D-LIMONENE

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.[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.

m UICPA    1-méthyl-4-prop-1-èn-2-yl-cyclohexène
No CAS    5989-27-5 (R)
5989-54-8 (S)(–)
138-86-3 (RS)
No ECHA    100.028.848
No CE    227-813-5 (R)
227-815-6 (–)
PubChem    440917 [archive]
FEMA    2633
Apparence    liquide incolore, d'odeur caractéristique (d-limonene)
D-LIMONENE
CAS number: 5989-27-5 - Limonene

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.

D-Limonene is harsh terpene citrusy fruity orange berry tarty fresh light sweet strong peel oil commercial grade d-limonene may redistilled citrus terpenes will then carry orange-likeodor highly purified limon-ene.

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.), 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.

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The odour and uses of D-Limonene
Odour=> harsh terpene citrusy fruity orange berry tarty Fresh light and sweet citrusy odor with strong resemblance to Orange peel oil Commercial grade d-Limonene may be redistilled 'Citrus Terpenes' and will then carry more Orange-likeodor than a highly purified Limon-ene
Perfume-Uses=> Eau-de-colognes fresh-topnotes Citrus, Orange, Household-perfumes, Add-lift, Floral-types, Jasmin, Lavender, Pine, Woody-blends, As-Modifier, Lime, Grapefruit,
Orange, Corn, Spice, Chewing-gum,
Blends-well-with=> Citrus-notes, Gums,

Synonyms
d-Limonene : d-1-Methyl-4-isopropenyl-1-cyclohexene : d-p-Mentha-1,8(9)-diene : Limonene d pure 1-Methyl para iso propenyl-1-cyclohexene : d para Mentha-1,8-diene : d Limonene : Kautschin : Hesperidene : Citrene : Carvene : Cajeputene : PerfumersWorld
Contains=> *D-LIMONENE@100% :

Limonene, (+/-)- is a racemic mixture of limonene, a natural cyclic monoterpene and major component of the oil extracted from citrus rind with chemo-preventive and antitumor activities. 
The metabolites of DL-limonene, perillic acid, dihydroperillic acid, uroterpenol and limonene 1,2-diol are suggested to inhibit tumor growth through inhibition of p21-dependent signaling,
 induce apoptosis via the induction of the transforming growth factor beta-signaling pathway, inhibit post-translational modification of signal transduction proteins, result in G1 cell 
cycle arrest as well as cause differential expression of cell cycle- and apoptosis-related genes.

NCI Thesaurus (NCIt)
Polylimonene, also known as dipentene or cajeputene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Polylimonene exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, polylimonene is primarily located in the membrane (predicted from logP) and cytoplasm. Polylimonene participates in a number of enzymatic reactions. In particular, polylimonene can be biosynthesized from p-menthane. Polylimonene can also be converted into limonene monoterpenoid and limonene-1, 2-diol. Polylimonene is a camphor, citrus, and herbal tasting compound that can be found in a number of food items such as dill, winter savory, summer savory, and cumin. This makes polylimonene a potential biomarker for the consumption of these food products.

Human Metabolome Database (HMDB)
Limonene is a monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively. It has a role as a human metabolite. It is a monoterpene and a cycloalkene. It derives from a hydride of a p-menthane.

D-Limonene

(+)-Limonene

5989-27-5

(R)-(+)-Limonene

(+)-carvene

(+)-(4R)-Limonene

(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

r-(+)-limonene

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

PARA-MENTHA-1,8-DIENE

DTXSID1020778

(R)-(+)-Limonene, 95%

(R)-(+)-Limonene, 97%

(R)-(+)-Limonene, >=93%

Tox21_200400

(R)-(+)-Limonene, analytical standard

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

(+)-(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