23094-69-1

Basic information

• Product Name: CORILAGIN
• Synonyms: 1-O-Galloyl-3-O,6-O-[2,2',3,3',4,4'-hexahydroxy[1,1'-biphenyl]-6,6'-diylbiscarbonyl]-β-D-glucopyranose;Galloyl 3-O,6-O-[(4,4',5,5',6,6'-hexahydroxy-1,1'-biphenyl-2,2'-diyl)biscarbonyl]-β-D-glucopyranoside;CORILAGIN(SH);CORILAGIN;B-D-GLUCOPYRANOSE, CYCLIC 3,6-(4,4',5,5',6,6'-HEXAHYDROXY[1,1'-BIPHENYL]-2,2'-DICARBOXYLATE)1-(3,4,5-TRIHYDROXYBENZOATE), (R)-;1-O-GALLOYL-3,6-HEXAHYDROXYDIPHENOYL-BETA-D-GLUCOPYRANOSE;CORILAGIN: B-D-GLUCOPYRANOSE, CYCLIC3,6-(4,4',5,5',6,6'-HEXAHYDROXY[1,1'-BIPHENYL]-2,2'-DICARBOXYLATE)1-(3,4,5-TRIHYDROXYBENZOATE), (R)-,;1-O-Galloyl-3,6-hexahydroxydiphenol-b-D-Glucopyranose
• CAS NO: 23094-69-1
• Molecular Formula: C₂₇H₂₂O₁₈
• Molecular Weight: 634.45
• Product Categories: Carbohydrates & Derivatives;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Miscellaneous Natural Products
• Mol File: 23094-69-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: >200°C dec
• Boiling Point: 1297.4°Cat760mmHg
• Flash Point: 426.3°C
• Appearance: Off-White Solid
• Density: 2.17g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.88
• Storage Temp.: -20°C Freezer
• Solubility: H2O: soluble1mg/mL, clear, colorless
• PKA: 7.53±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: CORILAGIN(CAS DataBase Reference)
• NIST Chemistry Reference: CORILAGIN(23094-69-1)
• EPA Substance Registry System: CORILAGIN(23094-69-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23094-69-1(Hazardous Substances Data)

Usage

Description

Corilagin is a polyphenol and hydrolyzable tannin that can be isolated from a variety of plants. It inhibits squalene epoxidase (IC50 = 4.0 μM), a key enzyme in cholesterol synthesis. Corilagin also has various anti-inflammatory and anti-cancer effects.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 23094-69-1 differently. You can refer to the following data:
1. Thrombolytic
2. Thrombolytic.

Definition

ChEBI: An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.

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

Upstream product

• 2485-62-3 L-Cysteine methyl ester 
• 81905-83-1 geraniin 
• 60976-49-0 geraniin 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 133145-19-4 Phyllanthusiin D 
• 132185-49-0 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose 
• 106647-18-1 geraniinic acid A 
• 60976-49-0 Granatin B 
• 100227-56-3 1-O-galloyl-2,4;3,6-bis-(R)-4,5,6,4,5,6-hexahydroxydiphenoyl-β-D-glucose 
• 70-18-8 GLUTATHIONE 

Downstream Products

• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 76692-72-3 corilagin nonamethyl ether 
• 97152-19-7 dimethyl 4,4',5,5',6,6'-hexakis(benzyloxy)-[1,1'-biphenyl]-2,2'-dicarboxylate 
• 23094-70-4 corilagin undeca-acetate 

Relevant articles and documents

Furosonin, a novel hydrolyzable tannin from geranium thunbergii

Furosonin (2), a novel hydrolyzable tannin, was isolated from Geranium thunbergii (Geraniaceae) leaves, and the structure was determined based on spectroscopic data. The effects of geraniin (1), furosonin (2), and related hydrolyzable tannins on antibiotic resistance were examined, and repandusinic acid A (4) was found to suppress oxacillin resistance of methicillin-resistant Staphylococcus aureus.

Total Synthesis of Mallotusinin

The total synthesis of mallotusinin, which bears a tetrahydroxydibenzofuranoyl (THDBF) bridge between the 2-oxygen and 4-oxygen of glucose on corilagin with a 3,6-O-(R)-hexahydroxydiphenoyl (HHDP) bridge, is described. The key features of the total synthesis are: 1) improvements of our previously reported method to synthesize corilagin; 2) establishment of the THDBF skeleton via an unusual intramolecular SNAr reaction of an HHDP analogue, and 3) the application of a two-step bislactonization strategy for a HHDP bridge construction into the 2,4-O-THDBF bridge. Oxidative phenol coupling of 1,2,4-orthoacetyl-3,6-di-(4-O-benzylgalloyl)-α-d-glucopyranose and the orthoester cleavage of the coupling product without the pyranose-furanose ring transformation are key reactions for the improved synthesis of corilagin, which enabled the adequate supply of a corilagin precursor that was required to develop the mallotusinin synthesis. These established methods are expected to help develop the synthesis of other ellagitannins with a bridge between the two oxygens of corilagin.

Glutathione-mediated conversion of the ellagitannin geraniin into chebulagic acid

Geraniin (1), a widely distributed ellagitannin having a dehydrohexahydroxydiphenoyl (DHHDP) ester moiety, was converted into chebulagic acid (2), an ellagitannin having a chebuloyl ester moiety, which was reported to be a potent inhibitor of DNA topoisomerases. This was achieved by addition of the thiol group of glutathione to the six-membered acetal ring form of the DHHDP moiety (1a) with concomitant hydrolytic ring cleavage and subsequent reductive desulfurization with Raney nickel. The concurrent addition of the thiol to the five-membered acetal ring form of the DHHDP group (1b) generated the product 14 and its precursor 13, which are structurally related to naturally occurring ellagitannins isolated from Euphorbiaceous plants. Thus, the rearrangements observed in these reactions may be relevant to the metabolism of DHHDP esters in plants.