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Limonene (Terpene) has a pleasant, lemon-like odors free from campho raceous and turpentine-like.
Limonene (Terpene) may be obtained by steam distillation of citrus peels and pulp resulting from the pro duction of juice and cold-pressed oils, or from deterpenation of citrus oils; it is sometimes redistilled.
The most important and widespread terpene; Limonene (Terpene) is known in the el and I- optically active forms and in the optically inactive dl-form (known as dipentene); it has been reported found in more than 300 essential oils in amounts ranging from 90 - 95% (lemon, orange, mandarin) to as low as 1% (palmarosa);1 the most widespread form is the d-limonene, followed by the racemic form, and then ι- limonene.
CAS: 5989-27-5
MF: C10H16
MW: 136.23
EINECS: 227-813-5
Synonyms
(+)-1,8-p-menthadiene,(R)-(+)-limonene;(+)-4-isopropenyl-1-methylcyclohexene;(+)-limonen;(4R)-(+)-limonene;(gamma)-Carvene;(R)-(+)-1-methyl-4-(1-methylethenyl)cyclohexene;(r)-(+)-p-mentha-8-diene;(R)-1-methyl-4-(1-methylethenyl)cyclohexene
Limonene (Terpene) is a monoterpene that has been found in citrus oils and Cannabis and has diverse biological activities, including anticancer, antimicrobial, antioxidant, anti-inflammatory, and chemoprotective properties.
Limonene (Terpene) inhibits the growth of bacteria including S. aureus, B. cereus, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, M. catarrhalis, and C. neoformans with MIC values ranging from 3 to 27 mg/ml.
In a human BGC-823 gastric cancer nude mouse orthotopic transplantation model, Limonene (Terpene) inhibits tumor growth by 47.6% compared to controls and reduces the number of metastases in the liver, peritoneum, and other organs when administered by gastric perfusion at a dose of 15 ml/kg of a 1% emulsion.
Dietary administration of Limonene (Terpene) (5 and 10% in chow) reverses doxorubicin-induced decreases in glutathione (GSH) levels in rat kidney.
Formulations containing Limonene (Terpene) have been used as flavoring and fragrance agents and in the treatment of gallstones, heartburn, and gastroesophageal reflux disorder.
An optically active form of limonene having (4R)-configuration.
Limonene (Terpene) 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.
Limonene (Terpene) 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 (Terpene) takes its name from Italian limone ("lemon").
Limonene (Terpene) 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 (Terpene) is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
Limonene (Terpene) is a natural compound that has shown to have anti-inflammatory properties in mice.
The optimum concentration of Limonene (Terpene) was found to be 0.5% in the diet of CD-1 mice, which showed reduced locomotor activity and pain model scores.
Limonene (Terpene) has also been shown to inhibit the enzyme arachidonic acid 15-lipoxygenase, thereby reducing production of leukotrienes and prostaglandins, which are inflammatory mediators.
Limonene (Terpene) has been shown to have clinical relevance for the treatment of inflammation in humans and rats.
Limonene (Terpene) is metabolized by cytochrome P450 enzymes, but not by human liver microsomes or rat liver microsomes.
Limonene (Terpene) is oxidized by trifluoroacetic acid (TFA) into carboxylic acids such as limonene oxide, perillic acid, and decanoic acid, which are less reactive than limonene.
Limonene (Terpene) Chemical Properties
Melting point: -75--73°C
Boiling point: 176-177 °C(lit.)
Alpha: 112o (10% IN ETHANOL)
Density: 0.842 g/mL at 20 °C(lit.)
Vapor density: 4.7 (vs air)
Vapor pressure: 1 mm Hg ( 20 °C)
Refractive index: n20/D 1.473(lit.)
FEMA: 2633 | D-LIMONENE
Fp: 119 °F
Storage temp.: Store below +30°C.
Solubility water: insoluble
Form: liquid
Color: Colorless to Almost colorless
Specific Gravity: 0.842 (20/4℃)
Odor: at 100.00 %. citrus orange fresh sweet
Odor Type: citrus
Biological source: synthetic
Optical Rotation: [α]20/D +120°, neat
Explosive limit: 0.7-6.1%(V)
Water Solubility:Miscible with alcohol,chloroform,ether and carbondisulfide.Immiscible with water.
Merck: 14,5493
JECFA Number: 1326
BRN: 2204754
Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
LogP: 4.38 at 25℃
CAS DataBase Reference: 5989-27-5(CAS DataBase Reference)
IARC: 3 (Vol. 56, 73) 1999
EPA Substance Registry System: Limonene (Terpene) (5989-27-5)
d-, l- or Limonene (Terpene) has a pleasant, lemon-like odor free from camphoraceous and turpentine-like notes.
Limonene (Terpene) is the most important and widespread terpene; it is known in the d- and l- optically active forms and in the optically inactive dl-form (known as dipentene).
Chemical reactions
Limonene (Terpene) is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.
Limonene (Terpene) oxidizes easily in moist air to produce carveol, carvone, and limonene oxide.
With sulfur, Limonene (Terpene) undergoes dehydrogenation to p-cymene.
Limonene (Terpene) occurs commonly as the (R)-enantiomer, but racemizes 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.
Limonene (Terpene) 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.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.
The most widely practiced conversion of Limonene (Terpene) 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 a base, and the hydroxylamine is removed to give the ketone-containing carvone.
Biosynthesis
In nature, Limonene (Terpene) is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown.
The final step involves loss of a proton from the cation to form the alkene.
Uses
Chiral building block. Biodegradable solvent.
Limonene (Terpene) is used as a solvent for filament-fused 3D printing, in cosmetic products, as a fragrance and as a biofuel.
Limonene (Terpene) is useful to promote weight loss, prevent cancer, treat cancer and treat bronchitis.
Limonene (Terpene) also finds use in foods, beverages, chewing gum, as a flavoring agent and a shrinking agent to dissolve polystyrene.
Limonene (Terpene) acts as a chiral intermediate for natural product synthesis.
Limonene (Terpene) has been used to investigate the in vitro and in vivo action of limonene against Leishmania species.
As the main fragrance of citrus peels, Limonene (Terpene) is used in food manufacturing and some medicines, such as a flavoring agent to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products.
Limonene (Terpene) is also used as a botanical insecticide.
Limonene (Terpene) is used in the organic herbicides.
Limonene (Terpene) is added to cleaning products, such as hand cleansers, to give a lemon or orange fragrance (see orange oil) and for its ability to dissolve oils.
In contrast, Limonene (Terpene) has a piny, turpentine-like odor.
Limonene (Terpene) is used as a solvent for cleaning purposes, such as adhesive remover, or the removal of oil from machine parts, as it is produced from a renewable source (citrus essential oil, as a byproduct of orange juice manufacture).
Limonene (Terpene) is used as a paint stripper and is also useful as a fragrant alternative to turpentine.
Limonene (Terpene) is also used as a solvent in some model airplane glues and as a constituent in some paints.
Commercial air fresheners, with air propellants, containing Limonene (Terpene) are used by stamp collectors to remove self-adhesive postage stamps from envelope paper.
Limonene (Terpene) is also used as a solvent for fused filament fabrication based 3D printing. Printers can print the plastic of choice for the model, but erect supports and binders from high impact polystyrene (HIPS), a polystyrene plastic that is easily soluble in Limonene (Terpene).
In preparing tissues for histology or histopathology, Limonene (Terpene) 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 (Terpene), from orange peel oil, is also combustible and has been considered as a biofuel.
Preparation
Limonene (Terpene) may be obtained by steam distillation of citrus peels and pulp resulting from the production of juice and cold pressed oils, or from deterpenation of citrus oils; it is sometimes redistilled.
Contact allergens
Limonene (Terpene) is contained in Citrus species such as citrus, orange, mandarin, and bergamot.
Limonene (Terpene), used as a solvent, may be found in cleansing or in degreasing agents.
Limonene (Terpene)'s sensitizing potential increases with prolonged air contact, which induces oxidation and leads to oxidation products.
The presence of Limonene (Terpene) has to be mentioned by name in cosmetics of the EU.
