CAS no.: 5989-27-5;CAS no.: 138-86-3;Limonene; DL-Limonene; Dipentene; d Limonene; d-limonene; dipentene; limonene;Orange oil;Citrus Terpenes; Citrusterpene. Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.
d-Limonene has been produced since 1995 and has been used as a flavor and fragrance additive in cleaning and cosmetic products, food, beverages, and pharmaceuticals. It is also increasingly used as a solvent. It is used in the manufacturing of resins, as a wetting and dispersing agent, and in insect control. It is present in most of the essential oils commonly used in Australia, particularly citrus oils. In the workplace, products such as hand cleaners, industrial cleaners, degreasers, and strippers may also contain limonene as a solvent. Industrial limonene is produced by alkaline extraction of citrus residues and steam distillation. This distillate contains more than 90% d-limonene.
Limonene is used as a substitute for chlorinated hydrocarbons, chlorofluorocarbons, and other solvents. It is used in degreasing metals (30% limonene) prior to industrial painting, for cleaning in the electronics industry (50–100% limonene), for cleaning in the printing industry (30–100% limonene), and in paint as a solvent. Limonene is also used as a solvent in histology laboratories and as a flavor and fragrance additive in food, household cleaning products, and perfumes. d-Limonene has been used as a gallstone solubilizer in humans.
d-Limonene has also been used as a sorption promoter or accelerant for improving transdermal drug delivery and works by penetrating the skin to reversibly decrease barrier resistance. Commercial mixtures of d-limonene molecules may contain other forms of limonene (l-limonene and d,l-limonene), which are called terpenes, and related compounds such as p-cumene.
Some studies have indicated that limonene has anticancer effects. Limonene increase the levels of liver enzymes involved in detoxifying carcinogens. The glutathione-S-transferase (GST) system eliminates carcinogens. The GST system can be promoted by limonene in the liver and small bowel leading to a decrease in the damaging effects of carcinogens. Animal studies demonstrated that dietary limonene reduced mammary tumor growth.
D-limonene is a clear colorless mobile liquid with a pleasant lemon-like odor.
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; 1-Methyl-4-(1-methylethenyl)cyclohexene; 4-Isopropenyl-1-methylcyclohexene; p-Menth-1,8-diene
Alpha-Limonene, Alpha-Limonène, Dipentene, D-Limonene, D-Limonène, L-Limonene, L-Limonène, Limonène, Limoneno, R-Limonene, R-Limonène, S-Limonene, S-Limonène.
CAS Number: 138-86-3; 5989-27-5; 5989-54-8
Chemical formula: C10H16
Molar mass: 136.238 g·mol−1
Appearance: colorless to pale-yellow 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)
Solubility in water: Insoluble
Solubility: Miscible with benzene, chloroform, ether, CS2, and oils
soluble in CCl4
Chiral rotation ([α]D): 87–102°
Refractive index (nD): 1.4727
dipentene; limonene
dl-Limonene (racemic)
Limonene
p-Mentha-1,8-diene
CAS no.: 5989-27-5
Mol. formula: C10H16
WHAT IS D-LIMONENE?
D-Limonene, also known as Citrus Terpenes, is the main chemical constituent found in the cold-pressed peel oils that can be derived from all edible citrus fruits, namely oranges, lemons, and limes. After the first pressing of the peels, it is obtained from the resultant oil through the process of distillation. The two chemical forms of Limonene are d-Limonene, which is found largely in orange peels, and L-Limonene, which is found largely in lemon peels. Limonene gets its name from the botanical name for “Lemon” – Citrus limon – due to the richness of this natural compound in lemon peels.
Its wide range of beneficial applications has made d-Limonene one of the most prominent natural Terpenes. With a light, pleasantly dry, and refreshingly-sweet citrusy scent, it is valued for its aroma and is mostly used in fragrances as well as green cleaning products rather than for therapeutic applications. NDA’s d-Limonene Raw Material is a thin, clear, colorless, oily fluid that is derived from steam distilled citrus rinds. It is safer to use, works more effectively, and is more environmentally-friendly than most commercial and industrial cleaners.
HOW DOES D-LIMONENE WORK?
D-Limonene is a fragrance agent, a degumming agent, and a gentle yet powerful cleaner that is reputed to effectively remove stains, grease, tar, and more, thus making a natural replacement for more popular solvents, which usually contain chlorine or petroleum. Its mildness has also made it a popular ingredient in water-free hand soaps, in which it is said to not only cleanse but to also leave the hands smelling fresh. When applied to various types of hard surfaces, such as counter tops, windows, mirrors, floors, bath tubs, refrigerators, cars, and electronic items, d-Limonene is reputed to bring a high shine to all cleaned items.
