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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16
Molecular Weight 136.2344
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIMONENE, (+)-

SMILES

C=C(C)[C@@]1([H])CC=C(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 136.2344
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
152
Targets

Targets

Primary TargetPharmacologyConditionPotency
Opener
32
Agonist
2470
Activator
1343
Inhibitor
7728
Inhibitor
7728
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
409
Unknown

Approved Use

Unknown
Primary
Phase I
409
Unknown

Approved Use

Unknown
Primary
Phase I
409
Rowachol

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Aroma compounds-proteins interaction using headspace techniques.
2001
Gc-olfactometry with solid phase microextraction of aroma volatiles from heated and unheated orange juice.
2001
Isotope ratio by HRGC-MS of citrus Junos tanaka (yuzu) essential oils: m/z 137/136 of terpene hydrocarbons.
2001 Dec
Perceptual correlates of neural representations evoked by odorant enantiomers.
2001 Dec 15
Composition and antimicrobial activity of the essential oil of Baccharis notosergila.
2001 Feb
Evaluation of individual components of plum odor as potential attractants for adult plum curculios.
2001 Jan
Characterization of some Italian types of wild fennel (Foeniculum vulgare Mill.).
2001 Jan
Odorant-induced hyperpolarization and suppression of cAMP-activated current in newt olfactory receptor neurons.
2001 Jan
Seasonal variation of monoterpene emission from Malus domestica and Prunus avium.
2001 Jul
Foliar and cortex oleoresin variability of silver fir (Abies alba Mill.) in Albania.
2001 Jul-Aug
Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I.
2001 Mar
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
Degradation of monoterpenes in orange juice by gamma radiation.
2001 May
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
2001 May
Indoor environmental quality in six commercial office buildings in the midwest United States.
2001 Nov
Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC.
2001 Nov-Dec
Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae).
2001 Nov-Dec
Seasonal changes in the composition of the essential oil extract of East Mediterranean sage (Salvia libanotica) and its toxicity in mice.
2001 Oct
Evaluation of in vitro percutaneous absorption of lorazepam and clonazepam from hydro-alcoholic gel formulations.
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
Health evaluation of volatile organic compound (VOC) emissions from wood and wood-based materials.
2001 Sep-Oct
Distribution and immune responses resulting from oral administration of D-limonene in rats.
2002 Apr
Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants.
2002 Apr
Spontaneous versus reinforced olfactory discriminations.
2002 Aug 15
Expression of cyclin D1/2 in the lungs of strain A/J mice fed chemopreventive agents.
2002 Feb
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation.
2002 Feb 12
Mammary carcinomas induced in human c-Ha-ras proto-oncogene transgenic rats are estrogen-independent, but responsive to d-limonene treatment.
2002 Jan
Additive toxicity of limonene and 50% oxygen and the role of glutathione in detoxification in human lung cells.
2002 Jan 15
A comparative analysis of glove permeation resistance to paint stripping formulations.
2002 Jan-Feb
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
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
Influence of flavour absorption on oxygen permeation through LDPE, PP, PC and PET plastics food packaging.
2002 Mar
Comparison of extraction methods for marker compounds in the essential oil of lemon grass by GC.
2002 Mar 13
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 Jun 25 21:51:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:51:24 UTC 2021
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
FCC  
Common Name English
(4R)-1-METHYL-4-(1-METHYLETHENYL)CYCLOHEXENE
Systematic Name English
LIMONENE, D-
Common Name English
LIMONENE [WHO-DD]
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 Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
JECFA EVALUATION D-LIMONENE
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
EPA PESTICIDE CODE 179701
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
Code System Code Type Description
HSDB
4186
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
NCI_THESAURUS
C61714
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
PUBCHEM
440917
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
RXCUI
1426476
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB08921
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
CAS
5989-27-5
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
FDA UNII
GFD7C86Q1W
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
EPA CompTox
5989-27-5
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
EVMPD
SUB126224
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
227-813-5
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL449062
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
PRIMARY
CAS
68647-72-3
Created by admin on Fri Jun 25 21:51:24 UTC 2021 , Edited by admin on Fri Jun 25 21:51:24 UTC 2021
NO STRUCTURE GIVEN
Related Record Type Details
EUCALYPTUS OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
LIMONENE
SUB_CONCEPT->SUBSTANCE
LEMON OIL, COLD PRESSED
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CARAWAY OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
MANDARIN OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CORIANDER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
JAVA CITRONELLA OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
LAVENDER OIL
PARENT -> CONSTITUENT MAY BE PRESENT
DWARF PINE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
JUNIPER BERRY OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
FOENICULUM VULGARE FRUIT OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
Related Record Type Details
Structure of PERILLIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of LIMONENE, (+)-
ACTIVE MOIETY
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