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

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 828
Adenosine A2a receptor 30 Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Agonist 2678
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Opener 34

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stress 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19763039 DOI: 10.1002/smi.1158	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro studies on penetration of terpenes from matrix-type transdermal systems through human skin.	2001 Aug 14	11472817
Electrophysiological and behavioral responses of female Helicoverpa armigera to compounds identified in flowers of African marigold, Tagetes erecta.	2001 Jun	11504018
Genomic organization of plant terpene synthases and molecular evolutionary implications.	2001 Jun	11404343
Xanthobacter sp. C20 contains a novel bioconversion pathway for limonene.	2001 Nov 30	11090685
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
Rapid determination of volatile constituents of Michelia alba flowers by gas chromatography-mass spectrometry with solid-phase microextraction.	2002 Jan 4	11822393
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.	2002 May	11950794
Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe.	2002 Nov	12399762
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.	2003 Nov 5	14583045
Characterisation of different clones of Picea abies (L.) Karst using head-space sampling of cortical tissues combined with enantioselective capillary gas chromatography for the separation of chiral and non-chiral monoterpenes.	2004 Apr 23	15116929
Flavor components of monoterpenes in citrus essential oils enhance the release of monoamines from rat brain slices.	2006 Feb-Apr	16913049
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).	2007 Sep	19259493
Sub-chronic effects of s-limonene on brain neurotransmitter levels and behavior of rats.	2009 Aug	19763039
Orange/lemon-scented beetles: opposite enantiomers of limonene as major constituents in the defensive secretion of related carabids.	2009 Dec	19690825
Volatiles released from Vaccinium corymbosum were attractive to Aegorhinus superciliosus (Coleoptera: Curculionidae) in an olfactometric bioassay.	2009 Jun	19508787
Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).	2010 Apr	20429462
The influence of Ceratocystis polonica inoculation and methyl jasmonate application on terpene chemistry of Norway spruce, Picea abies.	2010 Aug	20557909
Lung damage in mice after inhalation of nanofilm spray products: the role of perfluorination and free hydroxyl groups.	2010 Jul	20348230

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).

Name

Type

Language

LIMONENE, (-)-

Common Name

English

(-)-LIMONENE

Common 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