APPLICATIONS FOR D-LIMONENE
D-Limonene may be used at full strength, that is without dilution, as an eco-friendly detergent; however, direct application to painted surfaces, plexiglass, plastics, or fiberglass is not recommended. Conversely, it may be added to wetting agents, such as water or vinegar bases, to achieve better solubilization. Either method will make for a natural yet equally effective industrial-strength “green” surface disinfectant that is ideal for household cleaning.
Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-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 L-isomer is found in mint oils and has a piny, turpentine-like odor. The compound is one of the main volatile monoterpenes found in the resin of conifers, particularly in the Pinaceae, and of orange oil.
Limonene takes its name from French limon ("lemon"). 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. Racemic limonene is known as dipentene. D-Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
Chemical reactions
Limonene is a relatively stable monoterpene 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 commonly as the D- or (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.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.
Biosynthesis
In nature, limonene 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.
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 a base, and the hydroxylamine is removed to give the ketone-containing carvone.
In plants
D-Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees: red and silver maple (Acer rubrum, Acer saccharinum), cottonwoods (Populus angustifolia), aspens (Populus grandidentata, Populus tremuloides) sumac (Rhus glabra), spruce (Picea spp.), various pines (e.g., Pinus echinata, Pinus ponderosa), Douglas fir (Pseudotsuga menziesii), larches (Larix spp.), true firs (Abies spp.), hemlocks (Tsuga spp.), cannabis (Cannabis sativa spp.),[9] cedars (Cedrus spp.), various Cupressaceae, and juniper bush (Juniperus spp.). It contributes to the characteristic odor of orange peel, orange juice and other citrus fruits. To optimize recovery of valued components from citrus peel waste, d-limonene is typically removed.
Safety and research
D-Limonene applied to skin may cause irritation from contact dermatitis, but otherwise appears to be safe for human uses. Limonene is flammable as a liquid or vapor and it is toxic to aquatic life.
Uses
Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products. As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. D-Limonene is also used as a botanical insecticide. D-Limonene is used in the organic herbicide "Avenger". It 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, L-limonene has a piny, turpentine-like odor.
Limonene 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). It is used as a paint stripper and is also useful as a fragrant alternative to turpentine. Limonene 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 are used by philatelists to remove self-adhesive postage stamps from envelope paper.
Limonene 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 HIPS, a polystyrene plastic that is easily soluble in limonene. As it is combustible, limonene has also been considered as a biofuel.
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 is a colourless liquid hydrocarbon classified as a cyclic terpene possessing 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-li 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., bitter alkaloids, as a flavoring; it is also used as botanical 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. 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. As it is combustible, limonene has also been considered as a biofuel. Limonene can be used to dissolve polystyrene, and is a more ecologically friendly substitute for acetone. Safety 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.
Limonene is a chemical found in the peels of citrus fruits and in other plants. It is used to make medicine.
Limonene is used for obesity, cancer, and bronchitis, but there is no good scientific evidence to support these uses.
In foods, beverages, and chewing gum, limonene is used as a flavoring.
In pharmaceuticals, limonene is added to help medicinal ointments and creams penetrate the skin.
In manufacturing, limonene is used as a fragrance, cleaner (solvent), and as an ingredient in household cleaning products, cosmetics, and personal hygiene products.
Limonene
Limonene is one of the most abundant terpenes in cannabis, and it may be found in concentrations as high as 16% of the essential oil fraction. Ubiquitous in citrus rind, limonene is a monoterpene commonly used in perfumes, household cleaners, food, and medicines. Limonene has numerous medicinal benefits demonstrated in human and animal studies. Limonene is among a number of plant essential oils that have been identified as having antioxidant and anticancer properties. Limonene has therefore been suggested as an excellent dietary source for cancer prevention (Aggarwal and Shishodia, 2006)
Orange oil is an essential oil produced by cells within the rind of an orange fruit (Citrus sinensis fruit). In contrast to most essential oils, it is extracted as a by-product of orange juice production by centrifugation, producing a cold-pressed oil. It is composed of mostly (greater than 90%) d-limonene, and is often used in place of pure d-limonene. D-limonene can be extracted from the oil by distillation.
Composition
The compounds inside an orange oil vary with each different oil extraction. Composition varies as a result of regional and seasonal changes as well as the method used for extraction. Several hundred compounds have been identified with gas chromatograph-mass spectrometry. Most of the substances in the oil belong to the terpene group with limonene being the dominant one. Long chain aliphatic hydrocarbon alcohols and aldehydes like 1-octanol and octanal are second important group of substances.
Orange oil is used as a cleaner. It is also used as an additive to certain wax finish/polish such as Howard's Feed-N-Wax Wood Polish & Conditioner.
