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DL-Limonene Structure
  • CAS No.138-86-3
  • Chemical Name:DL-Limonene
  • CBNumber:CB2178358
  • Molecular Formula:C10H16
  • Formula Weight:136.23
  • MOL File:138-86-3.mol
DL-Limonene Property
  • Melting point: :-84--104 °C
  • Boiling point: :170-180 °C (lit.)
  • Density  :0.86 g/mL at 20 °C (lit.)
  • vapor density  :4.7 (vs air)
  • vapor pressure  :<3 mm Hg ( 14.4 °C)
  • refractive index  :n20/D 1.473(lit.)
  • Flash point: :119 °F
  • storage temp.  :Store below +30°C.
  • form  :Liquid
  • color  :Clear colorless to pale yellow
  • Odor :Pleasant, pine-like; lemon-like.
  • explosive limit :0.7-6.1%, 150°F
  • Odor Threshold :0.038ppm
  • Water Solubility  :<1 g/100mL
  • Merck  :14,5493
  • BRN  :3587825
  • Stability: :Stable. Flammable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference :138-86-3(CAS DataBase Reference)
  • Indirect Additives used in Food Contact Substances :DIPENTENE
  • FDA 21 CFR :182.60
  • EWG's Food Scores :1-2
  • NCI Drug Dictionary :limonene, (+)-
  • NIST Chemistry Reference :Limonene(138-86-3)
  • EPA Substance Registry System :Limonene (138-86-3)
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H334-H226-H315-H317-H410-H400
  • Precautionary statements P210-P233-P240-P241+P242+P243-P261-P264-P272-P284-P302+P352+P333+P313+P363-P304+P340+P342+P311-P370+P378-P391-P403+P235-P280a-P303+P361+P353-P501a-P273-P280-P501
DL-Limonene Price More Price(27)
  • Brand: Sigma-Aldrich
  • Product number: 62122
  • Product name : (R)-(+)-Limonene
  • Purity: technical, ~90% (sum of enantiomers, GC)
  • Packaging: 250 mL
  • Price: $32
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 334111
  • Product name : Dipentene
  • Purity: technical, for use as solvent (for the paint industry), mixture of various terpenes
  • Packaging: 1l
  • Price: $33.4
  • Updated: 2020/08/18
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 62118
  • Product name : (R)-(+)-Limonene
  • Purity: analytical standard
  • Packaging: 1 mL
  • Price: $41.7
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 8.18407
  • Product name : (R)-(+)-Limonene
  • Purity: for synthesis
  • Packaging: 100 mL
  • Price: $27.19
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 183164
  • Product name : (R)-(+)-Limonene
  • Purity: 97%
  • Packaging: 5 mL
  • Price: $42.8
  • Updated: 2021/03/22
  • Buy: Buy

DL-Limonene Chemical Properties,Usage,Production

  • Description D-limonene, which is a volatile oil, constitutes approximately 98% of orange peel oil by weight and has moderately good knockdown activity against ectoparasites of companion animals. The insecticidal activity of both d-limonene and linalool is enhanced when synergized by piperonyl butoxide. Apart from toxicoses reported in cats (65), d-limonene generally has a high margin of safety.
  • Chemical Properties colourless or light yellow liquid
  • Chemical Properties Limonene (4R)-(+)-limonene and (4S)-(?)-limonene as well as the racemate (dipentene) occur abundantly in many essential oils.The(+) isomer is present in citrus peel oils at a concentration of over 90%; a low concentration of the (?) isomer is found in oils from the Mentha species and conifers.
    Limonene is a liquid with lemon-like odor. It is a reactive compound; oxidation often yields more than one product. Dehydrogenation leads to p-cymene. Limonene can be converted into cyclic terpene alcohols by hydrohalogenation, followed by hydrolysis. Nitrosyl chloride adds selectively to the endocyclic double bond; this reaction is utilized in the manufacture of (?)-carvone from (+)- limonene.
    (+)-Limonene is obtained in large amounts as a by-product in the production of orange juice; (?)-limonene is isolated in relatively small quantities from essential oils. Racemic limonenes, which are commercially available under the name dipentene, are formed as by-products in many acid-catalyzed isomerizations of α- and β-pinene. Distillation of the so-called dipentene fraction yields limonenes in varying degrees of purity.
    The limonenes are used as fragrance materials for perfuming household products and as components of artificial essential oils.
  • Chemical Properties d-, l- or dl-Limonene has a pleasant, lemon-like odor free from camphoraceous and turpentine-like notes. Limonene 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).
