828939-85-1

Basic information

• Product Name: phenacyl (R)-3-hydroxyicosanoate
• Synonyms: phenacyl (R)-3-hydroxyicosanoate
• CAS NO: 828939-85-1
• Molecular Weight: 446.671
• Mol File: 828939-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: phenacyl (R)-3-hydroxyicosanoate(CAS DataBase Reference)
• NIST Chemistry Reference: phenacyl (R)-3-hydroxyicosanoate(828939-85-1)
• EPA Substance Registry System: phenacyl (R)-3-hydroxyicosanoate(828939-85-1)

Safety Data

• Hazardous Substances Data: 828939-85-1(Hazardous Substances Data)

Upstream product

• 112-76-5 Stearoyl chloride 
• 136890-22-7 (R)-β-hydroxyeicosanoic acid methyl ester 
• 14531-35-2 methyl 3-oxoicosanoate 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 828939-43-1 phenacyl (R)-3-(octadecanoyloxy)icosanoate 

Relevant articles and documents

Synthesis and purity assessment of tetra- and pentaacyl lipid A of Chlamydia containing (R)-3-hydroxyicosanoic acid

Based on structural data of lipid A from Chlamydia trachomatis strains, chemically pure tetra- and pentaacyl 1,4′-bisphosphoryl as well as the related 4′-monophosphoryl derivatives of lipid A were synthesized. (R)-3-Hydroxyicosanoic acid as a chiral constituent was prepared via Noyori-reduction of methyl-3-oxoicosanoic acid. Synthetic intermediates were O-acylated with myristoic acid residues at positions 3 and 3′ and N-acylated with (R)-3-hydroxyicosanoic acid at both glucosamine units. Efficient purification methods for highly hydrophobic long-chain tri-, tetra- and pentaacyl progenitors of lipid A have been developed. Purity and homogeneity of the synthetic target compounds were confirmed by NMR and MS-data as well as a sensitive immunostaining approach. The tetra- and pentaacyl species serve as biomedical probes to investigate the endotoxic potential of chlamydial lipid A and to clarify its role in Chlamydia associated infections. Graphical Abstract