3-MCPD

Source: Wikipedia, the free encyclopedia.
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 ?)

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

carcinogenic
in humans.

Accidental and intentional production

3-MCPD is thought to be produced when foods are treated at high temperatures with

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

In 2009, 3-MCPD was found in some

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

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

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

In 2000, a survey of soy sauces and similar products available in the UK was carried out by the Joint

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

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,

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,

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

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

  1. doi:10.1021/ma052448w
    .
  2. PMID 20163179
    .
  3. ^ IFST issues statement on 3-MCPD
  4. PMID 26196761
    .
  5. ^ "Food Standards Agency - 3-MCPD in soy sauce and related products - Q&As". Archived from the original on 2014-02-22.
  6. doi:10.2903/j.efsa.2013.3381
    .
  7. doi:10.1016/S0021-9673(97)00711-5
    .
  8. ^ "List of classifications". International Agency for Research on Cancer. Archived from the original on 2017-06-10. Retrieved 2017-12-19.
  9. PMID 12960406
    .
  10. PMID 1127646
    .
  11. ^
    S2CID 32271242
    .
  12. PMID 5520328.[permanent dead link
    ]
  13. PMID 5428943
    .
  14. S2CID 45724146
    .
  15. ^ "Food.gov.uk press release soysauce". Archived from the original on 2010-12-10. Retrieved 2008-10-16.
  16. ^ "Chart with five mentions of affected oyster sauces". Archived from the original on 2009-08-05. Retrieved 2008-10-16.
  17. ^ SOY SAUCE – PUBLIC HEALTH ADVICE Archived 2012-06-09 at the Wayback Machine Food Standards Agency 2001
  18. ^ 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.
  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. S2CID 20880307
    .
  21. ^ Soya sauce stirs worry and discontentment among public Archived May 15, 2010, at the Wayback Machine
  22. ^ Toxic soy sauce, chemical veggies -- food scares hit Vietnam Archived 2010-01-19 at the Wayback Machine
  23. ^ "'Cancer chemical' in soy sauce". Archived from the original on 2008-03-19. Retrieved 2008-11-22.
  24. S2CID 25763740
    .

External links
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