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Topic summary

Limonene

Limonene
Limonene (R)-isomer
Limonene extracted from orange peel
Names Pronunciation 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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.004.856KEGG
UNII
  • InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
    Key: XMGQYMWWDOXHJM-UHFFFAOYSA-N
  • CC1=CCC(CC1)C(=C)C
Properties C10H16Molar mass136.238 g·mol Appearance colorless liquid OdorOrangeDensity0.8411 g/cm Melting point−74.35 °C (−101.83 °F; 198.80 K) Boiling point176 °C (349 °F; 449 K) Insoluble SolubilityMiscible with benzene, chloroform, ether, CS2, and oils
soluble in CCl487–102° 1.4727 Thermochemistry −6.128 MJ mol Hazards Occupational safety and health (OHS/OSH):
Main hazards
Skin sensitizer / Contact dermatitis – After aspiration, pulmonary oedema, pneumonitis, and deathGHS labelling: DangerH226, H304, H315, H317, H410P210, 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, P501NFPA 704 (fire diamond)
2
2
0
Flash point50 °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).

Limonene () is a slightly yellow-green liquid aliphatichydrocarbon classified as a cyclic monoterpene, and is the major component in the fragrance and essential oil of citrus fruitpeels, taking its name from Italianlimone ("lemon").

Limonene is a chiral molecule, and most biological sources produce just one enantiomer (isomer). The (+)-isomer, d-limonene, which is the (R)-enantiomer, occurs more commonly in nature in citrus fruit peels, the principal commercial source, from which it is obtained commercially by two primary methods: centrifugal separation and steam distillation. d-Limonene is used as a flavoring agent in food manufacturing, in chemical synthesis as a precursor to carvone, and as a renewables-based solvent in cleaning products. It has a "citrus, orange, fresh, sweet, peely" aroma.

The less common (−)-isomer, l-limonene, which is the (S)-enantiomer, has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

Wikipedia source