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MedKoo Cat#: 461931 | Name: Diacetoxyscirpenol
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Description:

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

Diacetoxyscirpenol is a mycotoxin from the group of type A trichothecenes. It is a secondary metabolite product of fungi of the genus Fusarium.

Chemical Structure

Diacetoxyscirpenol
CAS#2270-40-8

Theoretical Analysis

MedKoo Cat#: 461931

Name: Diacetoxyscirpenol

CAS#: 2270-40-8

Chemical Formula: C19H26O7

Exact Mass: 366.1679

Molecular Weight: 366.41

Elemental Analysis: C, 62.28; H, 7.15; O, 30.56

Price and Availability

Size Price Availability Quantity
1mg USD 285.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Diacetoxyscirpenol; Anguidin; Anguidine; Diazetoxyskirpenol; Scirpenetriol 4,15-diacetate; DAS; NSC 141537; NSC141537; NSC-141537; NSC 177378; NSC177378; NSC-177378;
IUPAC/Chemical Name
((2S,2'R,3'R,4'S,5'S,5a'R,9a'R)-4'-acetoxy-3'-hydroxy-5',8'-dimethyl-2',3',4',5',7',9a'-hexahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-5a'(6'H)-yl)methyl acetate
InChi Key
AUGQEEXBDZWUJY-NMAPUUFXSA-N
InChi Code
InChI=1S/C19H26O7/c1-10-5-6-18(8-23-11(2)20)13(7-10)26-16-14(22)15(25-12(3)21)17(18,4)19(16)9-24-19/h7,13-16,22H,5-6,8-9H2,1-4H3/t13-,14-,15-,16-,17-,18-,19+/m1/s1
SMILES Code
C[C@@]12[C@H](OC(C)=O)[C@@H](O)[C@H]([C@@]23CO3)O[C@]4([H])C=C(C)CC[C@]14COC(C)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 366.41 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
1: Choi YJ, Shin HW, Chun YS, Leutou AS, Son BW, Park JW. Diacetoxyscirpenol as a new anticancer agent to target hypoxia-inducible factor 1. Oncotarget. 2016 Sep 20;7(38):62107-62122. doi: 10.18632/oncotarget.11529. PubMed PMID: 27613833; PubMed Central PMCID: PMC5308714. 2: Yang S, De Boevre M, Zhang H, De Ruyck K, Sun F, Wang Z, Cao X, Shen J, De Saeger S, Zhang S. Unraveling the in vitro and in vivo metabolism of diacetoxyscirpenol in various animal species and human using ultrahigh-performance liquid chromatography-quadrupole/time-of-flight hybrid mass spectrometry. Anal Bioanal Chem. 2015 Nov;407(28):8571-83. doi: 10.1007/s00216-015-9016-4. Epub 2015 Sep 11. PubMed PMID: 26362158. 3: Shams M, Mitterbauer R, Corradini R, Wiesenberger G, Dall'Asta C, Schuhmacher R, Krska R, Adam G, Berthiller F. Isolation and characterization of a new less-toxic derivative of the Fusarium mycotoxin diacetoxyscirpenol after thermal treatment. J Agric Food Chem. 2011 Sep 14;59(17):9709-14. doi: 10.1021/jf2022176. Epub 2011 Aug 9. PubMed PMID: 21800832; PubMed Central PMCID: PMC3175691. 4: Yang L, Zhao Z, Wu A, Deng Y, Zhou Z, Zhang J, Hou J. Determination of trichothecenes A (T-2 toxin, HT-2 toxin, and diacetoxyscirpenol) in the tissues of broilers using liquid chromatography coupled to tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Dec 30;942-943:88-97. doi: 10.1016/j.jchromb.2013.10.034. Epub 2013 Oct 25. Review. PubMed PMID: 24231141. 5: Ayral AM, Dubech N, Le Bars J, Escoula L. In vitro effect of diacetoxyscirpenol and deoxynivalenol on microbicidal activity of murine peritoneal macrophages. Mycopathologia. 1992 Nov;120(2):121-7. PubMed PMID: 1336129. 6: Hasan HA. Fungicide inhibition of aflatoxins, diacetoxyscirpenol and zearalenone production. Folia Microbiol (Praha). 