LIMONENE, (+)-

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

HIDE SMILES / InChI

Description

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 95	Opener 34
Adenosine A2a receptor 31	Agonist 2,752
regulation of glucuronosyltransferase activity 1	Activator 1,447
Ornithine decarboxylase 15	Inhibitor 8,504
protein prenylation 1	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432	Primary	Phase I 438	Unknown
Gastroesophageal reflux disease 68	Primary	Phase I 438	Unknown
Cholesterol gallstones 1	Primary	Phase I 438	Rowachol

C_max

Value	Dose	Analyte	Population
93.6 ng/mL	300 mg single, oral	LIMONENE, ( )- plasma	Homo sapiens
159.573 ng/mL	0.3 mL single, oral	LIMONENE, ( )- plasma	Homo sapiens
10.8 μM	2.67 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens
12 μM	2.67 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens
13.8 μM	3.33 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens
10.9 μM	3.33 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens
20.5 μM	4 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens
4.9 μM	4 g/m² 3 times / day multiple, oral	LIMONENE, ( )- plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
311.9 ng × h/mL	300 mg single, oral	LIMONENE, ( )- plasma	Homo sapiens
449.855 ng × h/mL	0.3 mL single, oral	LIMONENE, ( )- plasma	Homo sapiens
151 μM × h	8 g/m² single, oral	LIMONENE, ( )- plasma	Homo sapiens
165 μM × h	10 g/m² single, oral	LIMONENE, ( )- plasma	Homo sapiens
154.5 μM × h	12 g/m² single, oral	LIMONENE, ( )- plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.42 h	300 mg single, oral		LIMONENE, ( )- plasma	Homo sapiens
2.859 h	0.3 mL single, oral		LIMONENE, ( )- plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
12 g/m2 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Other AEs: Diarrhea...
8 g/m2 1 times / day multiple, oral MTD	unhealthy, ADULT	Other AEs: Nausea, Vomiting...

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AEs

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AE	Significance	Dose	Population
Diarrhea	grade 2, 1 pt	12 g/m2 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Vomiting	grade 1, 1 patient	8 g/m2 1 times / day multiple, oral MTD	unhealthy, ADULT
Nausea	grade 1, 3 patients	8 g/m2 1 times / day multiple, oral MTD	unhealthy, ADULT
Diarrhea	grade 1, 4 patients	8 g/m2 1 times / day multiple, oral MTD	unhealthy, ADULT
Diarrhea	grade 2, 2 patients	8 g/m2 1 times / day multiple, oral MTD	unhealthy, ADULT

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PubMed

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Title	Date	PubMed
Degradation of pinene by Bacillus pallidus BR425.	1998	10192895
Aroma compounds-proteins interaction using headspace techniques.	2001	11548158
Gc-olfactometry with solid phase microextraction of aroma volatiles from heated and unheated orange juice.	2001	11548149
Molecular cloning, functional expression and characterization of d-limonene synthase from Schizonepeta tenuifolia.	2001 Apr	11305598
Response of plum curculio (Coleoptera: Curculionidae) to odor-baited traps near woods.	2001 Dec	11777040

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Patents

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.

Show entries

Name

Type

Language

LIMONENE, (+)-

Common Name

English

LIMONENE

Preferred Name

English

DIPENTENE NO. 122

Brand Name

English

(+)-(R)-4-ISOPROPENYL-1-METHYLCYCLOHEXENE

Systematic Name

English

(D)-LIMONENE [HSDB]

Common Name

English

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Classification Tree

Code System

Code

Bioactive Food Component

NCI_THESAURUS

C68542

EPA PESTICIDE

EPA PESTICIDE CODE

79701

Chemical

DSLD

1215 (Number of products:28)

ESTABLISHED CONTACT ALLERGEN IN HUMANS

EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION

SCCS/1459/11

FUNCTIONAL CLASSIFICATION

JECFA EVALUATION

D-LIMONENE

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Code System

Code

Type

Description

HSDB

4186

PRIMARY

NCI_THESAURUS

C61714

PRIMARY

DAILYMED

GFD7C86Q1W

PRIMARY

PUBCHEM

440917

PRIMARY

RXCUI

1426476

PRIMARY

RxNorm

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ACTIVE MOIETY


					GFD7C86Q1W

LIMONENE, (+)-

METABOLITE (PARENT)


					PKS69DU4ZQ

PERILLIC ACID

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2