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 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
Liquid/air partition coefficients of four terpenes.	1990 Jan	2310709
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
Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis.	1999 Apr 15	10370194
Electrophysiological and behavioral responses of female Helicoverpa armigera to compounds identified in flowers of African marigold, Tagetes erecta.	2001 Jun	11504018
Effects of chiral fragrances on human autonomic nervous system parameters and self-evaluation.	2001 Mar	11287388
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
Wet effluent diffusion denuder technique and the determination of volatile organic compounds in air. II. Monoterpenes.	2002 Oct 11	12437180
Total syntheses of Yingzhaosu A and of its C(14)-epimer including the first evaluation of their antimalarial and cytotoxic activities.	2005 Apr 29	15844999
Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol.	2006 Mar 27	16451823
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 Oct	17031065
Increasing molecular weight parameters of a helical polymer through polymerization in a chiral solvent.	2006 Sep 27	16984183
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).	2007 Sep	19259493
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
Composition of essential oil from seeds and cones of Abies alba.	2010 Aug	20839638

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 `Fri Dec 15 20:19:25 UTC 2023` Edited by `admin` on `Fri Dec 15 20:19:25 UTC 2023`
Record UNII	47MAJ1Y2NE
Record Status	`Validated (UNII)`
Record Version

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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