10299-59-9

Basic information

• Product Name: 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one
• Synonyms: 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one
• CAS NO: 10299-59-9
• Molecular Weight: 272.301
• Mol File: 10299-59-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one(CAS DataBase Reference)
• NIST Chemistry Reference: 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one(10299-59-9)
• EPA Substance Registry System: 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one(10299-59-9)

Safety Data

• Hazardous Substances Data: 10299-59-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 39548-86-2 1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 115623-29-5 2-benzyloxy-4,6-bis(methoxymethyloxy)acetophenone 
• 77-78-1 dimethyl sulfate 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 100-39-0 benzyl bromide 

Downstream Products

• 25739-41-7 velutin 
• 57396-77-7 5‐hydroxy‐7‐methoxy‐2‐(3‐methoxyphenyl)‐4H‐chromen‐4‐one 
• 20243-59-8 7-methylluteoline 
• 169566-44-3 6-benzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxy-4-methoxyacetophenone 
• 16049-42-6 Flavocommelin 
• 1437307-75-9 5-benzoyl-4'-hydroxy-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-74-8 4'-acetoxy-5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-76-0 5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4'-O-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 1437307-72-6 5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-4'-hydroxy-7-methoxyflavone 
• 1437307-71-5 5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone 
• 381686-09-5 3,4,6'-tris-benzyloxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2'-hydroxy-4'-methoxychalcone 
• 381686-10-8 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one 
• 381686-11-9 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 

Relevant articles and documents

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

Synthesis of 8-C-glucosylflavones

The syntheses of orientin, parkinsonin A, isoswertiajaponin, and parkinsonin B, which are 8-C-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone, 5-methyl orientin, 7-methyl orientin, and 5,7-dimethyl orientin, respectively, are reported herein. The C-glucosyl phloroacetophenone derivatives were obtained via a regio- and stereoselective O → C glycosyl rearrangement. Aldol condensation of the C-glucosyl phloroacetophenone derivatives with 3,4-bisbenzyloxybenzaldehyde afforded the corresponding C-glucosylchalcones. Construction of the flavone system by reaction with I2-Me2SO, followed by the elimination of the 5-benzyl protecting group in the flavone structure, yielded an orientin derivative and a isoswertiajaponin derivative. Methylation of the orientin derivatives with dimethyl sulfate afforded the parkinsonin A derivative, the isoswertiajaponin derivative, and the parkinsonin B derivative. Finally, hydrogenolysis of these C-glucosylflavone derivatives led to the four 8-C-glucosylflavones. The NMR spectra of these C-glucosylflavones showed a duplication of signals corresponding to a major rotamer, along with a minor one. Based on NOESY experiments in Me2SO at ambient temperature, they adopted conformations in which the H-2″ and H-4″ protons in the glucose moiety were oriented toward the B-ring in the flavone structure.