Wikipedia

3-MCPD

(Redirected from Alpha-chlorohydrin)

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. The compound has attracted notoreity as the most common member of chemical food contaminants known as chloropropanols.[1] It is suspected to be carcinogenic in humans.[2]

3-MCPD
Skeletal formula
Ball-and-stick model
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 Edit this at Wikidata
EC Number
  • 202-492-4
68752
KEGG
UNII
  • InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2 checkY
    Key: SSZWWUDQMAHNAQ-UHFFFAOYSA-N checkY
  • InChI=1/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
    Key: SSZWWUDQMAHNAQ-UHFFFAOYAR
  • ClCC(O)CO
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:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
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).
☒N verify (what is checkY☒N ?)

Accidental and intentional production

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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:

HOCH(CH2OH)2 + HCl → HOCH(CH2Cl)(CH2OH) + H2O

The same compound can be produced by hydrolysis of epichlorohydrin.[3]

Occurrence

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In 2009, 3-MCPD was found in some East Asian and Southeast Asian sauces such as oyster sauce, Hoisin sauce, and soy sauce.[4] 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.[5]

3-MCPD can also be found in many paper products treated with polyamidoamine-epichlorohydrin wet-strength resins.[6]

Absorption and toxicity

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The International Agency for Research on Cancer has classified 3-MCPD as Group 2B, "possibly carcinogenic to humans".[7] 3-MCPD is carcinogenic in rodents via a non-genotoxic mechanism.[8] It is able to cross the blood-testis barrier and blood–brain barrier.[9] The oral LD50 of 3-chloro-1,2-propanediol is 152 mg/kg bodyweight in rats.[10]

3-MCPD also has male antifertility effects [10][11] and can be used as a rat chemosterilant.[12]

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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

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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.[13]

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.[14][15]

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.[16][17][18] Between 2002 and 2004, relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China.[19]

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,[20] 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."[21]

In March 2008, in Australia, "carcinogens" were found in soy sauces, and Australians were advised to avoid soy sauce.[22]

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 134μg/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.[23]

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 0.2-2μg/g.

Further reading

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  • 3-MCPD is a versatile multifunctional building block.[25]

