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
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
DescriptionSources: https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/tred_PC-079701_24-Jan-05.pdfCurator'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
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095177 |
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Target ID: CHEMBL302 |
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Target ID: GO:1904223 |
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Target ID: CHEMBL1869 |
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Target ID: GO:0018342 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Rowachol Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Degradation of pinene by Bacillus pallidus BR425. | 1998 |
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| 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 |
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| Joint effects of citrus peel use and black tea intake on the risk of squamous cell carcinoma of the skin. | 2001 |
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| Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials. | 2001 Apr 1 |
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| Volatile flavor constituents of acerola (Malpighia emarginata DC.) fruit. | 2001 Dec |
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| Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation. | 2001 Dec 15 |
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| Odorant-induced hyperpolarization and suppression of cAMP-activated current in newt olfactory receptor neurons. | 2001 Jan |
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| First isolation of an isoprene synthase gene from poplar and successful expression of the gene in Escherichia coli. | 2001 Jul |
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| Seasonal variation of monoterpene emission from Malus domestica and Prunus avium. | 2001 Jul |
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| Foliar and cortex oleoresin variability of silver fir (Abies alba Mill.) in Albania. | 2001 Jul-Aug |
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| Chemical and biological evaluation of a reaction mixture of R-(+)-limonene/ozone: formation of strong airway irritants. | 2001 Jun |
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| Enantioselectivity of odor perception in honeybees (Apis mellifera carnica). | 2001 Jun |
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| Permeation of oxygen, water vapor, and limonene through printed and unprinted biaxially oriented polypropylene films. | 2001 Jun |
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| Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans. | 2001 Jun |
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| 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 |
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| The effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities. | 2001 Mar 14 |
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| Biotransformation of (R)-(+)- and (S)-(-)-limonene by fungi and the use of solid phase microextraction for screening. | 2001 May |
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| Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka). | 2001 May |
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| Xanthobacter sp. C20 contains a novel bioconversion pathway for limonene. | 2001 Nov 30 |
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| Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC. | 2001 Nov-Dec |
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| Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae). | 2001 Nov-Dec |
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| Chiral discrimination of limonene by use of beta-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks. | 2001 Sep |
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| Lactones: Part 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones. | 2001 Sep |
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| Distribution and immune responses resulting from oral administration of D-limonene in rats. | 2002 Apr |
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| Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry. | 2002 Apr |
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| 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 |
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| Spontaneous versus reinforced olfactory discriminations. | 2002 Aug 15 |
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| Diastereoselectivity control in photosensitized addition of methanol to (R)-(+)-limonene. | 2002 Aug 9 |
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| Volatile components of peel and leaf oils of lemon and lime species. | 2002 Feb 13 |
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| 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 |
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| A comparative analysis of glove permeation resistance to paint stripping formulations. | 2002 Jan-Feb |
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| Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata. | 2002 Jul |
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| Acaricidal activity of pine essential oils and their main components against Tyrophagus putrescentiae, a stored food mite. | 2002 Jul 31 |
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| Chemical studies of essential oils of Juniperus oxycedrus ssp. badia. | 2002 Jun |
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| 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 |
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| Spontaneous and odour evoked activity in single avian olfactory bulb neurones. | 2002 Mar 1 |
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| Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa. | 2002 May |
Sample Use Guides
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.
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NCI_THESAURUS |
C68542
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JECFA EVALUATION |
D-LIMONENE
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EPA PESTICIDE CODE |
179701
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4186
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C61714
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GFD7C86Q1W
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440917
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1426476
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d-limonene
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DB08921
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5989-27-5
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GFD7C86Q1W
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DTXSID1020778
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757069
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SUB126224
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15382
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227-813-5
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1325
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100000151802
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CHEMBL449062
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68647-72-3
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NO STRUCTURE GIVEN |
ACTIVE MOIETY
METABOLITE (PARENT)
