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Dipentene, 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 Dipentene and linalool is enhanced when synergized by piperonyl butoxide.
Apart from toxicoses reported in cats (65), Dipentene generally has a high margin of safety.
CAS: 138-86-3
MF: C10H16
MW: 136.23
EINECS: 205-341-0
Synonyms
DL-LIMONENE (MIXTURE OF D- AND L-FORM CA;LIMONENE(P);Dipentene technical grade;(±)-LiMonene, Mixture of isoMers;DL-Limonene (mixture of D- and L-form ~1:1) for synthesis;acintenedpdipentene;alpha-Limonene;Cajeputen
Dipentene is a cyclic monoterpene that has been found in various plant oils and Cannabis and has antifungal activity.
Dipentene completely inhibits mycelial growth and aflatoxin B1 production in A. flavus when used at concentrations of 500 and 250 ppm, respectively.
Dipentene also inhibits the growth of various additional fungi in vitro, including S. cerevisiae, R. glutinis, and K. thermotolerans (MICs = 500-4,000 μg/ml).
Dipentene has been identified as a contact dermatitis allergen in honing oil, paint thinner, and turpentine.
Formulations containing Dipentene have been used as fragrance and flavoring ingredients.
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.
Dipentene 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.
Dipentene 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.
Dipentene takes its name from Italian limone ("lemon").
Dipentene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains (+)-limonene Dipentene, which is the (R)-enantiomer.
Dipentene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.
Chemical reactions
Dipentene is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.
Dipentene oxidizes easily in moist air to produce carveol, carvone, and limonene oxide.
With sulfur, Dipentene undergoes dehydrogenation to p-cymene.
Dipentene 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.
Dipentene 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 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.
Dipentene Chemical Properties
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.)
Fp: 119 °F
Storage temp.: Store below +30°C.
Solubility: Chloroform: Slightly Soluble
Form: Liquid
Color: Clear colorless to pale yellow
Odor: Pleasant, pine-like; lemon-like.
Odor Type: citrus
Odor Threshold: 0.038ppm
Biological source: synthetic
Explosive limit: 0.7-6.1%, 150°F
Water Solubility: <1 g/100mL
Merck: 14,5493
BRN: 3587825
Dielectric constant: 2.3（20℃）
Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
InChIKey: AJSJXSBFZDIRIS-UHFFFAOYSA-N
LogP: 4.57
CAS DataBase Reference: 138-86-3(CAS DataBase Reference)
NIST Chemistry Reference: Dipentene(138-86-3)
EPA Substance Registry System: Dipentene(138-86-3)
Dipentene 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.
Dipentene is a liquid with lemon-like odor.
Dipentene is a reactive compound; oxidation often yields more than one product.
Dehydrogenation leads to p-cymene.
Dipentene 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.
Dipentene is obtained in large amounts as a by-product in the production of orange juice; Dipentene 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.
d-, l- or Dipentene has a pleasant, lemon-like odor free from camphoraceous and turpentine-like notes.
Dipentene 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).
Uses
Dipentene is a flavoring agent that is a liquid, colorless with a pleasant odor resembling mild citrus.
Dipentene is miscible in alcohol, most fixed oils, and mineral oil; soluble in glycerin; and insoluble in water and propylene glycol.
Dipentene is obtained from citrus oil.
Dipentene is also termed d-p-mentha-1,8,diene and cinene.
Limonene is an antioxidant and flavoring agent that occurs in lemons, oranges, and pineapple juice, being obtained from the oils.
Dipentene 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.
Dipentene prevents or delays enzymatic browning-type oxidation.
Pharmaceutical Applications
Many studies have reported that Dipentene effectively plays a valuable role in the prevention of several chronic and degenerative diseases.
This review provides worthy information about the beneficial effects of Dipentene such as antioxidant, antidiabetic, anticancer, anti-inflammatory, cardioprotective, gastroprotective, hepatoprotective, immune modulatory, anti-fibrotic, anti-genotoxic etc.
This could in turn help in the application of D-limonene for clinical studies.
Various plant families contain Terpenes as their secondary metabolites.
Monoterpenes constitute an important part of these secondary metabolites.
Dipentene is a well-identified monoterpene that is commonly applied as a fragrance ingredient in essential oils.
Dipentene is known to possess remarkable biological activities.
Dipentene can be effectively used for treating various ailments and diseases.
Due to its diverse functions, it can be efficiently utilized for human health.
Numerous data on animal studies have highlighted the potential effects of D-limonene.
Dipentene is well tolerated in experimental animals and protective effects of limonene were observed in several preclinical models.
Animal studies showing the cardio protective and hepatoprotective effects of Dipentene are found to be inadequate.
Moreover, studies exploring the anticancer efficacy of Dipentene on animal models are also found to be limited.
The study on the effect of D-limonene on humans is also extremely limited.
Therefore, our present review will open new avenues to undertake further research on D-limonene in preclinical models and for subjecting this compound to effective clinical trials.
Production Methods
Dipentene 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.
Dipentene occurs as a by-product in the manufacture of terpineol and in various synthetic products made from α-pinene or turpentine oil.
Dipentene is found in the gas phase of tobacco smoke and has been detected in urban atmospheres.
Preparation
Dipentene 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.
Toxicology
Dipentene is a clear colorless mobile liquid with a pleasant lemon-like odor.
Dipentene is an optically active form of limonene having (4R)-configuration.
Dipentene has a role as a plant metabolite.
Dipentene is an enantiomer of a (4S)-limonene.
Dipentene is one of the most common terpenes in nature.
Dipentene is a major constituent in several citrus oils (orange, lemon, mandarin, lime, and grapefruit).
Dipentene is listed in the Code of Federal Regulations as generally recognized as safe (GRAS) for a flavoring agent and can be found in common food items such as fruit juices, soft drinks, baked goods, ice cream, and pudding.
Contact allergens
Dipentene is a racemic form of dand l-limonene.
Dipentene is contained in Citrus species such as citrus, orange, mandarin, and bergamot.
Dipentene is contained in Pinus pinea.
The racemic form (dand l-limonene) is also named dipentene.
