View source for 3-MCPD

{{chembox
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| ImageFile = alpha-Chlorohydrin.svg
| ImageSize =
| ImageName = Skeletal formula
| ImageFile1 = Alpha-chlorohydrin-3D-balls.png
| ImageName1 = Ball-and-stick model
| PIN= 3-Chloropropane-1,2-diol
| OtherNames= 3-Monochloropropane-1,2-diol; α-Chlorohydrin; Glycerol α-monochlorohydrin; Chlorodeoxyglycerol; 3-Chloro-1,2-propanediol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=96-24-2
| Beilstein = 635684
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI=18721
| ChEMBL = 3185949
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=7018
| EINECS=202-492-4
| Gmelin = 68752
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| KEGG = C18676
| PubChem=7290
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QGS78A3T6P
| InChIKey = SSZWWUDQMAHNAQ-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
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| StdInChIKey = SSZWWUDQMAHNAQ-UHFFFAOYSA-N
| InChI=1/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
| SMILES = ClCC(O)CO
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|Section2={{Chembox Properties
| C=3
| H=7
| Cl=1
| O=2
| Appearance=Viscous, colorless liquid
| Density=1.32&nbsp;g·cm<sup>−3</sup>
| MeltingPtC=−40
| BoilingPtC=213
| Solubility=
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|Section3={{Chembox Hazards
| ExternalSDS =[http://msds.chem.ox.ac.uk/GL/glycerol_alpha_monochlorohydrin.html External MSDS]
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| GHSSignalWord = Danger
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'''3-MCPD''' ('''3-monochloropropane-1,2-diol''' or '''3-chloropropane-1,2-diol''') is an [[Organic compound|organic]] [[chemical compound]] with the formula HOCH<sub>2</sub>CH(OH)CH<sub>2</sub>Cl.  It is a colorless liquid.  The compound has attracted notoreity as the most common member of chemical food contaminants known as [[chloropropanol]]s.<ref>{{cite journal|doi=10.1021/es903383a|pmid=20163179|title=Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce|journal=Environmental Science & Technology|volume=44|issue=7|pages=2277–2285|year=2010|last1=Howard|first1=Philip H.|last2=Muir|first2=Derek C. G.|bibcode=2010EnST...44.2277H|doi-access=free}}</ref>  It is suspected to be [[carcinogenic]] in humans.<ref>{{cite journal |doi=10.2903/j.efsa.2016.4426 |title=Risks for human health related to the presence of 3- and 2-monochloropropanediol (MCPD), and their fatty acid esters, and glycidyl fatty acid esters in food |journal=EFSA Journal |date=2016 |volume=14 |issue=5 |hdl=2164/7793 |hdl-access=free }}</ref>
==Accidental and intentional production==
3-MCPD, together with its [[isomer]] [[2-MCPD]], is thought to be produced when fat-containing 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 and 2-MCPD.
Chlorination of glycerol gives the 3-MCPD:
:{{chem2|HOCH(CH2OH)2  +  HCl ->  HOCH(CH2Cl)(CH2OH)  +  H2O}}
The same compound can be produced by hydrolysis of epichlorohydrin.<ref>{{cite journal |doi=10.1021/cr5004002 |title=Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies |date=2015 |last1=Sutter |first1=Marc |last2=Silva |first2=Eric Da |last3=Duguet |first3=Nicolas |last4=Raoul |first4=Yann |last5=Métay |first5=Estelle |last6=Lemaire |first6=Marc |journal=Chemical Reviews |volume=115 |issue=16 |pages=8609–8651 |pmid=26196761 |url=https://hal.archives-ouvertes.fr/hal-01312971/file/ChemRev_2015_115_8609-8651.pdf }}</ref>
==Occurrence==
In 2009, 3-MCPD was found in some [[East Asian]] and [[Southeast Asian]] sauces such as [[oyster sauce]], [[Hoisin sauce]], and [[soy sauce]].<ref>{{Cite web | url=http://www.food.gov.uk/multimedia/webpage/soyproductsqa/ | archive-url=https://web.archive.org/web/20140222035933/http://www.food.gov.uk/multimedia/webpage/soyproductsqa/ | url-status=dead | archive-date=2014-02-22 | title=Food Standards Agency - 3-MCPD in soy sauce and related products - Q&As}}</ref> 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.<ref>{{Cite journal | url = http://www.efsa.europa.eu/en/efsajournal/pub/3381| title = Analysis of occurrence of 3-monochloropropane-1,2-diol (3-MCPD) in food in Europe in the years 2009-2011 and preliminary exposure assessment | author = European Food Safety Authority | journal = EFSA Journal | date = 2013 | volume = 11 | issue = 9 | pages = 3381 | doi = 10.2903/j.efsa.2013.3381| doi-access = free }}</ref>
