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Substance Name: Patulin
RN: 149-29-1
UNII: 95X2BV4W8R
InChIKey: ZRWPUFFVAOMMNM-UHFFFAOYSA-N

Note

  • 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.

Molecular Formula

  • C7-H6-O4

Molecular Weight

  • 154.12
 

Classification Codes

Classification Codes

  • Drug / Therapeutic Agent
  • Mutagens
  • Mutation Data
  • Natural Product
  • Noxae
  • Poisons
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Name of Substance

  • Patulin

MeSH Heading

  • Patulin

Synonyms

  • (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone
  • (2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone
  • 2,4-Dihydroxy-2H-pyran-delta-3(6H),alpha-acetic acid-3,4-lactone
  • 2H-Pyran-delta(sup 3(6H),alpha)-acetic acid, 2,4-dihydroxy-, 3,4-lactone
  • 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one
  • 4H-Furo(3,3-c)pyran-2(6H)-one, 4-hydroxy-
  • 5-18-03-00005 (Beilstein Handbook Reference)
  • Acetic acid, (2,4-dihydroxy-2H-pyran-3(6H)-ylidene)-, 3,4-lactone
  • BRN 0149675
  • CCRIS 4940
  • Clairformin
  • Clavacin
  • Clavatin
  • Claviform
  • Claviformin
  • EINECS 205-735-2
  • Expansin
  • Expansine
  • Gigantin
  • HSDB 3522
  • Leucopin
  • Mycoin
  • Mycoin C
  • Mycoin C3
  • Mycoine C3
  • Mycosin
  • NSC 32951
  • NSC 8120
  • Patulin
  • Patuline
  • Penatin
  • Penicidin
  • Tercinin
  • Terinin
  • UNII-95X2BV4W8R

Systematic Names

  • 4,6-Dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one
  • 4H-Furo(3,2-c)pyran-2(6H)-one, 4-hydroxy-
  • Patulin

Superlist Name

  • Patulin

Registry Numbers

CAS Registry Number

  • 149-29-1

FDA UNII

  • 95X2BV4W8R

System Generated Number

  • 0000149291

Structure Descriptors

InChI

1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2

InChIKey

ZRWPUFFVAOMMNM-UHFFFAOYSA-N

Smiles

C1=2C(=CC(O1)=O)[C@@H](OCC2)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 unreported 170mg/kg (170mg/kg)   Reviews of Environmental Contamination and Toxicology. Vol. 113, Pg. 47, 1990.
dog LD50 intravenous 10mg/kg (10mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Food and Cosmetics Toxicology. Vol. 17, Pg. 605, 1979.
hamster LD50 intraperitoneal 10mg/kg (10mg/kg)   Food and Cosmetics Toxicology. Vol. 18, Pg. 173, 1980.
hamster LD50 oral 31500ug/kg (31.5mg/kg)   Food and Cosmetics Toxicology. Vol. 18, Pg. 173, 1980.
hamster LD50 subcutaneous 23mg/kg (23mg/kg)   Food and Cosmetics Toxicology. Vol. 18, Pg. 173, 1980.
mouse LD50 intracrebral 570ug/kg (0.57mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toxicology. Vol. 13, Pg. 91, 1979.
mouse LD50 intraperitoneal 5mg/kg (5mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 2, Pg. 109, 1946.
mouse LD50 intravenous 5mg/kg (5mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 439, 1981.
mouse LD50 oral 17mg/kg (17mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

LIVER: FATTY LIVER DEGERATION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Toxicology and Applied Pharmacology. Vol. 45, Pg. 275, 1978.
mouse LD50 subcutaneous 10mg/kg (10mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Food and Cosmetics Toxicology. Vol. 18, Pg. 181, 1980.
mouse LDLo unreported 8mg/kg (8mg/kg)   British Journal of Cancer. Vol. 15, Pg. 85, 1961.
rabbit LDLo intravenous 12mg/kg (12mg/kg) LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Lancet. Vol. 245, Pg. 631, 1943.
rat LD50 intraperitoneal 4590ug/kg (4.59mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: OTHER CHANGES
Annales Recherches Veterinaires. Vol. 8, Pg. 41, 1977.
rat LD50 intravenous 8570ug/kg (8.57mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Annales Recherches Veterinaires. Vol. 8, Pg. 41, 1977.
rat LD50 oral 27790ug/kg (27.79mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: OTHER CHANGES
Annales Recherches Veterinaires. Vol. 8, Pg. 41, 1977.
rat LD50 subcutaneous 11mg/kg (11mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Food and Chemical Toxicology. Vol. 20, Pg. 289, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 111 deg C   EXP
log P (octanol-water) -2.400 (none)   EST
Atmospheric OH Rate Constant 1.38E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.