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Wikipedia

3-MCPD

January 01, 1970

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

3-MCPD
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
  • 96-24-2 Y
3D model (JSmol)
  • Interactive image
635684
ChEBI
  • CHEBI:18721 Y
ChEMBL
  • ChEMBL3185949
ChemSpider
  • 7018 Y
ECHA InfoCard 100.002.267
EC Number
  • 202-492-4
68752
KEGG
  • C18676 Y
  • 7290
UNII
  • QGS78A3T6P Y
  • DTXSID4020664
  • InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2 Y
    Key: SSZWWUDQMAHNAQ-UHFFFAOYSA-N Y
  • 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:
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 YN ?)

Accidental and intentional production edit

3-MCPD is thought to be produced when 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. 3-MCPD is also thought to arise in foods that 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.[3]

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.[4]

Occurrence edit

In 2009, 3-MCPD was found in some East Asian and Southeast Asian sauces such as oyster sauce, Hoisin sauce, and soy sauce.[5] 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.[6]

3-MCPD can also be found in many paper products treated with polyamidoamine-epichlorohydrin wet-strength resins.[7]

Absorption and toxicity edit

The International Agency for Research on Cancer has classified 3-MCPD as Group 2B, "possibly carcinogenic to humans".[8] 3-MCPD is carcinogenic in rodents via a non-genotoxic mechanism.[9] It is able to cross the blood-testis barrier and blood–brain barrier.[10] The oral LD50 of 3-chloro-1,2-propanediol is 152 mg/kg bodyweight in rats.[11]

3-MCPD also has male antifertility effects [11][12] and can be used as a rat chemosterilant.[13]

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.

History edit

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.[14]

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.[15][16]

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.[17][18][19] Between 2002 and 2004, relatively high levels of 3-MCPD and other chloropropanols were found in soy sauce and other foods in China.[20]

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,[21] 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."[22]

In March 2008, in Australia, "carcinogens" were found in soy sauces, and Australians were advised to avoid soy sauce.[23]

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.[citation needed]

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 0.2-2 μg/g.

References edit

  1. ^ 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.
  2. ^ 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.
  3. ^ IFST issues statement on 3-MCPD
  4. ^ 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.
  5. ^ . Archived from the original on 2014-02-22.
  6. ^ 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.
  7. ^ 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.
  8. ^ . International Agency for Research on Cancer. Archived from the original on 2017-06-10. Retrieved 2017-12-19.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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]
  13. ^ 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.
  14. ^ 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.
  15. ^ . Archived from the original on 2010-12-10. Retrieved 2008-10-16.
  16. ^ . Archived from the original on 2009-08-05. Retrieved 2008-10-16.
  17. ^ SOY SAUCE – PUBLIC HEALTH ADVICE 2012-06-09 at the Wayback Machine Food Standards Agency 2001
  18. ^ Junelyn S. de la Rosa (May 2004). . Bar.gov.ph. Archived from the original on 2015-01-15. Retrieved 1 January 2015.
  19. ^ "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.
  20. ^ 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.
  21. ^ Soya sauce stirs worry and discontentment among public May 15, 2010, at the Wayback Machine
  22. ^ Toxic soy sauce, chemical veggies -- food scares hit Vietnam 2010-01-19 at the Wayback Machine
  23. ^ . Archived from the original on 2008-03-19. Retrieved 2008-11-22.
  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.

External links edit

  •   Media related to 3-Chloro-1,2-propandiol at Wikimedia Commons
  • Chloropropanols (WHO Food Additive Series 32)

