A bicyclic monoterpene with diverse biological activities
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α-Pinene

Item No. 21576

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ene
CAS Number
80-56-8
Synonyms
  • NSC 7727
Molecular Formula
C10H16
Formula Weight
136.2
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.33 mg/ml
SMILES
CC1=CCC2C(C)(C)C1C2
InChi Code
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3
InChi Key
GRWFGVWFFZKLTI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $39

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    5 g

    $135

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    10 g

    $211

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    Cayman Chemical
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    Product Description

    α-Pinene is a bicyclic monoterpene found in pine trees and other plants, including Cannabis with diverse biological activities.1 It reduces the growth of a panel of seven Gram-positive bacteria, seven Gram-negative bacteria, and eight yeast strains with MIC values of 0.75-1.29, 1.05-1.59, and 0.7-1.17%, respectively.2 It has insecticidal activity against C. molestus larvae with LC50 values ranging from 47 to 49 mg/L.3 α-Pinene (100 μg/ml) induces apoptosis, increases anion superoxide production and DNA fragmentation, and activates caspase-3 in B16/F10 melanoma cells.4 In a B16/F10 mouse xenograft model, α-pinene (100 ml of a 10 mg/ml solution) reduces the number of metastatic lung nodules by approximately 7-fold. α-Pinene (8.6 mg/L, aerosol) also increases the time spent in the open arms of the elevated plus maze by approximately 2-fold in mice, indicating anxiolytic-like activity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Russo, E.B. Taming THC: Potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br. J. Pharmacol. 163(7), 1344-1364 (2011).

    2. Nissen, L., Zatta, A., Stefanini, I., et al. Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.). Fitoterapia 81(5), 413-419 (2010).

    3. Traboulsi, A.F., Taoubi, K., el-Haj, S., et al. Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae). Pest Manag. Sci. 58(5), 491-495 (2002).

    4. Matsuo, A.L., Figueiredo, C.R., Arruda, D.C., et al. α-Pinene isolated from Schinus terebinthifolius Raddi (Anacardiaceae) induces apoptosis and confers antimetastatic protection in a melanoma model. Biochem. Biophys. Res. Commun. 411(2), 4749-4454 (2011).

    5. Satou, T., Kasuya, H., Maeda, K., et al. Daily inhalation of α-pinene in mice: Effects on behavior and organ accumulation. Phytother. Res. 28(9), 1284-1287 (2014).