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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.

CNS Activity

Originator

Wallach, O.|Brass, W.
2
Sources: DOI: 10.1002/jlac.18842250304

Approval Year

1999
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Opener
34
Agonist
2678
Activator
1430
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Rowachol

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Molecular cloning, functional expression and characterization of d-limonene synthase from Schizonepeta tenuifolia.
2001 Apr
Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials.
2001 Apr 1
Isotope ratio by HRGC-MS of citrus Junos tanaka (yuzu) essential oils: m/z 137/136 of terpene hydrocarbons.
2001 Dec
Composition and antimicrobial activity of the essential oil of Baccharis notosergila.
2001 Feb
Stability of monoterpenes encapsulated in gum Arabic by spray-drying.
2001 Feb
Flavor, color, and vitamin C retention of pulsed electric field processed orange juice in different packaging materials.
2001 Feb
Evaluation of individual components of plum odor as potential attractants for adult plum curculios.
2001 Jan
Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
2001 Jan
Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor.
2001 Jul
Enantioselectivity of odor perception in honeybees (Apis mellifera carnica).
2001 Jun
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
2001 Jun
Effect of in situ composting on reducing offensive odors and volatile organic compounds in swineries.
2001 Mar-Apr
Biotransformation of (R)-(+)- and (S)-(-)-limonene by fungi and the use of solid phase microextraction for screening.
2001 May
Degradation of monoterpenes in orange juice by gamma radiation.
2001 May
Indoor environmental quality in six commercial office buildings in the midwest United States.
2001 Nov
Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae).
2001 Nov-Dec
Lactones: Part 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones.
2001 Sep
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
Spontaneous versus reinforced olfactory discriminations.
2002 Aug 15
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
Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety.
2002 Jan 2
A comparative analysis of glove permeation resistance to paint stripping formulations.
2002 Jan-Feb
Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata.
2002 Jul
Chemical studies of essential oils of Juniperus oxycedrus ssp. badia.
2002 Jun
Muscle relaxing activity of Hyssopus officinalis essential oil on isolated intestinal preparations.
2002 Mar
Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa.
2002 May
Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation.
2002 May 8
Patents

Patents

US2382641 A
2
US4379168 B1
1
US4511488 A
1
US4533487 A
1
US8273687 B2
1

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:49 GMT 2023
Record UNII
GFD7C86Q1W
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
LIMONENE, (+)-
WHO-DD  
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
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 Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
JECFA EVALUATION D-LIMONENE
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
EPA PESTICIDE CODE 179701
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
Code System Code Type Description
HSDB
4186
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
NCI_THESAURUS
C61714
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
DAILYMED
GFD7C86Q1W
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
PUBCHEM
440917
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
RXCUI
1426476
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY RxNorm
ALANWOOD
d-limonene
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
DRUG BANK
DB08921
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
CAS
5989-27-5
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
FDA UNII
GFD7C86Q1W
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID1020778
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
NSC
757069
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
EVMPD
SUB126224
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
CHEBI
15382
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-813-5
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
JECFA MONOGRAPH
1325
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
SMS_ID
100000151802
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL449062
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
PRIMARY
CAS
68647-72-3
Created by admin on Fri Dec 15 15:24:49 GMT 2023 , Edited by admin on Fri Dec 15 15:24:49 GMT 2023
NO STRUCTURE GIVEN
Related Record Type Details
EUCALYPTUS OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
LIMONENE
SUB_CONCEPT->SUBSTANCE
CARAWAY OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
MANDARIN OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CORIANDER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
LEMON OIL, COLD PRESSED
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
JAVA CITRONELLA OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
LAVENDER OIL
PARENT -> CONSTITUENT MAY BE PRESENT
DWARF PINE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
FOENICULUM VULGARE FRUIT OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
JUNIPER BERRY OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of PERILLIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of LIMONENE, (+)-
ACTIVE MOIETY
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