리모넨 C화학적 특성, 용도, 생산
개요
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.
화학적 성질
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).
출처
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.
Toxicology
D-limonene is a clear colorless mobile liquid with a pleasant lemon-like odor. （(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.）D-limonene is one of the most common terpenes in nature. It is a major constituent in several citrus oils (orange, lemon, mandarin, lime, and grapefruit). D-limonene 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.
용도
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.
정의
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.
제조 방법
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.
생산 방법
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.
일반 설명
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.
공기와 물의 반응
Flammable. Insoluble in water.
반응 프로필
Cinene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.
건강위험
Liquid irritates eyes; prolonged contact with skin causes irritation. Ingestion causes irritation of gastrointestinal tract.
화재위험
Behavior in Fire: Containers may explode.
화학 반응
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.
색상 색인 번호
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
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).
환경귀착
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.
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