Showing Compound Patulin (FDB012642)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:17 UTC

Update date

2019-11-26 03:07:16 UTC

Primary ID

FDB012642

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Patulin

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.

CAS Number

149-29-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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-3(6H)-ylidene)acetic acid, 3,4-lactone	ChEBI
(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone	ChEBI
2,4-Dihydroxy-2H-pyran-alpha -acetic acid, 3, 4-lactone	HMDB
2,4-Dihydroxy-2H-pyran-α-acetic acid, 3, 4-lactone	biospider
2H-Pyran-alpha )-acetic acid, 2, 4-dihydroxy-,3,4-lactone	HMDB
2H-Pyran-alpha )-acetic acid, 2,4-dihydroxy-, 3,4-lactone	HMDB
2H-Pyran-α)-acetic acid, 2, 4-dihydroxy-,3,4-lactone	biospider
2H-Pyran-α)-acetic acid, 2,4-dihydroxy-, 3,4-lactone	biospider

Showing 1 to 10 of 53 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H6O4

IUPAC name

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

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

Isomeric SMILES

OC1OCC=C2OC(=O)C=C12

Average Molecular Weight

154.1201

Monoisotopic Molecular Weight

154.02660868

Classification

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Observation:

Skin irritation

Ingestion

Source:

Food

Biological:

Plant

Fungi:

Aspergillus:

Penicillium

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Environmental role:

Environmental contaminant

Industrial application:

Household products:

Antimicrobial agent:

Antibiotic

Indirect biological role:

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 54.55%; H 3.92%; O 41.52%	DFC
Melting Point	Mp 111°	DFC
Optical Rotation	[a]21D -6.2 (CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Patulin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9700000000-5a48339184b0b8962504	Spectrum
Predicted GC-MS	Patulin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gr-9600000000-3451d632d4f834dc62cc	Spectrum
Predicted GC-MS	Patulin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Patulin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-06be4453ffa97f478a45	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d4bddadeb22df078c3c9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-0775e607edc3b24dad13	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9100000000-37c4497452b5b85a32f7	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a5039689c3996db29872	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1900000000-d8df1f0a351c47943c80	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06uu-9200000000-cd27858111b7a99f8a9a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-77b51b14a11efa7e4bd7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-f1deb55458afa0cf487a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9200000000-ec01329ad017386b5211	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-5328d4e45a2fa398896e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-1000-3900000000-b2db7ade21b45c80a316	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-780f5433ebd56a09e203	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4534

ChEMBL ID

Not Available

KEGG Compound ID

C16748

Pubchem Compound ID

4696

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34299

CRC / DFC (Dictionary of Food Compounds) ID

HJM69-Q:HJM69-Q

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00024000

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Patulin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Patulin (FDB012642)

Structure for FDB012642 (Patulin)