파라시멘 C화학적 특성, 용도, 생산
화학적 성질
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.
출처
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.
용도
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
정의
ChEBI: A monoterpene that is toluene substituted by an isopropyl group at position 4.
제조 방법
Obtained chiefly from the wash water of sulfite paper.
일반 설명
Colorless liquid with a mild pleasant odor. Floats on water.
공기와 물의 반응
Insoluble in water.
반응 프로필
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.
건강위험
Inhalation causes impairment of coordination, headache. Contact with liquid causes mild irritation of eyes and skin. Ingestion causes irritation of mouth and stomach.
화재위험
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.
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.
Safety Profile
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.
신진 대사
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).
Purification Methods
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.]
파라시멘 준비 용품 및 원자재
원자재
준비 용품
