13405-60-2

Basic information

• Product Name: 1-Galloyl-glucose
• Synonyms: 1-Galloyl-glucose;.beta.-D-Glucogallin;.beta.-D-Glucopyranose, 1-(3,4,5-trihydroxybenzoate);.beta.-D-Glucose, 1-gallate;Aids085620;Aids-085620;b-Glucogallin;1-O-Galloyl-b-D-glucose
• CAS NO: 13405-60-2
• Molecular Formula: C₁₃H₁₆O₁₀
• Molecular Weight: 332.26014
• Product Categories: Aromatics, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals;carbohydrate
• Mol File: 13405-60-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 214℃
• Boiling Point: 736.4°C at 760 mmHg
• Flash Point: 278.9°C
• Appearance: /
• Density: 1.85
• Vapor Pressure: 9.04E-23mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Water (Slightly)
• PKA: 7.70±0.25(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 1-Galloyl-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Galloyl-glucose(13405-60-2)
• EPA Substance Registry System: 1-Galloyl-glucose(13405-60-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13405-60-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13405-60-2 differently. You can refer to the following data:
1. β-Glucogalin is used as a novel aldose reductase (ALR2) inhibitor, one of the factors regulating the secondary complications arising from diabetes mellitus.
2. β-Glucogallin is used as a novel aldose reductase (ALR2) inhibitor, one of the factors regulating the secondary complications arising from diabetes mellitus.

InChI:InChI=1/C13H16O10/c14-3-7-9(18)10(19)11(20)13(22-7)23-12(21)4-1-5(15)8(17)6(16)2-4/h1-2,7,9-11,13-20H,3H2/t7-,9-,10+,11-,13+/m1/s1

Synthetic route

2,3,4,6-tetra-O-benzyl-1-(3’,4’,5’-tri-O-benzylgalloyl)-β-D-glucopyranose (1195367-79-3) → β-glucogallin (13405-60-2)

Conditions	Yield
With 20% palladium hydroxide-activated charcoal; hydrogen In tetrahydrofuran at 20 - 25℃; for 12h;	96%
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate under 2585.81 Torr; for 5h; Inert atmosphere;	95%

L-Cysteine methyl ester (2485-62-3) + furosin (148077-26-3) → (R)-1,2,6-Trihydroxy-4,11-dioxo-4,8,9,11-tetrahydro-7H-5,12-dioxa-10-thia-7-aza-benzo[def]chrysene-8-carboxylic acid methyl ester (141968-72-1) + β-glucogallin (13405-60-2)

Conditions	Yield
With ammonium formate In water; acetonitrile at 80℃;	A 60% B 74%

furosin (148077-26-3) → (R)-1,2,6-Trihydroxy-4,11-dioxo-4,8,9,11-tetrahydro-7H-5,12-dioxa-10-thia-7-aza-benzo[def]chrysene-8-carboxylic acid methyl ester (141968-72-1) + β-glucogallin (13405-60-2)

Conditions	Yield
With L-Cysteine methyl ester; ammonium formate In water; acetonitrile at 80℃;	A 60% B 74%

1-galloyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (79814-54-3) → β-glucogallin (13405-60-2)

Conditions	Yield
With methanol; sodium methylate

3,4,5-trihydroxybenzoic acid (149-91-7) + hairy root cultures of Lobelia sessilifolia → gallic acid 3-O-β-D-glucopyranoside + β-glucogallin (13405-60-2)

Conditions	Yield
In water for 96h;	A 190 mg B 230 mg

+ 3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 3.33 h / Inert atmosphere; Molecular sieve 2.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 5 h / 2585.81 Torr / Inert atmosphere View Scheme

1-O-(3,4,5-tribenzyloxybenzoyl)-β-D-glucopyranoside → β-glucogallin (13405-60-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 2585.81 Torr; for 4h;
With 10 wt% Pd(OH)2 on carbon; hydrogen In ethanol; acetone at 20℃; for 4h;

3,4,5-trihydroxybenzoic acid (149-91-7) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 2: thionyl chloride / dichloromethane 3: dichloromethane / 72 h / Inert atmosphere 4: perchloric acid; silica gel / acetonitrile / 24 h 5: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme

