Vinaxanthone | CAS#133293-89-7 | antibacterial

MedKoo Cat#: 585388 | Name: Vinaxanthone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Vinaxanthone

CAS#133293-89-7

Theoretical Analysis

MedKoo Cat#: 585388

Name: Vinaxanthone

CAS#: 133293-89-7

Chemical Formula: C28H16O14

Exact Mass: 576.0540

Molecular Weight: 576.42

Elemental Analysis: C, 58.34; H, 2.80; O, 38.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Vinaxanthone; Ro 09-1450; Ro-09-1450; Ro09-1450; Ro 091450; Ro-091450; Ro091450; SM 345431; SM345431; SM-345431; SPF3059-5; SPF-3059-5; SPF 3059-5; SPF30595; SPF-30595; SPF 30595;

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

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 576.42 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: 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.