68676-88-0

Basic information

• Product Name: Trichostatin C
• Synonyms: 7-[4-(Dimethylamino)phenyl]-N-(β-D-glucopyranosyloxy)-4,6-dimethyl-7-oxo-2,4-heptadienamide;145-A
• CAS NO: 68676-88-0
• Molecular Formula: C23H32N2O8
• Molecular Weight: 464.512
• Mol File: 68676-88-0.mol

Chemical Properties

• Melting Point: 171-173°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.33g/cm³
• Refractive Index: 1.608
• PKA: 12.85±0.70(Predicted)
• CAS DataBase Reference: Trichostatin C(CAS DataBase Reference)
• NIST Chemistry Reference: Trichostatin C(68676-88-0)
• EPA Substance Registry System: Trichostatin C(68676-88-0)

Safety Data

• Hazardous Substances Data: 68676-88-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trichostatin C is used as an inducer of erythroid differentiation and histone H4 acetylation level. This application is significant because it can potentially be utilized in the treatment of various diseases and conditions related to abnormal cell differentiation and gene expression regulation.
Used in Anticancer Applications:
Trichostatin C is used as an antitumor agent due to its ability to inhibit histone deacetylases, which are often dysregulated in cancer cells. By modulating the acetylation levels of histones, trichostatin C can help regulate gene expression and potentially suppress tumor growth.
Used in Antifungal Applications:
Trichostatin C is used as an antifungal agent, providing a natural alternative for the treatment of fungal infections. Its ability to inhibit histone deacetylases in fungi can help control the growth and proliferation of fungal pathogens.
Used in Antiprotozoan Applications:
Trichostatin C is used as an antiprotozoan agent, particularly against protozoan parasites that cause various diseases in humans and animals. Its inhibitory effect on histone deacetylases can help disrupt the life cycle and survival of these parasites.

InChI:InChI=1/C23H32N2O8/c1-13(11-14(2)19(28)15-6-8-16(9-7-15)25(3)4)5-10-18(27)24-33-23-22(31)21(30)20(29)17(12-26)32-23/h5-11,14,17,20-23,26,29-31H,12H2,1-4H3,(H,24,27)/b10-5+,13-11+/t14-,17-,20-,21+,22-,23+/m1/s1

Upstream product

• 833476-60-1 (3aR,7aS)-2-[(2R,3R,4S,5R,6R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-isoindole-1,3-dione 
• 833476-56-5 (3aR,7aS)-2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-isoindole-1,3-dione 
• 833476-62-3 O-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-hydroxylamine 
• 833476-58-7 (3aR,7aS)-2-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-isoindole-1,3-dione 
• 794525-07-8 (4S,1'E,3'E)-(-1'-{[tert-butyl(dimethyl)silyl]oxy}-2'-methyl-1',3'-pentadienyl)-4-isopropyl-1,3-oxazolidin-2-one 
• 114127-17-2 (S)-trichostatic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 58880-19-6 trichostatin A 
• 120221-14-9 (2-chloro-4-nitrophenyl)-β-D-glucopyranoside 
• 833476-46-3 (R)-3-[(E)-(4R,5R)-5-(4-Bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enoyl]-4-isopropyl-oxazolidin-2-one 
• 833476-69-0 (2E,4E)-(6R,7R)-7-(4-Bromo-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hepta-2,4-dienoic acid ethyl ester 
• 833476-52-1 (2E,4E)-(6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-(4-dimethylamino-phenyl)-4,6-dimethyl-hepta-2,4-dienoic acid 
• 833476-50-9 (2E,4E)-(6R,7R)-7-(4-Bromo-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hepta-2,4-dienoic acid 

Relevant articles and documents

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

We describe the ability of an engineered glycosyltransferase (OleD Loki) to catalyze the N-glycosylation of tertiary-amine-containing drugs and trichostatin hydroxamate glycosyl ester formation. As such, this study highlights the first bacterial model catalyst for tertiary-amine N-glycosylation and further expands the substrate scope and synthetic potential of engineered OleDs. In addition, this work could open the door to the discovery of similar capabilities among other permissive bacterial glycosyltransferases.

The first total synthesis of trichostatin D

Trichostatin D and 6-epi-trichostatin D have been stereoselectively synthesized through a remote stereoinduction with a chiral vinylketene silyl N,O-acetal and glycosylation of hydroxyimide under Mitsunobu conditions.