Biological pest control
Orange oil can be used in green pesticides for biological pest control. It can kill ants, and by erasing their scent-pheromone trail indicators disrupts re-infestation.[8]
Orange oil is also known to be useful to control, but not exterminate Drywood termites (Incisitermes.), killing only those who come into direct contact with it.[9]
Aromatherapy material for humans
In the practice of aromatherapy, orange oil is described as providing various benefits, including the possibility of "reducing stress", controlling "anxiety", enabling "relaxation" and "lifting mood". Aromatherapy is a pseudoscience, and much of the purported evidence cited for these claims comes from research which is not double-blinded or controlled.
Hazards
The limonene which is the main component of the oil is a mild irritant, as it dissolves protective skin oils. Limonene and its oxidation products are skin 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.
Limonene is also flammable.
Use: Dipentene is a terpene liquid found in various volatile oils such as cardamon, mace, nutmeg , turpentine oil. Dipentene is mainly composed of limonene, beta phellandrene, myrcene and other terpenes. Dipentene is used as a solvent for resins, alkyds and waxes and to make paints, enamels, lacquers and polishes. Dipentine is used as a perfumery composition for soaps, personal care products and cosmetics. It is used as an intermediate for terpene resins, carvone, terylene, and rubber chemicals. It is used as an oils dispersant, metal dryer. It is used as a substitute for chlorinated solvents in degreasing metals for cleaning in the electronic industry and the printing industry while it can also be used as starting material for the synthesis of terpene resin. alpha-Limonene has been used as a gallstone solubilizer in pharmaceutical industry.
Limonene, (+)- is an oral dietary supplement containing a natural cyclic monoterpene and major component of the oil extracted from citrus peels with potential chemopreventive and antitumor activities. Although the mechanism of action has yet to be fully elucidated, limonene and its metabolites perillic acid, dihydroperillic acid, uroterpenol and limonene 1,2-diol may inhibit tumor growth through inhibition of p21-dependent signaling and may induce apoptosis via the induction of the transforming growth factor beta-signaling pathway. In addition, they inhibit post-translational modification of signal transduction proteins, resulting in G1 cell cycle arrest as well as differential expression of cell cycle- and apoptosis-related genes.
Use: Limonene is found in citrus essential oil, the contents can be up to 90%. (-)-Limonene is naturally found in Pine needle oil, Turpentine, Cajeput oil and other essential oils. It appears liquid and has orange smell. It is make from Terpenes of orange oils by the method of fractionation.
(4R)-limonene is an optically active form of limonene having (4R)-configuration. It has a role as a plant metabolite. It is an enantiomer of a (4S)-limonene.
(4R)-1-Methyl-4-(1-methylethenyl) cyclohexene
(d)-Limonene
(R)-p-mentha-1,8-diene
(R)-p-mentha-1,8-diene; d-limonene
Translated names
(+)-limonén (sk)
(<I>R</I>)-p-menta-1,8-dien (hr)
(R)-1-metyl-4-(prop-1-én-2-yl)cyklohexén (sk)
(R)-p-menta-1,8-dieen (et)
(R)-p-menta-1,8-dieeni (fi)(R)-p-menta-1,8-dien (no)
(R)-p-menta-1,8-diena (ro)
(R)-p-menta-1,8-dienas (lt)
(R)-p-menta-1,8-diene (it)
(R)-p-menta-1,8-dieno (es)
(R)-p-menta-1,8-dién (hu)
(R)-p-mentadiēns-1,8 (lv)
(R)-p-mentha-1,8-dieen (nl)
(R)-p-mentha-1,8-dien (cs)
(R)-p-mentha-1,8-diène;d-limonène; (fr)
(R)-p-μενθα-1,8-διένιο (el)
(R)-p-мeнта-1,8-диен (bg)
d-limoneen (et)
d-limonen (cs)
d-limonene (pl)
d-limonitas (lt)
d-limonén (hu)
d-limonēns (lv)
d-лимонен (bg)
CAS names
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
IUPAC names
(+)-Limonene
(+)-Limonene; (+)-(4R)-Limonene; (+)-carvene ...
(+)-p-Mentha-1,8-dien
(4R)-(+)-1-methyl-4-prop-1-en-2-ylcyclohexene
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexene
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexene
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
(4R)-4-Isopropenyl-1-methylcyclohexene
(4R)-isopropenyl-1-methylcyclohexene
(R)-(+)-4-isopropenyl-1-methylcyclohexene
(R)-(+)-Limonen
(R)-(+)-para-mentha-1,8-diene
(R)-1-methyl-4-(1-methylethenyl)-cyclohexene
(R)-4-Isopropenyl-1-methyl-1-cyclohexene
(R)-4-Isopropenyl-1-methylcyclohexene
(R)-p-mentha-1,8-diene ; d-limonene
(S)-p-mentha-1,8-diene
1-methyl-4(prop-1-en-2-yl)-cyclonexene
1-Methyl-4-(1-methylethenyl)-cyclohexene
1-methyl-4-([1R]-methylethenyl)-cyclohexene
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
1-Methyl-4-prop-1-en-2-ylcyclohexene
1-méthyl-4-prop-1-èn-2-yl-cyclohexène
4-Isopropenyl-1-methylcyclohexene
4-isopropenyl-1-methylcyclohexene
4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
BITTER ORANGE E.O.
