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D-Limonene

D-Limonene is a terpene found in the rind of various species of Citrus. D-Limonene is commercially used as a flavorant, odorant, cleaning solvent, and insecticide; it exhibits anti-inflammatory, antioxidative, hepatoprotective, anti-diabetic, anti-obesity, immunosuppressive, anticancer chemotherapeutic, chemopreventive, anti-metastatic, and anti-angiogenic activities. D-Limonene inhibits cell growth, induces mitochondria-dependent apoptosis, and causes cell cycle arrest in gastric carcinoma cells. In other in vitro models, D-limonene inhibits VEGF, tube formation, and metastasis. Additionally, this compound decreases DMBA-induced tumor formation and tumor burden, potentially through decreasing Ras, Raf, and phosphorylated ERK1/2 levels. In other animal models, D-limonene induces phase II enzyme expression, increasing levels of glutathione; it also decreases levels of KIM-1, Bun, creatinine, NO, iNOS, COX, and NF-κB, limiting doxycycline-induced renal damage. This compound also decreases adipocyte size and levels of blood glucose, LDL, and triglycerides, increases levels of HDL, activates PPARα signaling, and suppresses LXR-β signaling in vivo. D-Limonene inhibits cytokine production by CD4+ and CD8+ T cells and induces T cell death at high doses.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18855172

Cas No.

5989-27-5

Purity

≥96%

Formula

C10H16

Formula Wt.

136.23

Chemical Name

(+)-4-Isopropenyl-1-methylcyclohexene

IUPAC Name

(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene

Synonym

(+)-Dipentene; (+)-Limonene; (+)-R-Limonene; (+)-α-Limonene

Melting Point

-40°C

Solubility

Insoluble in water.

Appearance

Liquid

Zhang XZ, Wang L, Liu DW, Tang GY, Zhang HY. Synergistic Inhibitory Effect of Berberine and d-Limonene on Human Gastric Carcinoma Cell Line MGC803. J Med Food. 2014 Sep;17(9):955-62. PMID: 25045784.

Rehman MU, Tahir M, Khan AQ, et al. D-limonene suppresses doxorubicin-induced oxidative stress and inflammation via repression of COX-2, iNOS, and NFκB in kidneys of Wistar rats. Exp Biol Med (Maywood). 2014 Apr;239(4):465-76. PMID: 24586096.

Jing L, Zhang Y, Fan S, et al. Preventive and ameliorating effects of citrus D-limonene on dyslipidemia and hyperglycemia in mice with high-fat diet-induced obesity. Eur J Pharmacol. 2013 Sep 5;715(1-3):46-55. PMID: 23838456.

Lappas CM, Lappas NT. D-Limonene modulates T lymphocyte activity and viability. Cell Immunol. 2012 Sep;279(1):30-41. PMID: 23059811.

Chaudhary SC, Siddiqui MS, Athar M, et al. D-Limonene modulates inflammation, oxidative stress and Ras-ERK pathway to inhibit murine skin tumorigenesis. Hum Exp Toxicol. 2012 Aug;31(8):798-811. PMID: 22318307.

Sun J. D-Limonene: safety and clinical applications. Altern Med Rev. 2007 Sep;12(3):259-64. PMID: 18072821.

Y27632 dihydrochloride