3-MCPD
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3-MCPD (3-monochloropropane-1,2-diol or 3-chloropropane-1,2-diol) is an organic
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula HOCH2CH(OH)CH2Cl. It is a colorless liquid. It is a versatile multifunctional building block. The compound has attracted attention as the most common member of chemical food contaminants known as chloropropanols. It is suspected to be
carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...
in humans. It is produced in foods treated at high temperatures with hydrochloric acid to speed up
protein hydrolysis Hydrolyzed protein is a solution derived from the hydrolysis of a protein into its component amino acids and peptides. While many means of achieving this exist, most common is prolonged heating with hydrochloric acid, sometimes with an enzyme ...
. As a byproduct of this process, chloride can react with the
glycerol Glycerol (), also called glycerine in British English and glycerin in American English, 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 ...
backbone of
lipids Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include ...
to produce 3-MCPD. 3-MCPD can also occur in foods that have been in contact with materials containing epichlorohydrin-based wet-strength resins which are used in the production of some
tea bag A tea bag, or the compound teabag, is a small, porous, sealed bag or packet, typically containing tea leaves or the leaves of other herbs, which is immersed in water to steep and make an infusion. Originally used only for tea (''Camellia ...
s and
sausage A sausage is a type of meat product usually made from ground meat—often pork, beef, or poultry—along with salt, spices and other flavourings. Other ingredients, such as grains or breadcrumbs may be included as fillers or extenders. ...
casings. In 2009, 3-MCPD was found in some East Asian and Southeast Asian sauces such as oyster sauce,
Hoisin sauce Hoisin sauce is a thick, fragrant sauce commonly used in Cantonese cuisine as a glaze for meat, an addition to stir fry, or as dipping sauce. It is dark-coloured in appearance and sweet and salty in taste. Although regional variants exist, ho ...
, and soy sauce. Using hydrochloric acid is far faster than traditional slow fermentation. A 2013
European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, ...
report indicated margarine, vegetable oils (excluding
walnut oil Walnut oil is oil extracted from walnuts, '' Juglans regia''. The oil contains polyunsaturated fatty acids, monounsaturated fatty acids, and saturated fats. Composition Walnut oil is composed largely of polyunsaturated fatty acids (72% of tota ...
), preserved meats, bread, and fine bakery wares as major sources in Europe. 3-MCPD can also be found in many paper products treated with polyamidoamine-epichlorohydrin wet-strength resins.


Absorption and toxicity

The
International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...
has classified 3-MCPD as Group 2B, "possibly carcinogenic to humans". 3-MCPD is carcinogenic in rodents via a non-
genotoxic Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, but some genotoxic s ...
mechanism. It is able to cross the blood-testis barrier and blood–brain barrier. The oral of 3-chloro-1,2-propanediol is 152 mg/kg bodyweight in rats. 3-MCPD also has male antifertility effects and can be used as a rat
chemosterilant A chemosterilant is a chemical compound that causes reproductive sterility in an organism. Chemosterilants are particularly useful in controlling the population of species that are known to cause disease, such as insects, or species that are, in g ...
.


Legal limits

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.


History

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 An agriculture ministry (also called an) agriculture department, agriculture board, agriculture council, or agriculture agency, or ministry of rural development) is a ministry charged with agriculture. The ministry is often headed by a minister ...
/
Department of Health A health department or health ministry is a part of government which focuses on issues related to the general health of the citizenry. Subnational entities, such as states, counties and cities, often also operate a health department of their ow ...
Food Safety and Standards Group (JFSSG) and reported more than half of the samples collected from retail outlets contained various levels of 3-MCPD. In 2001, the United Kingdom
Food Standards Agency , type = Non-ministerial government department , nativename = , nativename_a = , nativename_r = , logo = Food Standards Agency.svg , logo_width = , logo_caption = , seal = , seal_width = , seal_caption = , picture = , picture_width = ...
(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 The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
. 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 Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...
and the Agency recommended that the affected products be withdrawn from shelves and avoided. 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 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, ...
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. Between 2002 and 2004, relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China. 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, 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." In March 2008, in Australia, "carcinogens" were found in soy sauces, and Australians were advised to avoid soy sauce. 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 Mother's Pride is a brand name for a variety of breads produced by British Bakeries, a division of Premier Foods. The company also bakes Nimble (reduced calorie) and Hovis branded loaves as well as supermarket 'own brand' ranges. British Bake ...
, 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 Tesco plc () is a British multinational groceries and general merchandise retailer headquartered in Welwyn Garden City, England. In 2011 it was the third-largest retailer in the world measured by gross revenues and the ninth-largest in th ...
char-grilled beefburgers,
Sainsbury's J Sainsbury plc, trading as Sainsbury's, is the second largest chain of supermarkets in the United Kingdom, with a 14.6% share of UK supermarket sales. Founded in 1869 by John James Sainsbury with a shop in Drury Lane, London, the company ...
Hot 'n Spicy Chicken Drumsticks and
digestive biscuit A digestive biscuit, sometimes described as a sweet-meal biscuit, is a semi- sweet biscuit that originated in Scotland. The digestive was first developed in 1839 by two Scottish doctors to aid digestion. The term ''digestive'' is derived from th ...
s from
Asda Asda Stores Ltd. () (often styled as ASDA) is a British supermarket chain. It is headquartered in Leeds, England. The company was founded in 1949 when the Asquith family merged their retail business with the Associated Dairies company of Yorks ...
. 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 will be 20 μg per kg, but the safety guideline on daily intake is 120 μg for a 60 kg person per day. 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. 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.


References


External links

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Chloropropanols (WHO Food Additive Series 32)
{{DEFAULTSORT:MCPD Vicinal diols IARC Group 2B carcinogens Organochlorides Spermatotoxicants Halohydrins