3-MCPD can also be found in many paper products treated with polyamidoamine-epichlorohydrin wet-strength resins.<ref>{{Cite journal|last1=Bodén|first1=Lennart|last2=Lundgren|first2=Michael|last3=Stensiö|first3=Karl-Erland|last4=Gorzynski|first4=Marek|date=1997-11-14|title=Determination of 1,3-dichloro-2-propanol and 3-chloro-1,2-propanediol in papers treated with polyamidoamine-epichlorohydrin wet-strength resins by gas chromatography-mass spectrometry using selective ion monitoring|journal=Journal of Chromatography A|volume=788|issue=1|pages=195–203|doi=10.1016/S0021-9673(97)00711-5}}</ref>
==Absorption and toxicity==
The [[International Agency for Research on Cancer]] has classified 3-MCPD as [[List of IARC Group 2B carcinogens|Group 2B]], "possibly carcinogenic to humans".<ref>{{cite web | url = http://monographs.iarc.fr/ENG/Classification/latest_classif.php | title = List of classifications | publisher = International Agency for Research on Cancer | access-date = 2017-12-19 | archive-url = https://web.archive.org/web/20170610015529/http://monographs.iarc.fr/ENG/Classification/latest_classif.php | archive-date = 2017-06-10 | url-status = dead }}</ref> 3-MCPD is carcinogenic in rodents via a non-[[genotoxic]] mechanism.<ref name="pmid12960406">{{cite journal
| vauthors=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
| date=September 2003
| pmid=12960406
| doi=10.1093/mutage/geg017
| doi-access=free
}}</ref>  It is able to cross the [[blood-testis barrier]] and [[blood–brain barrier]].<ref>{{cite journal|last1=Edwards|first1=Elizabeth M.|last2=Jones|first2=A. R.|last3=Waites|first3=G. M. H.|title=The entry of alpha-chlorohydrin into body fluids of male rats and its effect upon the incorporation of glycerol into lipids|journal=J Reprod Fertil|date=May 1975|volume=43|issue=2|pages=225–232|doi=10.1530/jrf.0.0430225|pmid=1127646|url=http://www.reproduction-online.org/content/43/2/225.long|doi-access=free}}</ref>  The oral {{LD50}} of 3-chloro-1,2-propanediol is 152&nbsp;mg/kg bodyweight in rats.<ref name="pmid5443210" />
3-MCPD also has male antifertility effects <ref name="pmid5443210">{{cite journal
| vauthors=Ericsson RJ, Baker VF
| title=Male antifertility compounds: biological properties of U-5897 and U-15,646
| journal= Journal of Reproduction and Fertility
| volume=21
| issue=2
| pages=267–73
| date=March 1970
| pmid=5443210
| doi=10.1530/jrf.0.0210267
| s2cid=32271242
}}</ref><ref name="pmid5520328">{{cite journal
|vauthors = 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
|date     = April 1970
|pmid     = 5520328
|doi      = 10.1095/biolreprod2.2.299
|doi-access= free
}}{{Dead link|date=September 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> and can be used as a rat [[chemosterilant]].<ref name="pmid5428943">{{cite journal
| vauthors=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
| date=July 1970
| pmid=5428943
| doi=10.1530/jrf.0.0220213
| doi-access=free
}}</ref>
==Legal limits==
The joint [[Food Standards Australia New Zealand]] (FSANZ) set a limit for 3-MCPD in soy sauce of 0.02&nbsp;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 (United Kingdom)|Ministry of Agriculture, Fisheries and Food]]/[[Department of Health (United Kingdom)|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.<ref name="pmid11271703">{{cite journal
| vauthors=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
| date=November 2000
| pmid=11271703
| doi=10.1080/026520300750038072
| s2cid=45724146
}}</ref>
In 2001, the United Kingdom [[Food Standards Agency]] (FSA) found in tests of various oyster sauces and [[soy sauce]]s 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.<ref>{{Cite web |url=http://www.food.gov.uk/news/pressreleases/2001/jun/soysaucerecall |title=Food.gov.uk press release soysauce |access-date=2008-10-16 |archive-date=2010-12-10 |archive-url=https://web.archive.org/web/20101210132240/http://www.food.gov.uk/news/pressreleases/2001/jun/soysaucerecall |url-status=dead }}</ref><ref>{{Cite web |url=http://www.food.gov.uk/multimedia/bigimages/soysauceproducts.gif |title=Chart with five mentions of affected oyster sauces |access-date=2008-10-16 |archive-date=2009-08-05 |archive-url=https://web.archive.org/web/20090805213829/http://www.food.gov.uk/multimedia/bigimages/soysauceproducts.gif |url-status=dead }}</ref>
