ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Acyclic hydrocarbons > DL-Limonene
DL-Limonene Chemical Properties
- Melting point:-84--104 °C
- Boiling point:176-177 °C(lit.)
- Density 0.844 g/mL at 25 °C(lit.)
- vapor density 4.7 (vs air)
- vapor pressure <3 mm Hg ( 14.4 °C)
- refractive index n
- Flash point:119 °F
- storage temp. 2-8°C
- form Liquid
- color Clear colorless to pale yellow
- OdorPleasant, pine-like; lemon-like.
- Odor Threshold0.038ppm
- explosive limit0.7-6.1%, 150°F
- Water Solubility <1 g/100mL
- Merck 14,5493
- BRN 3587825
- Stability:Stable. Flammable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference138-86-3(CAS DataBase Reference)
- NIST Chemistry ReferenceLimonene(138-86-3)
- EPA Substance Registry SystemLimonene (138-86-3)
- Hazard Codes Xi,N
- Risk Statements 10-38-43-50/53
- Safety Statements 24-37-60-61
- RIDADR UN 2052 3/PG 3
- WGK Germany 2
- RTECS OS8350000
- F 8-10-23
- Autoignition Temperature458 °F
- TSCA Yes
- HazardClass 3
- PackingGroup III
- HS Code 29021990
- Hazardous Substances Data138-86-3(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 5300 mg/kg
DL-Limonene Usage And Synthesis
- DescriptionD-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 Propertiescolourless 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 Propertiesd-, 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).
- OccurrenceIt 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.
- Usesd-limonene is used for perfuming and to mask odor. It is a chemical constituent of citrus oil.
- Usesd-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.
- UsesLimonene 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.
- DefinitionChEBI: 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 MethodsLimonene 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.
- Preparationd-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 valuesDetection: 4 to 229 ppb
- Taste threshold valuesTaste 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 DescriptionA 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 ReactionsFlammable. Insoluble in water.
- Reactivity ProfileCinene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.
- Health HazardLiquid irritates eyes; prolonged contact with skin causes irritation. Ingestion causes irritation of gastrointestinal tract.
- Fire HazardBehavior in Fire: Containers may explode.
- Chemical ReactivityReactivity 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 allergensDipentene 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 allergensLimonene 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 ResearchTested 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 ProfileA 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.
- CarcinogenicityInduction 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).
DL-Limonene Preparation Products And Raw materials
- Terpenes and Terpenoids, turpentine-oil, limonene fraction, sulfurized, reaction products with hydrogen tetrachloroaurate(-1) ,Terpenes and Terpenoids, turpentine-oil, limonene fraction, sulfurized, reaction products with hydrogen tetrachloroaurate(-1) (-)-PERILLYL ALCOHOL RARECHEM AQ BC 9125 L-CARVYL ACETATE 4,4,10-TRIMETHYL TRICYCLO[7,3,1,0(1-6)]-6,10-TRIDECADIENE-2,8-DIONE CARVEOL (-)-PERILLALDEHYDE Perillartine (+)-PERILLAALDEHYDE DIHYDRO CUMINYL ALCOHOL D(+)-Carvone (+)-(4R)-Limonene,(+)-1,8-p-menthadiene,(R)-(+)-limonen PERILLIC ACID CARVONE LIMONENE, S-(-)-,(S)-(-)-LIMONENE,(-)-1,8-p-menthadiene,(S)-(-)-limonen (-)-CARVYL PROPIONATE L(-)-Carvone MENTHADIENE-7-CARBINOL
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