3,4,5-tribenzyloxybenzoic acid (1486-48-2) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane 2: dichloromethane / 72 h / Inert atmosphere 3: perchloric acid; silica gel / acetonitrile / 24 h 4: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme

3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 72 h / Inert atmosphere 2: perchloric acid; silica gel / acetonitrile / 24 h 3: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 48 h / Reflux 2: hydrogen; 20% palladium hydroxide-activated charcoal / tetrahydrofuran / 12 h / 20 - 25 °C View Scheme

1-O-(3,4,5-tris(benzyloxy)benzoyl)-4,6-O-benzylidene-β-D-glucopyranose (1555352-04-9) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid; silica gel / acetonitrile / 24 h 2: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme

UDP-glucose (133-89-1) + 3,4,5-trihydroxybenzoic acid (149-91-7) → β-glucogallin (13405-60-2)

Conditions	Yield
With recombinant Quercus robur UGT84A13 In glycerol at 30℃; pH=6; Kinetics; Enzymatic reaction;
With Punica granatum UDP-glucosyltransferase 84A23; 2-hydroxyethanethiol In aq. buffer at 30℃; for 1h; pH=7; Enzymatic reaction;

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 48 h / Reflux 2: hydrogen; 20% palladium hydroxide-activated charcoal / tetrahydrofuran / 12 h / 20 - 25 °C View Scheme

Heptabenzyl-α-D-glucogallin (106822-42-8) → β-glucogallin (13405-60-2) + 1-O-galloyl-α-D-glucopyranose (53318-36-8)

Conditions	Yield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol

alpha-D-glucopyranose (492-62-6) + 3,4,5-tribenzyloxybenzoic acid (1486-48-2) → β-glucogallin (13405-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere 2: 10 wt% Pd(OH)2 on carbon; hydrogen / acetone; ethanol / 4 h / 20 °C View Scheme

1,6-di-O-galloyl-(α/β)-glucopyranose (23363-08-8) + β-glucogallin (13405-60-2) → 3,4,5-trihydroxybenzoic acid (149-91-7) + 6-O-galloyl-D-glucopyranose (7253-25-0) + 1,2,6-tri-O-galloyl β-D-glucopyranoside (79886-49-0, 81571-75-7, 82008-89-7, 135093-93-5)

Conditions	Yield
In water at 40℃; for 5h; 2-O-galloyltransferase, citrate buffer, pH 5.0; Yield given;

tannic acid + β-glucogallin (13405-60-2) → 4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose (99877-83-5) + 2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose (52238-31-0) + hexagalloyl β-D-glucose

Conditions	Yield
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation;

4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose (99877-83-5) + β-glucogallin (13405-60-2) → C55H40O34

Conditions	Yield
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation;

2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose (52238-31-0) + β-glucogallin (13405-60-2) → C55H40O34 (99877-84-6) + C55H40O34 (99877-87-9)

Conditions	Yield
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation;

hexagalloyl β-D-glucose (99877-82-4) + β-glucogallin (13405-60-2) → C55H40O34 (99877-85-7)

Conditions	Yield
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation;

β-glucogallin (13405-60-2) → ellagic acid

Conditions	Yield
In aq. buffer at 22℃; pH=10; Kinetics; pH-value; Time;

cyanidin-3-glucoside (47705-70-4, 142506-26-1) + β-glucogallin (13405-60-2) → 3,5-di-O-β-D-glucopyranoside of cyanidin (20905-74-2)

Conditions	Yield
With citric acid at 30℃; for 0.25h; pH=5.6; Catalytic behavior; Enzymatic reaction;

Upstream product

• 79814-54-3 1-galloyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 1195367-79-3 2,3,4,6-tetra-O-benzyl-1-(3’,4’,5’-tri-O-benzylgalloyl)-β-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 106822-42-8 Heptabenzyl-α-D-glucogallin 
• 492-62-6 alpha-D-glucopyranose 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 133-89-1 UDP-glucose 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 1555352-04-9 1-O-(3,4,5-tris(benzyloxy)benzoyl)-4,6-O-benzylidene-β-D-glucopyranose 
• 148077-26-3 furosin 
• 2485-62-3 L-Cysteine methyl ester 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 7253-25-0 6-O-galloyl-D-glucopyranose 
• 79886-49-0 1,2,6-tri-O-galloyl β-D-glucopyranoside 
• 20905-74-2 3,5-di-O-β-D-glucopyranoside of cyanidin 
• 476-66-4 ellagic acid 
• 99877-85-7 C₅₅H₄₀O₃₄ 
• 99877-84-6 C₅₅H₄₀O₃₄ 
• 99877-87-9 C₅₅H₄₀O₃₄ 
• 99877-83-5 4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose 
• 52238-31-0 2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose 
• 99877-82-4 hexagalloyl β-D-glucose 

