4297-61-4

Basic information

• Product Name: 3-A-ACETYLDIACETOXYSCIRPENOL
• Synonyms: triacetoxyscirpenol;3-A-ACETYLDIACETOXYSCIRPENOL;3,4,15-TRIACETOXYSCIRPENOL;12,13-Epoxytrichothec-9-ene-3α,4β,15-triol triacetate;3α,4β,15-Triacetoxy-12,13-epoxytrichothec-9-ene
• CAS NO: 4297-61-4
• Molecular Formula: C21H28O9
• Molecular Weight: 424.44162
• Mol File: 4297-61-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 477.352°C at 760 mmHg
• Flash Point: 206.022°C
• Appearance: /
• Density: 1.291g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-A-ACETYLDIACETOXYSCIRPENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-A-ACETYLDIACETOXYSCIRPENOL(4297-61-4)
• EPA Substance Registry System: 3-A-ACETYLDIACETOXYSCIRPENOL(4297-61-4)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• RIDADR: 3172
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 4297-61-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H28O8/c1-11-6-7-20(9-25-12(2)22)15(8-11)29-18-16(27-13(3)23)17(28-14(4)24)19(20,5)21(18)10-26-21/h8,15-18H,6-7,9-10H2,1-5H3/t15?,16-,17?,18-,19-,20?,21+/m0/s1

Upstream product

• 2270-40-8 4,15-diacetoxyscirpenol 
• 557-34-6 zinc diacetate 
• 1972-28-7 diethylazodicarboxylate 
• 85925-77-5 (6R,7S,8S,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-9-((R)-4-hydroxy-1-hydroxymethyl-4-methyl-cyclohex-2-enyl)-9-methyl-1,4-dioxa-spiro[4.4]nonane-6,7-diol 
• 85925-86-6 C₂₄H₄₀O₇Si 
• 85925-85-5 Acetic acid (R)-1-[(6S,7S,8S,9R)-7-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-6-methyl-1,4-dioxa-spiro[4.4]non-6-yl]-4-hydroxy-4-methyl-cyclohex-2-enylmethyl ester 
• 85925-73-1 C₂₄H₃₄O₇Si 
• 85925-84-4 Acetic acid (6R,7S,8S,9S)-7-acetoxy-9-((R)-1-acetoxymethyl-4-hydroxy-4-methyl-cyclohex-2-enyl)-8-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,4-dioxa-spiro[4.4]non-6-yl ester 
• 85925-74-2 C₂₈H₄₀O₈Si 
• 85925-76-4 C₂₉H₄₂O₇Si 
• 85925-75-3 C₂₈H₃₈O₇Si 
• 85925-79-7 C₂₆H₄₂O₈Si 
• 85925-72-0 C₂₆H₃₉NO₆Si 
• 85925-88-8 Acetic acid (1S,2R,7R,9S,10R,11S)-10-acetoxy-11-hydroxy-1,5-dimethyl-12-methylene-8-oxa-tricyclo[7.2.1.0^2,7]dodec-5-en-2-ylmethyl ester 

Relevant articles and documents

Chemical Deoxygenation of the Trichothecenes, Diacetoxyscirpenol and Deoxynivalenol

Based on a model study using the bicyclic epoxides (9) and (10), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene toxins has been devised.

Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene

The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.

Synthesis and Biological Evaluation of a Trichothecene epi-Epoxide, 3α,4β,15-Triacetoxy-12,13-epi-epoxytrichothec-9-ene

In order to provide additional insight into the mode of action of the trichothecene mycotoxins, one of the first semi-synthetic trichothecene epi-epoxides (8) has been prepared; in dramatic contrast to its natural isomer (9), this compound proved tobe devoid of significant biological activity.