1993;38(4):295-8. PubMed PMID: 8112694. 7: Coppock RW, Swanson SP, Gelberg HB, Buck WB. Tissue residues of diacetoxyscirpenol in pigs and calves after intravenous dosing. Am J Vet Res. 1988 Nov;49(11):1997-9. PubMed PMID: 3247925. 8: Hoerr FJ, Carlton WW, Yagen B, Joffe AZ. Mycotoxicosis caused by either T-2 toxin or diacetoxyscirpenol in the diet of broiler chickens. Fundam Appl Toxicol. 1982 May-Jun;2(3):121-4. PubMed PMID: 7185610. 9: Bottex C, Martin A, Fontanges R. Action of a mycotoxin (diacetoxyscirpenol) on the immune response of the mouse--interaction with an immunomodulator (OM-89). Immunopharmacol Immunotoxicol. 1990;12(2):311-25. PubMed PMID: 2229926. 10: Coppock RW, Swanson SP, Gelberg HB, Koritz GD, Buck WB, Hoffmann WE. Pharmacokinetics of diacetoxyscirpenol in cattle and swine: effects of halothane. Am J Vet Res. 1987 Apr;48(4):691-5. PubMed PMID: 3592368. 11: Janse van Rensburg DF, Thiel PG, Jaskiewicz K. Short-term effects of two fusarium toxins, diacetoxyscirpenol and neosolaniol monoacetate, in male Wistar rats. Food Chem Toxicol. 1987 Oct;25(10):767-71. PubMed PMID: 3679023. 12: Hernández F, Cannon M. Inhibition of protein synthesis in Saccharomyces cerevisiae by the 12,13-epoxytrichothecenes trichodermol, diacetoxyscirpenol and verrucarin A. Reversibility of the effects. J Antibiot (Tokyo). 1982 Jul;35(7):875-81. PubMed PMID: 6757231. 13: Bauer J, Bollwahn W, Gareis M, Gedek B, Heinritzi K. Kinetic profiles of diacetoxyscirpenol and two of its metabolites in blood serum of pigs. Appl Environ Microbiol. 1985 Apr;49(4):842-5. PubMed PMID: 4004216; PubMed Central PMCID: PMC238455. 14: Moré J, Galtier P, Eeckhoutte C. Effect of low doses of a trichothecene mycotoxin (diacetoxyscirpenol) on rat gastric glycoproteins: a histochemical study. Toxicol Lett. 1990 Feb;50(2-3):173-8. PubMed PMID: 1689879. 15: Kubena LF, Harvey RB, Edrington TS, Rottinghaus GE. Influence of ochratoxin A and diacetoxyscirpenol singly and in combination on broiler chickens. Poult Sci. 1994 Mar;73(3):408-15. PubMed PMID: 8177819. 16: Hoerr FJ, Carlton WW, Yagen B. Mycotoxicosis caused by a single dose of T-2 toxin or diacetoxyscirpenol in broiler chickens. Vet Pathol. 1981 Sep;18(5):652-64. doi: 10.1177/030098588101800510. PubMed PMID: 7281462. 17: Vidal D, Creach O, Genton A, Beaudry Y, Fontanges R. [Destruction and cutaneous decontamination of diacetoxyscirpenol (mycotoxin from the trichothecene group) by sodium hypochlorite]. C R Acad Sci III. 1985;301(5):183-6. French. PubMed PMID: 3933775. 18: Gürbüzel M, Uysal H, Kızılet H. Assessment of genotoxic potential of two mycotoxins in the wing spot test of Drosophila melanogaster. Toxicol Ind Health. 2015 Mar;31(3):261-7. doi: 10.1177/0748233712472528. Epub 2013 Jan 8. PubMed PMID: 23299195. 19: Rosenstein Y, Kretschmer RR, Lafarge-Frayssinet C. Effect of Fusarium toxins, T2-toxin and diacetoxyscirpenol on murine T-independent immune responses. Immunology. 1981 Nov;44(3):555-60. PubMed PMID: 6976308; PubMed Central PMCID: PMC1554958. 20: Coppock RW, Hoffmann WE, Gelberg HB, Bass D, Buck WB. Hematologic changes induced by intravenous administration of diacetoxyscirpenol in pigs, dogs, and calves. Am J Vet Res. 1989 Mar;50(3):411-5. PubMed PMID: 2930030.