Limonene
Sign in to saveAlso known as 1-methyl-4-(1-methylethenyl)cyclohexene, (+-)-(RS)-limonene, 4-isopropenyl-1-methylcyclohexene, 1,8-p-menthadiene, (+/-)-limonene, limonene, (+)-, (+/-)-1-Methyl-4-(1-methylvinyl)cyclohexene, dipentene
Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the fragrance and essential oil of citrus fruit peels, taking its name from Italian limone ("lemon").
OverviewAI-generated
Limonene is a small molecule with the chemical formula C₁₀H₁₆ and a mass of 136.125201. Its IUPAC name is 1-methyl-4-prop-1-en-2-ylcyclohexene. The compound consists of carbon and hydrogen, with a density of 0.84. It has a melting point of -74.25, a flash point of 42, and an autoignition temperature of 255. Limonene serves as an aroma compound.
The substance is found in several taxa, including Homo sapiens, Enydra fluctuans, Vitex agnus-castus, and Baccharis dracunculifolia. Its MCN code is 2902.19.10. According to PubChem data, limonene has an xlogp of 3.4, a tpsa of 0, and no hydrogen bond donors or acceptors. It carries a charge of 0.
Synthesized by Vinony from 28 facts across 5 sources: Wikidata, PubMed, PubChem, ChEMBL, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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Chemical data
- Formula
- C10H16
- Molecular weight
- 136.23 g/mol
- IUPAC name
- 1-methyl-4-prop-1-en-2-ylcyclohexene
- SMILES
- CC1=CCC(CC1)C(=C)C
- InChIKey
- XMGQYMWWDOXHJM-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
6,579 papers- Limonene Hydroperoxides.Dermatitis : contact, atopic, occupational, drug · 2019
- D-limonene: A multifunctional compound with potent therapeutic effects.Journal of food biochemistry · 2021
- Limonene and Perillyl Alcohol Derivatives: Synthesis and Anticancer Activity.Mini reviews in medicinal chemistry · 2021
- Limonene.Journal of applied toxicology : JAT · 1995
- Use of Limonene Epoxides and Derivatives as Promising Monomers for Biobased Polymers.ChemPlusChem · 2022
via PubMed
~6 min read
Encyclopedic overview
9 sectionsContents
- In plants
- Chemical reactions
- Biosynthesis
- Uses
- Safety and research
- Cancer
- See also
- References
- External links
Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the fragrance and essential oil of citrus fruit peels, taking its name from Italian limone ("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.
Excerpted from Wikipedia’s “Limonene” article, available under the CC BY-SA 4.0 licence.