References

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  1. ^ Howard, Philip H.; Muir, Derek C. G. (2010). "Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce". Environmental Science & Technology. 44 (7): 2277–2285. Bibcode:2010EnST...44.2277H. doi:10.1021/es903383a. PMID 20163179.
  2. ^ "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". EFSA Journal. 14 (5). 2016. doi:10.2903/j.efsa.2016.4426. hdl:2164/7793.
  3. ^ Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015). "Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies" (PDF). Chemical Reviews. 115 (16): 8609–8651. doi:10.1021/cr5004002. PMID 26196761.
  4. ^ "Food Standards Agency - 3-MCPD in soy sauce and related products - Q&As". Archived from the original on 2014-02-22.
  5. ^ European Food Safety Authority (2013). "Analysis of occurrence of 3-monochloropropane-1,2-diol (3-MCPD) in food in Europe in the years 2009-2011 and preliminary exposure assessment". EFSA Journal. 11 (9): 3381. doi:10.2903/j.efsa.2013.3381.
  6. ^ Bodén, Lennart; Lundgren, Michael; Stensiö, Karl-Erland; Gorzynski, Marek (1997-11-14). "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 of Chromatography A. 788 (1): 195–203. doi:10.1016/S0021-9673(97)00711-5.
  7. ^ "List of classifications". International Agency for Research on Cancer. Archived from the original on 2017-06-10. Retrieved 2017-12-19.
  8. ^ Robjohns S, Marshall R, Fellows M, Kowalczyk G (September 2003). "In vivo genotoxicity studies with 3-monochloropropan-1,2-diol". Mutagenesis. 18 (5): 401–4. doi:10.1093/mutage/geg017. PMID 12960406.
  9. ^ Edwards, Elizabeth M.; Jones, A. R.; Waites, G. M. H. (May 1975). "The entry of alpha-chlorohydrin into body fluids of male rats and its effect upon the incorporation of glycerol into lipids". J Reprod Fertil. 43 (2): 225–232. doi:10.1530/jrf.0.0430225. PMID 1127646.
  10. ^ a b Ericsson RJ, Baker VF (March 1970). "Male antifertility compounds: biological properties of U-5897 and U-15,646". Journal of Reproduction and Fertility. 21 (2): 267–73. doi:10.1530/jrf.0.0210267. PMID 5443210. S2CID 32271242.
  11. ^ Samojlik E, Chang MC (April 1970). "Antifertility activity of 3-chloro-1,2-propanediol (U-5897) on male rats". Biology of Reproduction. 2 (2): 299–304. doi:10.1095/biolreprod2.2.299. PMID 5520328.[permanent dead link‍]
  12. ^ Ericsson RJ (July 1970). "Male antifertility compounds: U-5897 as a rat chemosterilant". Journal of Reproduction and Fertility. 22 (2): 213–22. doi:10.1530/jrf.0.0220213. PMID 5428943.
  13. ^ Macarthur R, Crews C, Davies A, Brereton P, Hough P, Harvey D (November 2000). "3-monochloropropane-1,2-diol (3-MCPD) in soy sauces and similar products available from retail outlets in the UK". Food Additives and Contaminants. 17 (11): 903–6. doi:10.1080/026520300750038072. PMID 11271703. S2CID 45724146.
  14. ^ "Food.gov.uk press release soysauce". Archived from the original on 2010-12-10. Retrieved 2008-10-16.
  15. ^ "Chart with five mentions of affected oyster sauces". Archived from the original on 2009-08-05. Retrieved 2008-10-16.
  16. ^ SOY SAUCE – PUBLIC HEALTH ADVICE Archived 2012-06-09 at the Wayback Machine Food Standards Agency 2001
  17. ^ Junelyn S. de la Rosa (May 2004). "Is your soy sauce safe?". Bar.gov.ph. Archived from the original on 2015-01-15. Retrieved 1 January 2015.
  18. ^ "Tests Show More Soy Sauces are Unsafe". Food Standards Australia New Zealand. 8 October 2001. Archived from the original on 2013-06-24. Retrieved 2013-06-23.
  19. ^ Fu WS, Zhao Y, Zhang G, et al. (August 2007). "Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004". Food Additives and Contaminants. 24 (8): 812–9. doi:10.1080/02652030701246039. PMID 17613068. S2CID 20880307.
  20. ^ Soya sauce stirs worry and discontentment among public Archived May 15, 2010, at the Wayback Machine
  21. ^ Toxic soy sauce, chemical veggies -- food scares hit Vietnam Archived 2010-01-19 at the Wayback Machine
  22. ^ "'Cancer chemical' in soy sauce". Archived from the original on 2008-03-19. Retrieved 2008-11-22.
  23. ^ "3-monochloropropane diol (3-MCPD), 3-MCPD esters and glycidyl esters". Retrieved 2024-07-07.
  24. ^ Becalski, Adam; Zhao, Tony; Breton, Francois; Kuhlmann, Jan (2016-09-01). "2- and 3-Monochloropropanediols in paper products and their transfer to foods". Food Additives & Contaminants: Part A. 33 (9): 1499–1508. doi:10.1080/19440049.2016.1223353. ISSN 1944-0049. PMID 27598381. S2CID 25763740.
  25. ^ Fernandez-Megia, Eduardo; Correa, Juan; Rodríguez-Meizoso, Irene; Riguera, Ricardo (2006). "A Click Approach to Unprotected Glycodendrimers†". Macromolecules. 39 (6): 2113–2120. Bibcode:2006MaMol..39.2113F. doi:10.1021/ma052448w.
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