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3,4-Benzopyrene , CAS 50-32-8, molecular formula C20H12, is a polycyclic aromatic hydrocarbon containing a benzene ring and has strong carcinogenicity. Food is prone to produce benzo [a] pyrene when cooked at high temperatures. According to the different condensation positions of the benzene ring, benzo [a] pyrene has multiple isomers, with two common ones being benzo [a] pyrene, with a CAS number of 50-32-8; Another type of benzo [e] pyrene, CAS number: 192-97-2. Yellow to brown powder, insoluble in methanol and ethanol, insoluble in water, easily soluble in organic solvents such as benzene, toluene, xylene, acetone, ether, chloroform, dimethyl sulfoxide, etc.
It was originally isolated from coal tar and can be detected in coal smoke, tar, asphalt, and cigarette smoke. It has a strong carcinogenic effect and can induce lung cancer. Its concentration in the atmosphere has been included in routine environmental monitoring projects. On October 27, 2017, the International Agency for Research on Cancer of the World Health Organization released a preliminary list of carcinogens for reference, and benzo [a] pyrene and benzo [a] pyrene in alcoholic beverages were included in the first group of carcinogens list.
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Chemical Formula |
C20H12 |
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Exact Mass |
252 |
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Molecular Weight |
252 |
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m/z |
252 (100.0%), 253 (21.6%), 254 (2.2%) |
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Elemental Analysis |
C, 95.21; H, 4.79 |
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3,4-Benzopyrene exists widely in the environment, and its sources mainly include two aspects: first, the exhaust gas generated by incomplete combustion of coal, oil, natural gas and other fuels in the process of industrial production and life, including automobile exhaust, rubber production and smoke generated by smoking. Through the pollution of water source, atmosphere and soil, it can enter into vegetables, fruits, grains, aquatic products, meat and other food that human beings rely on for survival; Secondly, during the smoking, baking, and frying processes of food, fats, cholesterol, proteins, and carbohydrates undergo thermal cracking reactions under high temperature conditions, and then undergo cyclization and polymerization reactions to form polycyclic aromatic hydrocarbons including benzo [a] pyrene. Especially when food is burnt during smoking and baking, the amount of benzo [a] pyrene produced will increase by 10-20 times compared to ordinary food.
Pollution from smoked food
The smoked and baked products formed by smoking and baking include smoked fish slices, smoked sausage, smoked chicken, ham and other animal based foods. Baked products include moon cakes, bread, cakes, roast meat, roast chicken, roast duck, Mutton shashlik and other foods. The commonly used fuels for smoking and baking include coal, charcoal, coke, coal gas, and electric heating. Due to direct contact between combustion products and food, benzo [a] pyrene in smoke and dust can directly contaminate food.
Someone analyzed the high-temperature cracking products produced during wood combustion and found that benzo [a] pyrene can be produced at all combustion temperatures.
In addition, due to the high baking temperature, the fat, cholesterol and other components in food can undergo high-temperature pyrolysis or thermal polymerization during cooking and processing, forming benzo [a] pyrene.
According to research reports, the content of benzo [a] pyrene in the oil droplets dropped from animal food during the baking process is 10 to 70 times higher than that of animal food itself. When food is burnt or carbonized during smoking and baking, the production of benzo [a] pyrene will significantly increase, especially when the smoking temperature is between 400 ℃ and 1000 ℃, the production of benzo [a] pyrene can increase sharply with the rise of temperature. When starch is heated to 390 ℃, it can produce 0.7 μ g/kg of benzo [a] pyrene, and when heated to 650 ℃, it can produce 7mg/kg of benzo [a] pyrene.
Pollution from feed
Feed, as an important part of the human food chain, is mainly contaminated by raw material pollution, feed formula pollution, feed production pollution, and feed sales pollution. When animal feed is contaminated with benzo [a] pyrene, if the animal consumes this feed for a long time, the benzo [a] pyrene in its body gradually accumulates through enrichment. Meat products, dairy products, and poultry and egg products made from such animals will be contaminated with 3,4-Benzopyrene to varying degrees. Humans will also be harmed to a certain extent through the enrichment of the food chain.
Pollution in the processing stage
Some equipment pipelines and packaging materials contain benzo [a] pyrene. For example, when using rubber pipelines to transport raw materials or finished products, the filling material carbon black for rubber and the heavy oil used for processing rubber both contain benzo [a] pyrene. When liquid foods such as soy sauce, vinegar, wine, beverages, etc.
Are transported through these pipelines, benzo [a] pyrene may transfer to the food, especially if the rubber pipes are soaked in food for a long time, which is more harmful. Packaging candies, popsicles, bread, etc. requires wax paper, as mineral wax has a high content of benzo [a] pyrene. The lubricating oil used in food processing machinery has a high content of benzo [a] pyrene. If the sealing is not good, the lubricating oil can also contaminate the food after dripping in.
Food storage and transportation process
Smoked and baked animal food, benzo [a] pyrene initially mainly adheres to the surface of the food, with a content of about 90% in the cortex not exceeding 1.5 mm deep. With the extension of storage time, benzo [a] pyrene can penetrate deep into food, and after 40 days of storage, the content of the inner layer can increase to 40%~45% of the total amount, resulting in more serious pollution.
