Xantocillin

    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.


Price and Availability

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Xantocillin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

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


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


Technical Data

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).

Harmonized System Code:
2934990300


References

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.