ISOPULEGOL CAS 89-79-2
Introduction：Basic information about ISOPULEGOL CAS 89-79-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 | n |
| FEMA | 2962 | ISOPULEGOL |
| Fp | 195 °F |
| storage temp. | -20°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | 15.11±0.60(Predicted) |
| form | Liquid |
| color | Colourless |
| Odor | at 10.00 % in dipropylene glycol. minty cooling medicinal woody |
| Odor Type | minty |
| Optical Rotation | [α]20/D 22°, neat |
| biological source | synthetic |
| Water Solubility | 3g/L at 21.9℃ |
| JECFA Number | 755 |
| BRN | 1906573 |
| Stability: | Light sensitive |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | FRAGRANCE |
| InChI | 1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1 |
| InChIKey | ZYTMANIQRDEHIO-KXUCPTDWSA-N |
| SMILES | C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C |
| LogP | 2.4 at 23℃ |
| CAS DataBase Reference | 89-79-2(CAS DataBase Reference) |
| EPA Substance Registry System | Isopulegol (89-79-2) |
Safety Information
| 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 |
| TSCA | TSCA listed |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| 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 |
| Description | Synthesis: Several stereoisomers are possible; only l-isopulegoland 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 is used in perfume compositions as a "lift" to Rose notes, Geraniumnotes, Reseda and Oriental types, variousfloral fragrances, including Tuberose, etc.It is also used in flavor compositions inconcentrations equal to 5 to 30 ppm in thefinished product. The application is mainly inthe minty types and in a few Berry flavortypes. |
| Preparation | Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcoholsobtained by cyclization of d-citronellal. |
| Definition | ChEBI: A natural product found in Citrus hystrix. |
| 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 | Non flammable |
| References | [1] R NAIGRE. Comparison of antimicrobial properties of monoterpenes and their carbonylated products.[J]. Planta medica, 1996, 62 3: 275-277. DOI: 10.1055/s-2006-957877 [2] JAYANT S RAUT. Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans.[J]. Biofouling, 2013, 29 1: 87-96. DOI: 10.1080/08927014.2012.749398 [3] MARIA IZABEL GOMES SILVA . Central nervous system activity of acute administration of isopulegol in mice[J]. Pharmacology Biochemistry and Behavior, 2007, 88 2: Pages 141-147. DOI: 10.1016/j.pbb.2007.07.015 [4] MARIA IZABEL GOMES SILVA. Gastroprotective activity of isopulegol on experimentally induced gastric lesions in mice: investigation of possible mechanisms of action.[J]. Naunyn-Schmiedeberg’s archives of pharmacology, 2009, 380 3: 233-245. DOI: 10.1007/s00210-009-0429-5 |
ISOPULEGOL Preparation Products And Raw materials
| Preparation Products | Citronellol-->trans-5-methyl-2-(1-methylvinyl)cyclohexan-1-one-->DL-Menthol-->4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture) |
