Names | |
---|---|
Preferred IUPAC name 3-Chloropropane-1,2-diol | |
Other names 3-Monochloropropane-1,2-diol; α-Chlorohydrin; Glycerol α-monochlorohydrin; Chlorodeoxyglycerol; 3-Chloro-1,2-propanediol | |
Identifiers | |
3D model (JSmol) | |
635684 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.267 |
EC Number |
|
68752 | |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C3H7ClO2 | |
Molar mass | 110.54 g·mol−1 |
Appearance | Viscous, colorless liquid |
Density | 1.32 g·cm−3 |
Melting point | −40 °C (−40 °F; 233 K) |
Boiling point | 213 °C (415 °F; 486 K) |
Hazards | |
GHS labelling: | |
Danger | |
H300, H312, H315, H318, H330, H351, H360, H370, H372 | |
P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P311, P312, P314, P320, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, P501 | |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
3-MCPD (3-monochloropropane-1,2-diol or 3-chloropropane-1,2-diol) is an organic chemical compound with the formula HOCH2CH(OH)CH2Cl. It is a colorless liquid. It is a versatile multifunctional building block. [1] The compound has attracted attention as the most common member of chemical food contaminants known as chloropropanols. [2] It is suspected to be carcinogenic in humans.
3-MCPD is thought to be produced when foods are treated at high temperatures with hydrochloric acid. Such treatments are sometimes used to accelerate protein hydrolysis, making food more digestable. In such a treatment chloride is thought to react with the glycerol backbone of lipids to produce 3-MCPD. 3-MCPD is also thought to arise in foods that have been in contact with materials containing epichlorohydrin-based wet-strength resins which are used in the production of some tea bags and sausage casings. [3]
Chlorination of glycerol gives the 3-MCPD:
The same compound can be produced by hydrolysis of epichlorohydrin. [4]
In 2009, 3-MCPD was found in some East Asian and Southeast Asian sauces such as oyster sauce, Hoisin sauce, and soy sauce. [5] Using hydrochloric acid is far faster than traditional slow fermentation. A 2013 European Food Safety Authority report indicated margarine, vegetable oils (excluding walnut oil), preserved meats, bread, and fine bakery wares as major sources in Europe. [6]
3-MCPD can also be found in many paper products treated with polyamidoamine-epichlorohydrin wet-strength resins. [7]
The International Agency for Research on Cancer has classified 3-MCPD as Group 2B, "possibly carcinogenic to humans". [8] 3-MCPD is carcinogenic in rodents via a non-genotoxic mechanism. [9] It is able to cross the blood-testis barrier and blood–brain barrier. [10] The oral LD50 of 3-chloro-1,2-propanediol is 152 mg/kg bodyweight in rats. [11]
3-MCPD also has male antifertility effects [11] [12] and can be used as a rat chemosterilant. [13]
The joint Food Standards Australia New Zealand (FSANZ) set a limit for 3-MCPD in soy sauce of 0.02 mg/kg, in line with European Commission standards which came into force in the EU in April 2002.