Atmospheric environment and industrial wastewater and exhaust gas
The wastewater and exhaust gas from industries such as carbon black production, oil refining, coking, synthetic rubber, and asphalt burning in heavy industry enterprises contain a large amount of benzo [a] pyrene. These wastewater are discharged into rivers, lakes, and seas, and accumulate benzo [a] pyrene in aquatic products through the food chain.
According to investigations, the benzo [a] pyrene content in eels in a certain area is 1.0 μ g/kg~2.7 μ g/kg. In addition, the content of benzo [a] pyrene in asphalt is 2.5% to 3.5%. When burning and spraying asphalt, a large amount of benzo [a] pyrene will be emitted into the air, which can cause pollution to the environment and food. Grain and rapeseed are dried on asphalt roads, and the melted asphalt at high temperatures can adhere to the grain, leading to a significant increase in benzo [a] pyrene content.
3,4-Benzopyrene is a kind of polycyclic aromatic hydrocarbon, which is usually synthesized by multi-step reaction of alkylbenzene and acrylate. The following is a possible synthesis route, including detailed steps:
Synthesis of benzo [b] pyrene-7,12-diphenol: benzo [b] pyrene-7,12-diphenol is produced by heating benzo [b] pyrene and excess 2-hydroxybenzoic acid under acid catalysis at high temperature. After the reaction, the product is cooled with water and extracted with ether.
Oxidation of benzo [b] pyrene-7,12-diphenol: the reaction of benzo [b] pyrene-7,12-diphenol and oxidant (such as chromium tetroxide or oxygen) under alkaline conditions. This reaction produces benzo [b] pyrene-7,12-dione. After the reaction, the product is cooled with water and extracted with ether.
Reduction of benzo [b] pyrene-7,12-dione: reaction of benzo [b] pyrene-7,12-dione and reducing agent (such as sodium sulfite) in ethanol or ether. This reaction produces benzo [b] pyrene-7,12-diol. After the reaction, the product is cooled with water and extracted with ether.
Oxidation of benzo [b] pyrene-7,12-diol: the reaction of benzo [b] pyrene-7,12-diol and oxidant (such as chromium tetroxide or oxygen) under alkaline conditions. This reaction produces benzo [a] pyrene-4,5-dione. After the reaction, the product is cooled with water and extracted with ether.
Reduction of benzo [a] pyrene-4,5-dione: reaction of benzo [a] pyrene-4,5-dione and reducing agent (such as sodium sulfite) in ethanol or ether. This reaction produces benzo [a] pyrene-4,5-diol. After the reaction, the product is cooled with water and extracted with ether.
Condensation of benzo [a] pyrene-4,5-diol: condensation of benzo [a] pyrene-4,5-diol in the presence of weak acid (such as hydrochloric acid) or weak base (such as sodium hydroxide) to form benzo [a] pyrene. After the reaction, the product is cooled with water and extracted with ether.
3,4-Benzopyrene was first discovered in 1933. At that time, American chemist John William Gulland isolated this compound from coal tar and named it "1,2-benzopyrene".
In the next few years, the chemical properties and toxicity of Benzo [a] pyrene have been extensively studied. In 1935, American chemist James Lorin Sanderson first proved that Benzo [a] pyrene has carcinogenic effect on mice and rabbits. In the following decades, people conducted in-depth research on the carcinogenicity and toxicity of Benzo [a] pyrene, and determined its presence in tobacco smoke. In addition, Benzo [a] pyrene is also found to be one of the main pollutants in automobile exhaust and one of the air pollutants generated when burning coal and oil.
Due to the carcinogenicity of Benzo [a] pyrene, it has been listed as a carcinogen of the International Agency for Research on Cancer (IARC). People's extensive exposure in the environment and industry has made it an important issue of public health and environmental protection.
FAQ
What is benzopyrene?
(BEN-zoh-ay-PY-reen) A chemical that comes from certain substances when they are not burned completely. It is found in car exhaust, smoke from wood fires, tobacco, oil and gas products, charred or grilled foods, and other sources. It may also be found in water and soil.
What is a BaP chemical?
Benzo[a]pyrene (BaP) is a polycyclic aromatic hydrocarbon found in coal tar with the formula C20H12. The compound is one of the benzopyrenes, formed by a benzene ring fused to pyrene, and is the result of incomplete combustion at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F).
Why is CCl4 called pyrene?
Most commonly CC l 4 is known as Pyrene. It is the industrial name of this compound. It is used for dry cleaning, degreasing metals, fumigating, and in the manufacture of refrigerants and aerosol propellants. CC l 4 is also used in fire extinguishers because it is heavy non-combustible liquid.
Is benzopyrene in cigarettes?
Benzo(a)pyrene (BP) is a highly carcinogenic polycyclic aromatic hydrocarbon (PAH) present in emission exhausts, in charbroiled food, and in small quantity of cigarette smoke (2–5), typically <10 ng/cigarette (6). BP is 1 of >60 carcinogens in cigarette smoke that is involved in the etiology of lung cancer (7).
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