<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:17 UTC</creation_date>
  <update_date>2025-11-18 23:38:28 UTC</update_date>
  <accession>FDB012642</accession>
  <name>Patulin</name>
  <description>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.</description>
  <synonyms>
    <synonym>2,4-Dihydroxy-2H-pyran-&amp;alpha;-acetic acid, 3, 4-lactone</synonym>
    <synonym>2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactone</synonym>
    <synonym>2H-Pyran-&amp;alpha;)-acetic acid, 2, 4-dihydroxy-,3,4-lactone</synonym>
    <synonym>2H-Pyran-&amp;alpha;)-acetic acid, 2,4-dihydroxy-, 3,4-lactone</synonym>
    <synonym>2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactone</synonym>
    <synonym>2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactone</synonym>
    <synonym>4-Hydroxy-4,6-dihydrofuro[4,5-c]pyran-2-one</synonym>
    <synonym>4-Hydroxy-4H-furo(3,2-C)pyran-2(6H)-one</synonym>
    <synonym>4-Hydroxy-4H-furo(3,3-c)pyran-2(6H)-one</synonym>
    <synonym>4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one</synonym>
    <synonym>4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 9CI, 8CI</synonym>
    <synonym>4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one</synonym>
    <synonym>4H-Furo(3,2-c)pyran-2(6H)-one, 4-hydroxy-</synonym>
    <synonym>4H-Furo(3,3-c)pyran-2(6H)-one, 4-hydroxy-</synonym>
    <synonym>4H-Furo[3,2-c]pyran-2(6H)-one, 4-hydroxy-</synonym>
    <synonym>Antibiotic Sch 351633</synonym>
    <synonym>Antibiotic YS 1649</synonym>
    <synonym>Clairformin</synonym>
    <synonym>Clavacin</synonym>
    <synonym>Clavatin</synonym>
    <synonym>Clavicin</synonym>
    <synonym>Claviform</synonym>
    <synonym>Claviformin</synonym>
    <synonym>Clavitin</synonym>
    <synonym>Expansin</synonym>
    <synonym>Expansine</synonym>
    <synonym>Expansion</synonym>
    <synonym>Flavicin</synonym>
    <synonym>Gigantic acid?</synonym>
    <synonym>Gigantin</synonym>
    <synonym>Leucopin</synonym>
    <synonym>Mycoin</synonym>
    <synonym>Mycoin c</synonym>
    <synonym>Mycoin C3</synonym>
    <synonym>Mycoine C3</synonym>
    <synonym>Mycosin</synonym>
    <synonym>PAT</synonym>
    <synonym>Patuline</synonym>
    <synonym>Penatin</synonym>
    <synonym>Penicidin</synonym>
    <synonym>Sch 351633</synonym>
    <synonym>Tercinin</synonym>
    <synonym>Terinin</synonym>
    <synonym>YS 1649</synonym>
  </synonyms>
  <chemical_formula>C7H6O4</chemical_formula>
  <average_molecular_weight>154.1201</average_molecular_weight>
  <monisotopic_moleculate_weight>154.02660868</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one</iupac_name>
  <traditional_iupac>patulin</traditional_iupac>
  <cas_registry_number>149-29-1</cas_registry_number>
  <smiles>OC1OCC=C2OC(=O)C=C12</smiles>
  <inchi>InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2</inchi>
  <inchikey>ZRWPUFFVAOMMNM-UHFFFAOYSA-N</inchikey>
  <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.</description>
    <direct_parent>Pyrans</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyrans</class>
    <sub_class/>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Butenolides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Enol esters</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-furanone</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dihydrofuran</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Enol ester</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pyran</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Mycotoxins</external_descriptor>
      <external_descriptor>furopyran</external_descriptor>
      <external_descriptor>gamma-lactone</external_descriptor>
      <external_descriptor>lactol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.63e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 111°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>154.1201</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>154.02660868</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1OCC=C2OC(=O)C=C12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C7H6O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>ZRWPUFFVAOMMNM-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>55.76</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>37.03</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2664184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2664185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2664186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3017214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3017215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3017216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>125577</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34299</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32471ed0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32471d18&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32471b60&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Pomes</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
