29388-59-8

Basic information

• Product Name: SECOISOLARICIRESINOL
• Synonyms: 4,4',9,9'-TETRHYDROXY-3,3'-DIMETHOXYLIGNAN;(2R,3R)-2,3-BIS(4-HYDROXY-3-METHOXYBENZYL)-1,4-BUTANEDIOL;SECO-ISOLARICIRESINOL (SECO);(-)-SECO-ISOLARICIRESINOL;(+/-)-SECOISOLARICIRESINOL;SECOISOLARICIRESINOL;[R-(R*,R*)]-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;SECOISOLARICIRESINOL 95+%
• CAS NO: 29388-59-8
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.42
• EINECS: 249-599-2
• Product Categories: Miscellaneous Natural Products
• Mol File: 29388-59-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 609.1 °C at 760 mmHg
• Flash Point: 322.1 °C
• Appearance: White powder
• Density: 1.251 g/cm³
• Vapor Pressure: 1.09E-15mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.81±0.20(Predicted)
• BRN: 6611290
• CAS DataBase Reference: SECOISOLARICIRESINOL(CAS DataBase Reference)
• NIST Chemistry Reference: SECOISOLARICIRESINOL(29388-59-8)
• EPA Substance Registry System: SECOISOLARICIRESINOL(29388-59-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 29388-59-8(Hazardous Substances Data)

Usage

Description

Secoisolariciresinol, a natural phenolic compound, is derived from the heartwood of the Mongolian pine tree (Pinus sylvestris). It exhibits a range of biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. Its unique structure, featuring two phenolic rings connected by a dihydrofuran ring, contributes to its diverse pharmacological effects.

Uses

Used in Pharmaceutical Industry:
Secoisolariciresinol is used as a therapeutic agent for its anti-myocardial ischemia effects, which can help in the treatment of heart diseases by reducing the damage caused by ischemic conditions.
Used in Antioxidant Applications:
Secoisolariciresinol is used as an antioxidant, protecting cells from oxidative stress and damage caused by reactive oxygen species. Its antioxidant properties can be beneficial in various health and skincare products, as well as in the food industry to extend the shelf life of products.
Used in Antimicrobial Applications:
Secoisolariciresinol is used as an antimicrobial agent, exhibiting activity against a range of bacteria and fungi. This makes it a potential candidate for use in the development of new antimicrobial drugs and in the formulation of natural preservatives for various applications.
Used in Mongolian Folk Medicine:
Secoisolariciresinol is used as a traditional medicine in Mongolia, where it has been employed for centuries to treat various ailments, including heart diseases and infections, due to its multifaceted health-promoting properties.

InChI:InChI=1/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1

Upstream product

• 487-36-5 (+/-)-pinoresinol 
• 1243054-22-9 trans-(E)-dimethyl 2,3-bis(4-benzyloxy-3-methoxybenzylidene)-1,4-butanediol 
• 1243054-20-7 trans-(E)-dimethyl 2,3-bis(4'-benzyloxy-3'-methoxybenzylidene)succinic acid 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 96917-15-6 (E)-2-(4'-benzyloxy-3'-methoxybenzylidene)succinic acid 
• 121-33-5 vanillin 
• 888483-54-3 trans-(E)-2,3-bis(4'-benzyloxy-3'-methoxybenzylidene)succinic acid 
• 111194-08-2 (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol 
• 1391062-42-2 C₂₁H₂₂O₆ 
• 190004-70-7 dimethyl 2,3-bis-(4-hydroxy-3-methoxybenzyl)succinate 
• 190004-90-1 C₂₂H₂₂O₈ 
• 160097-43-8 C₂₁H₂₀O₈ 
• 190004-89-8 C₁₄H₁₆O₆ 
• 111194-03-7 C₁₃H₁₄O₆ 

Downstream Products

• 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 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 1206712-52-8 secoisolariciresinol-4',4''-diacetate 
• 3688-23-1 (-)-secoisolariciresinol 
• 145265-02-7 (-)-secoisolariciresinol 
• 347359-71-1 7'-hydroxymatairesinol 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 36469-60-0 (8R,8'S)-dihydroguaiaretic acid 
• 34730-78-4 4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol 

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.