| Identification | More | [Name]
ISOPULEGOL | [CAS]
89-79-2 | [Synonyms]
1-METHYL-4-ISOPROPENYLCYCLOHEXAN-3-OL
(1R,2S,5R)-2-ISOPROPENYL-5-METHYLCYCLOHEXANOL
(1R,3R,4S)-P-MENTH-8-EN-3-OL
DL-ISOPULEGOL
FEMA 2962
(-)-ISOPULEGOL
ISOPULEGOL
ISOPULEGOL, (-)-
L-ISOPULEGOL
P-MENTH-8-EN-3-OL
5-methyl-2-(1-methylethenyl)-,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol
cyclohexanol,5-methyl-2-(1-methylethenyl)-,[1theta-(1alpha,2beta,5alpha)]
p-Menth-8(9)-en-3-ol
p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-
(-)-ISOPULEGOL, TERPENE STANDARD
(-)-ISOPULEGOL 95+%
ISOPULEGOL 99+%
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-
ISOPULEGOL, (-)-(SG)
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1-alpha, 2-bets, 5-alpha)] | [EINECS(EC#)]
201-940-6 | [Molecular Formula]
C10H18O | [MDL Number]
MFCD00134655 | [Molecular Weight]
154.25 | [MOL File]
89-79-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Water-white liquid; mint-like odor. Combustible.
Available forms: The acetate. | [Melting point ]
78°C | [Boiling point ]
212 °C(lit.) | [density ]
0.912 g/mL at 25 °C(lit.)
| [vapor pressure ]
13.97Pa at 20℃ | [FEMA ]
2962 | [refractive index ]
n20/D 1.471(lit.)
| [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℃ | [Uses]
Perfumery (geranium and rose compounds), flavoring. | [CAS DataBase Reference]
89-79-2(CAS DataBase Reference) | [EPA Substance Registry System]
Isopulegol (89-79-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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 |
| Hazard Information | Back Directory | [Description]
(–)-Isopulegol is a monoterpene that has been found in the essential oils of several aromatic plants, including Cannabis, with diverse biological activities.1,2,3,4,5 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).2 (–)-Isopulegol inhibits C. albicans morphogenesis, adhesion, and biofilm formation (MICs = 0.125, 4, and 0.25 mg/ml, respectively).3 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.4 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.5 | [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. | [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 | [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 |
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