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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:06:19 UTC
Update Date2023-02-21 17:24:08 UTC
HMDB IDHMDB0034299
Secondary Accession Numbers
  • HMDB34299
Metabolite Identification
Common NamePatulin
DescriptionPatulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice
Structure
Thumb
Synonyms
Chemical FormulaC7H6O4
Average Molecular Weight154.1201
Monoisotopic Molecular Weight154.02660868
IUPAC Name4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one
Traditional Namepatulin
CAS Registry Number149-29-1
SMILES
OC1OCC=C2OC(=O)C=C12
InChI Identifier
InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
InChI KeyZRWPUFFVAOMMNM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassNot Available
Direct ParentPyrans
Alternative Parents
Substituents
  • 2-furanone
  • Pyran
  • Dihydrofuran
  • Enol ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012642
KNApSAcK IDC00024000
Chemspider ID4534
KEGG Compound IDC16748
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPatulin
METLIN IDNot Available
PubChem Compound4696
PDB IDNot Available
ChEBI ID74926
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1272171
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ozsoy N, Selmanoglu G, Kockaya EA, Gul N, Cebesoy S: Effect of patulin on the interdigitating dendritic cells (IDCs) of rat thymus. Cell Biochem Funct. 2008 Mar-Apr;26(2):192-6. [PubMed:17702051 ]
  2. McKinley ER, Carlton WW, Boon GD: Patulin mycotoxicosis in the rat: toxicology, pathology and clinical pathology. Food Chem Toxicol. 1982 Jun;20(3):289-300. [PubMed:7201955 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .