Xantocillin

Xantocillin
Names
	Preferred IUPAC name 4,4′-[(1Z,3Z)-2,3-Diisocyanobuta-1,3-diene-1,4-diyl]diphenol
	Other names Xanthocillin X, Ophthocillin
Identifiers
CAS Number	580-74-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1977264;
ChemSpider	21106491;
EC Number	234-271-3;
PubChem CID	5378293;
UNII	06Z55VZ40D ;
CompTox Dashboard (EPA)	DTXSID801018149 ;
	InChI InChI=1S/C18H12N2O2/c1-19-17(11-13-3-7-15(21)8-4-13)18(20-2)12-14-5-9-16(22)10-6-14/h3-12,21-22H/b17-11-,18-12- Key: YBMVKDUTYAGKEW-WHYMJUELSA-N;
	SMILES [C-]#[N+]C(=CC1=CC=C(C=C1)O)C(=CC2=CC=C(C=C2)O)[N+]#[C-];
Properties
Chemical formula	C18H12N2O2
Molar mass	288.306 g·mol−1
Appearance	Yellow crystals
Melting point	200 °C (392 °F; 473 K) (decomposes)
	Except where otherwise noted, 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 Rothe in 1950 and subsequently from several other sources. It possesses antibiotic properties.^{[citation needed]}

References

↑ PubChem. "Xantocillin". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-11-03.
↑ W. ROTHE (1950). "Vorläufige Mitteilung über eine neues Antibiotikum". Pharmazie. 5: 190.
↑ Paul J. Scheuer (1992). "Isocyanides and cyanides as natural products". Accounts of Chemical Research. 25 (10): 433–439. doi:10.1021/ar00022a001.
↑ Kozlovskiĭ AG, Zhelifonova VP, Antipova TV, Adanin VM, Novikova ND, Deshevaia EA, et al. (2004). "[Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocillin X and questiomycin A]". Prikl Biokhim Mikrobiol. 40 (3): 344–9. PMID 15283339.

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[1] PubChem. "Xantocillin". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-11-03.

[2] W. ROTHE (1950). "Vorläufige Mitteilung über eine neues Antibiotikum". Pharmazie. 5: 190.

[3] Paul J. Scheuer (1992). "Isocyanides and cyanides as natural products". Accounts of Chemical Research. 25 (10): 433–439. doi:10.1021/ar00022a001.

[pmid15283339-4] Kozlovskiĭ AG, Zhelifonova VP, Antipova TV, Adanin VM, Novikova ND, Deshevaia EA, et al. (2004). "[Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocillin X and questiomycin A]". Prikl Biokhim Mikrobiol. 40 (3): 344–9. PMID 15283339.