12,13-Epoxytrichothec-9-en-4-ol

Base Information

• Chemical Name: 12,13-Epoxytrichothec-9-en-4-ol
• CAS No.: 2198-93-8
• Molecular Formula: C15H22O3
• Molecular Weight: 250.338
• DSSTox Substance ID: DTXSID70944568
• Wikidata: Q105341269
• Mol file: 2198-93-8.mol

Synonyms:BRN 1287601;12,13-Epoxytrichothec-9-en-4-beta-ol;Trichothec-9-en-4-beta-ol, 12,13-epoxy-;(4-beta)-12,13-Epoxytrichothec-9-en-4-ol;Trichothec-9-en-4-ol, 12,13-epoxy-, (4-beta)-;DTXSID70944568;12,13-Epoxytrichothec-9-en-4-ol;LS-157033

Chemical Property of 12,13-Epoxytrichothec-9-en-4-ol

Chemical Property:

• Vapor Pressure: 4.28E-07mmHg at 25°C
• Melting Point: 124-125°
• Boiling Point: 373.2°Cat760mmHg
• Flash Point: 179.5°C
• PSA: 41.99000
• Density: 1.2g/cm³
• LogP: 2.04010
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 250.15689456
• Heavy Atom Count: 18
• Complexity: 445

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)O)C)C
• Isomeric SMILES: CC1=C[C@@H]2[C@](CC1)(C3([C@@H](C[C@H](C34CO4)O2)O)C)C

Technology Process of 12,13-Epoxytrichothec-9-en-4-ol

There total 35 articles about 12,13-Epoxytrichothec-9-en-4-ol 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: 99.0%

(4β)-12,13-epoxytrichothec-9-en-4-yl acetate → (4β)-12,13-epoxytrichothec-9-en-4-ol (2198-93-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.75h;

DOI:10.3390/molecules24203811

Reference yield:

4β-hydroxytrichotheca-9,12-diene (33809-40-4) → (+/-)-trichodermol (2198-93-8,38757-97-0,74501-22-7)

Guidance literature:

DOI:10.1021/jo00280a039

Reference yield:

4-(dimethyl-tert-butoxysilyl)trichotheca-9,12-diene (118714-92-4) → (+/-)-trichodermol (2198-93-8,38757-97-0,74501-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

2: 80 percent / 30percent aq. H₂O₂, KF, NaHCO₃ / tetrahydrofuran; methanol / 24 h / 60 °C

3: MCPBA, NaHPO₄ / CH₂Cl₂ / Ambient temperature

With potassium fluoride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja00186a057

upstream raw materials:

trichodermadiene

trichodermadiene

trichodermadienediol A

trichodermadienediol B

Downstream raw materials:

C₁₅H₂₀O₃

C₂₂H₂₅FO₄

C₂₂H₂₅ClO₄

C₂₂H₂₆O₄

Refernces

• 1、 Jarvis, Bruce B.,Midiwo, Jacob O.,Stahly, G. Patrick,Pavanasasivam, Gowsala,Mazzola, Eugene P.. "TRICHODERMADIENE: A NEW TRICHOTHECENE". . p. 787 - 788. Retrieved 1980.
• 2、 Xu, Xiaojun,Cheng, Jingli,Zhou, Yong,Zhang, Chulong,Ou, Xiaoming,Su, Weike,Zhao, Jinhao,Zhu, Guonian. "Synthesis and antifungal activities of trichodermin derivatives as fungicides on rice". . p. 600 - 611. Retrieved 2013/06/05.