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, an ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core, is a polyphenol and hydrolyzable tannin that can be isolated from a variety of plants. It is an off-white solid that inhibits squalene epoxidase, a key enzyme in cholesterol synthesis, and exhibits various anti-inflammatory and anti-cancer effects.

Uses

Used in Pharmaceutical Industry:
Corilagin is used as a thrombolytic agent for its ability to dissolve blood clots and improve blood flow, making it a potential candidate for the treatment of various cardiovascular diseases.
Used in Cholesterol-Lowering Applications:
Corilagin is used as a cholesterol-lowering agent due to its inhibitory effect on squalene epoxidase, a key enzyme in cholesterol synthesis, which can help reduce high cholesterol levels and support cardiovascular health.
Used in Anti-Inflammatory Applications:
Corilagin is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Anti-Cancer Applications:
Corilagin is used as an anti-cancer agent for its potential to inhibit the growth and proliferation of cancer cells, making it a promising candidate for cancer prevention and treatment.

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

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

Downstream Products

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