951288-55-4

Basic information

• Product Name: (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate
• Synonyms: (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate
• CAS NO: 951288-55-4
• Molecular Weight: 450.534
• Mol File: 951288-55-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate(951288-55-4)
• EPA Substance Registry System: (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate(951288-55-4)

Safety Data

• Hazardous Substances Data: 951288-55-4(Hazardous Substances Data)

Upstream product

• 331-39-5 caffeic acid 
• 100-39-0 benzyl bromide 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 5396-89-4 benzyl acetoacetate 

Downstream Products

• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 1339946-92-7 benzyl (2R)-hydroxy-3-(3,4-dibenzyloxyphenyl)propionate 
• 1241892-06-7 benzyl (2R,3S)-2,3-dihydroxy-3-(3,4-dibenzyloxyphenyl)-propionate 
• 1241892-07-8 benzyl (2S,3R)-2,3-dihydroxy-3-(3,4-dibenzyloxyphenyl)-propionate 
• 42085-50-7 (2S)-3-(3,4-dihydroxyphenyl)-2-hydroxypropionic acid 
• 23028-17-3 danshensu 
• 732298-08-7 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 1236312-48-3 C₂₃H₂₂O₄ 
• 1309058-48-7 C₃₈H₄₆O₇S 
• 362632-36-8 C₂₃H₂₄O₅ 
• 154-23-4 catechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 1423162-28-0 (E)-N-[(3-(3,4-bis(benzyloxy)phenyl)allyl)oxy]-4-toluenesulfonamide 
• 1423162-19-9 (E)-2-[(3-(3,4-bis(benzyloxy)phenyl)allyl)oxy]isoindoline-1,3-dione 

Relevant articles and documents

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The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regio

Synthesis method of procyanidine compound Catechin

The invention relates to a synthesis method of a procyanidine compound Catechin and belongs to the field of chemical synthesis. The method is as below: conducting benzyl protection reaction on trans-caffeic acid to produce O-Bz caffeic acid; subjecting O-Bz caffeic acid to an ester reduction reaction for synthesis of allyl alcohol; subjecting allyl alcohol to a Sharpless dihydroxylation reaction to synthesize a trihydroxy compound; subjecting the trihydroxy compound to a selective sulfonylation reaction to synthesize sulfonate; subjecting the sulfonate to an O-Ts leaving reaction to synthesize ternary epoxy; conducting a hydroxy mitsunobu reaction to synthesiz O-Ph epoxy; subjecting O-Ph epoxy to a ring-forming reaction to synthesize O-Bz Catechi; subjecting O-Bz Catechin to a palladium carbon deprotection reaction to synthesize the procyanidine compound Catechin (shown in figure). The invention has the characteristics of few reaction steps, high total yield, good product selectivity, and suitability for industrial production.

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation

This work describes the chemical synthesis of O-aryl-β-D-glucosides and 1-O-β-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-β-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-β-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-β-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the π-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.