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
Acaricidal and quantitative structure activity relationship of monoterpenes against the two-spotted spider mite, Tetranychus urticae.	2010-11	20431924
Composition of essential oil from seeds and cones of Abies alba.	2010-08	20839638
The influence of Ceratocystis polonica inoculation and methyl jasmonate application on terpene chemistry of Norway spruce, Picea abies.	2010-08	20557909
A chamber study of secondary organic aerosol formation by limonene ozonolysis.	2010-08	20557377
Lung damage in mice after inhalation of nanofilm spray products: the role of perfluorination and free hydroxyl groups.	2010-07	20348230
Fumigant toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).	2010-06	20568624
Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).	2010-04	20429462
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens.	2010-03	20079506
Expressed sequence tags from cephalic chemosensory organs of the northern walnut husk fly, Rhagoletis suavis, including a putative canonical odorant receptor.	2010	20569128
Orange/lemon-scented beetles: opposite enantiomers of limonene as major constituents in the defensive secretion of related carabids.	2009-12	19690825
Sub-chronic effects of s-limonene on brain neurotransmitter levels and behavior of rats.	2009-08	19763039
Volatiles released from Vaccinium corymbosum were attractive to Aegorhinus superciliosus (Coleoptera: Curculionidae) in an olfactometric bioassay.	2009-06	19508787
Fumigant and contact toxicities of monoterpenes to Sitophilus oryzae (L.) and Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase activity.	2009-05	19412756
Components of lemon essential oil attenuate dementia induced by scopolamine.	2009-04	19356307
Isolation of cDNAs and functional characterisation of two multi-product terpene synthase enzymes from sandalwood, Santalum album L.	2008-09-01	18541135
Identification of the airborne aggregation pheromone of the common bed bug, Cimex lectularius.	2008-06	18470566
Novel spectropolarimeter employing fixed polarizers for the determination of optically active samples.	2008-04	18416899
A male-produced aggregation pheromone blend consisting of alkanediols, terpenoids, and an aromatic alcohol from the cerambycid beetle Megacyllene caryae.	2008-03	18253798
Control of H- and J-type pi stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregates.	2008	19009569
Physical and chemical responses of Sitka spruce (Picea sitchensis) clones to colonization by Heterobasidion annosum as potential markers for relative host susceptibility.	2007-12	17938101
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).	2007-09	19259493
Limonene: attractant kairomone for white pine cone beetles (Coleoptera: Scolytidae) in an eastern white pine seed orchard in western North Carolina.	2007-06	17598543
Not only oxidized R-(+)- but also S-(-)-limonene is a common cause of contact allergy in dermatitis patients in Europe.	2006-11	17026692
Determination of the absolute configuration of quercivorol, (1S,4R)-p-menth-2-en-1-ol, an aggregation pheromone of the ambrosia beetle Platypus quercivorus (Coleoptera: Platypodidae).	2006-10	17031065
Increasing molecular weight parameters of a helical polymer through polymerization in a chiral solvent.	2006-09-27	16984183
Flavor components of monoterpenes in citrus essential oils enhance the release of monoamines from rat brain slices.	2006-08-18	16913049
Influence of fungal infection and wounding on contents and enantiomeric compositions of monoterpenes in phloem of Pinus sylvestris.	2006-08	16900432
Defensive secretion components of the host Parastizopus armaticeps as kairomones for the cleptoparasite Eremostibes opacus.	2006-04	16718570
Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol.	2006-03-27	16451823
(-)-Menthol biosynthesis and molecular genetics.	2005-12	16292524
Regio- and stereoselective fungal oxyfunctionalisation of limonenes.	2005-07-27	16042348
Total syntheses of Yingzhaosu A and of its C(14)-epimer including the first evaluation of their antimalarial and cytotoxic activities.	2005-04-29	15844999
Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole.	2004-08	15299125
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.	2004-04-23	15116929
Cosuppression of limonene-3-hydroxylase in peppermint promotes accumulation of limonene in the essential oil.	2004-03	15003417
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.	2003-11-05	14583045
Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH.	2003-09-19	12968887
Monoterpene biosynthesis pathway construction in Escherichia coli.	2003-09	12943759
Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.	2003-08-27	12926889
Stereoselective biotransformation of limonene and limonene oxide by cyanobacterium, Synechococcus sp. PCC 7942.	2003	16233578
Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe.	2002-11	12399762
Wet effluent diffusion denuder technique and the determination of volatile organic compounds in air. II. Monoterpenes.	2002-10-11	12437180
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.	2002-05	11950794
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation.	2002-02-12	11827526
Rapid determination of volatile constituents of Michelia alba flowers by gas chromatography-mass spectrometry with solid-phase microextraction.	2002-01-04	11822393
Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes.	2002-01	11800592
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
Terpene penetration enhancers in propylene glycol/water co-solvent systems: effectiveness and mechanism of action.	1995-12	8932680
Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment.	1994-12	7536240
Liquid/air partition coefficients of four terpenes.	1990-01	2310709

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