p-シメン 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
溶解性
水に不溶, エタノール, アセトンに易溶。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
解説
芳香族炭化水素．ベンゼン環にメチル基とイソプロピル基が置換したもの，CH
3C
6H
4CH(CH
3)
2．o-シメン，m-シメン，p-シメンの3種の異性体があるが，通常はp-シメンを指す．p-シメンは植物精油の中にも存在し，水素化された飽和化合物p-メンタンは，典型的なモノテルペンの母体である．香料原料となる．
用途
香料、有機合成原料
用途
有機合成原料。
化学的特性
p-Cymene is a monoterpene that is found in a variety of plants, including C. sativa, and has diverse biological activities, including antimicrobial, anticancer, antioxidant, anti-inflammatory, antinociceptive, and anxiolytic properties.p-Cymene inhibits the growth of S. typhimurium, E. coli, L. monocytogenes, S. epidermidis, and S. aureus with MIC values ranging from 0.266 to 0.608% v/v.It decreases the invasive activity of HT-1080 human fibrosarcoma cells in vitro by 87% when used at a concentration of 600 μM.In mouse hippocampus, p-Cymene (50 mg/kg, i.p.) reduces lipid peroxidation and nitrite content by 65.5 and 71.2%, respectively, and increases superoxide dismutase (SOD) and catalase activities by 22.7 and 119.3%, respectively, compared to vehicle control animals.Formulations containing p-cymene have been used as flavoring agents.
天然物の起源
Widespread in nature; reported in the oils of cypress, Artemisia cina Bg., Ceylon cinnamon, boldo leaf, cascarilla,
Cuminum cyminum L. and lemon; in the oils for seeds of coriander and Cicuta virosa; in the ether-extracted oils of Monarda
fisulosa and Monarda puncata; in the star anise and nutmeg essential oils. Note that p-cymene reported in essential oil may be
formed from the conversion of a cyclic terpene; its presence is indicative of aging in lemon essential oil. Reported found in citrus
juices and peel oils, guava, papaya, black currant, pineapple, blueberry, blackberry, carrot, tomato, celery seed, cumin seed, mace,
ginger, coriander seed, anise, nutmeg, mace, parsley, cardamom, cinnamon root and bark, pepper, peppermint oil, spearmint oil,
cassia leaf and Thymus vulgaris.
使用
As a diluent for lacquers, varnishes,
and dyes; in the production of resins; as a component
of fragrances; also found as a byproduct
in the manufacture of sulfite paper
pulp
製造方法
Obtained chiefly from the wash water of sulfite paper.
定義
ChEBI: A monoterpene that is toluene substituted by an isopropyl group at position 4.
一般的な説明
Colorless liquid with a mild pleasant odor. Floats on water.
空気と水の反応
Insoluble in water.
反応プロフィール
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as CYMENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.
健康ハザード
Inhalation causes impairment of coordination, headache. Contact with liquid causes mild irritation of eyes and skin. Ingestion causes irritation of mouth and stomach.
火災危険
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
化学反応性
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.
安全性プロファイル
Mildly toxic by
ingestion. Humans sustain central nervous
system effects at low doses. A skin irritant.
Flammable liquid. Explosion Hazard:
Slight in the form of vapor. To fight fire,
use foam, CO2, dry chemical. When heated
to decomposition it emits acrid smoke and
fumes.
代謝
In this compound both an isopropyl and a methyl group occur together and the available evidence shows that only the methyl group is oxidized, cumic acid (pisopropylbenzoic acid) and its conjugate (cuminuric acid) being the main metabolites in dogs and in sheep (Williams, 1959). Following inhalation, only a small part is excreted unchanged, the remainder being oxidized to water-soluble metabolites. As early as 1873, Ziegler suggested that the readily oxidized propyl side-chain formed a -COO H group (Browning, 1965): The ultimate product in the case of dogs and sheep is cumic acid, which is probably excreted as a conjugate with glycine (Gerarde, 1960).
純化方法
Wash p-cymene with cold, conc H2SO4 until there is no further colour change, then repeatedly with H2O, 10% aqueous Na2CO3 and H2O again. Dry it over Na2SO4, CaCl2 or MgSO4, and distil it. Further purification steps include steam distillation from 3% NaOH, percolation through silica gel or activated alumina, and a preliminary reflux for several days over powdered sulfur. Store it over CaH2. [Beilstein 5 IV 1060.]
p-シメン 上流と下流の製品情報
原材料
準備製品