177943-50-9

Basic information

• Product Name: 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid
• Synonyms: 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid
• CAS NO: 177943-50-9
• Molecular Weight: 520.536
• Mol File: 177943-50-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid(177943-50-9)
• EPA Substance Registry System: 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid(177943-50-9)

Safety Data

• Hazardous Substances Data: 177943-50-9(Hazardous Substances Data)

Upstream product

• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 86404-07-1 O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 100-39-0 benzyl bromide 
• 15771-06-9 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 100-44-7 benzyl chloride 

Downstream Products

• 177943-51-0 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-L-ascorbic acid 

Relevant articles and documents

Design of novel hybrid vitamin C derivatives: Thermal stability and biological activity

Novel hybrid L-ascorbic acid (vitamin C) derivatives with other biologically active substances, 5-hydroxy-2-hydroxymethyl-β-pyrone (kojic acid) and α-tocopherol (vitamin E), linked at the C-2 or C-3 hydroxyl group were synthesized, and their thermal stability and inhibitory effects on tyrosinase activity, active oxygen species (AOS), and free radicals were estimated in vitro. It was found that a hydrophilic derivative, 2-O-(5- hydroxy-4H-pyran-4-one-2-methyl)-L-ascorbic acid (1), exhibited good thermal stability and inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals compared to vitamin C and its conventional derivatives (such as the 2-phosphate, 6-stearate and 2,6-dipalmitate, and 2- O-octadecylascorbic acid), as well as vitamin E, kojic acid, and arbutin. It is apparent that 1 has the biological properties of vitamin C and kojic acid, and acts synergistically. The hydroxyl groups at the C-3 position of the vitamin C moiety and the C-5 position of the kojic acid moiety are critical for the biological activities. We consider that the kojic acid moiety of 1 counterbalances the diminution of the biological activity due to shielding of the biologically important C-2 hydroxyl group of the vitamin C moiety. In addition, the thermal stability was significantly improved relative to not only vitamin C but also kojic acid. Further, a lipophilic derivative, 3-O- [(α-tocopheryloxy)-2-hydroxypropyl]-D-ascorbic acid, 2, was far more stable than vitamin C and its typical lipophilic derivatives. Compound 2 exhibited almost the same inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals as typical lipophilic derivatives, although these biological activities of 2 were lower than those of vitamin C.