View source for 3-MCPD

{{chembox
| verifiedrevid = 325602923
| ImageFile = alpha-Chlorohydrin.svg
| ImageSize = 
| ImageName = Skeletal formula
| ImageFile1 = Alpha-chlorohydrin-3D-balls.png
| ImageName1 = Ball-and-stick model
|IUPACName=3-chloropropane-1,2-diol
|OtherNames=α-Chlorohydrin, glycerol α-monochlorohydrin, chlorodeoxyglycerol
|Section1={{Chembox Identifiers
|  InChIKey = SSZWWUDQMAHNAQ-UHFFFAOYAR
| CASNo_Ref = {{cascite}}
| CASNo=96-24-2
|  PubChem=7290
|  EINECS=202-492-4
|  ChEBI=18721
|  ChemSpiderID=7018
|  SMILES = ClCC(O)CO
|  InChI=1/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
  }}
|Section2={{Chembox Properties
|  Formula=C<sub>3</sub>H<sub>7</sub>ClO<sub>2</sub>
|  MolarMass=110.539&nbsp;g·mol<sup>−1</sup>
|  Appearance=Viscous, colorless liquid
|  Density=1.32&nbsp;g·cm<sup>−3</sup>
|  MeltingPtC=−40
|  BoilingPtC=213
|  Solubility=
  }}
|Section3={{Chembox Hazards
|  ExternalMSDS=[http://msds.chem.ox.ac.uk/GL/glycerol_alpha_monochlorohydrin.html External MSDS]
|  MainHazards=
|  FlashPt=
|  Autoignition=
|  RPhrases = {{R26/27/28}}, {{R36/37/38}}
|  SPhrases = {{S24}}, {{S45}}
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}}
'''3-MCPD''' or (3-monochloropropane-1,2-diol or 3-chloro-1,2-propanediol) is an [[Organic compound|organic]] [[chemical compound]] which is [[carcinogenic]] and highly suspected to be [[genotoxic]] in humans, has male anti-fertility effects, and is a chemical byproduct which may be formed in foods, the most commonly found member of chemical contaminants known as [[chloropropanol]]s.

It is primarily created in foods by [[protein hydrolysis]] by adding hydrochloric acid to speed up the reaction of the (soy) protein with [[lipids]] at high temperatures.  Another method 3-MCPD can also occur in foods which have been in contact with materials containing [[epichlorohydrin]]-based [[wet strength|wet-strength]] resins - used in the production of some [[tea bags]] and [[sausage]] casings.<ref>[http://www.foodnavigator.com/Science-Nutrition/IFST-issues-statement-on-3-MCPD IFST issues statement on 3-MCPD]</ref> 

It has been found far exceeding health standards by in some cases thousand of times in many Chinese and [[Southeast Asian]] sauces such as [[Oyster sauce]], [[Hoisin sauce]] and [[Soy sauce]], but Korean or Japanese sauces do not utilize hydrochloric acid in production and therefore do not produce chloropropanols{{Citation needed|date=January 2010}}.  Using hydrochloric acid is a far cheaper and faster method but inevitably creates carcinogens, which is why artificial soy sauce can sell for far cheaper than traditionally fermented soy sauce.  The manufacturing process for acid-hydrolyzed protein can be modified to reduce the levels of 3-MCPD that are formed, but cannot completely eliminate them.

==Absorption and toxicity==
3-MCPD is considered to be carcinogenic to rodents via a non-[[genotoxic]] mechanism<ref name="pmid12960406">{{cite journal
|author=Robjohns S, Marshall R, Fellows M, Kowalczyk G
|title=In vivo genotoxicity studies with 3-monochloropropan-1,2-diol
|journal=Mutagenesis
|volume=18
|issue=5
|pages=401–4
|year=2003
|month=September
|pmid=12960406
|doi=10.1093/mutage/geg017
|url=http://mutage.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12960406
|issn=
}}</ref>.  It is able to cross the [[blood-testis barrier]] and [[blood-brain barrier]]. (Edwards  et al. 1975).  The oral [[LD50]] of 3-chloro-1,2-propanediol was reported to be 152&nbsp;mg/kg bodyweight in rats (Ericsson & Baker, 1970).

3-MCPD also has male antifertility effects <ref name="pmid5443210">{{cite journal
|author=Ericsson RJ, Baker VF
|title=Male antifertility compounds: biological properties of U-5897 and U-l5,646
|journal= Journal of reproduction and fertility
|volume=21
|issue=2
|pages=267–73
|year=1970
|month=March
|pmid=5443210
|doi=
10.1530/jrf.0.0210267|url=
|issn=
}}</ref><ref name="pmid5520328">{{cite journal
|author=Samojlik E, Chang MC
|title=Antifertility activity of 3-chloro-1, 2-propanediol (U-5897) on male rats
|journal= Biology of reproduction
|volume=2
|issue=2
|pages=299–304
|year=1970
|month=April
|pmid=5520328
|doi=10.1095/biolreprod2.2.299
|url=http://www.biolreprod.org/cgi/pmidlookup?view=long&pmid=5520328
|issn=
}}</ref> and can be used as a rat [[chemosterilant]]<ref name="pmid5428943">{{cite journal
|author=Ericsson RJ
|title=Male antifertility compounds: U-5897 as a rat chemosterilant
|journal= Journal of reproduction and fertility
|volume=22
|issue=2
|pages=213–22
|year=1970
|month=July
|pmid=5428943
|doi=
10.1530/jrf.0.0220213|url=
|issn=
}}</ref>.

