Xanthocillin

Title: Xanthocillin
CAS Registry Number: 11042-38-9
Additional Names: Xantocillin
Trademarks: Brevicid (AWD)
Literature References: Antibiotic complex produced by Penicillium notatum Westling: Rothe, Pharmazie 5, 190 (1950); Barwald, GB 898498 (1962 to Arzneimittelwerk VEB), C.A. 57, 9013a (1962). Consists of at least three antibiotics, xanthocillins X, Y1 and Y2; the first being the major component (about 70%).
Derivative Type: Xanthocillin X
CAS Registry Number: 580-74-5
CAS Name: 4,4¢-(2,3-Diisocyano-1,3-butadiene-1,4-diyl)bisphenol
Additional Names: bis(p-hydroxybenzylidene)ethylene isocyanide; 1,4-bis(p-hydroxyphenyl)-2,3-diisonitrilo-1,3-butadiene
Molecular Formula: C18H12N2O2
Molecular Weight: 288.30
Percent Composition: C 74.99%, H 4.20%, N 9.72%, O 11.10%
Literature References: Structure: Hagedorn, Tönjes, Pharmazie 11, 409 (1956); 12, 567 (1957); Hagedorn et al., Ber. 93, 1584 (1960). Synthesis: Hagedorn, Eholzer, Angew. Chem. 74, 215 (1962). Biosynthetic studies: Achenbach, Grisebach, Z. Naturforsch. 20b, 137 (1965); Achenbach, König, Ber. 105, 784 (1972). Crystal structure: D. Britton et al., Cryst. Struct. Commun. 10, 1497 (1981). Studies on antiviral activity: Takatsuki et al., J. Antibiot. 21, 671 (1968); eidem, ibid. 22, 151 (1969); Kitahara, ibid. 34, 1556 (1981).
Properties: Clusters of yellow needles from alc; yellow rhombs from ethyl acetate. Chars at about 210°. Sol (up to 1%) in alc, ether, acetone, dioxane. Freely sol in aqueous alkaline solns. Practically insol in water, petr ether, benzene, chloroform. Forms a water-sol dipotassium salt, the concd solns of which have a pH of 10.5.
Derivative Type: Dimethyl ether
Molecular Formula: C20H16N2O2
Molecular Weight: 316.35
Percent Composition: C 75.93%, H 5.10%, N 8.86%, O 10.11%
Properties: Yellow needles from dioxane + alcohol, dec 181°.
Derivative Type: Xanthocillin Y1
CAS Registry Number: 38965-69-4
CAS Name: 4-[4-(4-Hydroxyphenyl)-2,3-diisocyano-1,3-butadienyl]-1,2-benzenediol
Molecular Formula: C18H12N2O3
Molecular Weight: 304.30
Percent Composition: C 71.05%, H 3.97%, N 9.21%, O 15.77%
Derivative Type: Xanthocillin Y2
CAS Registry Number: 38965-70-7
CAS Name: 4,4¢-(2,3-Diisocyano-1,3-butadiene-1,4-diyl)bis-1,2-benzenediol
Molecular Formula: C18H12N2O4
Molecular Weight: 320.30
Percent Composition: C 67.50%, H 3.78%, N 8.75%, O 19.98%
Literature References: Structure of xanthocillins Y1 and Y2: Achenbach et al., Ber. 105, 3061 (1972).
Use: In feed supplements.
Therap-Cat: Antibacterial.
Xanthone Xanthophyll Xanthopterin Xanthosine Xanthoxyletin

Xantocillin
Xantocillin.svg
Xantocillin-from-xtal-3D-balls.png
Xantocillin-from-xtal-3D-vdW.png
Identifiers
CAS number 580-74-5
PubChem 5378293
ChemSpider 21106491
Jmol-3D images Image 1
Properties
Molecular formula C18H12N2O2
Molar mass 288.30 g mol−1
Appearance Yellow crystals
Melting point 200 °C (decomposes)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Xantocillin (INN), also known as xanthocillin X or ophthocillin, was the first reported natural product found to contain the isocyanide functional group. It was first isolated from Penicillium notatum by Westling in 1950[1] and subsequently from several other sources.[2][3]