WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 341317
CAS#: 580-74-5
Description: Xantocillin (INN), also known as xanthocillin X or ophthocillin, was the first reported natural product found to contain the isocyanide functional group.
MedKoo Cat#: 341317
Name: Xantocillin
CAS#: 580-74-5
Chemical Formula: C18H12N2O2
Exact Mass: 288.0899
Molecular Weight: 288.306
Elemental Analysis: C, 74.99; H, 4.20; N, 9.72; O, 11.10
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Synonym: Xantocillin; NSC 179485; NSC 227183; BRN 3700094.
IUPAC/Chemical Name: Ethylene isocyanide, bis(p-hydroxybenzylidene)-
InChi Key: YBMVKDUTYAGKEW-MJZABRMRSA-N
InChi Code: 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+
SMILES Code: OC1=CC=C(C=C1)/C=C([N+]#[C-])/C([N+]#[C-])=C/C2=CC=C(O)C=C2
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 288.306 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Zhao Y, Chen H, Shang Z, Jiao B, Yuan B, Sun W, Wang B, Miao M, Huang C. SD118-xanthocillin X (1), a novel marine agent extracted from Penicillium commune, induces autophagy through the inhibition of the MEK/ERK pathway. Mar Drugs. 2012 Jun;10(6):1345-59. doi: 10.3390/md10061345. Epub 2012 Jun 11. PubMed PMID: 22822377; PubMed Central PMCID: PMC3397444.
2: Isaka M, Boonkhao B, Rachtawee P, Auncharoen P. A xanthocillin-like alkaloid from the insect pathogenic fungus Cordyceps brunnearubra BCC 1395. J Nat Prod. 2007 Apr;70(4):656-8. Epub 2007 Feb 1. PubMed PMID: 17266369.
3: Sakai R, Nakamura T, Nishino T, Yamamoto M, Miyamura A, Miyamoto H, Ishiwata N, Komatsu N, Kamiya H, Tsuruzoe N. Xanthocillins as thrombopoietin mimetic small molecules. Bioorg Med Chem. 2005 Dec 1;13(23):6388-93. Epub 2005 Aug 22. PubMed PMID: 16115772.
4: Kozlovskiĭ AG, Zhelifonova VP, Antipova TV, Adanin VM, Novikova ND, Deshevaia EA, Schlegel B, Dahse HM, Gollmick FA, Grafe U. [Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocillin X and questiomycin A]. Prikl Biokhim Mikrobiol. 2004 May-Jun;40(3):344-9. Russian. PubMed PMID: 15283339.
5: HEIJER A. Sensitization to xantocillin in salve. Acta Derm Venereol. 1961;41:201-4. PubMed PMID: 13712825.
6: BEIERSDORF R. [Detection of xanthocillin X in the body fluids and in secretions]. Pharmazie. 1954 Mar;9(3):193-8. Undetermined Language. PubMed PMID: 13177142.
