80226-00-2

Basic information

• Product Name: ENTERODIOL
• Synonyms: (-)-ENTERODIOL;ENTERODIOL;4,4',9,9'-TETRAHYDROXYLIGNAN;3,3'-[2,3-BIS(HYDROXYMETHYL)BUTANE-1,4-DIYL]DIPHENOL;ENTERODIOL, >95% (HPLC);ENTERODIOL hplc;2,3-Bis(3-hydroxybenzyl)-1,4-butanediol;2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol
• CAS NO: 80226-00-2
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.36
• Product Categories: Miscellaneous Natural Products
• Mol File: 80226-00-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 554.9 °C at 760 mmHg
• Flash Point: 262.5 °C
• Appearance: solid
• Density: 1.251 g/cm³
• Vapor Pressure: 3.79E-13mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: 2-8°C
• PKA: 9.68±0.10(Predicted)
• BRN: 8997364
• CAS DataBase Reference: ENTERODIOL(CAS DataBase Reference)
• NIST Chemistry Reference: ENTERODIOL(80226-00-2)
• EPA Substance Registry System: ENTERODIOL(80226-00-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 80226-00-2(Hazardous Substances Data)

Usage

General Description

Enterodiol is a natural lignan compound that is produced in the human gut through the microbial metabolism of plant lignans found in the diet. It is known for its potential health benefits, including anti-inflammatory, antioxidant, anti-cancer, and hormone-regulating properties. Enterodiol has been studied for its role in reducing the risk of hormone-related cancers such as breast and prostate cancer, as well as its ability to modulate the gut microbiota and reduce inflammation in the body. Overall, enterodiol is a promising compound with potential therapeutic applications in various health conditions.

InChI:InChI=1/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2

Upstream product

• 76543-15-2 trans-2,3-bis[(3-hydroxyphenyl)methyl]-γ-butyrolactone 
• 77756-17-3 trans-2,3-bis(3-methoxybenzyl)-4-butanolide 
• 86653-16-9 4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one 
• 77756-14-0 Toluene-4-sulfonic acid 2-hydroxymethyl-3-(3-methoxy-phenyl)-propyl ester 
• 77756-15-1 3-Hydroxymethyl-4-(3-methoxy-phenyl)-butyronitrile 
• 77756-13-9 2-<(3-methoxyphenyl)methyl>-1,3-propanediol 
• 61227-48-3 [(3-methoxyphenyl)methyl]propanedioic acid diethyl ester 
• 77545-17-6 bis-(3'-benzyloxybenzylidene)-succinic acid 
• 77545-18-7 (+/-)-2,3-bis-(3'-hydroxybenzyl)-succinic acid 
• 78032-13-0 2-[1-(3-Benzyloxy-phenyl)-meth-(Z)-ylidene]-succinic acid dimethyl ester 
• 78032-12-9 3'-benzyloxybenzylidene succinic acid 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 96995-01-6 (+/-)-trans-2-(3-benzyloxybenzyl)-3-<3-benzyloxy-α,α-bis(phenylthio)benzyl>butyrolactone 
• 96995-00-5 3-benzyloxybenzaldehyde bis(phenylthio) acetal 

Relevant articles and documents

Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate)

A series of trans-3,4-dibenzyltetrahydrofurans has been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate), affording dibenzocyclooctadiene lignans belonging to the isostegane series, in high yields. Since no evidence was found for the formation of the corresponding stegane isomers it is assumed that the reactions proceed with complete diastereoselectivity.

CHEMICAL SYNTHESIS OF THE FIRST LIGNANS TO BE FOUND IN HUMANS AND ANIMALS

Trans-2,3-bis-(3'-hydroxybenzyl)-butyrolactone (1) and 2,3-bis-(3'-hydroxybenzyl)-butane-1,4-diol (2), recently identified in urine, have been synthesised in racemic form.