Citrinin

Title: Citrinin
CAS Registry Number: 518-75-2
CAS Name: (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
Trademarks: Antimycin
Molecular Formula: C13H14O5
Molecular Weight: 250.25
Percent Composition: C 62.39%, H 5.64%, O 31.97%
Literature References: Antibiotic substance produced by a white spore aspergillus which has been placed under the species name Aspergillus niveus (Thorn and Raper). Also produced in small quantities by Penicillium citrinum: Hetherington, Raistrick, Trans. R. Soc. London B220, 269 (1931); Raistrick, Smith, Chem. Ind. (London) 60, 828 (1941); Timonin, Science 96, 494 (1942); Timonin, Rovatt, Can. J. Public Health 35, 80 (1944). Identity with antimycin: Haese, Arch. Pharm. 296, 227 (1963). Structure: Brown et al., J. Chem. Soc. 1949, 867; Warren et al., J. Am. Chem. Soc. 79, 3812 (1957); Kovac et al., Nature 190, 1104 (1961). Synthesis: Cartwright et al., J. Chem. Soc. 1949, 1563; J. A. Barber et al., J. Chem. Soc. Perkin Trans. 1 1986, 2101. Stereochemistry: Cram, J. Am. Chem. Soc. 72, 1001 (1950); Mehta, Whalley, J. Chem. Soc. 1963, 3777; Mathieson, Whalley, ibid. 1964, 4640. Physical characteristics and toxicity: Nagai et al., Chem. Zentralbl. 1958, 8088, C.A. 55, 1914 (1961). Crystal and molecular structure: Rodig, Chem. Commun. 1971, 1553. Biosynthesis: J. Barber et al., J. Chem. Soc. Perkin Trans. 1 1981, 2577; L. Colombo et al., ibid. 2594. Physicochemical data: A. E. Pohland et al., Pure Appl. Chem. 54, 2219 (1982). Toxicology: A. M. Ambrose, F. De Eds, J. Pharmacol. Exp. Ther. 88, 173 (1946). Review: Saito et al., "Yellowed Rice Toxins" in Microbial Toxins vol. VI, A. Ciegler, S. Kadis, A. Ajl, Eds. (Academic Press, New York, 1971) pp 357-367.
Properties: Lemon-yellow needles from alcohol, dec 175°. [a]D18 -37.4° (c = 1.15 in alc.). uv max: 250, 331 nm (E1%1cm 370, 418). Strong acid. Practically insol in water. Sol in alcohol, dioxane, dilute alkali. Solns change color with changes in pH, from lemon-yellow at pH 4.6 to cherry-red at pH 9.9. Poisonous! LD50 in mice, rats (mg/kg): 35, 67 i.p. (Ambrose, De Eds).
Optical Rotation: [a]D18 -37.4° (c = 1.15 in alc.)
Absorption maximum: uv max: 250, 331 nm (E1%1cm 370, 418)
Toxicity data: LD50 in mice, rats (mg/kg): 35, 67 i.p. (Ambrose, De Eds)
Derivative Type: Methyl citrinin
Molecular Formula: C14H16O5
Molecular Weight: 264.27
Percent Composition: C 63.63%, H 6.10%, O 30.27%
Properties: Plates from benzene, dec 139°. [a]D18 +217.1° (c = 0.38 in acetone). uv max: 260, 334 nm (E1%1cm 520, 151.6). Sol in hot alcohol; moderately sol in chloroform. Practically insol in petr ether.
Optical Rotation: [a]D18 +217.1° (c = 0.38 in acetone)
Absorption maximum: uv max: 260, 334 nm (E1%1cm 520, 151.6)
Derivative Type: Dihydrocitrinin
Molecular Formula: C13H16O5
Molecular Weight: 252.26
Percent Composition: C 61.90%, H 6.39%, O 31.71%
Properties: Prisms from benzene, dec 171°. [a]D18 -18.8° (c = 4.148 in chloroform). uv max: 260, 330 nm (E1%1cm 400, 100). Sol in alcohol, acetone, chloroform; sparingly sol in benzene, petr ether.
Optical Rotation: [a]D18 -18.8° (c = 4.148 in chloroform)
Absorption maximum: uv max: 260, 330 nm (E1%1cm 400, 100)
Citromycetin Citronellal Citrulline Citrullol Citrus Red 2

Citrinin[1]
Citrinin structure.svg
Identifiers
CAS number 518-75-2 YesY
PubChem 54680783
ChemSpider 10222475 N
UNII 3S697X6SNZ N
KEGG C16765 N
ChEMBL CHEMBL510139 N
Jmol-3D images Image 1
Properties
Molecular formula C13H14O5
Molar mass 250.25 g mol−1
Appearance Lemon-yellow needles
Melting point 175 °C (decomp.)
Solubility in water Insoluble
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Citrinin is a mycotoxin originally isolated in 1931 by Hetherington and Raistrick from a culture of Penicillium citrinum.[2] It has since been found to be produced by a variety of other fungi that are found or used in the production of human foods, such as grain, cheese, sake, and red pigments. Citrinin has also been found in commercial red yeast rice supplements.[3]