2270-41-9

Basic information

• Product Name: scirpentriol
• Synonyms: scirpentriol;12,13-Epoxytrichothec-9-ene-3α,4β,15-triol;Anguidol;Scirpenetriol
• CAS NO: 2270-41-9
• Molecular Formula: C15H22O5
• Molecular Weight: 282.334
• Mol File: 2270-41-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 459.4°Cat760mmHg
• Flash Point: 231.6°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 2.28E-10mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: scirpentriol(CAS DataBase Reference)
• NIST Chemistry Reference: scirpentriol(2270-41-9)
• EPA Substance Registry System: scirpentriol(2270-41-9)

Safety Data

• Hazardous Substances Data: 2270-41-9(Hazardous Substances Data)

Usage

Uses

Scirpentriol is a trichothecene mycotoxin.

InChI:InChI=1/C15H22O5/c1-8-3-4-14(6-16)9(5-8)20-12-10(17)11(18)13(14,2)15(12)7-19-15/h5,9-12,16-18H,3-4,6-7H2,1-2H3/t9-,10-,11-,12-,13-,14-,15-/m1/s1

Upstream product

• 2270-40-8 ((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 
• 2270-40-8 4,15-diacetoxyscirpenol 

Downstream Products

• 81452-35-9 C₁₅H₂₀O₅ 
• 38818-51-8 calonectrin 
• 38818-51-8 calonectrin 
• 80178-14-9 15-(chloroacetoxy)scirpene-3α,4β-diol 
• 80178-15-0 3α-(chloroacetoxy)scirpene-4β,15-diol 
• 80178-16-1 3α,15-bis(chloroacetoxy)scirpen-4β-ol 
• 80178-18-3 3α,4β,15-tris(chloroacetoxy)scirpene 
• 80178-17-2 4β-(chloroacetoxy)scirpene-3α,15-diol 
• 81331-27-3 3α,15-bis(chloroacetoxy)scirpen-4-one 

Relevant articles and documents

Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay

Many Fusarium species produce trichothecenes, sesquiterpene epoxides that differ in patterns of oxygenation and esterification at carbon positions C-3, C-4, C-7, C-8, and C-15. For the first comprehensive and quantitative comparison of the effects of oxygenation and esterification on trichothecene phytotoxicity, we tested 24 precursors, intermediates, and end products of the trichothecene biosynthetic pathway in an Arabidopsis thaliana detached leaf assay. At 100 μM, the highest concentration tested, only the trichothecene precursor trichodiene was nontoxic. Among trichothecenes, toxicity varied more than 200-fold. Oxygenation at C-4, C-8, C-7/8, or C-15 was, on average, as likely to decrease as to increase toxicity. Esterification at C-4, C-8, or C-15 generally increased toxicity. Esterification at C-3 increased toxicity in one case and decreased toxicity in three of eight cases tested. Thus, the increase in structural complexity along the trichothecene biosynthetic pathway in Fusarium is not necessarily associated with an increase in phytotoxicity.

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.

Antitumor agents

Novel mono-, di- and triacylated derivatives of scirpentriol are provided for use as antitumor agents. Also provided are methods for the production of such derivatives.