Structure via PubChem · Public domain (PubChem)
patulin
Sign in to saveAlso known as PAT, expansine, clavatin, expansin, (2,4-dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone, 4,6-dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one, clavacin, claviformin
Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, Penicillium patulum. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened. It is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, the amount of patulin in apple products is generally viewed as a measure of the quali
Chemical data
- Formula
- C7H6O4
- Molecular weight
- 154.12 g/mol
- IUPAC name
- 4-hydroxy-4,6-dihydrofuro[3,2-c]pyran-2-one
- SMILES
- C1C=C2C(=CC(=O)O2)C(O1)O
- InChIKey
- ZRWPUFFVAOMMNM-UHFFFAOYSA-N
- XLogP
- -1
- Polar surface area
- 55.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
1,500 papers- Removal of patulin by thiol-compounds: A review.Toxicon : official journal of the International Society on Toxinology · 2022
- Patulin.IARC monographs on the evaluation of the carcinogenic risk of chemicals to man · 1976
- Patulin-degrading enzymes sources, structures, and mechanisms: A review.International journal of biological macromolecules · 2025
- Mycotoxin patulin in food matrices: occurrence and its biological degradation strategies.Drug metabolism reviews · 2019
- Patulin in food: A mycotoxin concern for human health and its management strategies.Toxicon : official journal of the International Society on Toxinology · 2021
via PubMed
Wikidata facts
- Mass
- 154.027
Show 4 more facts
- melting point
- 110.5
- chemical formula
- C₇H₆O₄
- Commons category
- Patulin
- canonical SMILES
- C1C=C2C(=CC(=O)O2)C(O1)O
via Wikidata · CC0
~7 min read
Article
13 sectionsContents
- Biosynthesis, synthesis, and reactivity
- Uses
- Sources of exposure
- Toxicity
- Acute
- Subacute
- Genotoxicity
- Reproduction studies
- Immunotoxicity
- Human health
- Risk management and regulations
- References
- External links
Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, Penicillium patulum. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened. It is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. Its presence is highly regulated.
==Biosynthesis, synthesis, and reactivity== Patulin is biosynthesized from 6-methylsalicylic acid via multiple chemical transformations.