Basic information
- CAS
5989-54-8- Standard SMILES
C=C(C)[C@@H]1CC=C(C)CC1- InChIKey
XMGQYMWWDOXHJM-SNVBAGLBSA-N- Molecular formula
- C10H16
- Average molar mass
- 136.23 g/mol
- Monoisotopic mass
- 136.12520051
Overview
(4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene.
Names & identifiers
- Preferred name
- Limonene, (-)-
- IUPAC
- (4S)-1-methyl-4-prop-1-en-2-ylcyclohexene
- English name
- (S)-(-)-Limonene
- Molecular formula
- C10H16
- Molecular weight
- 136.23
Names & synonyms
(-)-Limonenel-Limonenebeta-LimoneneLimonene, (-)-Limonene, L-P-Mentha-1,8-diene, (S)-(-)-UNII-47MAJ1Y2NE47MAJ1Y2NECyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-EINECS 227-815-6AI3-25390EC 227-815-6
Show more names
(-)-Dipentene(s)-(-)-p-mentha-8-diene(-)-1,8-p-menthadiene,(S)-(-)-limonene(S)-(-)-4-ISOPROPENYL-1-METHYL-1-CYCLOHEXENE1-methyl-4-(1-methylethenyl)-,(S)-Cyclohexenecyclohexene,1-methyl-4-(1-methylethenyl)-,(S)-
1-Methyl-4-(1-methylethenyl)cyclohexene, (S)-RefChem:41455227-815-65989-54-8(S)-(-)-Limonene(S)-Limonene(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene(-)-(4S)-Limonene
Database identifiers
- CAS
5989-54-8- PubChem CID
- 439250
- DTXSID
DTXSID6047078- ChEMBL
CHEMBL236688- ChEBI
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 163
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Terpenes
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsCosmetics ingredient -> Base; Colorant; Conditioning/Emollient; Emulsifier; Flavor; Fragrance; Moisturizing/Humectant; Opacifying Agent; Other (Specify); Preservative/Stabilizer; Solvent
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (l-Limonene) -> IFRA transparency List
LogP4.57
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility0.0138 mg/mL at 25 °C
Flash Point48 °C
Safety & regulation
GHS classification
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P302+P352, P303+P361+P353, P321, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P321, P331, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 28-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10807
(S)-(-)-Limonene: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationPEC / SN / Other assessments - Limonene: Health and Environment
Hazards Summary
A skin sensitizer; A mild skin, eye, and respiratory tract irritant; [CHEMINFO] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; Effects in high-dose animal studies include acute tubular necrosis; [MSDSonline] The racemic mixture of d-limonene and l-limonene is called dipentene or limonene (138-86-3). [Kanerva, p. 1789] See Limonene and d-Limonene.
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flammable liquid - category 3
Flam. Liq. 3
Toxicology
Chemistry & industry
Pharmacology
Metabolism/Metabolites(-)-limonene has known human metabolites that include Carveol and Perillyl alcohol.
Cellular LocationsExtracellular
Uses & manufacturing
Uses
Used in artificial essential oils and to make (+)-carvone; Occurs naturally in essential oils of pine, peppermint, spearmint, and other plants; A minor constituent of turpentine; [CHEMINFO] Used in flavorings, fragrances, cosmetics and as a solvent and wetting agent; Also used to make resins, insecticides, insect repellants, and animal repellants; [HSDB]
Painting (Solvents) [Category: Paint]
Household Products
Cosmetics product ingredient: Limonene (1-methyl-4-prop-1-en-2-yl-cyclohexene; dl-limonene (racemic); Dipentene; (R)-p-mentha-1,8-diene; (d-limonene); (S)-p-mentha-1,8-diene; (l-limonene))
Information on 16 consumer products that contain L-Limonene in the following categories is provided:
Use ClassificationFragrance Ingredients
General Manufacturing InformationCyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-: ACTIVE
Applications
Description(S)-(-)-Limonene is one of the most popular natural occurring cyclic terpenes and its chemical name is D-Limonene. It is a colorless liquid at room temperature with a characteristic lemon-like odor. Although it is insoluble in ether and alcohol, (S)-(-)-Limonene is soluble in water and has a boiling point of 74oC. (S)-(-)-Limonene can be recovered from orange peel from the conversion of press liquor to molasses. It is a major constituent of numerous citrus oils such as lemon, orange, lime, mandarin, and grapefruit, which are fruits from the Rutaceae family. (S)-(-)-Limonene can be obtained by stream distillation of pulp and citrus peels resulting from production of cold-pressed oils and juice or from deterpenation of citrus oils. The compound also occurs in other essences and oils obtained during the processing of citrus juice, including deoiler, essence oil, aroma, and juice oil.
Related reactions
2 records
Compound notes
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