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

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

Uses

Used in Cancer Prevention:
Enterodiol is used as a chemopreventive agent for reducing the risk of hormone-related cancers such as breast and prostate cancer. Its hormone-regulating properties help in maintaining hormonal balance and preventing the development of hormone-sensitive tumors.
Used in Anti-Inflammatory Applications:
Enterodiol is used as an anti-inflammatory agent to reduce inflammation in the body. Its ability to modulate the gut microbiota and reduce inflammation makes it a potential candidate for treating inflammatory conditions.
Used in Antioxidant Therapy:
Enterodiol is used as an antioxidant to neutralize free radicals and protect the body from oxidative stress. Its antioxidant properties help in preventing cellular damage and reducing the risk of various diseases.
Used in Gut Microbiota Modulation:
Enterodiol is used as a modulator of gut microbiota to maintain a healthy balance of gut bacteria. Its ability to modulate the gut microbiota can contribute to overall gut health and immune function.

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

• 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 
• 76543-15-2 trans-2,3-bis[(3-hydroxyphenyl)methyl]-γ-butyrolactone 

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.

Oxidative metabolism of the mammalian lignans enterolactone and enterodiol by rat, pig, and human liver microsomes

Hepatic microsomes from aroclor-treated male Wistar rats biotransform enterolactone to 12 metabolites, six of which carry an additional hydroxy group at the aromatic and six at the aliphatic moiety according to HPLC/MS and GC/MS analysis. The aromatic hyd

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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.

SYNTHESIS OF COMPOUND X, A NON-STEROIDAL CONSTITUENT OF FEMALE URINE, AND CONGENERS

The synthesis of trans-(+/-)- and (-)-3,4-bisdihydro-2-(3H)-furanone (1), a recently discovered constituent of female urine, and some related compounds of biological interest is described.