  • Occurrence It has been reported found in more than 300 essential oils in amounts ranging from 90 to 95% (lemon, orange, mandarin) to as low as 1% (palmarosa); the most widespread form is the d-limonene, followed by the racemic form and then l-limo nene. Also reported found in ginger, nutmeg, pepper, mace, hop oil, coriander seed, calamus, dill herb, caraway seed and rosemary.
  • Uses d-limonene is used for perfuming and to mask odor. It is a chemical constituent of citrus oil.
  • Uses d-Limonene is a flavoring agent that is a liquid, colorless with a pleasant odor resembling mild citrus. It is miscible in alcohol, most fixed oils, and mineral oil; soluble in glycerin; and insoluble in water and propylene glycol. It is obtained from citrus oil. It is also termed d-p-mentha-1,8,diene and cinene.
  • Uses Limonene is an antioxidant and flavoring agent that occurs in lemons, oranges, and pineapple juice, being obtained from the oils. It is a colorless liquid which is insoluble in water and propylene glycol, very slightly soluble in glycerin, and miscible with alcohol, most fixed oils, and mineral oil. It prevents or delays enzymatic browning-type oxidation.
  • Definition ChEBI: 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.
  • Production Methods Limonene occurs in the oil of many plants and is the main constituent (≤86%) of the terpenoid fraction of fruit, flowers, leaves, bark, and pulp from shrubs, annuals, or trees including anise, mint, caraway, polystachya, pine, lime, and orange oil. It occurs as a by-product in the manufacture of terpineol and in various synthetic products made from α-pinene or turpentine oil. It is found in the gas phase of tobacco smoke and has been detected in urban atmospheres.
  • Preparation d-Limonene 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.
  • Aroma threshold values Detection: 4 to 229 ppb
  • Taste threshold values Taste characteristics at 30 ppm: sweet, orange, citrus and terpy.
  • Synthesis Reference(s) Canadian Journal of Chemistry, 39, p. 1860, 1961 DOI: 10.1139/v61-249
    Tetrahedron Letters, 20, p. 3519, 1979 DOI: 10.1016/S0040-4039(01)95450-4
  • General Description A colorless liquid with an odor of lemon. Flash point 113°F. Density about 7.2 lb /gal and insoluble in water. Hence floats on water. Vapors heavier than air. Used as a solvent for rosin, waxes, rubber; as a dispersing agent for oils, resins, paints, lacquers, varnishes, and in floor waxes and furniture polishes.
  • Air & Water Reactions Flammable. Insoluble in water.
  • Reactivity Profile Cinene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.
  • Health Hazard Liquid irritates eyes; prolonged contact with skin causes irritation. Ingestion causes irritation of gastrointestinal tract.
  • Fire Hazard Behavior in Fire: Containers may explode.
  • Chemical Reactivity Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Contact allergens Dipentene corresponds to a racemic mixture of d-limonene and l-limonene. Dipentene can be prepared from wood turpentine or by synthesis. It is used as a solvent for waxes, rosin and gums, in printing inks, perfumes, rubber compounds, paints, enamels, and lacquers. An irritant and sensitizer, dipentene caused contact dermatitis mainly in painters, polishers, and varnishers
  • Contact allergens Limonene is a racemic form of dand l-limonene. d-Limonene is contained in Citrus species such as citrus, orange, mandarin, and bergamot. l-Limonene is contained in Pinus pinea. The racemic form (dand l-limonene) is also named dipentene.
  • Anticancer Research Tested as promising antitumor molecules in induced tumor on rat tissues, D-limonenewas tested in preclinical studies in patients with advanced cancer. Limonene inhibitsthe activity of HMG-CoA reductase, subsequently reducing the possibility of cancergrowth. The mechanism of action involves the inhibition of prenyltransferases withthe activation of glutathione-S transferase and uridine diphospho-glucuronosyltransferase.More interest was pointed on the principal metabolite:perillyl alcohol which is more potent than limonene. The interest on perillyl alcoholis based on the necessity of a very high dosage of D-limonene in preclinical studies(about 1000 mg/kg/day in human mammary tumor) that can cause notably importantside effects. The more active perillyl alcohol and the less low active doseshypothesized this molecule as a clinical candidate (Pattanayak et al. 2009; Chenet al. 2013; Fontes et al. 2013; Rani and Sharma 2013).
