3-MCPD

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3-MCPD
Skeletal formula
Ball-and-stick model
Names
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
96-24-2 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:18721 YesY
ChemSpider 7018 YesY
ECHA InfoCard 100.002.267
EC Number 202-492-4
KEGG C18676 N
PubChem 7290
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
Safety data sheet External MSDS
R-phrases R26/27/28-R36/37/38
S-phrases S24-S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

3-MCPD (3-monochloropropane-1,2-diol or 3-chloropropane-1,2-diol) is an 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 chloropropanols.

It is primarily created in foods by protein hydrolysis by adding hydrochloric acid at high temperature to speed up the breakdown of proteins into amino acids. Under these conditions, chloride can react with the glycerol backbone of lipids to produce 3-MCPD. 3-MCPD can also occur in foods which have been in contact with materials containing epichlorohydrin-based wet-strength resins which are used in the production of some tea bags and sausage casings.[1]

It has been found in some East Asian and Southeast Asian sauces such as oyster sauce, Hoisin sauce and soy sauce.[2] Using hydrochloric acid rather than traditional slow fermentation is a far cheaper and faster method but unavoidably creates chloropropanols. An EFSA report indicated margarine, vegetable oils (excluding walnut oil), preserved meats, breads, and fine bakery wares as major sources in Europe.[3]

3-MCDP dinitrate is called Clonitrate, is a vasodilator (c.f. nitroglycerin).

Absorption and toxicity[edit]

3-MCPD is carcinogenic in rodents via a supposed non-genotoxic mechanism.[4] It is able to cross the blood-testis barrier and blood–brain barrier.[5] The oral LD50 of 3-chloro-1,2-propanediol is 152 mg/kg bodyweight in rats.[6]

3-MCPD also has male antifertility effects [7][8] and can be used as a rat chemosterilant.[9]

Legal limits[edit]

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.

Incidents[edit]

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) in 2000 and reported more than half of the samples collected from retail outlets contained various levels of 3-MCPD.[10]

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.[11][12]

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 (金蘭）, Golden Swan, Sinsin, Tung Chun, and Wanjasham soy sauce. 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.[13][14][15]

Relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China between 2002 and 2004.[16]

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,[17] 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." [18]

In March 2008 in Australia, "carcinogens" were found in soy sauces there, and Australians were advised to avoid soy sauce.[19]

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 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[when?] will be 20 µg per kg, but the safety guideline on daily intake is 120 µg for a 60 kg person per day.[20]

Current status[edit]

Some companies[which?] 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 1,3-DCP, a byproduct of 3-MCPD, there is no standard to meet as it is unregulated, although, according to research, it could cause cancer and mutations.[14]

References[edit]

  1. ^ IFST issues statement on 3-MCPD
  2. ^ http://www.food.gov.uk/multimedia/webpage/soyproductsqa/
  3. ^ Analysis of occurrence of 3-monochloropropane-1,2-diol (3-MCPD) in food in Europe in the years 2009-2011 and preliminary exposure assessment
  4. ^ 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. 
  5. ^ Edwards et al. 1975[full citation needed]
  6. ^ Ericsson & Baker, 1970
  7. ^ Ericsson RJ, Baker VF (March 1970). "Male antifertility compounds: biological properties of U-5897 and U-l5,646". Journal of reproduction and fertility. 21 (2): 267–73. doi:10.1530/jrf.0.0210267. PMID 5443210. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ Food.gov.uk press release soysauce
  12. ^ Chart with five mentions of affected oyster sauces
  13. ^ SOY SAUCE – PUBLIC HEALTH ADVICE Food Standards Agency 2001
  14. ^ a b Junelyn S. de la Rosa (May 2004). "Is your soy sauce safe?". Bar.gov.ph. Retrieved 1 January 2015. 
  15. ^ TESTS SHOW MORE SOY SAUCES ARE UNSAFE Food Standards Australia New Zealand, 8 October 2001
  16. ^ 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. 
  17. ^ Soya sauce stirs worry and discontentment among public Archived May 15, 2010, at the Wayback Machine.
  18. ^ Toxic soy sauce, chemical veggies -- food scares hit Vietnam
  19. ^ 'Cancer chemical' in soy sauce
  20. ^ The cancer chemical lurking in our food

External links[edit]

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