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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 elemen ...
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
chloropropanol Chloropropanols are chlorohydrins related to propanol There are two isomers of propanol. *1-Propanol, ''n''-propanol, or propan-1-ol : CH3CH2CH2OH, the most common meaning *2-Propanol, Isopropyl alcohol, isopropanol, or propan-2-ol : (CH3)2CHOH ...
s. 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 substan ...
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 su ...
. 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 Epichlorohydrin (abbreviated ECH) 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 orga ...
-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 East Asia is the eastern region of Asia, which is defined in both geographical and ethno-cultural terms. The modern states of East Asia include China, Japan, Mongolia, North Korea, South Korea, and Taiwan. China, North Korea, South Korea and ...
and
Southeast Asian Southeast Asia, also spelled South East Asia and South-East Asia, and also known as Southeastern Asia, South-eastern Asia or SEA, is the geographical south-eastern region of Asia, consisting of the regions that are situated south of mainland ...
sauces such as
oyster sauce 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,The Times, 22 January 1981; ''Cook Accidentally on purpose'' sugar, salt and water thick ...
,
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, hoisi ...
, and
soy sauce Soy sauce (also called simply soy in American English and soya sauce in British English) is a liquid condiment of Chinese origin, traditionally made from a fermented paste of soybeans, roasted grain, brine, and ''Aspergillus oryzae'' or '' Asp ...
. 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 su ...
mechanism. It is able to cross the blood-testis barrier and
blood–brain barrier The blood–brain barrier (BBB) is a highly selective semipermeable border of endothelial cells that prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of the central nervous system where neu ...
. 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 Food Standards Australia New Zealand (FSANZ) ( Māori: ''Te Mana Kounga Kai – Ahitereiria me Aotearoa''), formerly Australia New Zealand Food Authority (ANZFA), is the statutory authority in the Australian Government Health portfolio that is ...
(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 o ...
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 sauce Soy sauce (also called simply soy in American English and soya sauce in British English) is a liquid condiment of Chinese origin, traditionally made from a fermented paste of soybeans, roasted grain, brine, and ''Aspergillus oryzae'' or '' Asp ...
s 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 ...
. About two-thirds of these samples also contained a second chloropropanol called
1,3-dichloropropane-2-ol 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. 1,3-DCP is a believed to be a carcinogen and mutagen. The Internati ...
(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. 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
chloropropanol Chloropropanols are chlorohydrins related to propanol There are two isomers of propanol. *1-Propanol, ''n''-propanol, or propan-1-ol : CH3CH2CH2OH, the most common meaning *2-Propanol, Isopropyl alcohol, isopropanol, or propan-2-ol : (CH3)2CHOH ...
s 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 The second incarnation of Kraft Foods is an American food manufacturing and processing conglomerate, split from Kraft Foods Inc. in 2012 and headquartered in Chicago, Illinois. It became part of Kraft Heinz in 2015. A merger with Heinz, arra ...
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 corporation, 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 an ...
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 wa ...
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 In the metric system, a microgram or microgramme is a unit of mass equal to one millionth () of a gram. The unit symbol is μg according to the International System of Units (SI); the recommended symbol in the United States and United Kingdom whe ...
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

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