In 2000, a survey of soy sauces and similar products available in the UK was carried out by the Joint Ministry of Agriculture, Fisheries and Food/Department of Health Food Safety and Standards Group (JFSSG) and reported more than half of the samples collected from retail outlets contained various levels of 3-MCPD. [14]
In 2001, the United Kingdom Food Standards Agency (FSA) found in tests of various oyster sauces and soy sauces that 22% of samples contained 3-MCPD at levels considerably higher than those deemed safe by the European Union. About two-thirds of these samples also contained a second chloropropanol called 1,3-dichloropropane-2-ol (1,3-DCP) which experts advise should not be present at any levels in food. Both chemicals have the potential to cause cancer and the Agency recommended that the affected products be withdrawn from shelves and avoided. [15] [16]
In 2001, the FSA and Food Standards Australia New Zealand (FSANZ) singled out brands and products imported from Thailand, China, Hong Kong, and Taiwan. Brands named in the British warning include Golden Mountain, King Imperial, Pearl River Bridge, Golden Mark, Kimlan, Golden Swan, Sinsin, Tung Chun, and Wanjasham soy sauce. Knorr soy sauce was also implicated, as well as Uni-President Enterprises Corporation creamy soy sauce from Taiwan, Silver Swan soy sauce from the Philippines, Ta Tun soy bean sauce from Taiwan, Tau Vi Yeu seasoning sauce and Soya bean sauce from Vietnam, Zu Miao Fo Shan soy superior sauce and Mushroom soy sauce from China and Golden Mountain and Lee Kum Kee chicken marinade. [17] [18] [19] Between 2002 and 2004, relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China. [20]
In 2007, in Vietnam, 3-MCPD was found in toxic levels. In 2004, the HCM City Institute of Hygiene and Public Health found 33 of 41 sample of soy sauce with high rates of 3-MCPD, including six samples with up to 11,000 to 18,000 times more 3-MPCD than permitted, an increase over 23 to 5,644 times in 2001, [21] The newspaper Thanh Nien Daily commented, "Health agencies have known that Vietnamese soy sauce, the country's second most popular sauce after fish sauce, has been chock full of cancer agents since at least 2001." [22]
In March 2008, in Australia, "carcinogens" were found in soy sauces, and Australians were advised to avoid soy sauce. [23]
In November 2008, Britain's Food Standards Agency reported a wide range of household name food products from sliced bread to crackers, beefburgers and cheese with 3-MCPD above safe limits. Relatively high levels of the chemical were found in popular brands such as Mother's Pride, Jacobs crackers, John West, Kraft Dairylea and McVitie's Krackawheat. The same study also found relatively high levels in a range of supermarket own-brands, including Tesco char-grilled beefburgers, Sainsbury's Hot 'n Spicy Chicken Drumsticks and digestive biscuits from Asda. The highest levels of 3-MCPD found in a non- soy sauce product, crackers, was 134 μg per kg. The highest level of 3-MCPD found in soy sauce was 93,000 μg per kg, 700 times higher. The legal limit for 3-MCPD coming in next year[ when? ] will be 20 μg per kg, but the safety guideline on daily intake is 120 μg for a 60 kg person per day.[ citation needed ]
In 2016, the occurrence of 3-MCPD in selected paper products (coffee filters, tea bags, disposable paper hot beverage cups, milk paperboard containers, paper towels) sold on the Canadian and German market was reported and the transfer of 3-MCPD from those products to beverages was investigated. [24] Exposure to 3-MCPD from packaging material would likely constitute only a small percentage of overall dietary exposure when compared to the intake of processed oils/fats containing 3-MCPD equivalent (in form of fatty acid esters) which are often present at levels of about 0.2-2 μg/g.
Soy sauce is a liquid condiment of Chinese origin, traditionally made from a fermented paste of soybeans, roasted grain, brine, and Aspergillus oryzae or Aspergillus sojae molds. It is recognized for its pronounced umami taste.
Glycerol, also called glycerine or glycerin, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known as glycerides. Because it has antimicrobial and antiviral properties, it is widely used in wound and burn treatments approved by the U.S. Food and Drug Administration. Conversely, it is also used as a bacterial culture medium. Its presence in blood can be used as an effective marker to measure liver disease. It is also widely used as a sweetener in the food industry and as a humectant in pharmaceutical formulations. Because of its three hydroxyl groups, glycerol is miscible with water and is hygroscopic in nature.
Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classed as a diol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.
Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.
1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers are rarely encountered.
Substances, mixtures and exposure circumstances in this list have been classified by the International Agency for Research on Cancer (IARC) as group 2B: The agent (mixture) is "possibly carcinogenic to humans". The exposure circumstance entails exposures that are possibly carcinogenic to humans. This category is used for agents, mixtures and exposure circumstances for which there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is inadequate evidence of carcinogenicity in humans but there is sufficient evidence of carcinogenicity in experimental animals. In some instances, an agent, mixture or exposure circumstance for which there is inadequate evidence of carcinogenicity in humans but limited evidence of carcinogenicity in experimental animals together with supporting evidence from other relevant data may be placed in this group. Further details can be found in the preamble to the IARC Monographs.