Relevant articles and documents

Two UGT84 family glycosyltransferases catalyze a critical reaction of hydrolyzable tannin biosynthesis in pomegranate (Punica granatum)

Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cloned and biochemically characterized four candidate UGTs from pomegranate (Punica granatum), of which only UGT84A23 and UGT84A24 exhibited β-glucogallin forming activities in enzyme assays. Although overexpression and single RNAi knockdown pomegranate hairy root lines of UGT84A23 or UGT84A24 did not lead to obvious alterations in punicalagin (the prevalent HT in pomegranate) accumulation, double knockdown lines of the two UGTs resulted in largely reduced levels of punicalagins and bis-hexahydroxydiphenyl glucose isomers. An unexpected accumulation of galloyl glucosides (ether-linked gallic acid and glucose) was also detected in the double knockdown lines, suggesting that gallic acid was utilized by an unidentified UGT activity for glucoside formation. Transient expression in Nicotiana benthamiana leaves and immunogold labeling in roots of pomegranate seedlings collectively indicated cytosolic localization of UGT84A23 and UGT84A24. Overall, functional characterization and localization of UGT84A23 and UGT84A24 open up opportunities for further understanding the regulatory control of HT metabolism in plants and its coordination with other biochemical pathways in the metabolic network.

NOVEL GLYCOSYLTRANSFERASE, NOVEL GLYCOSYLTRANSFERASE GENE, AND NOVEL GLYCOSYL DONOR COMPOUND

An object of the present invention is to provide a sugar donating reagent comprising a sugar donor compound other than a sugar nucleotide and an enzyme capable of catalyzing a glycosyl transfer reaction using a sugar donor compound other than a sugar nucleotide. The present invention provides the following: a sugar donating reagent containing a compound of formula (A): wherein R 1 is independently selected from hydrogen, or C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl in which each of the groups is unsubstituted or substituted with one or more groups selected from OH, F, Cl, Br, I, CN, NO 2 , and SO 2 , n is 0, 1, 2, 3, 4 or 5, m is 0 or 1, and X represents a monosaccharide bound via a 2 bond on its anomeric carbon; a glycosyltransferase capable of catalyzing a glycosyl transfer reaction using the sugar donor; and a glycosyltransferase gene comprising DNA encoding the glycosyltransferase.

Identification of UGT84A13 as a candidate enzyme for the first committed step of gallotannin biosynthesis in pedunculate oak (Quercus robur)

A cDNA encoding the ester-forming hydroxybenzoic acid glucosyltransferase UGT84A13 was isolated from a cDNA library of Quercus robur swelling buds and young leaves. The enzyme displayed high sequence identity to resveratrol/hydroxycinnamate and hydroxybenzoate/hydroxycinnamate glucosyltransferases from Vitis species and clustered to the phylogenetic group L of plant glucosyltransferases, mainly involved in the formation of 1-O-β-d-glucose esters. In silico transcriptome analysis confirmed expression of UGT84A13 in Quercus tissues which were previously shown to exhibit UDP-glucose:gallic acid glucosyltransferase activity. UGT84A13 was functionally expressed in Escherichia coli as N-terminal His-tagged protein. In vitro kinetic measurements with the purified recombinant enzyme revealed a clear preference for hydroxybenzoic acids as glucosyl acceptor in comparison to hydroxycinnamic acids. Of the preferred in vitro substrates, protocatechuic, vanillic and gallic acid, only the latter and its corresponding 1-O-?-D-glucose ester were found to be accumulated in young oak leaves. This indicates that in planta UGT84A13 catalyzes the formation of, 1-O-galloyl-?-D-glucose, the first committed step of gallotannin biosynthesis.