(lit.) | | FEMA | 2962 | ISOPULEGOL | | Fp | 195 °F | | storage temp. | -20°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | neat | | pka | 15.11±0.60(Predicted) | | color | Colourless | | Odor | at 10.00 % in dipropylene glycol. minty cooling medicinal woody | | Odor Type | minty | | optical activity | [α]20/D 22°, neat | | Water Solubility | 3g/L at 21.9℃ | | JECFA Number | 755 | | BRN | 1906573 | | Stability: | Light sensitive | | InChIKey | ZYTMANIQRDEHIO-KXUCPTDWSA-N | | LogP | 2.4 at 23℃ | | CAS DataBase Reference | 89-79-2(CAS DataBase Reference) | | EPA Substance Registry System | Isopulegol (89-79-2) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26-36/37/39 | | RIDADR | NA 1993 / PGIII | | WGK Germany | 2 | | F | 10-23 | | toxicity | The acute oral LD50 in rats was reported as 1.03 ± 0.10 ml/kg and the acute dermal LD50 in rabbits as approximately 3 ml/kg |
| | ISOPULEGOL Usage And Synthesis |
| 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. | | Description | (–)-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. | | Chemical Properties | Isopulegol is a cyclic nonaromatic alcohol. | | Chemical Properties | Water-white liquid; mint-like odor. Combustible.
Available forms: The acetate. | | Occurrence | l-Isopulegol has been reported found in the essences of lemongrass, East African geranium and Eucalyptus
citriodora; d-isopulegol is present in the oils of Backhousia and Baeckea citriodorae; d-neoisopulegol is found in Mentha rotundifolia. Also reported found in mint, mandarin, orange juice, citrus peel oils, currant bud, ginger, corn mint oil, cognac, rum, buchu oil,
lemon balm and mastic gum oil | | 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.
| | Uses | Perfumery (geranium and rose compounds), flavoring. | | Definition | ChEBI: A natural product found in Citrus hystrix. | | Preparation | Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols
obtained by cyclization of d-citronellal. | | Aroma threshold values | Detection: 1 ppm | | Taste threshold values | Taste characteristics at 30 ppm: minty cooling, herbaceous peppermint nuance. | | Synthesis Reference(s) | Synthetic Communications, 18, p. 2309, 1988 DOI: 10.1080/00397918808082375 | | General Description | Isopulegol is monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste. | | Flammability and Explosibility | Nonflammable |
| | ISOPULEGOL Preparation Products And Raw materials |
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