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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 of LIMONENE, (+)-

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

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
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

Sources: DOI: 10.1002/jlac.18842250304

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
93.6 ng/mL
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
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
311.9 ng × h/mL
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.42 h
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
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

Doses

DosePopulationAdverse 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...
Other AEs:
Diarrhea (grade 2, 1 pt)
Sources:
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)
Vomiting (grade 1, 1 patient)
Diarrhea (grade 1, 4 patients)
Nausea (grade 2, 2 patients)
Diarrhea (grade 2, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Joint effects of citrus peel use and black tea intake on the risk of squamous cell carcinoma of the skin.
2001
Identification of volatile constituents of Tambourissa leptophylla.
2001 Apr
Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials.
2001 Apr 1
Response of plum curculio (Coleoptera: Curculionidae) to odor-baited traps near woods.
2001 Dec
Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation.
2001 Dec 15
First isolation of an isoprene synthase gene from poplar and successful expression of the gene in Escherichia coli.
2001 Jul
Low-resolution gas-phase FT-IR method for the determination of the limonene/carvone ratio in supercritical CO2-extracted caraway fruit oils.
2001 Jul
Chemical variability in the essential oil of Hyptis suaveolens.
2001 Jul
Seasonal variation of monoterpene emission from Malus domestica and Prunus avium.
2001 Jul
Age and space distributions of monoterpenes in fresh needles of Picea abies (L) Karst. Determined by gas chromatography-mass spectrometry.
2001 Jul-Aug
Foliar and cortex oleoresin variability of silver fir (Abies alba Mill.) in Albania.
2001 Jul-Aug
Chemical and biological evaluation of a reaction mixture of R-(+)-limonene/ozone: formation of strong airway irritants.
2001 Jun
Permeation of oxygen, water vapor, and limonene through printed and unprinted biaxially oriented polypropylene films.
2001 Jun
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
2001 Jun
Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans.
2001 Jun
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
Effect of in situ composting on reducing offensive odors and volatile organic compounds in swineries.
2001 Mar-Apr
Indoor environmental quality in six commercial office buildings in the midwest United States.
2001 Nov
Fragrance chemicals in domestic and occupational products.
2001 Oct
Aromatic profile of aqueous banana essence and banana fruit by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O).
2001 Oct
Seasonal changes in the composition of the essential oil extract of East Mediterranean sage (Salvia libanotica) and its toxicity in mice.
2001 Oct
Transdermal delivery of ketoprofen using microemulsions.
2001 Oct 9
Chiral discrimination of limonene by use of beta-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks.
2001 Sep
High-speed GC and GC/time-of-flight MS of lemon and lime oil samples.
2001 Sep 15
Health evaluation of volatile organic compound (VOC) emissions from wood and wood-based materials.
2001 Sep-Oct
Direct analysis of highly oxidised organic aerosol constituents by on-line ion trap mass spectrometry in the negative-ion mode.
2002
Distribution and immune responses resulting from oral administration of D-limonene in rats.
2002 Apr
Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry.
2002 Apr
Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants.
2002 Apr
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
Spontaneous versus reinforced olfactory discriminations.
2002 Aug 15
Diastereoselectivity control in photosensitized addition of methanol to (R)-(+)-limonene.
2002 Aug 9
Expression of cyclin D1/2 in the lungs of strain A/J mice fed chemopreventive agents.
2002 Feb
Composition and antifungal activity of the essential oil of Solidago chilensis.
2002 Feb
Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo.
2002 Feb
Mammary carcinomas induced in human c-Ha-ras proto-oncogene transgenic rats are estrogen-independent, but responsive to d-limonene treatment.
2002 Jan
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
Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety.
2002 Jan 2
Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata.
2002 Jul
Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice.
2002 Jul
Acute necrotizing dermatitis and septicemia after application of a d-limonene-based insecticidal shampoo in a cat.
2002 Jul 15
Acaricidal activity of pine essential oils and their main components against Tyrophagus putrescentiae, a stored food mite.
2002 Jul 31
Background odour induces adaptation and sensitization of olfactory receptors in the antennae of houseflies.
2002 Jun
Diet and breast cancer.
2002 Jun
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
Muscle relaxing activity of Hyssopus officinalis essential oil on isolated intestinal preparations.
2002 Mar
Comparison of extraction methods for marker compounds in the essential oil of lemon grass by GC.
2002 Mar 13
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.
2002 May
Characteristic odor components of Citrus sphaerocarpa Tanaka (Kabosu) cold-pressed peel oil.
2002 May 8
Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation.
2002 May 8
Patents

Sample Use Guides

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 Mon Mar 31 17:56:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:52 GMT 2025
Record UNII
GFD7C86Q1W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIMONENE, (+)-
WHO-DD  
Common Name English
LIMONENE
INCI  
INCI  
Preferred Name English
DIPENTENE NO. 122
Brand 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
FCC  
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
JAN  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68542
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
EPA PESTICIDE CODE 79701
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
DSLD 1215 (Number of products:28)
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
JECFA EVALUATION D-LIMONENE
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
EPA PESTICIDE CODE 179701
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
Code System Code Type Description
HSDB
4186
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
NCI_THESAURUS
C61714
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
DAILYMED
GFD7C86Q1W
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
PUBCHEM
440917
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
RXCUI
1426476
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY RxNorm
ALANWOOD
d-limonene
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
DRUG BANK
DB08921
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
RXCUI
28730
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
ALTERNATIVE
CAS
5989-27-5
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
FDA UNII
GFD7C86Q1W
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
CHEBI
15384
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
WIKIPEDIA
LIMONENE
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID1020778
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
EVMPD
SUB37237
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
NSC
757069
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
EVMPD
SUB126224
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
CHEBI
15382
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-813-5
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
JECFA MONOGRAPH
1325
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
SMS_ID
100000151802
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL449062
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
CAS
68647-72-3
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
NO STRUCTURE GIVEN
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