CYCLOHEXEN,1-METHYL-4-(1-METHYLETHENYL)-,(R)
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
Cyclohexene,1-methyl-4-(1-methylethenyl)-,(r)
D'-limonene
d-limonene (R)-p-mentha-1,8-diene
D-Limoneno
Limonene
LIMONENE, D-
ORANGE OILORANGE BRAZIL OILCITRUS TERPENES
R)-p-mentha-1,8-diene
R)-p-mentha-1,8-diene, D-Limonene
r-p-mentha-1,8-dien
Trade names
Aceite d-Limoneno de Naranja
Citrus Terpenes; Citrusterpene
CLEARON M105
CLEARON P105
CLEARON P125
Cold Pressed Peel Oil
D'Limonene
D-LIMONENE BRAZIL
LIMONENE-D
NANOLET R1050-CH
ORANGE TERPENES
Piccolyte C115
YS RESIN PX1150
(+)-(R)-4-isopropenyl-1-methylcyclohexene
(+)-limonene
(-)-limonene
(4R)-1-methyl-4-(1-methylethenyl)cyclohexene
(4S)-1-methyl-4-isopropenylcyclohex-1-ene
(D)-limonene
(R)-(+)-limonene
(R)-4-isopropenyl-1-methylcyclohexene
1-methyl-4-(1-methylethenyl)cyclohexene
4 Mentha 1,8 diene
4-mentha-1,8-diene
AISA 5203-L (+)limonene
cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
d Limonene; d-limonene; dipentene; limonene
limonene, (+)-
limonene, (+-)-
limonene, (+-)-isomer
limonene, (R)-isomer
limonene, (S)-isomer
D-Limonene
(+)-Limonene
5989-27-5
(R)-(+)-Limonene
(+)-(4R)-Limonene
(+)-carvene
(4R)-Limonene
D-(+)-Limonene
(R)-Limonene
(R)-p-Mentha-1,8-diene
Citrene
(+)-p-Mentha-1,8-diene
(R)-4-Isopropenyl-1-methyl-1-cyclohexene
D-Limonen
Carvene
Glidesafe
Glidsafe
Kautschiin
Refchole
(+)-R-Limonene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
d-p-Mentha-1,8-diene
(D)-Limonene
Limonene, D-
(+)-4-Isopropenyl-1-methylcyclohexene
(+)-Dipentene
(4R)-4-isopropenyl-1-methylcyclohexene
(R)-(+)-p-Mentha-1,8-diene
Biogenic SE 374
(+)-alpha-Limonene
d-Limonene (natural)
d-Limoneno [Spanish]
Limonene, (+)-
(R)-1-Methyl-4-(1-methylethenyl)cyclohexene
(+)-(R)-Limonene
Hemo-sol
(4R)-(+)-Limonene
UNII-GFD7C86Q1W
MFCD00062991
CCRIS 671
r-(+)-limonene
FEMA No. 2633
EC 7
HSDB 4186
D-1,8-p-Menthadiene
NCI-C55572
EINECS 227-813-5
p-Mentha-1,8-diene, (R)-(+)-
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
4betaH-p-mentha-1,8-diene
(+)-1,8-para-Menthadiene
AI3-15191
CHEBI:15382
1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-
(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
(+) Limonene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
(4R)-1-methyl-4-isopropenylcyclohex-1-ene
(R)-(+)-4-Isopropenyl-1-methylcyclohexene
(4R)-1-methyl-4-(1-methylethenyl)cyclohexene
(+)-Limonene, stabilized with 0.03% tocopherol
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-
(+)-Limonene, 96%, unstabilized
d-Limoneno
D-limonene [JAN]
(4R)-4-isopropenyl-1-methyl-cyclohexene
Citrus stripper oil
Terpenes and Terpenoids, limonene fraction
Sulfate turpentine, distilled
Dextro-limonene
d limonene
citre ne
65996-98-7
EINECS 266-034-5
D-(+)-Limonen
limonene, (R)-isomer
D-Limonene Reagent Grade
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
(4R)-limonene derivatives
EC 227-813-5
CHEMBL449062
PARA-MENTHA-1,8-DIENE
DTXSID1020778
(R)-(+)-Limonene, 95%
(R)-(+)-Limonene, 97%
(R)-(+)-Limonene, >=93%
(R)-(+)-Limonene, analytical standard
SC-65387
CAS-5989-27-5
(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene
(4R)-1-methyl-4-(1-methylvinyl)cyclohex-1-ene
(R)-(+)-Limonene, primary pharmaceutical reference standard
UNII-9MC3I34447 component XMGQYMWWDOXHJM-JTQLQIEISA-N
(R)-(+)-Limonene, purum, >=96.0% (sum of enantiomers, GC)
(R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC)
d-Limonene;D-LIMONENE;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-;D-Limonene
