LIMONENE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H16
Molecular Weight	136.234
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)[C@H]1CCC(C)=CC1

InChI

InChIKey=XMGQYMWWDOXHJM-SNVBAGLBSA-N

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H16
Molecular Weight	136.234
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19763039
Curator's Comment: description was created based on several sources, including: http://www.who.int/ipcs/publications/cicad/en/cicad05.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26526880 | https://www.ncbi.nlm.nih.gov/pubmed/19874194 | https://www.ncbi.nlm.nih.gov/pubmed/21376365 | https://www.ncbi.nlm.nih.gov/pubmed/7482582

(-)-Limonene is found in mint oils and has a piney, turpentine-like odor. (-)-Limonene has an antioxidant effect and it cause rat myometrial contraction through activation of the A2A receptor and opening of the voltage-gated Ca(2+) channel. It is a natural larvicidal agents against A. aegypti. (-)-Limonene induced accumulation of protein droplets containing alpha 2 mu-globulin in proximal tubular epithelial cells in male rats, inducing nephropathy.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
regulation of neurotransmitter levels 1 Target ID: GO:0001505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16913049 \| https://www.ncbi.nlm.nih.gov/pubmed/19763039	Modulator 846
Adenosine A2a receptor 31 Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Agonist 2752
Voltage-gated L-type calcium channel 95 Target ID: CHEMBL2095177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Opener 34

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stress 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19763039 DOI: 10.1002/smi.1158	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment.	1994 Dec	7536240
Terpene penetration enhancers in propylene glycol/water co-solvent systems: effectiveness and mechanism of action.	1995 Dec	8932680
In vitro studies on penetration of terpenes from matrix-type transdermal systems through human skin.	2001 Aug 14	11472817
Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites.	2001 Mar 1	11368174
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.	2001 Nov	11672734
Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans.	2002	15618705
Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe.	2002 Nov	12399762
Wet effluent diffusion denuder technique and the determination of volatile organic compounds in air. II. Monoterpenes.	2002 Oct 11	12437180
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).	2007 Sep	19259493
Novel spectropolarimeter employing fixed polarizers for the determination of optically active samples.	2008 Apr	18416899
Components of lemon essential oil attenuate dementia induced by scopolamine.	2009 Apr	19356307
Expressed sequence tags from cephalic chemosensory organs of the northern walnut husk fly, Rhagoletis suavis, including a putative canonical odorant receptor.	2010	20569128
Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).	2010 Apr	20429462
Composition of essential oil from seeds and cones of Abies alba.	2010 Aug	20839638
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens.	2010 Mar	20079506

Patents

Sample Use Guides

In Vivo Use Guide

5, 25 or 50 mg/kg once daily (one week)

Route of Administration: Oral

In Vitro Use Guide

S-limonene is a weak inhibitor of the prenylation enzymes geranylgeranyltransferase type I enzyme and farnesyltransferase (IC50 > 40mM for both).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:07:42 GMT 2025` Edited by `admin` on `Mon Mar 31 20:07:42 GMT 2025`
Record UNII	47MAJ1Y2NE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIMONENE, (-)-

Common Name

English

(-)-LIMONENE

Preferred Name

English

L-LIMONENE

Common Name

English

(S)-LIMONENE

Common Name

English

P-MENTHA-1,8-DIENE, (S)-(-)-

Systematic Name

English

(-)-LIMONENE [FCC]

Common Name

English

LIMONENE, L-

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID6047078