Limonene Identifiers CAS number PubChem , (S-isomer) ChemSpider , (S-isomer), (R-isomer)(Racemic) UNII KEGG ChEBI Jmol-3D images Image 1 Properties Molecular formula C10H16 Molar mass 136.24 g/mol Density 0.8411 g/cm³ Melting point
-74.35 °C, 199 K, -102 °F
176 °C, 449 K, 349 °F
Hazards R-phrases S-phrases NFPA 704 Flash point 50 °C (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Limonene is a colourless liquid hydrocarbon classified as a cyclic terpene. The more common D isomer possesses a strong smell of oranges. It is used in chemical synthesis as a precursor to carvone and as a renewably-based solvent in cleaning products.
Limonene takes its name from the lemon, as the rind of the lemon, like other citrus fruits, contains considerable amounts of this compound, which contributes to their odor. Limonene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains D-limonene ((+)-limonene), which is the (R)-enantiomer (CAS number 5989-27-5, EINECS number 227-813-5). Racemic limonene is known as dipentene. D-Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
Limonene is a relatively stable terpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene. It oxidizes easily in moist air to produce carveol, carvone, and limonene oxide. With sulfur, it undergoes dehydrogenation to p-cymene.
Limonene occurs naturally as the (R)-enantiomer, but racemizes to dipentene at 300 °C. When warmed with mineral acid, limonene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene). Evidence for this isomerization includes the formation of Diels-Alder adducts between α-terpinene adducts and maleic anhydride.
It is possible to effect reaction at one of the double bonds selectively. Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene, whereas epoxidation with MCPBA occurs at the trisubstituted alkene.
The most widely practiced conversion of limonene is to carvone. The three step reaction begins with the regioselective addition of nitrosyl chloride across the trisubstituted double bond. This species is then converted to the oxime with base, and the hydroxylamine is removed to give the ketone-containing carvone.
Limonene is common in cosmetic products. As the main odor constituent of citrus (plant family Rutaceae), D-limonene is used in food manufacturing and some medicines, e.g. as a flavoring to mask the bitter taste of alkaloids, and as a fragrant in perfumery; it is also used as botanical insecticide., particularly the (R)-(+)-enantiomer is most active as an insecticide. It is added to cleaning products such as hand cleansers to give a lemon-orange fragrance (see orange oil). In contrast, L-limonene has a piney, turpentine-like odor.
Limonene is increasingly being used as a solvent for cleaning purposes, such as the removal of oil from machine parts, as it is produced from a renewable source (citrus oil, as a byproduct of orange juice manufacture). It also serves as a paint stripper when applied to painted wood and is also useful as a fragrant alternative to turpentine. Limonene is also used as a solvent in some model airplane glues. All-natural commercial air fresheners, with air propellants, containing limonene are used by philatelists to remove self-adhesive postage stamps from envelope paper.
Limonene can be used to dissolve polystyrene, and is a more ecologically friendly substitute for acetone.
In preparing tissues for histology or histopathology, D-limonene is often used as a less toxic substitute for xylene when clearing dehydrated specimens. Clearing agents are liquids miscible with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens are embedded to facilitate cutting of thin sections for microscopy.
Limonene and its oxidation products are skin and respiratory irritants, and limonene-1,2-oxide (formed by aerial oxidation) is a known skin sensitizer. Most reported cases of irritation have involved long-term industrial exposure to the pure compound, e.g. during degreasing or the preparation of paints. However a study of patients presenting dermatitis showed that 3% were sensitized to limonene.
Although high doses have been shown to cause renal cancer in male rats, limonene is considered by some researchers to be a potential chemopreventive agent  with value as a dietary anti-cancer tool in humans. There is no evidence for carcinogenicity or genotoxicity in humans. The IARC classifies D-limonene as a Group 3 carcinogen: not classifiable as to its carcinogenicity to humans.
No information is available on the health effects of inhalation exposure to D-limonene in humans,[dubious ] and no long-term inhalation studies have been conducted in laboratory animals.
D-Limonene is biodegradable, but due to its low flash point, it must be treated as hazardous waste for disposal.
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Limonène — Structure du R Limonène Général Nom IUPAC 1 méthyl 4 prop 1 èn 2 yl cyclohexène … Wikipédia en Français
Limonene — Limonène Limonène Structure du R Limonène Général Nom IUPAC 1 méthyl 4 prop 1 èn 2 yl cyclohexène … Wikipédia en Français
limonène — [ limɔnɛn ] n. m. • 1905; de 3. limon et ène ♦ Chim. Hydrocarbure de la famille des terpènes, qu on rencontre dans les essences de citron, de bergamote, etc. ● limonène nom masculin (arabe līmūn, citron) Hydrocarbure terpénique C10H16, employé… … Encyclopédie Universelle
limonene — n. a liquid terpene with a lemon odor; found in lemons and oranges and other essential oils. [WordNet 1.5] … The Collaborative International Dictionary of English
limonene — [lim′ə nēn΄] n. [< ModL Limonum (< Fr limon, LEMON) + ENE] any of three isomeric terpenes, C10H16, present in many plant products such as lemon peel, orange oil, pine needles, peppermint, etc … English World dictionary
limonene — /lim euh neen /, n. Chem. a liquid terpene, C40H16, occurring in two optically different forms, the dextrorotatory form being present in the essential oils of lemon, orange, etc., and the levorotatory form in Douglas fir needle oil. [1835 45; <… … Universalium
limonene — limonenas statusas T sritis chemija formulė CH₃C₆H₈C(CH₃)=CH₂ atitikmenys: angl. carvene; citrene; limonene rus. карвен; лимонен ryšiai: sinonimas – karvenas sinonimas – (+)4 izopropenil 1 metilcikloheksenas … Chemijos terminų aiškinamasis žodynas
limonene — noun Etymology: International Scientific Vocabulary, from French limon lemon, from Middle French Date: 1845 a widely distributed terpene hydrocarbon C10H16 that occurs in essential oils (as of oranges or lemons) and has a lemon odor … New Collegiate Dictionary
limonene — noun 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 … Wiktionary
limonene — lim·o·nene lim ə .nēn n a liquid terpene hydrocarbon C10H16 that has an odor like a lemon, exists in dextrorotatory, levorotatory, and racemic forms, and occurs in many essential oils compare DIPENTENE … Medical dictionary