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Limonene is the second most abundant terpene in all cannabis strains, but not all strains necessarily have it. As its name says, limonene gives strains a citrusy smell that resembles lemons, which is no surprise as all citrus fruits contain large amounts of this compound. Limonene is used in cosmetics and also in cleaning products. For therapeutic purposes, limonene is known to improve mood and reduce stress. Researchers also found it to have antifungal and antibacterial properties and one research even found it to have a role in reducing tumor size.
Limonene (/ˈlɪmənˌiːn/) is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common (−)-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.
Limonene (R)-isomer
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![]() Limonene extracted from orange peel
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Names | |||
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Preferred IUPAC name
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene | |||
Other names
1-Methyl-4-(1-methylethenyl)cyclohexene
4-Isopropenyl-1-methylcyclohexene p-Menth-1,8-diene Racemic: DL-Limonene; Dipentene | |||
Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChEMBL |
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ChemSpider | |||
ECHA InfoCard | 100.004.856 ![]() | ||
KEGG |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C10H16 | |||
Molar mass | 136.238 g·mol−1 | ||
Appearance | colorless liquid | ||
Odor | Orange | ||
Density | 0.8411 g/cm3 | ||
Melting point | −74.35 °C (−101.83 °F; 198.80 K) | ||
Boiling point | 176 °C (349 °F; 449 K) | ||
Insoluble | |||
Solubility | Miscible with benzene, chloroform, ether, CS2, and oils soluble in CCl4 | ||
Chiral rotation ([α]D)
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87–102° | ||
Refractive index (nD)
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1.4727 | ||
Thermochemistry | |||
Std enthalpy of
combustion (ΔcH⦵298) |
−6.128 MJ mol−1 | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Skin sensitizer / Contact dermatitis – After aspiration, pulmonary oedema, pneumonitis, and death | ||
GHS labelling: | |||
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Danger | |||
H226, H304, H315, H317, H410 | |||
P210, P233, P235, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P312, P333+P313, P362, P370+P378, P391, P403+P233, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 50 °C (122 °F; 323 K) | ||
237 °C (459 °F; 510 K) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Limonene takes its name from Italian limone ("lemon"). Limonene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains (+)-limonene (d-limonene), which is the (R)-enantiomer. (+)-Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
English
Etymology
From German Limonen.
Noun
limonene (countable and uncountable, plural limonenes)
- (organic chemistry) A monoterpene hydrocarbon 1-methyl-4-prop-1-en-2-yl-cyclohexene found in the essential oils of oranges, lemons and similar fruit, and mainly responsible for their fragrance
Translations
See also
- lemonene