Structure via PubChem · Public domain (PubChem)
3-MCPD
Sign in to saveAlso known as chlorodeoxyglycerol, 1-chloro-2,3-propanediol, 3-chloro-1,2-propanediol, (RS)-3-chloro-1,2-propanediol, 3-Monochloro-1,2-propanediol
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. It is suspected to be carcinogenic in humans.
Chemical data
- Formula
- C3H7ClO2
- Molecular weight
- 110.54 g/mol
- IUPAC name
- 3-chloropropane-1,2-diol
- SMILES
- C(C(CCl)O)O
- InChIKey
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N
- XLogP
- -0.5
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
787 papers- 3-MCPD as contaminant in processed foods: State of knowledge and remaining challenges.Food chemistry · 2023
- 3-MCPD exposure enhances ovarian fibrosis and reduces oocyte quality in mice.Environmental pollution (Barking, Essex : 1987) · 2023
- 3-MCPD: A Worldwide Problem of Food Chemistry.Critical reviews in food science and nutrition · 2016
- Alleviating 3-MCPD-induced male reproductive toxicity: Mechanistic insights and resveratrol intervention.Ecotoxicology and environmental safety · 2024
- 3-MCPD Induced Mitochondrial Damage of Renal Cells Via the Rhythmic Protein BMAL1 Targeting SIRT3/SOD2.Journal of agricultural and food chemistry · 2023
via PubMed
Wikidata facts
Show 8 more facts
- Commons category
- 3-Chloro-1,2-propandiol
- found in taxon
- Eunicea mammosa
- chemical formula
- C₃H₇ClO₂
- density
- 1.32
- canonical SMILES
- C(C(CCl)O)O
- boiling point
- 213
- subject has role
- carcinogen
- melting point
- -40
via Wikidata · CC0
~6 min read
Encyclopedic overview
8 sectionsContents
- Accidental and intentional production
- Occurrence
- Absorption and toxicity
- Legal limits
- History
- Other uses
- References
- External links
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. It is suspected to be carcinogenic in humans.
==Accidental and intentional production== 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:
Excerpted from Wikipedia’s “3-MCPD” article, available under the CC BY-SA 4.0 licence.
Available in 14 languages
via Wikidata sitelinks · CC0