Scirpene-3,4,15-triol

Base Information

• Chemical Name: Scirpene-3,4,15-triol
• CAS No.: 2270-41-9
• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.337
• UNII: YDE8TG6S26
• Nikkaji Number: J34.229G
• Wikidata: Q105216132
• Mol file: 2270-41-9.mol

Synonyms:3,4,15-trihydroxy-8-(3-methylbutyryloxy)-1,2,3-epoxytrichothec--9-ene;scirpentriol;T-2 triol

Chemical Property of Scirpene-3,4,15-triol

Chemical Property:

• Vapor Pressure: 2.28E-10mmHg at 25°C
• Boiling Point: 459.4°Cat760mmHg
• Flash Point: 231.6°C
• PSA: 82.45000
• Density: 1.39g/cm³
• LogP: -0.01670
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 282.14672380
• Heavy Atom Count: 20
• Complexity: 491

Purity/Quality:

99% ^*data from raw suppliers

Scirpentriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2C(CC1)(C3(C(C(C(C34CO4)O2)O)O)C)CO
• Isomeric SMILES: CC1=C[C@@H]2[C@](CC1)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)O)O)C)CO
• Uses: Scirpentriol is a trichothecene mycotoxin.

Technology Process of Scirpene-3,4,15-triol

There total 5 articles about Scirpene-3,4,15-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

((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 (2270-40-8,28776-47-8) → scirpentriol (2270-41-9)

Guidance literature:

With ammonium hydroxide; In acetonitrile; at 60 ℃; for 2h;

DOI:10.1021/jf061347+

Reference yield:

4,15-diacetoxyscirpenol (2270-40-8,28776-47-8) → scirpentriol (2270-41-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 0.25h;

Reference yield:

((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 (2270-40-8,28776-47-8) → 12,13-epoxytrichothec-9-ene-3α,4β,15-triol 15 acetate (2623-22-5) + scirpentriol (2270-41-9)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/jf0709193

upstream raw materials:

4,15-diacetoxyscirpenol

((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

Downstream raw materials:

calonectrin

C₁₅H₂₀O₅

calonectrin

3α,15-bis(chloroacetoxy)scirpen-4-one

Refernces

• 1、 Asam, Stefan,Rychlik, Michael. "Synthesis of four carbon-13-labeled type A trichothecene mycotoxins and their application as internal standards in stable isotope dilution assays". . p. 6535 - 6546. Retrieved 2008/09/21.
• 2、 -. "Antitumor agents". . . Retrieved 2008/06/13.