36001-47-5

Basic information

• Product Name: vescalagin
• Synonyms: vescalagin;Nsc297812
• CAS NO: 36001-47-5
• Molecular Formula: C₄₁H₂₆O₂₆
• Molecular Weight: 934.63
• Mol File: 36001-47-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.034g/cm³
• Refractive Index: 1.858
• Storage Temp.: -20°C
• PKA: 4.07±0.40(Predicted)
• CAS DataBase Reference: vescalagin(CAS DataBase Reference)
• NIST Chemistry Reference: vescalagin(36001-47-5)
• EPA Substance Registry System: vescalagin(36001-47-5)

Safety Data

• Hazardous Substances Data: 36001-47-5(Hazardous Substances Data)

Usage

General Description

Vescalagin is a polyphenolic compound found in a variety of plants, including oak trees and grapevines. It is classified as a hydrolysable tannin and is abundant in red wine and oak-aged spirits. Vescalagin has been studied for its potential health benefits, including antioxidant, anti-inflammatory, and anti-cancer properties. It has also been shown to have antimicrobial and antiviral effects. Research on vescalagin is ongoing, and its potential therapeutic applications continue to be investigated.

InChI:InChI=1/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11?,31-,34-,35-,36?/m1/s1

Synthetic route

33-carboxy-33-deoxyvescalagin (118964-19-5) → dehydrocastalagin + deoxyvescalagin + castalagin (24312-00-3) + castalagin (36001-47-5)

Conditions	Yield
at 180℃;

β-1-S-butylvescalagin → castalagin (36001-47-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2: water / 20 °C View Scheme

C50H37N2O27S2(1+)*Cl(1-) → castalagin (24312-00-3) + castalagin (36001-47-5)

Conditions	Yield
With water at 20℃;

methanol (67-56-1) + castalagin (36001-47-5) → methylvescalagin (139643-88-2)

Conditions	Yield
With trifluoroacetic acid at 37℃; for 6h; other substrates;	100%
With trifluoroacetic acid at 37℃; for 6h;	100%

castalagin (36001-47-5) → (–)-vescalin (19086-75-0, 34112-28-2) + castalin (19086-75-0, 34112-28-2)

Conditions	Yield
With hydrogenchloride at 60℃; for 65h;	A 32% B 53%

2-thiolomethyl-furan (98-02-2) + castalagin (36001-47-5) → C46H30O27S + C51H34O28S2 + C56H38O29S3

Conditions	Yield
With iron(III) chloride In water at 20℃; for 8h; Inert atmosphere;	A 12% B 19% C 4%

(+)-(S)-3-mercaptohexan-1-ol (90180-90-8) + castalagin (36001-47-5) → C47H38O27S

Conditions	Yield
With iron(III) chloride In water at 20℃; for 4h; Inert atmosphere;	9%

ethanol (64-17-5) + castalagin (36001-47-5) → C43H30O27

Conditions	Yield
In water at 20℃; for 720h; pH=4.5; Oxidation; ethoxylation;

castalagin (36001-47-5) → castalin (19086-75-0, 34112-28-2)

Conditions	Yield
With hydrogenchloride at 60℃; for 24h;

castalagin (36001-47-5) → dehydrocastalagin

Conditions	Yield
at 180℃;

castalagin (36001-47-5) → dehydrocastalin

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / 24 h / 60 °C 2: 1 h / 180 °C View Scheme

castalagin (36001-47-5) → vescalene

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / aq. HCl / 65 h / 60 °C 2: 21 percent / aq. HCl / 144 h / 60 °C View Scheme

castalagin (36001-47-5) → (–)-vescalin (19086-75-0, 34112-28-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / aq. HCl / 65 h / 60 °C 2: 65 percent / aq. HCl / 144 h / 60 °C View Scheme

castalagin (36001-47-5) → ellagic acid (476-66-4) + castalin (19086-75-0, 34112-28-2)

Conditions	Yield
With hydrogenchloride; water for 6h;

castalagin (36001-47-5) + catechin (154-23-4) → (13'S;14'S)-corklin

Conditions	Yield
Stage #1: castalagin In ethanol; water at 35℃; for 240h; pH=3.2; Acidic conditions; Stage #2: catechin In ethanol; water for 480h;

ethanol (64-17-5) + castalagin (36001-47-5) → C43H30O27

Conditions	Yield
In water at 35℃; for 240h; pH=3.2; Acidic conditions;

methanol (67-56-1) + castalagin (36001-47-5) → C42H28O27 + C43H30O27

Conditions	Yield
In water at 35℃; pH=3.2; Acidic conditions;

ethanol (64-17-5) + castalagin (36001-47-5) → C43H30O27

Conditions	Yield
In aq. buffer for 60h; pH=6;	2.8 mg

Upstream product

• 118964-19-5 33-deoxy-33-carboxyvescalagin 

Downstream Products

• 476-66-4 ellagic acid 
• 19086-75-0 castalin 
• 124960-56-1 C₅₂H₄₀N₂O₂₉ 
• 118964-15-1 C₅₆H₃₆O₃₂ 
• 118964-13-9 mongolicin A 

Relevant articles and documents

Protecting-group-free solid-phase anchoring of polyphenolic C-glucosidic ellagitannins and synthesis of 1-alkylamino-vescalagin derivatives

The C-glucosidic ellagitannins vescalagin and vescalin are among the plant polyphenols that have been shown to interact with protein targets in a specific manner. This work describes a protecting-group-free method to immobilize these protein-binding natural products on a solid support, and a functionalizing cleavage method, which is adaptable to the solution-phase synthesis of vescal(ag)in derivatives, and which advantageously permitted the preparation of 1-alkylamino derivatives of vescalagin.