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 (brand)|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.<ref>[http://www.food.gov.uk/multimedia/pdfs/soyadviceleaflet.pdf SOY SAUCE – PUBLIC HEALTH ADVICE] {{webarchive|url=https://web.archive.org/web/20120609110044/http://www.food.gov.uk/multimedia/pdfs/soyadviceleaflet.pdf |date=2012-06-09 }} Food Standards Agency 2001</ref><ref name="bar.gov.ph">{{cite web |url=http://www.bar.gov.ph/chronicle-home/archives-list/393-may-2004-issue/2970-is-your-soy-sauce-safe |title=Is your soy sauce safe? |author=Junelyn S. de la Rosa |publisher=Bar.gov.ph |date=May 2004 |access-date=1 January 2015 |archive-url=https://web.archive.org/web/20150115192331/http://www.bar.gov.ph/chronicle-home/archives-list/393-may-2004-issue/2970-is-your-soy-sauce-safe |archive-date=2015-01-15 |url-status=dead }}</ref><ref>{{cite web|title=Tests Show More Soy Sauces are Unsafe|url=http://archive.foodstandards.gov.au/scienceandeducation/mediacentre/mediareleases/archivedmediareleases/mediareleases2001/testsshowmoresoysauc1077.cfm|website=Food Standards Australia New Zealand|date=8 October 2001|access-date=2013-06-23|archive-url=https://archive.today/20130624143305/http://archive.foodstandards.gov.au/scienceandeducation/mediacentre/mediareleases/archivedmediareleases/mediareleases2001/testsshowmoresoysauc1077.cfm|archive-date=2013-06-24|url-status=dead}}</ref>
Between 2002 and 2004, relatively high levels of 3-MCPD and other [[chloropropanol]]s were found in soy sauce and other foods in China.<ref name="pmid17613068">{{cite journal
| vauthors=Fu WS, Zhao Y, Zhang G
| 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
| date=August 2007
| pmid=17613068
| doi=10.1080/02652030701246039
| s2cid=20880307
| display-authors=etal}}</ref>
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,<ref>[http://english.vietnamnet.vn/reports/2007/05/699774/ Soya sauce stirs worry and discontentment among public] {{webarchive |url=https://web.archive.org/web/20100515090016/http://english.vietnamnet.vn/reports/2007/05/699774/ |date=May 15, 2010 |url-status=dead}}</ref> 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."<ref>[https://www.smh.com.au/world/toxic-soy-sauce-chemical-veggies--food-scares-hit-vietnam-20070912-yib.html Toxic soy sauce, chemical veggies -- food scares hit Vietnam] {{webarchive|url=https://web.archive.org/web/20100119040101/http://afp.google.com/article/ALeqM5iiMrrBvLTLGX3P0uXmSqeT1Zjayw |date=2010-01-19 |url-status=dead}}</ref>
In March 2008, in Australia, "carcinogens" were found in soy sauces, and Australians were advised to avoid soy sauce.<ref>{{Cite web |url=http://www.news.com.au/story/0,23599,23392636-29277,00.html |title='Cancer chemical' in soy sauce |access-date=2008-11-22 |archive-date=2008-03-19 |archive-url=https://web.archive.org/web/20080319011524/http://www.news.com.au/story/0,23599,23392636-29277,00.html |url-status=dead }}</ref>
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 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 biscuit]]s from [[Asda]]. The highest levels of 3-MCPD found in a non- soy sauce product, crackers, was 134[[μg]]/kg. The highest level of 3-MCPD found in soy sauce was 93,000μg/kg, 700 times higher.
In 2006 the legal limit for 3-MCPD contained in acid-hydrolysed vegetable protein (HVP) and soy sauce was set at 20μg/kg, the legislation was revised further in 2020 to limit the amount of 3-MCPD across all vegetable oils and fats as well as oils made from marine life which are either produced and made available for consumers or added as an ingredient to other foods.<ref>{{Cite web|url=https://www.ifst.org/resources/information-statements/3-monochloropropane-diol-3-mcpd-3-mcpd-esters-and-glycidyl-esters |title=3-monochloropropane diol (3-MCPD), 3-MCPD esters and glycidyl esters |access-date=2024-07-07}}</ref>
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.<ref>{{Cite journal|last1=Becalski|first1=Adam|last2=Zhao|first2=Tony|last3=Breton|first3=Francois|last4=Kuhlmann|first4=Jan|date=2016-09-01|title=2- and 3-Monochloropropanediols in paper products and their transfer to foods|journal=Food Additives & Contaminants: Part A|volume=33|issue=9|pages=1499–1508|doi=10.1080/19440049.2016.1223353|issn=1944-0049|pmid=27598381|s2cid=25763740}}</ref> 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 0.2-2μg/g.
==Further reading==
*3-MCPD is a versatile multifunctional building block.<ref>{{cite journal|doi=10.1021/ma052448w|title=A Click Approach to Unprotected Glycodendrimers†|journal=Macromolecules|volume=39|issue=6|pages=2113–2120|year=2006|last1=Fernandez-Megia|first1=Eduardo|last2=Correa|first2=Juan|last3=Rodríguez-Meizoso|first3=Irene|last4=Riguera|first4=Ricardo|bibcode=2006MaMol..39.2113F}}</ref>
==References==
{{reflist|30em}}
==External links==
*{{Commonscatinline|3-Chloro-1,2-propandiol}}
<!-- * [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] -->
{{Consumer Food Safety}}
{{DEFAULTSORT:MCPD}}
[[Category:Vicinal diols]]
[[Category:IARC Group 2B carcinogens]]
[[Category:Organochlorides]]
[[Category:Spermatotoxicants]]
[[Category:Halohydrins]]