Xantocillin

{{chembox

| ImageFile =Xantocillin.svg

| ImageSize =250

| ImageFile1 =Xantocillin-from-xtal-3D-balls.png

| ImageFile2 =Xantocillin-from-xtal-3D-vdW.png

| PIN =4,4′-[(1Z,3Z)-2,3-Diisocyanobuta-1,3-diene-1,4-diyl]diphenol

| OtherNames =Xanthocillin X, Ophthocillin

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =580-74-5

| PubChem =5378293

| ChemSpiderID =21106491

| ChEMBL = 1977264

| SMILES =[C-]#[N+]C(=CC1=CC=C(C=C1)O)C(=CC2=CC=C(C=C2)O)[N+]#[C-]

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 06Z55VZ40D

}}

|Section2={{Chembox Properties

| C =18 |H=12 |N=2 |O=2

| Appearance =Yellow crystals

| Density =

| MeltingPtC = 200

| MeltingPt_notes = (decomposes)

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Xantocillin{{Cite web |last=PubChem |title=Xantocillin |url=https://pubchem.ncbi.nlm.nih.gov/compound/5378293 |access-date=2023-11-03 |website=pubchem.ncbi.nlm.nih.gov |language=en}} (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{{cite journal

| author = W. ROTHE

| title =Vorläufige Mitteilung über eine neues Antibiotikum

| journal = Pharmazie

| volume = 5

| year = 1950

| pages = 190

}} and subsequently from several other sources.{{cite journal

| author = Paul J. Scheuer

| title = Isocyanides and cyanides as natural products

| journal = Accounts of Chemical Research

| volume = 25

| year = 1992

| issue = 10

| pages = 433–439

| doi = 10.1021/ar00022a001

}}{{cite journal |vauthors=Kozlovskiĭ AG, Zhelifonova VP, Antipova TV, Adanin VM, Novikova ND, Deshevaia EA, etal | title=[Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocillin X and questiomycin A]. | journal=Prikl Biokhim Mikrobiol | year= 2004 | volume= 40 | issue= 3 | pages= 344–9 | pmid=15283339 | url=https://pubmed.ncbi.nlm.nih.gov/15283339 }}

See also

References