2-MCPD

2-MCPD
Names
Preferred IUPAC name
2-Chloropropane-1,3-diol
Other names
2-monochloropropane-1,3-diol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.123 Edit this at Wikidata
EC Number
  • 207-834-6
UNII
  • InChI=1S/C3H7ClO2/c4-3(1-5)2-6/h3,5-6H,1-2H2
    Key: DYPJJAAKPQKWTM-UHFFFAOYSA-N
  • C(C(CO)Cl)O
Properties
C3H7ClO2
Molar mass 110.54 g·mol−1
Appearance colorless liquid
Boiling point 146 °C; 295 °F; 419 K 18 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-MCPD (2-chloropropane-1,3-diol) is an organic chemical compound with the formula ClCH(CH2(OH))2. It is a colorless liquid. The compound has attracted notoreity as a food contaminant. Together with the 3-MCPD, it is one of two chloropropanols food contaminants.[1] It is suspected to be carcinogenic in humans.[2]

2-MCPD, together with its isomer 3-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 2- and 3-MCPD.

Further reading

  • Kuhlmann, Jan (2019). "2-Monochloropropanediol (2-MCPD), 3-Monochloropropanediol (3-MCPD), and Glycidol in Infant and Adult/Pediatric Nutritional Formula: Single-Laboratory Validation, First Action 2018.12". Journal of AOAC International. 102 (4): 1205–1220. doi:10.5740/jaoacint.19-0026. PMID 30992094.
  • Buhrke, T.; Frenzel, F.; Kuhlmann, J.; Lampen, A. (2015). "2-Chloro-1,3-propanediol (2-MCPD) and its fatty acid esters: Cytotoxicity, metabolism, and transport by human intestinal Caco-2 cells". Archives of Toxicology. 89 (12): 2243–2251. doi:10.1007/s00204-014-1395-3. PMID 25354796.

References

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

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