Sambutoxin

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

MedKoo CAT#: 461745

CAS#: 160047-56-3

Description: Sambutoxin is a mycotoxin produced by toxic Fusarium isolates obtained from rotted potato tubers.


Chemical Structure

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Sambutoxin
CAS# 160047-56-3

Theoretical Analysis

MedKoo Cat#: 461745
Name: Sambutoxin
CAS#: 160047-56-3
Chemical Formula: C28H39NO4
Exact Mass: 453.2879
Molecular Weight: 453.62
Elemental Analysis: C, 74.14; H, 8.67; N, 3.09; O, 14.11

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sambutoxin;

IUPAC/Chemical Name: 3-((2S,5R,6R)-6-((4R,6S,Z)-4,6-dimethyloct-2-en-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)-4-hydroxy-5-(4-hydroxyphenyl)-1-methylpyridin-2(1H)-one

InChi Key: FVYDVAOTXPELMH-DBCNXVKXSA-N

InChi Code: InChI=1S/C28H39NO4/c1-7-17(2)14-18(3)15-20(5)27-19(4)8-13-24(33-27)25-26(31)23(16-29(6)28(25)32)21-9-11-22(30)12-10-21/h9-12,15-19,24,27,30-31H,7-8,13-14H2,1-6H3/b20-15-/t17-,18+,19+,24-,27+/m0/s1

SMILES Code: O=C1C([C@@H]2CC[C@@H](C)[C@H](/C(C)=C\[C@H](C)C[C@@H](C)CC)O2)=C(O)C(C3=CC=C(O)C=C3)=CN1C

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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 453.62 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.

Recalculate based on batch purity %
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

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1: Wijeratne EM, Gunatilaka AA. Biomimetic conversion of (-)-fusoxypyridone and (-)-oxysporidinone to (-)-sambutoxin: further evidence for the structure of the tricyclic pyridone alkaloid, (-)-fusoxypyridone. Bioorg Med Chem Lett. 2011 Apr 15;21(8):2327-9. doi: 10.1016/j.bmcl.2011.02.091. Epub 2011 Mar 16. PubMed PMID: 21419624; PubMed Central PMCID: PMC3359017.

2: Kim JC, Lee YW. Sambutoxin, a new mycotoxin produced by toxic Fusarium isolates obtained from rotted potato tubers. Appl Environ Microbiol. 1994 Dec;60(12):4380-6. PubMed PMID: 7811078; PubMed Central PMCID: PMC201996.

3: Kim J, Lee Y, Yu S. Sambutoxin-producing isolates of fusarium species and occurrence of sambutoxin in rotten potato tubers. Appl Environ Microbiol. 1995 Oct;61(10):3750-1. PubMed PMID: 16535155; PubMed Central PMCID: PMC1388717.

4: Abbas HK, Shier WT, Gronwald JW, Lee YW. Comparison of phytotoxicity and mammalian cytotoxicity of nontrichothecene mycotoxins. J Nat Toxins. 2002 Aug;11(3):173-86. PubMed PMID: 12182537.

5: Williams DR, Turske RA. Construction of 4-hydroxy-2-pyridinones. Total synthesis of (+)-sambutoxin. Org Lett. 2000 Oct 5;2(20):3217-20. Erratum in: Org Lett 2001 Aug 9;3(16):2619. PubMed PMID: 11009385.

6: Jayasinghe L, Abbas HK, Jacob MR, Herath WH, Nanayakkara NP. N-Methyl-4-hydroxy-2-pyridinone analogues from Fusarium oxysporum. J Nat Prod. 2006 Mar;69(3):439-42. PubMed PMID: 16562855; PubMed Central PMCID: PMC2564868.

7: Stahl M, Schopfer U, Frenking G, Hoffmann RW. Assignment of Relative Configuration to Acyclic Compounds Based on (13)C NMR Shifts. A Density Functional and Molecular Mechanics Study. J Org Chem. 1996 Nov 15;61(23):8083-8088. PubMed PMID: 11667793.