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Compound Summary

General Compound Information

(R)-limonene

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Description

(4R)-limonene is an optically active form of limonene having (4R)-configuration. It has a role as a plant metabolite. It is an enantiomer of a (4S)-limonene.

Synonyms

D-Limonene; 5989-27-5; (R)-(+)-Limonene; (+)-Limonene; (D)-Limonene;

(+)-(4R)-Limonene;(+)-carvene;(4R)-Limonene;D-(+)-Limonene;(R)-Limonene;Limonene, D-;(+)-Dipentene;Citrene;(+)-p-Mentha-1,8-diene;D-Limonen;Limonene, (+)-;(R)-4-Isopropenyl-1-methyl-1-cyclohexene;(R)-p-Mentha-1,8-diene;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-;(+)-R-Limonene;FEMA No. 2633;d-p-Mentha-1,8-diene;(+)-4-Isopropenyl-1-methylcyclohexene;r-(+)-limonene;(4R)-4-isopropenyl-1-methylcyclohexene;(R)-(+)-p-Mentha-1,8-diene;(R)-1-Methyl-4-(1-methylethenyl)cyclohexene;(+)-(R)-Limonene;(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene;D-limonene [JAN];(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;(4R)-1-methyl-4-(1-methylethenyl)cyclohexene;MFCD00062991;GFD7C86Q1W;4betaH-p-mentha-1,8-diene;DTXSID1020778;CHEBI:15382;(+) Limonene;NSC-757069;Carvene;Glidesafe;Glidsafe;Kautschiin;Refchole;(4R)-1-methyl-4-isopropenylcyclohex-1-ene;Orange x;Biogenic SE 374;(+)-alpha-Limonene;d-Limonene (natural);d-Limoneno [Spanish];d limonene;d-Limoneno;Hemo-sol;(4R)-(+)-Limonene;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-;(4R)-4-isopropenyl-1-methyl-cyclohexene;CCRIS 671;EC 7;HSDB 4186;D-1,8-p-Menthadiene;NCI-C55572;EINECS 227-813-5;UNII-GFD7C86Q1W;p-Mentha-1,8-diene, (R)-(+)-;Sulfate turpentine, distilled;(+)-1,8-para-Menthadiene;Dextro-limonene;AI3-15191;1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-;EINECS 266-034-5;(R)-4-isopropenyl-1-methylcyclohexene;D-(+)-Limonen;Dipentene no. 122;(+)-(R)-4-isopropenyl-1-methylcyclohexene;D-Limonene Reagent Grade;D-LIMONENE [IARC];EC 227-813-5;(+)-Limonene, stabilized with 0.03% tocopherol;DTXCID50778;(D)-LIMONENE [HSDB];(+)-LIMONENE [FCC];CHEMBL449062;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-;(R)-(+)-Limonene, 95%;(R)-(+)-Limonene, 97%;ZINC967513;CS-M3273;(R)-(+)-Limonene, >=93%;Tox21_200400;LIMONENE, (+)- [WHO-DD];AKOS015899935;CCG-266134;DB08921;LMPR0102090013;NSC 757069;(R)-(+)-Limonene, analytical standard;NCGC00248591-01;NCGC00248591-02;NCGC00257954-01;BS-22387;CAS-5989-27-5;(R)-(+)-4-Isopropenyl-1-methylcyclohexene;L0047;L0105;(R)-Limonene 2000 microg/mL in Acetonitrile;C06099;D91245;EN300-106573;(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene;J-502148;W-105295;Q27888324;Z1255486311;(R)-(+)-Limonene, primary pharmaceutical reference standard;(R)-(+)-Limonene, purum, >=96.0% (sum of enantiomers, GC);(R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC);68647-72-3;9IR;

FlavorDB ID

277 PUBCHEM ID

Molecular Weight

136.23 Molecular Formula

C10H16

Openeye Can Smiles

CC1=CCC(CC1)C(=C)C

IUPAC Inchikey

XMGQYMWWDOXHJM-JTQLQIEISA-N

Network

Similarity

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
smell	citrus-like	1.300e+1 µmol/L		details
smell	citrus		water	details

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: D-Limonene is a colorless liquid or oil with citrus odor. D-Limonene, a major constituent of citrus oils, is a monoterpene widely used as a flavor/fragrance additive in cosmetics, foods, and industrial solvents as it possesses a pleasant lemon-like odor. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. D-Limonene is also used as gallstone solubilizer in animals and humans. HUMAN EXPOSURE AND TOXICITY: Skin irritation or sensitizing potential was reported following widespread use of this agent in various consumer products. In humans, oxidation products or metabolites of d-limonene were shown to act as skin irritants. The potential occurrence of skin irritation necessitates regulation of this chemical as an ingredient in cosmetics. In humans, d-limonene has demonstrated low toxicity after single and repeated dosing for up to one year. D-Limonene was reported to significantly damage and increase permeability of membranes of human lung fibroblasts. ANIMAL STUDIES: In experimental animals oxidation products or metabolites of d-limonene were shown to act as skin irritants. D-Limonene has been designated as a chemical with low toxicity based upon lethal dose (LD50) and repeated-dose toxicity studies when administered orally to animals. Carcinogenic effects have also been observed in male rats, but the mode of action (MOA) is considered irrelevant for humans as the protein alpha(2u)-globulin responsible for this effect in rodents is absent in humans. d-Limonene induced hyaline droplet nephropathy in male rats. The liver was identified as a critical target organ following oral administration of d-limonene. D-Limonene (2363 mg/kg, orally) given to mice for 6 days from day 7-12 of gestation decreased body weight gain and increased incidence of abnormal bone formation in fetuses. D-Limonene also decreased body weight gain in male offspring; however, the toxicity of d-limonene was not severe. D-Limonene was not mutagenic in four strains of Salmonella typhimurium (TA 98, TA 100, TA 1535, or TA 1537), did not significantly increase the number of trifluorothymidine-resistant cells in the mouse L5178Y/TK + or - assay, and did not induce chromosomal aberrations or sister chromatid exchanges in cultured CHO cells. All assays were conducted in the presence and absence of exogenous metabolic activation.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

Food Additive Safety (OFAS)
D-LIMONENE is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: d-Limonene

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Output ID	SPECIES	Route	Duration Days	END POINT	QUALIFIER	VALUE	UNIT	EFFECT	Toxicity
2102	Rat	oral: gavage	721	NOAEL	=	215	mg/kg bw/day	mortality	systemic
2103	Mouse	intraperitoneal		NOAEL	=	215	mg/kg bw/day	not reported	not reported
2784	Mouse	Not reported		NOAEL	=	250	mg/kg bw/day	gross pathology	hepatotoxicity
2784	Rat	Not reported		NOAEL	=	250	mg/kg bw/day	histopathology non neoplastic	nephrotoxicity

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

OUTPUT ID	ASSESSMENT	QUALIFIER	VALUE	UNIT	POPULATION
2305	TTC Cramer Class I	=	30	µg/kg bw/day	Consumers
248	critical study not identified		0		Consumers
2784	MTD	=	22	mg/kg	Cats as pet

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA AFC	2009	2305	Negative
EFSA CEF	2011	2102	Negative
EFSA CEF	2011	2103	Negative
EFSA CEF	2015	2635	Negative
EFSA FEEDAP	2011	248	No data
EFSA FEEDAP	2015	2784	Not determined

EFSA Outputs

Output ID	Title	DOI	Published
248	Scientific Opinion on the safety and efficacy of FRESTA F for weaned piglets	doi:10.2903/j.efsa.2011.2139	19Apr2011
2102	Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31	doi:10.2903/j.efsa.2011.2177	29Jun2011
2103	Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF)	doi:10.2903/j.efsa.2011.2178	29Jun2011
2305	Flavouring Group Evaluation 78 (FGE.78): Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25. Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food	doi:10.2903/j.efsa.2009.931	20Jan2009
2635	Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3.	doi:10.2903/j.efsa.2015.4067	13Apr2015
2784	Scientific Opinion on the safety and efficacy of aliphatic and aromatic hydrocarbons (chemical group 31) when used as flavourings for all animal species	doi:10.2903/j.efsa.2015.4053	31Mar2015

Receptors

Receptor	REFERENCE	EC50 [µM]
OR1A1	details	Activated
OR1G1	details	Activated
OR2B11	details	Activated
OR2W1	details	Activated
OR5K1	details	Activated

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative

Content

Compound Summary

(R)-limonene

Description

(4R)-limonene is an optically active form of limonene having (4R)-configuration. It has a role as a plant metabolite. It is an enantiomer of a (4S)-limonene.

Synonyms

D-Limonene; 5989-27-5; (R)-(+)-Limonene; (+)-Limonene; (D)-Limonene;

FlavorDB ID

277

PUBCHEM ID

440917

Molecular Weight

136.23

Molecular Formula

C10H16

Openeye Can Smiles

CC1=CCC(CC1)C(=C)C

IUPAC Inchikey

XMGQYMWWDOXHJM-JTQLQIEISA-N

Network

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Similarity

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Content

Compound Summary

(R)-limonene

Description

(4R)-limonene is an optically active form of limonene having (4R)-configuration. It has a role as a plant metabolite. It is an enantiomer of a (4S)-limonene.

Synonyms

D-Limonene; 5989-27-5; (R)-(+)-Limonene; (+)-Limonene; (D)-Limonene;

FlavorDB ID

277

PUBCHEM ID

440917

Molecular Weight

136.23

Molecular Formula

C10H16

Openeye Can Smiles

CC1=CCC(CC1)C(=C)C

IUPAC Inchikey

XMGQYMWWDOXHJM-JTQLQIEISA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

Reference Details

Reference Details

OpenFoodTox: component d-Limonene

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

GC-MS Spectrum

GC-MS Spectrum

GC-MS Spectrum