A monoterpene with diverse biological activities
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(−)-Isopulegol

Item No. 23161

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5R-methyl-2S-(1R-methylethenyl)-cyclohexanol
CAS Number
89-79-2
Synonyms
  • l-Isopulegol
Molecular Formula
C10H18O
Formula Weight
154.3
Purity
≥98%
Formulation (Request formulation change)
A liquid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
SMILES
CC([C@@H]1CC[C@@H](C)C[C@H]1O)=C
InChi Code
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
InChi Key
ZYTMANIQRDEHIO-KXUCPTDWSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $54

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    50 g

    $102

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    100 g

    $190

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    250 g

    $392

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fletcher, R.S., and McKay, J. Industrial hemp cannabis cultivars and seeds with stable cannabinoid profiles. (2006).

    2. Naigre, R., Kalck, P., Rogues, C., et al. Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Planta Med. 62(3), 275-277 (1996).

    3. Raut, J.S., Shinde, R.B., Chauhan, N.M., et al. Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans. Biofouling 29(1), 87-96 (2013).

    4. Silva, M.I., de Aquino Neto, M.R., Teixieira Neto, P.F., et al. Central nervous system activity of acute administration of isopulegol in mice. Pharmacol. Biochem. Behav. 88(2), 141-147 (2007).

    5. Silva, M.I., Moura, B.A., Neto, M.R., et al. Gastroprotective activity of isopulegol on experimentally induced gastric lesions in mice: Investigation of possible mechanisms of action. Naunyn Schmiedebergs Arch. Pharmacol. 380(3), 233-245 (2009).