517-46-4

Basic information

• Product Name: Strictinin
• Synonyms: Strictinin;4-O,6-O-[(4,4',5,5',6,6'-Hexahydroxybiphenyl-2,2'-diyl)biscarbonyl]-β-D-glucopyranose 1-(3,4,5-trihydroxybenzoate)
• CAS NO: 517-46-4
• Molecular Formula: C₂₇H₂₂O₁₈
• Molecular Weight: 634.45278
• Mol File: 517-46-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 1280.8°Cat760mmHg
• Flash Point: 418.8°C
• Appearance: /
• Density: 2.11g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.88
• CAS DataBase Reference: Strictinin(CAS DataBase Reference)
• NIST Chemistry Reference: Strictinin(517-46-4)
• EPA Substance Registry System: Strictinin(517-46-4)

Safety Data

• Hazardous Substances Data: 517-46-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)21(37)23-13(43-27)5-42-25(40)7-3-11(30)17(33)19(35)14(7)15-8(26(41)44-23)4-12(31)18(34)20(15)36/h1-4,13,21-23,27-38H,5H2/t13-,21-,22-,23-,27+/m1/s1

Upstream product

• 79786-00-8 casuarictin 
• 113900-92-8 nobotanin G 
• 109742-46-3 3-O-galloyl-1,2;4,6-bis-O-(S)-(4,4’,5,5’,6,6’-hexabenzyloxy-1,1’-biphenyl-2,2’-dicarboxylate)-β-D-glucopyranose 
• 160657-48-7 3,5,4-tri(methoxymethyloxy)benzoic acid 
• 2280-44-6 D-Glucose 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 36378-48-0 4,6-O-<(S)-4,4',5,5',6,6'-hexahydroxydiphenoyl>-D-glucose 

Relevant articles and documents

First Total Synthesis of Neostrictinin

Herein, we describe the first total synthesis of neostrictinin, a natural ellagitannin bearing a (R)-hexahydroxydiphenoyl (HHDP) bridge between the 4- and 6-oxygens of d-glucose. Among the multitude of 4,6-O-HHDP bridged ellagitannins, (R)-axial chirality of the HHDP bridge is quite rare as it is less stable than the corresponding (S)-isomer. The labile bridge was constructed using a two-step bislactonization that involved: (1) monoacylation of the primary alcohol of ethyl 2,3-O-benzyl-1-thio-β-d-glucopyranoside using protected (R)-hexahydroxydiphenic anhydride and (2) intramolecular lactonization of the obtained seco acid by treatment with a Mukaiyama condensation reagent (2-chloro-N-methylpyridinium iodide) and 2,6-lutidine. Structural confirmation of the synthesized neostrictinin and the preparation of its epimer are also reported.

TANNIN INHIBITORS OF HIV

The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

Synthesis of enantiomerically pure strictinin using a stereoselective esterification reaction

The total synthesis of strictinin (4) has been achieved using a diastereoselective esterification of benzyl protected hexahydroxydiphenic acid 1 with D-glucose derived sugar 2.