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Substance Name: Citrinin
RN: 518-75-2
UNII: 3S697X6SNZ
InChIKey: CQIUKKVOEOPUDV-IYSWYEEDSA-N

Note

  • Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.

Molecular Formula

  • C13-H14-O5

Molecular Weight

  • 250.2486
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Germicide, Bactericide, Disinfectant
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Name of Substance

  • Citrinin

MeSH Heading

  • Citrinin

Synonyms

  • (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
  • 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
  • 5-18-09-00061 (Beilstein Handbook Reference)
  • BRN 0088597
  • CCRIS 175
  • Citrinin
  • EINECS 208-257-2
  • HSDB 3473
  • NSC 186
  • UNII-3S697X6SNZ

Systematic Names

  • 3,4-Dihydro-8-hydroxy-3,4,5-trimethyl-6H-6-oxobenzo(c)pyran-7-carboxylic acid
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R,4S)-
  • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
  • Citrinin

Superlist Name

  • Citrinin

Registry Numbers

CAS Registry Number

  • 518-75-2

FDA UNII

  • 3S697X6SNZ

System Generated Number

  • 0000518752

Structure Descriptors

InChI

1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

InChIKey

CQIUKKVOEOPUDV-IYSWYEEDSA-N

Smiles

C12=C(C(=O)C(=C(C1=CO[C@@H]([C@H]2C)C)O)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 subcutaneous 37mg/kg (37mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 173, 1946.
hamster LD50 intraperitoneal 66mg/kg (66mg/kg)   Food and Cosmetics Toxicology. Vol. 16, Pg. 355, 1978.
hamster LD50 oral 75mg/kg (75mg/kg)   Food and Cosmetics Toxicology. Vol. 16, Pg. 355, 1978.
mouse LD50 intraperitoneal 35mg/kg (35mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 173, 1946.
mouse LD50 oral 112mg/kg (112mg/kg)   Toxicology and Applied Pharmacology. Vol. 37, Pg. 139, 1976.
mouse LD50 subcutaneous 73mg/kg (73mg/kg)   Food and Cosmetics Toxicology. Vol. 15, Pg. 29, 1977.
rabbit LD50 intraperitoneal 50mg/kg (50mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Food and Chemical Toxicology. Vol. 21, Pg. 487, 1983.
rabbit LD50 intravenous 19mg/kg (19mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 173, 1946.
rabbit LD50 oral 134mg/kg (134mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Food and Chemical Toxicology. Vol. 21, Pg. 487, 1983.
rat LD50 intraperitoneal 50mg/kg (50mg/kg)   Pharmaceutical Bulletin. Vol. 3, Pg. 337, 1955.
rat LD50 subcutaneous 67mg/kg (67mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 173, 1946.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 178.5 dec deg C   EXP
log P (octanol-water) 0.450 (none)   EST
Atmospheric OH Rate Constant 8.36E-11 cm3/molecule-sec 25 EST

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