D-limonene
(+)-(R)-Limonene
(+)-Limonene
(4R)-4-isopropenyl-1-methylcyclohexene
(R)-4-isopropenyl-1-methyl-1-cyclohexene
(R)-(+)-limonene
4βH-p-mentha-1,8-diene
D-(+)-limonene
(4R)-1-methyl-4-isopropenylcyclohex-1-ene
(R)-1-methyl-4-(1-methylethenyl)cyclohexene
(4R)-limonene
(+)-(4R)-Limonene
D-Limonen
(+)-4-isopropenyl-1-methylcyclohexene
(R)-p-mentha-1,8-diene
(R)-(+)-p-mentha-1,8-diene
(±)-Limonene
(±)-(RS)-limonene
(±)-Limonene
(±)-Limonene
1,8-p-Mentadiene
138-86-3 [RN]
1-methyl-4-(prop-1-en-2-yl)cyclohexene
1-Methyl-4-methylethenylcyclohexene
229-977-3 [EINECS]
231-732-0 [EINECS]
4-(1-methylethenyl)-1-methyl-cyclohexene
4-Isopropenyl-1-methylcyclohexen [German] [ACD/IUPAC Name]
4-Isopropenyl-1-methylcyclohexene [ACD/IUPAC Name]
4-Isopropényl-1-méthylcyclohexène [French] [ACD/IUPAC Name]
6876-12-6 [RN]
7705-14-8 [RN]
a-limonene
Cyclohexene, 1-methyl-4-(1-methylethenyl)- [ACD/Index Name]
Cyclohexene, 4-Isopropenyl-1-methyl-
Dipentene [Wiki]
DL-p-mentha-1,8-diene
LIMONENE, (-)-
Limonene, (±)-
limonene, (±)-isomer
Limonene, dl-
Mentha-1,8-diene
Mentha-1,8-diene, DL
Methyl-4-(1-methylethenyl)cyclohexene
Methyl-4-isopropenyl-1-cyclohexene
Methyl-4-isopropenylcyclohexene
MFCD00062992 [MDL number]
p-mentha-1,8-diene
p-Mentha-1,8-diene, (±)-
p-Mentha-1,8-diene, (±)-
p-Mentha-1,8-diene, (±)-
p-Mentha-1,8-diene, DL-
α-Limonene
(±)-Dipentene
(¤)-LIMONENE
(±)-1-methyl-4-(1-methylvinyl)cyclohexene
(±)-Dipentene
(±)-Limonene
(±)-α-Limonene
(1)-1-Methyl-4-(1-methylvinyl)cyclohexene
(plusmn)-limonene
(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
1,8(9)-p-Menthadiene
1,8-p-menthadiene
1-methyl-4-(1-methylethenyl)-cyclohexene
1-Methyl-4-(1-methylethenyl)cyclohexene
1-Methyl-4-(1-methylethyl)cyclohexene
1-methyl-4-(1-methylvinyl)cyclohex-1-ene
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
1-Methyl-4-isopropenyl-1-cyclohexene
1-methyl-4-isopropenylcyclohex-1-ene
1-METHYL-4-ISOPROPENYLCYCLOHEXENE
1-methyl-4-prop-1-en-2-ylcyclohexene
1-Methyl-4-prop-1-en-2-yl-cyclohexene
1-Methyl-p-isopropenyl-1-cyclohexene
4-Isopropenyl-1-methyl-1-cyclohexene
4-mentha-1,8-diene
8008-57-9 [RN]
Achilles dipentene
Acintene DP
Biogenic SE 374
Cajeputen
Cajeputene
Carvene
Ciene
citrene
Cyclil decene
Cyclohexene, 1-methyl-4- (1-methylethenyl)-, (±)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (±)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (±)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, homopo
Cyclohexene, 1-methyl-4-(1-methylethynyl)
Cyclohexene,1-methyl-4-(1-methylethenyl)-
Dipanol
Dipenten
DIPENTENE (±)
Dipentene 200
DIPENTENE 38 PF
Di-p-mentha-1,8-diene
DL-4-Isopropenyl-1-methylcyclohexene
dl-Limonene
EC 7
ESSENCE DE PIN PF
Eulimen
Flavor orange
Glidesafe
Glidsafe
Goldflush II
Hemo-sol
Hesperidine
INACTIVE LIMONENE
Kautschiin
Kautschin
menthadiene
MFCD00001558 [MDL number]
NESOL
p-Mentha-1,8(9)-diene
Refchole
Terpodiene
trans-1-methyl-4-(1-methylvinyl)cyclohexene
Unitene
α-limonene
β-Limonene
δ-1,8-Terpodiene
δ-1,8-Terpodiene
(+/-)-Limonene
(D) 4-Isopropenyl-1-methyl-1-cyclohexene
-Methyl-4-isopropenyl-1-cyclohexene
1-methyl-4-(1-methylethenyl)-cyclohexene
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
1-methyl-4-(prop-1-en-2-yl)cyclohexene
1-methyl-4-isopentyl-1-cyclohexene
1-METHYL-4-ISOPROPENYL-1-CYCLOHEXENE(MAIN COMPONENT)
1-methyl-4-prop-1-en-2-ylcyclohexene
4-Isopropenyl-1-methylcyclohexene
CYCLOHEXANE, 1-METHYL-4-(1-METHYLETHENYL)-, (R)
