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
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
288.31
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.
