Vinaxanthone

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MedKoo CAT#: 585388

CAS#: 133293-89-7

Description: Vinaxanthone is a FabI inhibitor from Penicillium sp. and antibacterial.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-02-28. Prices are subject to change without notice.

Vinaxanthone 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#: 585388
Name: Vinaxanthone
CAS#: 133293-89-7
Chemical Formula: C28H16O14
Exact Mass: 576.054
Molecular Weight: 576.422
Elemental Analysis: C, 58.34; H, 2.80; O, 38.86


Synonym: Vinaxanthone

IUPAC/Chemical Name: 5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxochromen-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid

InChi Key: MEYYEMQDVMMNNR-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H16O14/c1-7(29)9-3-10-22(33)19-15(5-13(32)25(36)21(19)28(39)40)42-26(10)16(8(2)30)17(9)11-6-41-14-4-12(31)24(35)20(27(37)38)18(14)23(11)34/h3-6,31-32,35-36H,1-2H3,(H,37,38)(H,39,40)

SMILES Code: O=C(C1=C(O)C(O)=CC(OC2=C3C=C(C(C)=O)C(C4=COC5=C(C(C(O)=O)=C(O)C(O)=C5)C4=O)=C2C(C)=O)=C1C3=O)O


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:
>3 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


References

1: Chin MR, Zlotkowski K, Han M, Patel S, Eliasen AM, Axelrod A, Siegel D. Expedited access to vinaxanthone and chemically edited derivatives possessing neuronal regenerative effects through ynone coupling reactions. ACS Chem Neurosci. 2015 Apr 15;6(4):542-50. doi: 10.1021/cn500237z. Epub 2015 Feb 10. PubMed PMID: 25615693.

2: Zhang L, Kaneko S, Kikuchi K, Sano A, Maeda M, Kishino A, Shibata S, Mukaino M, Toyama Y, Liu M, Kimura T, Okano H, Nakamura M. Rewiring of regenerated axons by combining treadmill training with semaphorin3A inhibition. Mol Brain. 2014 Mar 10;7:14. doi: 10.1186/1756-6606-7-14. PubMed PMID: 24618249; PubMed Central PMCID: PMC4008261.

3: Axelrod A, Eliasen AM, Chin MR, Zlotkowski K, Siegel D. Syntheses of xanthofulvin and vinaxanthone, natural products enabling spinal cord regeneration. Angew Chem Int Ed Engl. 2013 Mar 18;52(12):3421-4. doi: 10.1002/anie.201205837. Epub 2012 Oct 19. PubMed PMID: 23086682.

4: Zheng CJ, Sohn MJ, Kim WG. Vinaxanthone, a new FabI inhibitor from Penicillium sp. J Antimicrob Chemother. 2009 May;63(5):949-53. doi: 10.1093/jac/dkp058. Epub 2009 Mar 12. PubMed PMID: 19282328.

5: Gammon G, Chandler G, Depledge P, Elcock C, Wrigley S, Moore J, Cammarota G, Sinigaglia F, Moore M. A fungal metabolite which inhibits the interaction of CD4 with major histocompatibility complex-encoded class II molecules. Eur J Immunol. 1994 Apr;24(4):991-8. PubMed PMID: 8149967.

6: Kumagai K, Hosotani N, Kikuchi K, Kimura T, Saji I. Xanthofulvin, a novel semaphorin inhibitor produced by a strain of Penicillium. J Antibiot (Tokyo). 2003 Jul;56(7):610-6. PubMed PMID: 14513903.

7: Yamazaki R, Yamazoe K, Yoshida S, Hatou S, Inagaki E, Okano H, Tsubota K, Shimmura S. The Semaphorin 3A inhibitor SM-345431 preserves corneal nerve and epithelial integrity in a murine dry eye model. Sci Rep. 2017 Nov 14;7(1):15584. doi: 10.1038/s41598-017-15682-1. PubMed PMID: 29138447; PubMed Central PMCID: PMC5686158.

8: Henao Muñoz LM, Montes Rojas CM, Bernal Bautista MH. Acute toxicity and sublethal effects of the mixture glyphosate (Roundup Active) and Cosmo-Flux 411F to anuran embryos and tadpoles of four Colombian species. Rev Biol Trop. 2015 Mar;63(1):223-33. PubMed PMID: 26299127.

9: Omoto M, Yoshida S, Miyashita H, Kawakita T, Yoshida K, Kishino A, Kimura T, Shibata S, Tsubota K, Okano H, Shimmura S. The semaphorin 3A inhibitor SM-345431 accelerates peripheral nerve regeneration and sensitivity in a murine corneal transplantation model. PLoS One. 2012;7(11):e47716. doi: 10.1371/journal.pone.0047716. Epub 2012 Nov 9. PubMed PMID: 23152758; PubMed Central PMCID: PMC3494696.