dipentene limonene
dipentene, crude
dipentene, limonene
dipentenelimonene
Limonene (AKA 1-methyl-4-(1-methylethyenyl)-cyclohexane)
D-LIMONENE CAS No: 5989-27-5
D-limonene synonyms: D-Limonene; Portakal kabuğu yağı; Narenciye kabuğu yağı; Sitrin; p-menta-1,8-dien ( bilimsel isim ); D-Limonene; 1-Methyl-4-(1-methylethenyl)cyclohexene; 4-Isopropenyl-1-methylcyclohexene; p-Menth-1,8-diene; Racemic: DL-Limonene; Dipentene; (+)-Limonene; 5989-27-5; (R)-(+)-Limonene; (+)-carvene; (+)-(4R)-Limonene; (4R)-Limonene; D-(+)-Limonene; (R)-Limonene; (R)-p-Mentha-1,8-diene; Citrene; sitren; (+)-p-Mentha-1,8-diene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; D-Limonen; karvin; karven; siklohekzen; sikloheksen; siklohegsen; Carvene; Glidesafe; Glidsafe; Kautschiin; Refchole; (+)-R-Limonene; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-d-p-Mentha-1,8-diene; (D)-Limonene; Limonene, D-(+)-4-Isopropenyl-1-methylcyclohexene (+)-Dipenten; (4R)-4-isopropenyl-1-methylcyclohexene; (R)-(+)-p-Mentha-1,8-diene; Biogenic SE 374; biyojenik; biyojen; (+)-alpha-Limonene; alfa-limonen; d-Limonene (natural); d-Limoneno [Spanish]; D-limonen (doğal); Limonene, (+)-(R)-1-Methyl-4-(1-methylethenyl)cyclohexene; (+)-(R)-Limonene; Hemo-sol; hemosol; (4R)-(+)-LimoneneUNII-GFD7C86Q1W; MFCD00062991, CCRIS 671; r-(+)-limonene; R-limonen; R-limonene; FEMA No. 2633; EC 7; HSDB 4186; D-1,8-p-Menthadiene; NCI-C55572; EINECS 227-813-5; p-Mentha-1,8-diene, (R)-(+)-; GFD7C86Q1W; (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; 4betaH-p-mentha-1,8-diene; (+)-1,8-para-Menthadiene; metadien; metadiyen; AI3-15191; CHEBI:15382; 1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-; (R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; (+) Limonene; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-; (4R)-1-methyl-4-isopropenylcyclohex-1-ene; (R)-(+)-4-Isopropenyl-1-methylcyclohexene; metilsikloheksen; metilsiklohegzen; metilsiklohekzen; (4R)-1-methyl-4-(1-methylethenyl)cyclohexene; (+)-Limonene, stabilized with 0.03% tocopherol; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-; (+)-Limonene, 96%, unstabilized; d-Limoneno; D-limonene [JAN]; (4R)-4-isopropenyl-1-methyl-cyclohexene; Citrus stripper oil; Terpenes and Terpenoids, limonene fraction; Sulfate turpentine, distilled; distile sülfat terpentin; Dextro-limonene; dekstro-limonen; dextro-limonen; d limonene; citre ne; 65996-98-7; EINECS 266-034-5; D-(+)-Limonen; limonene, (R)-isomer; D-Limonene Reagent Grade; DSSTox_CID_778; (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene; EC 227-813-5; DSSTox_RID_75785; DSSTox_GSID_20778; CHEMBL449062; PARA-MENTHA-1,8-DIENE; DTXSID1020778; (R)-(+)-Limonene, 95%; (R)-(+)-Limonene, 97%; ZINC967513; CS-M3273; KS-000001WP; (R)-(+)-Limonene, >=93%; Tox21_200400; 6458AE; SBB055254; AKOS015899935; CCG-266134; DB08921; LMPR0102090013; LS-1427; NE11118; (R)-(+)-Limonene, analytical standard; NCGC00248591-01; NCGC00257954-01; SC-65387; CAS-5989-27-5; L0047; L0105; C06099; (4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene; (4R)-1-methyl-4-(1-methylvinyl)cyclohex-1-ene; J-502148; W-105295; Q27888324; (R)-(+)-Limonene, primary pharmaceutical reference standard; UNII-9MC3I34447 component XMGQYMWWDOXHJM-JTQLQIEISA-N; (R)-(+)-Limonene, purum, >=96.0% (sum of enantiomers, GC); (R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC); d-Limonene;D-LIMONENE;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-;D-Limonen.
Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels.[1] The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.[1][2] It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products.[1] The less common L-isomer is found in mint oils and has a piny, turpentine-like odor.[1] The compound is one of the main volatile monoterpenes found in the resin of conifers, particularly in the Pinaceae, and of orange oil.
Chemical formula C10H16
Molar mass 136.238 g·mol-1
Appearance colorless to pale-yellow 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)
Solubility in water Insoluble
Solubility Miscible with benzene, chloroform, ether, CS2, and oils
soluble in CCl4
Chiral rotation ([α]D) 87-102°
Refractive index (nD) 1.4727
Limonene takes its name from French limon ("lemon"). 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. Racemic limonene is known as dipentene. D-Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
Alternate Names:(+)-Dipentene; (R)-(+)-Limonene
Application:D-Limonene is which activates UGT and hepatic GST
CAS Number:5989-27-5
Purity:≥96%
Molecular Weight:136.23
Molecular Formula:C10H16
Supplemental Information:This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
Chemical reactions
Limonene is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.[5] It oxidizes easily in moist air to produce carveol, carvone, and limonene oxide. With sulfur, it undergoes dehydrogenation to p-cymene.
Limonene occurs commonly as the D- or (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.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.
Biosynthesis
In nature, limonene 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.
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 a base, and the hydroxylamine is removed to give the ketone-containing carvone.
In plants
D-Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees: red and silver maple (Acer rubrum, Acer saccharinum), cottonwoods (Populus angustifolia), aspens (Populus grandidentata, Populus tremuloides) sumac (Rhus glabra), spruce (Picea spp.), various pines (e.g., Pinus echinata, Pinus ponderosa), Douglas fir (Pseudotsuga menziesii), larches (Larix spp.), true firs (Abies spp.), hemlocks (Tsuga spp.), cannabis (Cannabis sativa spp.),[9] cedars (Cedrus spp.), various Cupressaceae, and juniper bush (Juniperus spp.). It contributes to the characteristic odor of orange peel, orange juice and other citrus fruits. To optimize recovery of valued components from citrus peel waste, d-limonene is typically removed.
Safety and research
D-Limonene applied to skin may cause irritation from contact dermatitis, but otherwise appears to be safe for human uses. Limonene is flammable as a liquid or vapor and it is toxic to aquatic life.
Uses
Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products. As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. D-Limonene is also used as a botanical insecticide. D-Limonene is used in the organic herbicide "Avenger". It 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, L-limonene has a piny, turpentine-like odor.
Limonene 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). It is used as a paint stripper and is also useful as a fragrant alternative to turpentine. Limonene 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 are used by philatelists to remove self-adhesive postage stamps from envelope paper.
Limonene 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 HIPS, a polystyrene plastic that is easily soluble in limonene. As it is combustible, limonene has also been considered as a biofuel.
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.
D-limonene is a compound sourced from the peel of citrus fruits, including include oranges, mandarins, limes, and grapefruit. It takes its name from the lemon and is often used as a flavoring agent in foods. D-limonene differs from a less common type of limonene known as L-limonene, which is found in mint oil.
Sold as a dietary supplement, D-limonene is said to offer a variety of health benefits, in part because of its ability to dissolve fats, including cholesterol. Proponents believe that D-limonene can not only aid in weight loss but treat or prevent certain diseases, including cancer.
Health Benefits
Alternative practitioners have long touted the benefits of D-limonene, claiming that it not only burns fat but reduces inflammation and kills disease-causing germs. Many of these beliefs are culled from its use in industry, where D-limonene is commonly used to make hand sanitizers, perfumes, botanical pesticides, and chemical solvents.
Among some of the conditions that D-limonene is believed to prevent or treat are:
Bronchitis
Cancer
Diabetes
Gallstones
Gastroesophageal reflux disease (GERD)
Heartburn
High cholesterol
Inflammatory bowel disease (IBD)
Metabolic syndrome
Obesity
Peptic ulcers
Citrus essential oils rich in D-limonene are also used in aromatherapy to relieve stress.
To date, there is little solid evidence that D-limonene can treat any medical condition. With that said, a number of preliminary studies have hinted at benefits that may warrant further investigation.
