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Structure Database (LMSD)

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Common Name

gamma-Terpinene

Systematic Name

Synonyms

LM ID

LMPR0102090027

Formula

C₁₀H₁₆

Exact Mass

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136.1252

Status

Curated

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Classification

Biological Context

γ-Terpinene is a monoterpene that has been found in various plants, including C. sativa, with diverse biological activities.^1,2,3,4,5,6 It scavenges 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS+) free radicals (IC50s = 2.8 and 30 mM, respectively) and reduces hemolysis induced by AAPH in isolated human erythrocytes.² γ-Terpinene reduces the growth of T. evansi in a concentration-dependent manner.³ It increases membrane permeability and decreases growth of X. oryzae bacteria.⁴ In vivo, γ-terpinene (100 mg/kg) reduces Triton WR1339-induced increases in serum cholesterol and triglyceride levels in rats.⁵ It reduces paw edema induced by histamine, bradykinin , carrageenan, and prostaglandin E2 (PGE2) in mice.⁶ It also inhibits fluid extravasation in a mouse model of acetic acid microvascular permeability and reduces neutrophil migration in lung in a mouse model of acute lung injury.

This information has been provided by Cayman Chemical

References

1. Baldissera, M.D., Grando, T.H., Souza, C.F., et al. In vitro and in vivo action of terpinen-4-ol, γ-terpinene, and α-terpinene against Trypanosoma evansi. Exp. Parasitol. 162, 43-48 (2016).

2. Hazekamp, A., Tejkalová, K., and Papadimitriou, S. Cannabis: From cultivar to chemovar II—A metabolomics approach to Cannabis classification. Cannabis Cannabinoid Res. 1(1), 202-215 (2016).

3. Li, G.-X., and Liu, Z.-Q. Unusual antioxidant behavior of α- and γ-terpinene in protecting methyl linoleate, DNA, and erythrocyte. J. Agric. Food Chem. 57(9), 3943-3948 (2009).

4. Yoshitomi, K., Taniguchi, S., Tanaka, K., et al. Rice terpene synthase 24 (OsTPS24) encodes a jasmonate-responsive monoterpene synthase that produces an antibacterial γ-terpinene against rice pathogen. J. Plant Physiol. 191(1), 120-126 (2016).

5. Takahashi, Y., Inaba, N., Kuwahara, S., et al. Effects of γ-terpinene on lipid concentrations in serum using Triton WR1339-treated rats. Biosci. Biotechnol. Biochem. 67(11), 2448-2450 (2003).

6. Ramalho, T.R., Oliveira, M.T., Lima, A.L., et al. Gamma-terpinene modulates acute inflammatory response in mice. Planta. Med. 81(14), 1248-1254 (2015).