==Legal limits==
The joint [[Australia New Zealand Food Authority]] (ANZFA) set a limit for 3-MCPD in soy sauce of 0.02 milligrams per kilogram, in line with European Commission standards which came into force in the EU in April 2002.

==Incidents==
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 (United Kingdom)|Department of Health]] Food Safety and Standards Group (JFSSG) in 2000 and reported more than half of the samples collected from retail outlets contained various levels of 3-MCPD <ref name="pmid11271703">{{cite journal
|author=Macarthur R, Crews C, Davies A, Brereton P, Hough P, Harvey D
|title=3-monochloropropane-1,2-diol (3-MCPD) in soy sauces and similar products available from retail outlets in the UK
|journal=Food additives and contaminants
|volume=17
|issue=11
|pages=903–6
|year=2000
|month=November
|pmid=11271703
|doi=10.1080/026520300750038072
|url=
|issn=
}}</ref>.

* In 2001 the United Kingdom Food Standards Agency found in tests of various oyster sauces and [[soy sauce]]s that some 22% of samples contained a chemical called 3-MCPD (3-monochloropropane-1,2-diol) 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-DCP]] (1,3-dichloropropane-2-ol) 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.<ref>[http://www.food.gov.uk/news/pressreleases/2001/jun/soysaucerecall Food.gov.uk press release soysauce]</ref><ref>[http://www.food.gov.uk/multimedia/bigimages/soysauceproducts.gif Chart with five mentions of affected oyster sauces]</ref>

* Britain's Food Standards Agency (FSA) 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, Jammy Chai, [[Lee Kum Kee]] (李錦記), Golden Mark, [[Kimlan]] (金蘭）, Golden Swan, Sinsin, Tung Chun and Wanjasham soy sauce.  [[Knorr (brand)|Knorr]] soy sauce was also implicated, as well as [[Uni-President Enterprises Corporation]] (統一企業公司) [[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.<ref name="barchroniclePhilippine government">[http://www.bar.gov.ph/barchronicle/2004/may04_1-31_soysauce.asp barchronicle(Philippine government)]</ref>

* Relatively high levels of 3-MCPD and other [[chloropropanol]]s were found in soy sauce and other foods in China between 2002 and 2004<ref name="pmid17613068">{{cite journal
|unused_data=1B69BA326FFE69C3F0A8F227DF8201D0
|author=Fu WS, Zhao Y, Zhang G, ''et al.''
|title=Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004
|journal=Food additives and contaminants
|volume=24
|issue=8
|pages=812–9
|year=2007
|month=August
|pmid=17613068
|doi=10.1080/02652030701246039
|url=http://www.informaworld.com/openurl?genre=article&doi=10.1080/02652030701246039&magic=pubmed
|issn=

}}</ref>.

* In 2006, Certain batches of Marca Pina Soy Sauce (1 litre) have been found to be contaminated with levels of (3-MCPD) above EU statutory limits. According to the label, the affected brand of Soy sauce was manufactured in the Philippines by [[Pinakamasarap Corporation]].

* In 2007 in Vietnam, 3-MCPD was found in toxic levels (Testing since 2001, In 2004, the HCM City Institute of Hygiene and Public Health found 33 of 41 sample of soya 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) <ref>[http://english.vietnamnet.vn/reports/2007/05/699774/ Soya sauce stirs worry and discontentment among public]</ref> in soy sauces there in 2007, along with [[formaldehyde]] in the national dish [[Pho]], and banned pesticides in vegetables and fruits. A prominent 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," <ref>[http://afp.google.com/article/ALeqM5iiMrrBvLTLGX3P0uXmSqeT1Zjayw Toxic soy sauce, chemical veggies -- food scares hit Vietnam]</ref>

* In March 2008 in Australia, "carcinogens" were found in soy sauces there, and were advised to avoid soy sauce. <ref>[http://www.news.com.au/story/0,23599,23392636-29277,00.html 'Cancer chemical' in soy sauce]</ref>

* In Nov 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 Foods|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 mcg per kg. The highest level of 3-MCPD found in soy sauce was 93,000 mcg per kg, 700 times higher.  The legal limit for 3-MCPD coming in next year will be 20 mcg per kg. But the safety guideline on daily intake is 120mcg for a 60&nbsp;kg person per day.<ref>[http://www.dailymail.co.uk/health/article-61607/The-cancer-chemical-lurking-food.html The cancer chemical lurking in our food]</ref>

==Current status==
These companies continue to use the rapid soy protein hydrolyzation method, but modify methods to lower contaminants to meet standards. Hydrolyzing always produces some 3-MCPD, but for the 1,3-DCP, a byproduct of 3-MCPD, there is no standard to meet as it is unregulated, scientists said that cancer found in reproductive cells caused by 1,3-DCP can cause cancer and genetic damage that can be passed to generations of offspring who have never been exposed to the chemical.<ref name="barchroniclePhilippine government"/>

==See also==
* [[Food contamination]]

==External links==
* [http://www.foodsafety.gov/~dms/cpgmcpd.html US FDA Compliance Policy on 3-MCPD in Asian Sauces]
* [http://www.inchem.org/documents/jecfa/jecmono/v32je17.htm Chloropropanols (WHO Food Additive Series 32)]
* [http://www.centralanalytical.com/3_MCPD_Testing_News.html?gclid=CK6J3t7myJgCFQLObwodkCE71Q 3-MCPD detection and testing]

==References==
<references />

{{DEFAULTSORT:3-Mcpd}}
{{Consumer Food Safety}}

[[Category:Organochlorides]]
[[Category:Carcinogens]]
[[Category:Diols]]

[[de:3-Chlor-1,2-propandiol]]
[[zh:3-氯-1,2-丙二醇]]
[[Category:2Fix]]