Hydrolyzed vegetable protein (HVP) products are foodstuffs obtained by protein hydrolysis and are used as ingredients to create a bouillon (broth) taste without the vegetables, bones, simmering, or other standard elements of creating bouillon from scratch.
Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.
Uni-President Enterprises Corporation is an international food conglomerate based in Tainan, Taiwan. It is the largest food production company in Taiwan as well as Asia, and has a significant market share in dairy products, foods and snacks, and beverages. Through its subsidiary company President Chain Store Corporation, it is also responsible for running Starbucks, 7-Eleven, Mister Donut, Carrefour and Muji in Taiwan. In addition, Uni-President has subsidiaries in Mainland China, Vietnam, Thailand and the Philippines.
A food contaminant is a harmful chemical or microorganism present in food, which can cause illness to the consumer.
In enzymology, a 1,3-propanediol dehydrogenase (EC 1.1.1.202) is an enzyme that catalyzes the chemical reaction
The enzyme propanediol dehydratase (EC 4.2.1.28) catalyzes the chemical reaction
Drinking water quality standards describes the quality parameters set for drinking water. Water may contain many harmful constituents, yet there are no universally recognized and accepted international standards for drinking water. Even where standards do exist, the permitted concentration of individual constituents may vary by as much as ten times from one set of standards to another. Many countries specify standards to be applied in their own country. In Europe, this includes the European Drinking Water Directive and in the United States, the United States Environmental Protection Agency (EPA) establishes standards as required by the Safe Drinking Water Act. China adopted its own drinking water standard GB3838-2002 enacted by Ministry of Environmental Protection in 2002. For countries without a legislative or administrative framework for such standards, the World Health Organization publishes guidelines on the standards that should be achieved.
1,2,3-Trichloropropane (TCP) is an organic compound with the formula CHCl(CH2Cl)2. It is a colorless liquid that is used as a solvent and in other specialty applications.
Lee Kum Kee Company Limited is a Hong Kong-based food company which specializes in manufacturing a wide range of Chinese and Asian sauces. Founded by Lee Kum Sheung in 1888 in Nanshui, Guangdong, Lee Kum Kee produces over 200 Chinese-style sauces, including oyster sauce, soy sauce, hoisin sauce, XO sauce, one-step recipe sauce, chili sauce, cooking ingredients, and dipping sauce. The group also purchased London's landmark Walkie-Talkie skyscraper in July 2017 for £1.3bn, which was a record-breaking transaction for a single building in the UK.
Oyster sauce describes a number of sauces made by cooking oysters. The most common in modern use is a viscous dark brown condiment made from oyster extracts, sugar, salt and water, thickened with corn starch.
Chloropropanols are chlorohydrins related to propanols containing chloride functional group. Eight isomers are possible. Two of these derivatives, 1,3-dichloropropanol (1,3-DCP) and 3-chloropropane-1,2-diol (3-MCPD), are carcinogenic contaminants in processed foods. Several isomers are encountered in industrial chemistry.
1,3-Dichloropropan-2-ol (1,3-DCP) is an organic compound with the formula HOCH2CHClCH2Cl. It is a colorless liquid. It is an intermediate in the production of epichlorohydrin.
Ohio River Park is a Superfund Site located in Neville Island, Pennsylvania. Between the 1920s-1970s, the Site was used for municipal waste, pesticide manufacturing, coke sludge disposal, cement manufacturing disposal, and pesticide waste. In 1977, Neville Land Company donated the Site to Allegheny County who started developing the Site as a community park. In 1979, Allegheny County found various hazardous contaminants on the Site. On August 30, 1990, the Site was determined to be a Superfund Site due to VOCs, SVOCs, inorganics, and pesticides being present in the surface soil, subsurface soil, surface water, river sediment, and groundwater. Soil remediation began in February 1998 and ended in September 1999. Today, Ohio River Park has the Robert Morris University Island Sports Center and Coraopolis Bridge on top of it. Additionally, benzene continues to be monitored because it is still present in the Site's groundwater.