7530-92-9

Basic information

• Product Name: Octanethioic acid
• Synonyms: Octanethioic acid
• CAS NO: 7530-92-9
• Molecular Formula: C₈H₁₆OS
• Molecular Weight: 160.27704
• Mol File: 7530-92-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 95-96℃ (3 Torr)
• Flash Point: 87.5±18.7℃
• Appearance: /
• Density: 0.933±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: Octanethioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Octanethioic acid(7530-92-9)
• EPA Substance Registry System: Octanethioic acid(7530-92-9)

Safety Data

• Hazardous Substances Data: 7530-92-9(Hazardous Substances Data)

Upstream product

• 111-64-8 n-octanoic acid chloride 
• 62-55-5 thioacetamide 
• 124-07-2 Octanoic acid 

Downstream Products

• 59051-66-0 cyclohexanethiooctanoate 
• 1196806-30-0 5-[3-(1-phenyl-1 H-tetrazol-5-ylsulfonyl)propyl]octanethioate 
• 70659-87-9 N-benzyloctanoic amide 
• 1009815-87-5 largazole 
• 1429340-54-4 (-)-S-{4-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]butyl} octanethioate 
• 1429340-71-5 (-)-S-{5-[(3S,9S,14aR)-9-benzyl-6,6-dimethyl-1,4,7,10-tetraoxotetradecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]pentyl} octanethioate 
• 2432-83-9 S-methyl thiocaprylate 

Relevant articles and documents

Process Development and Scale-up Total Synthesis of Largazole, a Potent Class i Histone Deacetylase Inhibitor

Herein we describe the research and development of the process for the scale-up total synthesis of largazole, a potent class I selective histone deacetylase (HDAC) inhibitor, a potential anticancer agent and also useful for the treatment of other disorders where transcriptional reprogramming might be beneficial. The synthetic route and conditions for each fragment and final product were modified and optimized to make them suitable for larger-scale synthesis. With the process we developed, hundreds of grams of each fragment and decagrams of final product largazole were synthesized in good to excellent yields. The final target largazole was obtained in 21% overall yield over eight steps based on the longest sequence with over 95% HPLC purity.

Synthesis and biological characterization of the histone deacetylase inhibitor largazole and C7- modified analogues

Largazole 4a and analogues with modifications at the C7 position, as well as 2,4′-bithiazole 5a, have been synthesized using an acyclic cross-metathesis of the corresponding depsipeptide structures assembled by N-C6(O) or C15(O)-N lactam formation. Similar to the parent system 4a, the series of largazole depsipeptides 4b-d, but not 2,4′-bithiazole 5a, showed a marked inhibition of recombinant HDAC1 and selectivity over HDAC4, as well as strong pro-apoptotic effects on the NB4 leukemia cell line, but they failed to induce differentiation to mature granulocytes. Functional assays of the analogues correlated with the in vitro activities, as shown by increased H3 and α-tubulin acetylation levels and p21WAF1/CIP1 up-regulation in NB4 cells. The activity of the natural product HDACi largazole 4a is not significantly altered by the presence of groups of different size (H, Et, Ph) at C7 on the dihydrothiazole ring.

Synthesis and biological activity of largazole and derivatives

A modular synthesis of the marine natural product largazole and related synthetic analogues is described. Largazole was prepared in 19% overall yield through a synthetic route with a longest linear sequence of nine steps. Activity tests showed the necessity of the thiobutenyl moiety for antiproliferative activity. (Chemical Equation Presented).