Weight Loss
There is some evidence that D-limonene can promote weight loss by lowering blood sugar and lipids associated with metabolic syndrome. A 2013 study in the European Journal of Pharmacology reported that obese mice fed a high-diet diet supplemented with D-limonene experienced decreases in blood glucose, total cholesterol, and "bad" LDL cholesterol as well as increases in "good" HDL cholesterol.
These findings suggest that D-limonene may be useful in preventing or treating metabolic syndrome, although it is unclear what dose would be needed to achieve such benefit in humans. Further research is needed.
Peptic Ulcers
D-limonene may help reduce the risk of peptic ulcers and other inflammatory gastrointestinal diseases, suggests a 2009 study published in the Chemico-Biological Interactions. According to the researchers, high concentrations of D-limonene in the essential oil of bitter orange (C. aurantium) served to protect the lining of the stomach of lab rats fed high-doses of alcohol and nonsteroidal anti-inflammatory drugs (NSAIDs).
Contrary to popular belief, it did so not by suppressing stomach acid but by increasing the production of gastric mucus.
Despite the positive findings, it is unclear if D-limonene did so on its own or if some other component in the essential oil contributed. Further research is needed.
Cancer
Alternative practitioners have long touted the anticancer properties of D-limonene. The effect of is attributed to a substance known as perillic acid, which is released into the bloodstream when D-limonene is broken down by the body.
A number of test-tube studies have reported that D-limonene applied to cancer cells can trigger apoptosis (programmed cell death). This is considered significant given that apoptosis-a naturally occurring event that allows old cells to be replaced by new cells-does not occur with cancer cells. This effect was seen in recent studies involving colon cancer,1 skin cancer,2 and other common malignancies.
It remains unclear whether taking D-limonene by mouth might render the same benefit. A 2013 study in Cancer Prevention Research aimed to evaluate this effect by providing 43 women with breast cancer with 2 grams of D-limonene daily for two to six weeks.
At the end of the study period, a biopsy of breast tissue showed high concentrations of D-limonene but little of the perillic acid needed to arrest cancer growth. Further research is needed to determine whether higher doses or longer treatment may help improve these results.
Can Green Tea Prevent Colon Cancer?
Possible Side Effects
Widely used as a food flavoring, D-limonene is generally considered safe and has been used for up to a year in clinical research without incidence. Common side effects include stomach upset and reflux.
At excessively high doses, D-limonene has been known to hematuria (blood in urine).3
D-limonene may cause irritation if applied to the skin. This includes citrus essential oils that are characteristically high in D-limonene. To reduce irritation, always mix essential oils with a carrier oil (such as avocado oil or sweet almond oil) if you intend to use it for massage purposes.
The safety of D-limonene has not been established in children, pregnant women, or nursing mother. As a precaution, always speak with your doctor before using D-limonene or any other supplement if you are pregnant or breastfeeding. As the benefits of D-limonene in children is unknown, it is best to play it safe and avoid the supplement altogether.
Interactions
D-limonene is broken down by many of the same liver enzymes-called cytochrome P450 (CYP450)-that other drugs use for metabolization. Because of this, D-limonene may increase or decrease the concentration of certain drugs as they compete for the same enzyme.
Possible drug-drug interactions include:
Anticoagulants like Coumadin (warfarin)
Anticonvulsants like Tegretol (carbamazepine)
Antifungal drugs like Nizoral (ketoconazole)
Anti-hypertensive medications like Cozaar (losartan)
Antipsychotic drugs like Orap (pimozide)
Atypical antidepressants like nefazodone
Benzodiazepine tranquilizers like Halcion (triazolam)
H2 blockers like Tagamet (cimetidine)
Macrolide antibiotics like clarithromycin and telithromycin
Nonsteroid anti-inflammatory drugs (NSAIDs) like Advil (ibuprofen) and Voltaren (diclofenac)
Proton pump inhibitors like Prilosec (omeprazole)
Many of these interactions can be mitigated by separating the doses by two to four hours. Others may require a dose adjustment or substitution.
To avoid interactions, always advise your doctor about any medications you are taking, whether they are prescription, over-the-counter, nutritional, herbal, or recreational.
Dosage and Preparations
D-limonene supplements are most often sold in soft gel capsules and are easily sourced online or in stores specializing in dietary supplements.
While there are no guidelines for the appropriate use of D-limonene, most manufacturers recommend a dose of between 500 milligrams (mg) and 1,000 mg per day, taken with or without food.
As a rule of thumb, never exceed the dose on the product label. There is no evidence that higher doses confer to improved health benefits.
Most D-limonene soft gels can be stored safely at room temperature. You can also keep them in the refrigerator if there is a risk of heat exposure. Never use a supplement past its expiration date, and dispose of any soft gels that are either leaking, discolored, or misshapen.
