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
| 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 |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880 |
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Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26526880 |
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Target ID: GO:1904223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15161036 |
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Target ID: CHEMBL1869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10417763 |
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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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
93.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17540528/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
159.573 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18972832/ |
0.3 mL single, oral dose: 0.3 mL route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
2.67 g/m² 3 times / day multiple, oral dose: 2.67 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
2.67 g/m² 3 times / day multiple, oral dose: 2.67 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
13.8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
3.33 g/m² 3 times / day multiple, oral dose: 3.33 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
3.33 g/m² 3 times / day multiple, oral dose: 3.33 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20.5 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
4 g/m² 3 times / day multiple, oral dose: 4 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
4 g/m² 3 times / day multiple, oral dose: 4 g/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
311.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17540528/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
449.855 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18972832/ |
0.3 mL single, oral dose: 0.3 mL route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
151 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
8 g/m² single, oral dose: 8 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
165 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
10 g/m² single, oral dose: 10 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
154.5 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9654110/ |
12 g/m² single, oral dose: 12 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17540528/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.859 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18972832/ |
0.3 mL single, oral dose: 0.3 mL route of administration: Oral experiment type: SINGLE co-administered: |
LIMONENE, ( )- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 g/m2 1 times / day multiple, oral Highest studied dose Dose: 12 g/m2, 1 times / day Route: oral Route: multiple Dose: 12 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Diarrhea... |
8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (grade 1, 3 patients) Sources: Vomiting (grade 1, 1 patient) Diarrhea (grade 1, 4 patients) Nausea (grade 2, 2 patients) Diarrhea (grade 2, 2 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diarrhea | grade 2, 1 pt | 12 g/m2 1 times / day multiple, oral Highest studied dose Dose: 12 g/m2, 1 times / day Route: oral Route: multiple Dose: 12 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | grade 1, 1 patient | 8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | grade 1, 3 patients | 8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Diarrhea | grade 1, 4 patients | 8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Diarrhea | grade 2, 2 patients | 8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | grade 2, 2 patients | 8 g/m2 1 times / day multiple, oral MTD Dose: 8 g/m2, 1 times / day Route: oral Route: multiple Dose: 8 g/m2, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spontaneous versus reinforced olfactory discriminations. | 2002-08-15 |
|
| Diastereoselectivity control in photosensitized addition of methanol to (R)-(+)-limonene. | 2002-08-09 |
|
| Acaricidal activity of pine essential oils and their main components against Tyrophagus putrescentiae, a stored food mite. | 2002-07-31 |
|
| Acute necrotizing dermatitis and septicemia after application of a d-limonene-based insecticidal shampoo in a cat. | 2002-07-15 |
|
| Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata. | 2002-07 |
|
| Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice. | 2002-07 |
|
| Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases. | 2002-07 |
|
| 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. | 2002-06-03 |
|
| Background odour induces adaptation and sensitization of olfactory receptors in the antennae of houseflies. | 2002-06 |
|
| Diet and breast cancer. | 2002-06 |
|
| Chemical studies of essential oils of Juniperus oxycedrus ssp. badia. | 2002-06 |
|
| Characteristic odor components of Citrus sphaerocarpa Tanaka (Kabosu) cold-pressed peel oil. | 2002-05-08 |
|
| Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation. | 2002-05-08 |
|
| Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa. | 2002-05 |
|
| Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. | 2002-05 |
|
| Biosynthesis of marine natural products: isolation and characterization of a myrcene synthase from cultured tissues of the marine red alga Ochtodes secundiramea. | 2002-04-01 |
|
| Distribution and immune responses resulting from oral administration of D-limonene in rats. | 2002-04 |
|
| Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry. | 2002-04 |
|
| Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants. | 2002-04 |
|
| Comparison of extraction methods for marker compounds in the essential oil of lemon grass by GC. | 2002-03-13 |
|
| Spontaneous and odour evoked activity in single avian olfactory bulb neurones. | 2002-03-01 |
|
| Muscle relaxing activity of Hyssopus officinalis essential oil on isolated intestinal preparations. | 2002-03 |
|
| Influence of flavour absorption on oxygen permeation through LDPE, PP, PC and PET plastics food packaging. | 2002-03 |
|
| A comparative analysis of glove permeation resistance to paint stripping formulations. | 2002-02-15 |
|
| Volatile components of peel and leaf oils of lemon and lime species. | 2002-02-13 |
|
| Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC. | 2002-02-12 |
|
| Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae). | 2002-02-12 |
|
| Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. | 2002-02-12 |
|
| Expression of cyclin D1/2 in the lungs of strain A/J mice fed chemopreventive agents. | 2002-02 |
|
| Composition and antifungal activity of the essential oil of Solidago chilensis. | 2002-02 |
|
| Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo. | 2002-02 |
|
| Additive toxicity of limonene and 50% oxygen and the role of glutathione in detoxification in human lung cells. | 2002-01-15 |
|
| Health evaluation of volatile organic compound (VOC) emissions from wood and wood-based materials. | 2002-01-05 |
|
| Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety. | 2002-01-02 |
|
| Mammary carcinomas induced in human c-Ha-ras proto-oncogene transgenic rats are estrogen-independent, but responsive to d-limonene treatment. | 2002-01 |
|
| 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 |
|
| Direct analysis of highly oxidised organic aerosol constituents by on-line ion trap mass spectrometry in the negative-ion mode. | 2002 |
|
| Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation. | 2001-12-15 |
|
| Perceptual correlates of neural representations evoked by odorant enantiomers. | 2001-12-15 |
|
| Isotope ratio by HRGC-MS of citrus Junos tanaka (yuzu) essential oils: m/z 137/136 of terpene hydrocarbons. | 2001-12 |
|
| Response of plum curculio (Coleoptera: Curculionidae) to odor-baited traps near woods. | 2001-12 |
|
| Volatile flavor constituents of acerola (Malpighia emarginata DC.) fruit. | 2001-12 |
|
| Functional magnetic resonance imaging of odor identification: the effect of aging. | 2001-12 |
|
| Age and space distributions of monoterpenes in fresh needles of Picea abies (L) Karst. Determined by gas chromatography-mass spectrometry. | 2001-11-14 |
|
| Indoor environmental quality in six commercial office buildings in the midwest United States. | 2001-11 |
|
| Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan. | 2001-11 |
|
| Essential oil composition of sea fennel (Crithmum maritimum) form Turkey. | 2001-10 |
|
| Fragrance chemicals in domestic and occupational products. | 2001-10 |
|
| Chiral discrimination of limonene by use of beta-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks. | 2001-09 |
|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23554130
take 2 grams of limonene daily for two to six weeks
Route of Administration:
Oral
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.
| Substance Class |
Chemical
Created
by
admin
on
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Mon Mar 31 17:56:52 GMT 2025
by
admin
on
Mon Mar 31 17:56:52 GMT 2025
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| Record UNII |
GFD7C86Q1W
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Validated (UNII)
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68542
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EPA PESTICIDE CODE |
79701
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DSLD |
1215 (Number of products:28)
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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JECFA EVALUATION |
D-LIMONENE
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EPA PESTICIDE CODE |
179701
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| Code System | Code | Type | Description | ||
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4186
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PRIMARY | |||
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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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28730
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5989-27-5
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GFD7C86Q1W
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15384
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LIMONENE
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DTXSID1020778
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SUB37237
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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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