10061. Xanthocillin

Nomenclature

CAS number: 11042-38-9
Xantocillin; Brevicid (AWD).

Description and 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%).

Chemical structure

Derivative

Xanthocillin X.

Nomenclature

CAS number: 580-74-5
4,4′-(2,3-Diisocyano-1,3-butadiene-1,4-diyl)bisphenol; bis(p-hydroxybenzylidene)ethylene isocyanide; 1,4-bis(p-hydroxyphenyl)-2,3-diisonitrilo-1,3-butadiene.
C18H12N2O2; mol wt 288.30.
C 74.99%, H 4.20%, N 9.72%, O 11.10%.

Description and references

Structure: Hagedorn, Tnjes, 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, Knig, 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

Dimethyl ether.
C20H16N2O2; mol wt 316.35.
C 75.93%, H 5.10%, N 8.86%, O 10.11%.

Properties

Yellow needles from dioxane + alcohol, dec 181°.

Derivative

Xanthocillin Y1.

Nomenclature

CAS number: 38965-69-4
4-[4-(4-Hydroxyphenyl)-2,3-diisocyano-1,3-butadienyl]-1,2-benzenediol.
C18H12N2O3; mol wt 304.30.
C 71.05%, H 3.97%, N 9.21%, O 15.77%.

Derivative

Xanthocillin Y2.

Nomenclature

CAS number: 38965-70-7
4,4′-(2,3-Diisocyano-1,3-butadiene-1,4-diyl)bis-1,2-benzenediol.
C18H12N2O4; mol wt 320.30.
C 67.50%, H 3.78%, N 8.75%, O 19.98%.

Description and references

Structure of xanthocillins Y1 and Y2: Achenbach et al., Ber. 105, 3061 (1972).

Use

In feed supplements.

Therapeutic Category

Antibacterial.