LIMONENE, (+)-

First approved in 1999

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-JTQLQIEISA-N

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/tred_PC-079701_24-Jan-05.pdf
Curator's Comment: description was created based on several sources, including: https://archive.epa.gov/pesticides/reregistration/web/pdf/3083fact.pdf https://www.ncbi.nlm.nih.gov/pubmed/18072821

Limonene is a naturally occurring chemical which is used in many food products, soaps and perfumes for its lemon-like flavor and odor. Limonene also is a registered active ingredient in 15 pesticide products used as insecticides, insect repellents, and dog and cat repellents. Pesticide products containing limonene are used for flea and tick control on pets, as an insecticide spray, an outdoor dog and cat repellent. It has also been used for relief of heartburn and gastroesophageal reflux (GERD). D-limonene has well-established chemopreventive activity against many types of cancer. Limonene and its oxidation products are skin and respiratory irritants.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Opener 34
Adenosine A2a receptor 30 Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880	Agonist 2678
regulation of glucuronosyltransferase activity 1 Target ID: GO:1904223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15161036	Activator 1430
Ornithine decarboxylase 15 Target ID: CHEMBL1869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10417763	Inhibitor 8297
protein prenylation 1 Target ID: GO:0018342 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18072821 \| https://www.ncbi.nlm.nih.gov/pubmed/10082788	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23554130	Primary	Phase I 428	Unknown Approved Use Unknown
Gastroesophageal reflux disease 59 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21649454 https://www.ncbi.nlm.nih.gov/pubmed/18072821	Primary	Phase I 428	Unknown Approved Use Unknown
Cholesterol gallstones 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1988264 https://www.ncbi.nlm.nih.gov/pubmed/18072821 https://www.ncbi.nlm.nih.gov/pubmed/4022860 https://www.ncbi.nlm.nih.gov/pubmed/6430390 https://www.ncbi.nlm.nih.gov/pubmed/447112	Primary	Phase I 428	Rowachol Approved Use Unknown

