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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
Attraction of a leaf beetle (Oreina cacaliae) to damaged host plants.
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
[Allergic contact dermatitis to cosmetics containing Melaleuca alternifolia (tea tree oil)].
2001 Feb
Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor.
2001 Jul
Chemical and biological evaluation of a reaction mixture of R-(+)-limonene/ozone: formation of strong airway irritants.
2001 Jun
Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).
2001 Jun
Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.
2001 Jun 28
Multivariate calibration for the determination of total azadirachtin-related limonoids and simple terpenoids in neem extracts using vanillin assay.
2001 Mar
Effects of chiral fragrances on human autonomic nervous system parameters and self-evaluation.
2001 Mar
The effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities.
2001 Mar 14
Chemical intra-Mediterranean variation and insecticidal activity of Crithmum maritimum.
2001 Mar-Apr
Indoor environmental quality in six commercial office buildings in the midwest United States.
2001 Nov
Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan.
2001 Nov
Seasonal changes in the composition of the essential oil extract of East Mediterranean sage (Salvia libanotica) and its toxicity in mice.
2001 Oct
Chiral discrimination of limonene by use of beta-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks.
2001 Sep
Distribution and immune responses resulting from oral administration of D-limonene in rats.
2002 Apr
Composition and antifungal activity of the essential oil of Solidago chilensis.
2002 Feb
Additive toxicity of limonene and 50% oxygen and the role of glutathione in detoxification in human lung cells.
2002 Jan 15
Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety.
2002 Jan 2
Background odour induces adaptation and sensitization of olfactory receptors in the antennae of houseflies.
2002 Jun
Diet and breast cancer.
2002 Jun
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:49 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
JECFA EVALUATION D-LIMONENE
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
EPA PESTICIDE CODE 179701
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
Code System Code Type Description
HSDB
4186
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
NCI_THESAURUS
C61714
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
DAILYMED
GFD7C86Q1W
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
PUBCHEM
440917
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
RXCUI
1426476
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY RxNorm
ALANWOOD
d-limonene
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
DRUG BANK
DB08921
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
CAS
5989-27-5
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
FDA UNII
GFD7C86Q1W
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID1020778
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
NSC
757069
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
EVMPD
SUB126224
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
CHEBI
15382
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-813-5
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
JECFA MONOGRAPH
1325
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
SMS_ID
100000151802
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL449062
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 2023
PRIMARY
CAS
68647-72-3
Created by admin on Fri Dec 15 15:24:49 UTC 2023 , Edited by admin on Fri Dec 15 15:24:49 UTC 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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