Acrolein
描述
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. Acrolein is an herbicide and algicide used in water treatment. It is produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and a reactive one, hence its high toxicity. It is a good Michael acceptor, hence its useful reaction with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 mg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram.
类别
"Pesticide", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Synthetic Toxin"
同义词
"2-Propen-1-one", "2-Propenal", "2-Propenaldehyde", "Acquinite", "Acraldehyde", "Acrylaldehyde", "Acrylic Aldehyde", "Aldehyde, acrylic", "Allyl aldehyde", "Aqualin", "Aqualine", "Biocide", "CH2=CHCHO", "Crolean", "Ethylene aldehyde", "Magnacide", "Magnacide H", "Papite", "Prop-2-En-1-al", "Prop-2-enal", "Propenal", "Propenaldehyde", "Propylene aldehyde", "Slimicide", "trans-Acrolein Formylethylene"
InChI 标识符
InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
键
InChIKey=HGINCPLSRVDWNT-UHFFFAOYSA-N
大分类
Organic oxygen compounds
类型
Organooxygen compounds
另外分类
"Hydrocarbon derivatives", "Organic oxides", "Short-chain aldehydes"
取代基
"Aldehyde", "Aliphatic acyclic compound", "Enal", "Hydrocarbon derivative", "Organic oxide", "Short-chain aldehyde"
分子框架
Aliphatic acyclic compounds
外部描述符
"Pesticides", "a small molecule", "enal"
地位
Detected and Not Quantified
蜂窝位置
"Cytoplasm", "Extracellular"
外貌
Greenish-yellow when impure
熔点/沸点/溶解度
-87.7°C/52°C/212 mg/mL at 25°C
暴露途径
Oral (L121) ; inhalation (L121) ; dermal (L121)
毒性机制
Acrolein rapidly and irreversibly binds to lysine moieties and sulfhydryl groups found on many cellular molecules forming thiol ethers. By this mechanism acrolein can bind to messenger compounds to produce direct cytotoxic effects or secondary effects from interrupted cell signaling pathways. Perturbation of inflammatory responses in bronchial epithelial cells was demonstrated by direct action of acrolein on the inhibitor of nuclear factor kappa-B (IκB) kinase, which inhibits activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) transcription factor and suppresses interleukin 8 (IL-8) production. Rapid binding of acrolein to neural receptors in the corneal and nasal mucosa results in rapid depolarization of the associated neurons to produce ocular and nasal irritation. Acrolein also binds rapidly to glutathione, which may be inhibitory to the enzyme glutathione peroxidase and result in a lower level of cellular protection against oxygen radical toxicity. Further, the adduction of glutathione generates GS-propionaldehyde, which produces oxygen and possibly hydroxy radicals via cytosolic aldehyde dehydrogenase. Acrolein inhibits thioredoxin and thioredoxin reductase, which disrupts the cellular thiol redox balance necessary for cell survival. It interferes with normal reverse cholesterol transport by high density lipoprotein (HDL) by modifying specific sites in apolipoprotein A-I. Acrolein also inhibits aldehyde dehydrogenases and activates the transient receptor potential cation channel. (L121, A84, A85, A86)
代谢
Acrolein can be absorbed though oral, inhalation, or dermal routes. In the liver and kidneys, acrolein forms conjugates with glutathione, cysteine, N-acetylcysteine, and/or thioredoxin. Acrolein can also be transformed into acrylic acid by liver cytosol or microsomes, or it can be oxidized to glycidaldehyde by lung or liver microsomes. Acrolein metabolites are excreted in the urine. (L121)
毒性值
LC50: 130 ppm over 30 minutes (Inhalation, Rat) (T21)
LD50: 562 mg/kg (Dermal, Rabbit) (T22)
LD50: 46 mg/kg (Oral, Rat) (T22)
LD50: 30 mg/kg (Subcutaneous, Rat) (T22)
High levels of acrolein (>7 mg/m3) cause injury to lungs after short term exposures.
致死剂量
10 ppm for an adult human. (L138)
致癌性
3, not classifiable as to its carcinogenicity to humans. (L135)
用途/来源
Acrolein is used as a pesticide to control algae, weeds, bacteria, and mollusks. It is also used to make other chemicals, such as polyester resin, polyurethane, propylene glycol, acrylic acid, acrylonitrile, and glycerol. Small amounts of acrolein can be formed when trees, tobacco, other plants, gasoline, and oil are burned. (L121)
最低风险等级
Acute Inhalation: 0.003 ppm (L134)
Intermediate Inhalation: 0.00004 ppm (L134)
Intermediate Oral: 2 mg/kg/day (L134)
健康影响
Acrolein is a severe pulmonary irritant and lachrymatory agent. Breathing large amounts of acrolein damages the lungs and could cause death. (L121, L122)
症状
Ingestion of acrolein causes stomach irritation, vomiting, stomach ulcers and bleeding. Breathing acrolein may cause eye watering, burning of the nose and throat and a decreased breathing rate. (L121)
维基百科链接
http://en.wikipedia.org/wiki/acrolein
创建于
2009-03-06 18:57:58 UTC
更新于
2014-12-24 20:20:56 UTC