  • Safety Profile A skin irritant. Flammable when exposed to heat or flame; can react vigorously with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Carcinogenicity Induction of kidney neoplasias has been observed in male rats of strains that have significant concentrations of the protein a2u-globulin (158a). This protein is not expressed in females or species other than the rat; therefore, limonene carcinogenicity appears to be limited to the male of specific strains of this species. Subcutaneous injection of the compound or its hydroperoxide into C57BL/6 mice decreased the incidence of dibenzopyrene- induced tumors appreciably. Given orally either 15 min or 1 h prior to nitrosodiethylamine, D-limonene reduced forestomach tumor formation by about 60% and pulmonary adenoma formation by about 35%. Reduction of cancer incidence and metastasis by limonene has also been reported in other systems (158b).
  • Environmental Fate Limonene is insoluble and is stable in water. Substances like limonene that are monoterpenes are released in large amounts mainly to the atmosphere. The chemical and physical properties of limonene also indicate that limonene is distributed mainly to air. Based on the physical and chemical properties of limonene, when this substance is released to ground, it has low to very low mobility in soil. The soil adsorption coefficient (Koc), calculated on the basis of the solubility (13.8 mg l-1 at 25 ℃) and the log octanol/water partition coefficient (4.232), ranges from 1030 to 4780.3. Henry’s Law constant indicates that limonene rapidly volatilizes from both dry and moist soil; however, its strong adsorption to soil may slow this process. In the aquatic environment, limonene is expected to adsorb to sediment and suspended organic particles to rapidly volatilize to the atmosphere, based on its physical and chemical properties. The estimated half-life for volatilization of limonene from a model river (1 m deep, flow 1 ms-1, and wind speed 3 ms-1) is 3.4 h. The bioconcentration factor, calculated on the basis of water solubility and the log octanol/water partition coefficient, is 246–262, suggesting that limonene may accumulate in fish and other aquatic organisms.
  • Toxicity evaluation D-Limonene can cause a renal syndrome in male rats. Male rats have a background of spontaneous protein droplets in the proximal tubule, particularly within the cells of the P2 segment. D-Limonene can increase the formation of protein droplets, and experiments show that the only protein accumulating is α2u-globulin. α2u-Globulin is synthesized in the liver, then it is released into the general circulation and reabsorbed by renal proximal tubule cells. Synthesis of α2u-globulin occurs only in adult male rats and to understand the critical role of α2uglobulin in the renal effects of D-limonene the absence of histopathological changes can be studied in female rats, since they cannot produce α2u-globulin. It was concluded from these studies that D-limonene does not have a renal toxicity effect on species that do not synthesize α2u-globulin, for example, female rats, male and female mice, and dogs.
    To develop nephropathy, there is a prerequisite step in which an agent binds to α2u-globulin and in the case of D-limonene, this agent is 1,2-epoxide. Binding of this agent to α2u-globulin reduces the rate of degradation relative to that of native protein, thereby causing it to accumulate. Accumulation of α2u-globulin can be observed after a single oral dose of D-limonene and continued treatment results in additional histological changes in the kidney. Renal function can be observed by increasing the amount of α2u-globulin in urine. These functional changes occur only in male rats and only at doses that exacerbate protein droplet formation. In response to the cell death and functional changes, there is an increase in cell proliferation in the kidney. With continued treatment, cell proliferation persists but it does not restore renal function. Increasing cell proliferation is directly related to the development of renal tubular tumors and is dependent on the presence of α2u-globulin. α2u-Globulin nephropathy and renal cell proliferation occur at the same doses consistent with those that produce renal tubular tumors.
    α2u-Globulin is one type of superfamily proteins that bind and transport a variety of agents. Many of these proteins are synthesized in mammalian species, including humans. The protein that can be found in human urine is very different from that in rat urine. About 1% of the protein concentration in male rat urine can be found in human urine. Human urinary protein is predominantly a species of high molecular mass, and there is no protein in human plasma or urine identical to α2u-globulin and there is no protein-like α2u-globulin detected in human kidney tissue. Even though the binding of D-limonene- 1,2-epoxide to α2u-globulin can be shown in vitro, other superfamily proteins, especially those synthesized by humans, do not bind 1,2-epoxide.
    There is no verification that any human protein can contribute to a renal syndrome similar to α2u-globulin nephropathy, and consequently no evidence can be found that D-limonene is carcinogenic in humans by a mechanism similar to α2u-globulin nephropathy. The initiation of renal cell tumors in male rats by binding to agents that act through an α2u-globulin-associated response is not projected as a carcinogenic hazard to humans. This can be concluded based on an extensive evidence that the presence of α2u-globulin is an absolute requirement for the carcinogenic activity. Therefore, D-limonene has no carcinogenic activity in human since neither α2u-globulin nor any protein that can function like α2uglobulin is synthesized by humans.
DL-Limonene Preparation Products And Raw materials
Raw materials
Preparation Products
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