Xantocillin

Xantocillin
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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 Y;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1977264;
ChemSpider	21106491;
EC Number	234-271-3;
PubChem CID	5378293;
UNII	06Z55VZ40D Y;
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

Xantocillin¹ (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 1950² and subsequently from several other sources.³⁴

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.

[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.

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