Xantocillin

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[1] and subsequently from several other sources.[2][3]

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
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • [C-]#[N+]C(=CC1=CC=C(C=C1)O)C(=CC2=CC=C(C=C2)O)[N+]#[C-]
Properties
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

See also

References
  1. W. ROTHE (1950). "Vorläufige Mitteilung über eine neues Antibiotikum". Pharmazie. 5: 190.
  2. Paul J. Scheuer (1992). "Isocyanides and cyanides as natural products". Accounts of Chemical Research. 25 (10): 433–439. doi:10.1021/ar00022a001.
  3. 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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