PubMed

Title	Date	PubMed
Structural elucidation of monoterpene oxidation products by ion trap fragmentation using on-line atmospheric pressure chemical ionisation mass spectrometry in the negative ion mode.	2001	11746892
Isotope ratio by HRGC-MS of citrus Junos tanaka (yuzu) essential oils: m/z 137/136 of terpene hydrocarbons.	2001 Dec	11826956
Response of plum curculio (Coleoptera: Curculionidae) to odor-baited traps near woods.	2001 Dec	11777040
Volatile flavor constituents of acerola (Malpighia emarginata DC.) fruit.	2001 Dec	11743778
Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation.	2001 Dec 15	11755117
Perceptual correlates of neural representations evoked by odorant enantiomers.	2001 Dec 15	11739591
Indoor environmental quality in six commercial office buildings in the midwest United States.	2001 Nov	11757903
Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC.	2001 Nov-Dec	11837677
Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae).	2001 Nov-Dec	11837668
Essential oil composition of sea fennel (Crithmum maritimum) form Turkey.	2001 Oct	11715349
Aromatic profile of aqueous banana essence and banana fruit by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O).	2001 Oct	11600027
Transdermal delivery of ketoprofen using microemulsions.	2001 Oct 9	11576778
Chiral discrimination of limonene by use of beta-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks.	2001 Sep	11605760
Lactones: Part 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones.	2001 Sep	11561401
High-speed GC and GC/time-of-flight MS of lemon and lime oil samples.	2001 Sep 15	11575784
Health evaluation of volatile organic compound (VOC) emissions from wood and wood-based materials.	2001 Sep-Oct	11777023
Direct analysis of highly oxidised organic aerosol constituents by on-line ion trap mass spectrometry in the negative-ion mode.	2002	11870886
Distribution and immune responses resulting from oral administration of D-limonene in rats.	2002 Apr	12171437
Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry.	2002 Apr	11993758
Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants.	2002 Apr	11966698
Biosynthesis of marine natural products: isolation and characterization of a myrcene synthase from cultured tissues of the marine red alga Ochtodes secundiramea.	2002 Apr 1	11913979
Spontaneous versus reinforced olfactory discriminations.	2002 Aug 15	12177181
Diastereoselectivity control in photosensitized addition of methanol to (R)-(+)-limonene.	2002 Aug 9	12153274
Expression of cyclin D1/2 in the lungs of strain A/J mice fed chemopreventive agents.	2002 Feb	11872634
Composition and antifungal activity of the essential oil of Solidago chilensis.	2002 Feb	11859470
Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo.	2002 Feb	11801384
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation.	2002 Feb 12	11827526
Volatile components of peel and leaf oils of lemon and lime species.	2002 Feb 13	11829647
Mammary carcinomas induced in human c-Ha-ras proto-oncogene transgenic rats are estrogen-independent, but responsive to d-limonene treatment.	2002 Jan	11802805
Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes.	2002 Jan	11800592
Additive toxicity of limonene and 50% oxygen and the role of glutathione in detoxification in human lung cells.	2002 Jan 15	11750085
Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety.	2002 Jan 2	11754559
A comparative analysis of glove permeation resistance to paint stripping formulations.	2002 Jan-Feb	11843429
Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata.	2002 Jul	12142998
Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice.	2002 Jul	12122569
Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases.	2002 Jul	12084056
Acute necrotizing dermatitis and septicemia after application of a d-limonene-based insecticidal shampoo in a cat.	2002 Jul 15	12118590
Acaricidal activity of pine essential oils and their main components against Tyrophagus putrescentiae, a stored food mite.	2002 Jul 31	12137480
Background odour induces adaptation and sensitization of olfactory receptors in the antennae of houseflies.	2002 Jun	12109710
Diet and breast cancer.	2002 Jun	12095951
Chemical studies of essential oils of Juniperus oxycedrus ssp. badia.	2002 Jun	12020937
Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors.	2002 Jun 3	12180326
Muscle relaxing activity of Hyssopus officinalis essential oil on isolated intestinal preparations.	2002 Mar	11914956
Influence of flavour absorption on oxygen permeation through LDPE, PP, PC and PET plastics food packaging.	2002 Mar	11837243
Spontaneous and odour evoked activity in single avian olfactory bulb neurones.	2002 Mar 1	11852030
Comparison of extraction methods for marker compounds in the essential oil of lemon grass by GC.	2002 Mar 13	11879000
Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa.	2002 May	12033511
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.	2002 May	11950794
Characteristic odor components of Citrus sphaerocarpa Tanaka (Kabosu) cold-pressed peel oil.	2002 May 8	11982418
Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation.	2002 May 8	11982414

Patents

Sample Use Guides

In Vivo Use Guide

take 2 grams of limonene daily for two to six weeks

Route of Administration: Oral

In Vitro Use Guide

Fungal inhibiton range (in %) of limonene enantiomers at concentration 10ul/ml is 54-91. Antifungal action was assessed against eight different species of fungi: Aspergillus niger, A. ochraceus, A. flavus, A.parasiticus, Alternaria alternata, Chaetomium sp., Fusarium culmorum. and Penicillium citratum. The fungi were introduced at l flL mL and 10 flL mL in 10 mL of YES broth (2% yeast extract in 15% sucrose); after 10 days the weights of fungi were recorded after drying and compared with untreated fungal weights.

Name

Type

Language

LIMONENE, (+)-

Common Name

English

(+)-(R)-4-ISOPROPENYL-1-METHYLCYCLOHEXENE

Systematic Name

English

(D)-LIMONENE [HSDB]

Common Name

English

(+)-LIMONENE [FCC]

Common Name

English

FEMA NO. 2633

Code

English

ORANGE OIL DISTILLATE

Common Name

English

NSC-757069

Code

English

CYCLOHEXENE, 1-METHYL-4-(1-METHYLETHENYL)-, (4R)-

Systematic Name

English

D-LIMONENE [IARC]

Common Name

English

(R)-4-ISOPROPENYL-1-METHYLCYCLOHEXENE

Systematic Name

English

Limonene, (+)- [WHO-DD]

Common Name

English

(+)-LIMONENE

Common Name

English

(4R)-1-METHYL-4-(1-METHYLETHENYL)CYCLOHEXENE

Systematic Name

English

LIMONENE, D-

Common Name

English

D-LIMONENE [JAN]

Common Name

English

D-LIMONENE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68542