January 01, 1970
mcpd, monochloropropane, diol, chloropropane, diol, organic, chemical, compound, with, formula, hoch2ch, ch2cl, colorless, liquid, versatile, multifunctional, building, block, compound, attracted, attention, most, common, member, chemical, food, contaminants, . 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 It is a versatile multifunctional building block 1 The compound has attracted attention as the most common member of chemical food contaminants known as chloropropanols 2 It is suspected to be carcinogenic in humans 3 MCPD Names Preferred IUPAC name 3 Chloropropane 1 2 diol Other names 3 Monochloropropane 1 2 diol a Chlorohydrin Glycerol a monochlorohydrin Chlorodeoxyglycerol 3 Chloro 1 2 propanediol Identifiers CAS Number 96 24 2 Y 3D model JSmol Interactive image Beilstein Reference 635684 ChEBI CHEBI 18721 Y ChEMBL ChEMBL3185949 ChemSpider 7018 Y ECHA InfoCard 100 002 267 EC Number 202 492 4 Gmelin Reference 68752 KEGG C18676 Y PubChem CID 7290 UNII QGS78A3T6P Y CompTox Dashboard EPA DTXSID4020664 InChI InChI 1S C3H7ClO2 c4 1 3 6 2 5 h3 5 6H 1 2H2 YKey SSZWWUDQMAHNAQ UHFFFAOYSA N YInChI 1 C3H7ClO2 c4 1 3 6 2 5 h3 5 6H 1 2H2Key SSZWWUDQMAHNAQ UHFFFAOYAR SMILES ClCC O CO Properties Chemical formula C 3H 7Cl O 2 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 Pictograms Signal word Danger Hazard statements H300 H312 H315 H318 H330 H351 H360 H370 H372 Precautionary statements 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 Y N Infobox references Contents 1 Accidental and intentional production 2 Occurrence 3 Absorption and toxicity 4 Legal limits 5 History 6 References 7 External linksAccidental and intentional production edit3 MCPD is thought to be produced when 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 3 MCPD is also thought to arise in foods that 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 3 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 4 Occurrence editIn 2009 3 MCPD was found in some East Asian and Southeast Asian sauces such as oyster sauce Hoisin sauce and soy sauce 5 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 6 3 MCPD can also be found in many paper products treated with polyamidoamine epichlorohydrin wet strength resins 7 Absorption and toxicity editThe International Agency for Research on Cancer has classified 3 MCPD as Group 2B possibly carcinogenic to humans 8 3 MCPD is carcinogenic in rodents via a non genotoxic mechanism 9 It is able to cross the blood testis barrier and blood brain barrier 10 The oral LD50 of 3 chloro 1 2 propanediol is 152 mg kg bodyweight in rats 11 3 MCPD also has male antifertility effects 11 12 and can be used as a rat chemosterilant 13 Legal limits editThe 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 editIn 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 14 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 15 16 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 17 18 19 Between 2002 and 2004 relatively high levels of 3 MCPD and other chloropropanols were found in soy sauce and other foods in China 20 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 21 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 22 In March 2008 in Australia carcinogens were found in soy sauces and Australians were advised to avoid soy sauce 23 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 mg per kg The highest level of 3 MCPD found in soy sauce was 93 000 mg per kg 700 times higher The legal limit for 3 MCPD coming in next year when will be 20 mg per kg but the safety guideline on daily intake is 120 mg for a 60 kg person per day citation needed 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 2 mg g References edit Fernandez Megia Eduardo Correa Juan Rodriguez Meizoso Irene Riguera Ricardo 2006 A Click Approach to Unprotected Glycodendrimers Macromolecules 39 6 2113 2120 Bibcode 2006MaMol 39 2113F doi 10 1021 ma052448w Howard Philip H Muir Derek C G 2010 Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce Environmental Science amp Technology 44 7 2277 2285 Bibcode 2010EnST 44 2277H doi 10 1021 es903383a PMID 20163179 IFST issues statement on 3 MCPD Sutter Marc Silva Eric Da Duguet Nicolas Raoul Yann Metay 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 Food Standards Agency 3 MCPD in soy sauce and related products Q amp As Archived from the original on 2014 02 22 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 Boden Lennart Lundgren Michael Stensio 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 List of classifications International Agency for Research on Cancer Archived from the original on 2017 06 10 Retrieved 2017 12 19 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 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 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 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 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 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 Food gov uk press release soysauce Archived from the original on 2010 12 10 Retrieved 2008 10 16 Chart with five mentions of affected oyster sauces Archived from the original on 2009 08 05 Retrieved 2008 10 16 SOY SAUCE PUBLIC HEALTH ADVICE Archived 2012 06 09 at the Wayback Machine Food Standards Agency 2001 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 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 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 Soya sauce stirs worry and discontentment among public Archived May 15 2010 at the Wayback Machine Toxic soy sauce chemical veggies food scares hit Vietnam Archived 2010 01 19 at the Wayback Machine Cancer chemical in soy sauce Archived from the original on 2008 03 19 Retrieved 2008 11 22 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 amp Contaminants Part A 33 9 1499 1508 doi 10 1080 19440049 2016 1223353 ISSN 1944 0049 PMID 27598381 S2CID 25763740 External links edit nbsp Media related to 3 Chloro 1 2 propandiol at Wikimedia Commons Chloropropanols WHO Food Additive Series 32 Retrieved from https en wikipedia org w index php title 3 MCPD amp oldid 1194399601, wikipedia, wiki, book, books, library,

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