57759-55-4

Basic information

• Product Name: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol
• Synonyms: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol
• CAS NO: 57759-55-4
• Molecular Weight: 362.423
• Mol File: 57759-55-4.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol(57759-55-4)
• EPA Substance Registry System: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol(57759-55-4)

Safety Data

• Hazardous Substances Data: 57759-55-4(Hazardous Substances Data)

Upstream product

• 487-36-5 (+)-epipinoresinol 
• 4263-88-1 pinoresinol 
• 580-72-3 matairesinol 
• 111265-99-7 C₁₃H₁₄O₆^(2-)*2K⁽¹⁺⁾ 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 158932-33-3 secoisolariciresinol diglycoside 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1071726-15-2 (1S,2S,3R)-1-(4-benzyloxy-3-methoxyphenyl)-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(methoxymethoxy)methyl]-2-trityloxymethyl-1,4-butanediol 
• 1243054-22-9 trans-(E)-dimethyl 2,3-bis(4-benzyloxy-3-methoxybenzylidene)-1,4-butanediol 
• 33837-83-1 3-(1,1-dimethylethyl)-4-hydroxy-5-methoxybenzaldehyde 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 111266-03-6 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 111194-08-2 (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol 

Downstream Products

• 121621-31-6 L_g-threo-1,4-bis-benzoyloxy-2,3-bis-(4-benzoyloxy-3-methoxy-benzyl)-butane 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 62624-76-4 (8R,8'R)-9,9'-epoxy-3,4,3',4'-tetramethoxylignane 
• 29388-33-8 (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide 
• 67597-01-7 Secoisolarcinoltetraacetat 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 1243054-24-1 meso-2,3-bis(4'-benzyloxy-3'-methoxybenzyl)-1,4-butanediol 
• 1206712-52-8 secoisolariciresinol-4',4''-diacetate 

Relevant articles and documents

Antiestrogenic and antiproliferative potency of secoisolariciresinol diglucoside derivatives on MCF-7 breast cancer cells

Secoisolariciresinol diglucoside (SDG) is isolated from Linum usitatissimum seeds. The antiproliferative effects of SDG (1) and its derivatives secoisolariciresinol (2) and secoisolariciresinol-4′, 4″-diacetate (3) have been evaluated on MCF-7 breast cancer cells and normal breast epithelial line MCF-10A. Lignan 1 has not shown cytotoxic effects on MCF-7 cells, while derivatives 2 and 3 have inhibited cell growth with IC50 values of 25 and 11 μM, respectively. Estrogen receptor alpha is a key growth driver in MCF-7 cells. Compound 1 did not affect the activity of ERα, while derivatives 2 and 3 showed significant antiestrogenic effects. Compounds 2 and 3 caused apoptosis in the MCF-7 line, determined by the cleavage of PARP. SDG derivative 3 enhanced the effect of doxorubicin. SDG derivatives can be considered as promising agents that exhibit a combined antiestrogen and proapoptotic effect in hormone-dependent breast cancer cells.

Total Synthesis and Stereochemical Confirmation of (-)-Olivil, (+)-Cycloolivil, (-)-Alashinols F and G, (+)-Cephafortin A, and Their Congeners: Filling in Biosynthetic Gaps

For the first time, we describe the stereocontrolled total syntheses of olivil, cephafortin A, 4-des-O-methyl-4-O-rhamnosyl cephafortin A, and alashinol F from a common precursor using a combination of chemoenzymatic and biomimetic methods for the systematic introduction of functional groups on three vicinal stereogenic carbon atoms. We revised the previously assigned stereochemistry of (+)-cephafortin A, which was reported as the enantiomer. Natural and unnatural congeners provide insights into the biogenetic interrelations of members of this family.

Pharmaceutical compositions comprising 8-substituted dibenzylbutyrolactone lignans

Therapeutic compositions comprising at least one 8-substituted-dibenzylbutyrolactone lignan, preferably a lignan is selected from the group of nortrachelogenin, diasteromeric forms of nortrachelogenin, isomeric forms of nortrachelogenin and combinations thereof as well as 8-methylmatairesinol and 8-methyldimethylmatairesinol, for use in a method of treating cancer or a similar condition wherein the growth factor signaling pathway of a mammal is deregulated. The invention also provides therapeutic pharmaceutical combinations comprising a hydroxy-dibenzylbutyrolactone lignan and at least one TRAIL receptor agonist. The hydroxy-dibenzylbutyrolactone lignans and a TRAIL receptor agonist can be used as a combined preparation for administration to a patient simultaneously, separately or spaced out over a period of time in treating cancer.