66427-91-6

Basic information

• Product Name: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide
• Synonyms: Benzeneacetamide, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (αR)-
• CAS NO: 66427-91-6
• Molecular Formula: C₂₀H₂₉NO₁₂
• Molecular Weight: 475.4438
• Mol File: 66427-91-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 800°C at 760 mmHg
• Flash Point: 437.6°C
• Density: 1.61g/cm³
• Vapor Pressure: 5.3E-27mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(66427-91-6)
• EPA Substance Registry System: (2R)-2-{[6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]oxy}-2-phenylethanamide(66427-91-6)

Safety Data

• Hazardous Substances Data: 66427-91-6(Hazardous Substances Data)

Upstream product

• 51371-34-7 amygdalin 
• 61091-11-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester 
• 909100-37-4 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)trichloroacetimidate 
• 4358-86-5 (2R)-mandelamide 
• 18423-99-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and Biological Evaluation of Cyanogenic Glycosides

An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

Peptide T (ASTTTNYT) is a promising molecule to prevent the neuropsychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles.