76543-15-2

Basic information

• Product Name: 2,3-bis(3'-hydroxybenzyl)butyrolactone
• Synonyms: 2,3-bis(3'-hydroxybenzyl)butyrolactone;2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-;2,3-Bhbb;3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone;Bhmdf;trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone
• CAS NO: 76543-15-2
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 0
• Mol File: 76543-15-2.mol

Chemical Properties

• Boiling Point: 561.4°C at 760 mmHg
• Flash Point: 209°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 3.29E-13mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2,3-bis(3'-hydroxybenzyl)butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis(3'-hydroxybenzyl)butyrolactone(76543-15-2)
• EPA Substance Registry System: 2,3-bis(3'-hydroxybenzyl)butyrolactone(76543-15-2)

Safety Data

• Hazardous Substances Data: 76543-15-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2

Upstream product

• 77756-17-3 trans-2,3-bis(3-methoxybenzyl)-4-butanolide 
• 77756-15-1 3-Hydroxymethyl-4-(3-methoxy-phenyl)-butyronitrile 
• 77756-14-0 Toluene-4-sulfonic acid 2-hydroxymethyl-3-(3-methoxy-phenyl)-propyl ester 
• 344564-01-8 3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 158705-71-6 (3R,4R)-3,4-Bis<(3-(benzyloxy)phenyl)methyl>dihydro-2(3H)-furanone 
• 80704-91-2 (3R,4R)-3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 86653-16-9 4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one 
• 77756-13-9 2-<(3-methoxyphenyl)methyl>-1,3-propanediol 
• 61227-48-3 [(3-methoxyphenyl)methyl]propanedioic acid diethyl ester 
• 93578-36-0 1,2-bis[(3-methoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 104079-35-8 (2R,3R)-3-Hydroxymethyl-2-(3-methoxy-benzyl)-4-(3-methoxy-phenyl)-butyric acid methyl ester 
• 6099-04-3 3-methoxycinnamic acid 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 77545-17-6 bis-(3'-benzyloxybenzylidene)-succinic acid 

Downstream Products

• 856412-16-3 [2,4,5,6,2',4',5',6'-2H₈]-enterolactone 
• 1176223-72-5 (3R,4R)-3,4-bis(3-hydroxybenzyl)-tetrahydrofuran-2-ol 
• 104411-12-3 <2,2',4,4',6,6'-2H6>enterodiol 
• 96995-03-8 <1,1-(2)H2>-(+/-)-2,3-bis-(3-hydroxybenzyl)butane-1,4-diol 
• 76543-16-3 2,3-bis(3-hydroxybenzyl)-butane-1,4-diol 
• 77756-23-1 Meso-2,3-bis-[(3-hydroxyphenyl)methyl]-1,4-butane diol 

Relevant articles and documents

Using α- and β-Epimerizations of cis-2,3-Bis(hydroxymethyl)-γ-butyrolactone for the Synthesis of Both Enantiomers of Enterolactone

In the context of asymmetric synthesis, epimerization is usually problematic. Here, we describe the use of the epimerization of cis-2,3-bis(hydroxymethyl)-γ-butyrolactone for the synthesis of enterolactones with anti-carcinogenic, anti-inflammatory, anti-angiogenic, and antioxidant activity. Selective α- or β-epimerization of a γ-butyrolactone was used to selectively synthesize both enantiomers of enterolactone. Theoretical and kinetic studies were performed to elucidate the epimerization mechanism.

Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters

In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.

Isolation and characterization of a human intestinal bacterium Eggerthella sp. CAT-1 capable of cleaving the C-Ring of (+)-catechin and (-)-Epicatechin, followed by p-dehydroxylation of the B-ring

We isolated a human intestinal bacterium, capable of cleaving the C-ring and dehydroxylating the Bring of both (+)-catechin (2 R ,3S ) and (-)-epicatechin (2 R ,3R). Although the strain was classified as Eggerthella (Eg.) lenta [named Eg. sp. CAT-1 (JF798636)] by 16S ribosomal RNA (rRNA) gene similarity, it was quite different in substrate specificity from a previously isolated strain, Eg. sp. SDG-2, which takes part in cleavage of the C-ring and dehydroxylation of the 3,4-dihydroxyphenyl moiety (B-ring) of (3R)-flavan-3-ol derivatives. On the other hand, both Eg. sp. CAT-1 and Eg. sp. SDG-2 showed the same substrate specificity against dehydroxylation of enantiomeric lignans, (+)- and (-)-dihydroxyenterodiol, and (+)- and (-)-dihydroxyenterolactone.

An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone

Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.

Asymmetric syntheses of (-)-enterolactone and 7′R)-7′- hydroxyenterolactone via organocatalyzed aldol reaction

(Chemical Equation Presented) Short syntheses of (-)-enterolactone (1a) and (7′R)-7′-hydroxyenterolactone (1b) have been achieved utilizing organocatalyzed asymmetric cross-aldol reaction of aldehydes 2 and 3 and base-mediated alkylation of lactones 5 and 4.

Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans

A human intestinal bacterium Ruminococcus (R.) sp. END-1 capable of oxidizing (-)-enterodiol to (-)-enterolactone, enantioselectively, was further investigated from the perspective of transformation of plant lignans to mammalian lignans; A cell-free extra

SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES

There is provided a method of producing novel 13C-labelled estrogen analogues. The method preferably proceeds via an intermediate A or B or which is a mixture of (A) or (B): wherein a13C atom is located at one or more of positions 1, 2, 3 or 4 and wherein R is an optionally substituted alkane, alkene, alkyne or aryl group. Preferably R is -CH2Ph. An alternative preferred intermediate compound is 13C-resorcinol.

Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol.

[reaction: see text] We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was

Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria

After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (-)-arctigenin (2), (2R,3R)-2-(3′,4′- dihydroxybenzyl)-3-(3″,4″-dimethoxybenzyl)b

A short synthesis of both enantiomers of enterolactone

A short and efficient synthesis of both enantiomers of enterolactone, a mammalian lignan, is described. The overall yield for the natural enterolactone, over seven steps, was 19% and for its enantiomer 27%.