ContaminantDB: Patulin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (78)XML

Record Information

Version

1.0

Creation Date

2009-12-17 22:12:11 UTC

Update Date

2026-05-14 19:52:01 UTC

Accession Number

CHEM002630

Identification

Common Name

Patulin

Class

Small Molecule

Description

Patulin 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 ug/L in apple juice. Patulin has been shown to exhibit apoptotic and antibiotic functions (5, 6). Patulin belongs to the family of Pyrans. These 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.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Ester
Food Toxin
Fungal Toxin
Industrial/Workplace Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound
PFAS

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone	ChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone	ChEBI
4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one	ChEBI
Clavacin	ChEBI
Clavatin	ChEBI
Claviform	ChEBI
Claviformin	ChEBI
Expansin	ChEBI
Expansine	ChEBI
Mycoin C3	ChEBI
Mycoine C3	ChEBI
PAT	ChEBI
Patuline	ChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate, 3,4-lactone	Generator
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetate-3,4-lactone	Generator
2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactone	HMDB
2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactone	HMDB
2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactone	HMDB
4-Hydroxy-4,6-dihydrofuro[4,5-c]pyran-2-one	HMDB
4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo(3,3-c)pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one	HMDB
4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one, 9ci, 8ci	HMDB
Antibiotic SCH 351633	HMDB
Antibiotic ys 1649	HMDB
Clairformin	HMDB
Clavicin	HMDB
Clavitin	HMDB
Expansion	HMDB
Flavicin	HMDB
Gigantic acid?	HMDB
Gigantin	HMDB
Leucopin	HMDB
Mycoin	HMDB
Mycoin c	HMDB
Mycosin	HMDB
Penatin	HMDB
Penicidin	HMDB
SCH 351633	HMDB
Tercinin	HMDB
Terinin	HMDB
YS 1649	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Mass

154.120 g/mol

Monoisotopic Mass

154.027 g/mol

CAS Registry Number

149-29-1

IUPAC Name

4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one

Traditional Name

patulin

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 Key

ZRWPUFFVAOMMNM-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:74926 )
lactol (CHEBI:74926 )
furopyran (CHEBI:74926 )
Mycotoxins (C16748 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antibiotic

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Compact prisms.

Experimental Properties

Property	Value
Melting Point	111°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	163 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.38	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	13.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9700000000-5a48339184b0b8962504	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9600000000-3451d632d4f834dc62cc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-06be4453ffa97f478a45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d4bddadeb22df078c3c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-0775e607edc3b24dad13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9100000000-37c4497452b5b85a32f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a5039689c3996db29872	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1900000000-d8df1f0a351c47943c80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06uu-9200000000-cd27858111b7a99f8a9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-77b51b14a11efa7e4bd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-f1deb55458afa0cf487a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9200000000-ec01329ad017386b5211	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-5328d4e45a2fa398896e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-1000-3900000000-b2db7ade21b45c80a316	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-780f5433ebd56a09e203	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (4)

Mechanism of Toxicity

Patulin's strong affinity to sulfhydryl groups enables to to inhibit a number of enzymes, including succinate dehydrogenase, alcohol dehydrogenases, ATPases, acetylcholinesterase, aldolases, protein tyrosine phosphatases, RNA polymerases, aminoacyl-tRNA synthetase, ribonuclease H, and lactate dehydrogenase. This widespread enzyme inhibition has a number of effects, including inhibition of aerobic respiration, inhibition of RNA synthesis, and inhibition of protein synthesis. Patulin also affects some aspects of membrane permeability and causes DNA-strand breakage and chromosomal aberrations, likely contributing to it's genotoxicity. Patulin may also cause the development of allergies by inhibiting interferon-gamma production. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (11, 2, 3)

Metabolism

Metabolism of patulin is limited. No metabolic products have been identified. It is quite likely that the metabolic fragments or conjugated metabolites of patulin either are bound to the cell membrane or become incorporated into the cellular components. (11)

Toxicity Values

LD50: 29-48 mg/kg (Oral, Mouse) (12) LD50: 10 mg/kg (Subcutaneous, Mosue) (12) LD50: 5.7-8.17 mg/kg (Intraperitoneal, Mouse) (12) LD50: 8.57 mg/kg (Intravenous, Mouse) (12)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (8)

Uses/Sources

Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. Although patulin can occur in many molding fruits, grains and other foods, the major source of patulin contamination is in apples with brown rot, and in apple cider or apple juice. Patulin is also an antibiotic. (10, 11)

Minimum Risk Level

The World Health Organization recommends a maximum concentration of 50 µg/kg (50 ppb) in juices. (12)

Health Effects

Animals studies have shown patulin to cause gastrointestinal hyperemia, distension, hemorrhage and ulceration. It has also been shown to be immunotoxic, and neurotoxic. (12, 13)

Symptoms

Skin irritation occurs in cases of topical exposure. Patulin is also a stomach irritant and causes nausea and vomiting if ingested. (13)

Treatment

Symptomatic and supportive care is the mainstay of therapy. (1)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034299

FooDB ID