Trichostatic acid

Base Information

• Chemical Name: Trichostatic acid
• CAS No.: 114127-17-2
• Molecular Formula: C17H21 N O3
• Molecular Weight: 287.359
• European Community (EC) Number: 834-835-4
• DSSTox Substance ID: DTXSID501141808
• Nikkaji Number: J3.078.560F
• Wikidata: Q27119756
• Metabolomics Workbench ID: 56176
• Mol file: 114127-17-2.mol

Synonyms:trichostatic acid;trichostatic acid, (+)-isomer

Chemical Property of Trichostatic acid

Chemical Property:

• Vapor Pressure: 9.83E-11mmHg at 25°C
• Boiling Point: 497.9°Cat760mmHg
• Flash Point: 254.9°C
• PSA: 57.61000
• Density: 1.12g/cm³
• LogP: 3.15850
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 287.15214353
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C=C(C)C=CC(=O)O)C(=O)C1=CC=C(C=C1)N(C)C
• Isomeric SMILES: CC(/C=C(\C)/C=C/C(=O)O)C(=O)C1=CC=C(C=C1)N(C)C

Technology Process of Trichostatic acid

There total 38 articles about Trichostatic acid 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: 96.0%

(±)-(2E,4E)-methoxybenzyl 7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate (1312938-58-1) → Trichostatic acid (114127-17-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 22 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/ol200964m

Reference yield: 94.0%

C18H25NO3 (1208355-94-5) → Trichostatic acid (114127-17-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/ol9029116

Reference yield: 88.0%

4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid (122222-85-9,122222-86-0,122223-02-3,122223-03-4,125936-83-6) → (S)-trichostatic acid (114127-17-2,114127-18-3,68690-19-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89789-1

upstream raw materials:

C₁₈H₂₅NO₃

(2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate

(2E,4E)-5-bromo-4-methylpenta-2,4-dienoic acid

1-(4-dimethylaminophenyl)propan-1-one

Downstream raw materials:

trichostatin A

(S)-(-)-trichostatin A

6-epi-trichostatin D

O-(2-methoxypropyl)-(S)-trichostatin A

Refernces

• 1、 Cosner, Casey C.,Bhaskara Reddy Iska, Vijaya,Chatterjee, Anamitra,Markiewicz, John T.,Corden, Steven J.,Loefstedt, Joakim,Ankner, Tobias,Richer, Joshua,Hulett, Tyler,Schauer, Douglas J.,Wiest, Olaf,Helquist, Paul. "Evolution of concise and flexible synthetic strategies for trichostatic acid and the potent histone deacetylase inhibitor trichostatin A". . p. 162 - 172. Retrieved 2013/02/23.
• 2、 -. "SYNTHESIS OF HDAC INHIBITORS: TRICHOSTATIN A AND ANALOGUES". Page/Page column 8. . Retrieved 2011/10/12.