158932-33-3

Basic information

• Product Name: SECO-ISOLARICIRESINOL DIGLUCOSIDE
• Synonyms: SDG;Seco-isolariciresinol diglucoside;(2R,3R)-2,3-Bis[(4-hydroxy-3-Methoxyphenyl)Methyl]-1,4-butanediyl Bis-β-D-glucopyranoside;[R-(R*,R*)]-2,3-Bis[(4-Hydroxy-3-Methoxyphenyl) Methyl]-1,4-butanediyl Bis-β-D-glucopyranoside;rac Secoisolariciresinol Diglucoside;Secoisolarisiresinol Diglucoside;(2R,3R)-SDG;Secoisolariciresinol Diglucoside(SDG)
• CAS NO: 158932-33-3
• Molecular Formula: C32H46O16
• Molecular Weight: 686.7
• Product Categories: Miscellaneous Natural Products
• Mol File: 158932-33-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 989.171°C at 760 mmHg
• Flash Point: 552.031°C
• Appearance: /
• Density: 1.523g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.80±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: SECO-ISOLARICIRESINOL DIGLUCOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SECO-ISOLARICIRESINOL DIGLUCOSIDE(158932-33-3)
• EPA Substance Registry System: SECO-ISOLARICIRESINOL DIGLUCOSIDE(158932-33-3)

Safety Data

• Hazardous Substances Data: 158932-33-3(Hazardous Substances Data)

Usage

Description

Secoisolariciresinol diglucoside (SDG) is a lignan compound derived from flaxseed, which is recognized as the richest source of this particular lignan. SDG possesses a range of bioactive properties, including antioxidant, anti-inflammatory, and cardioprotective effects, making it a promising candidate for various applications in the functional food and pharmaceutical industries.

Uses

Used in Functional Food Industry:
Secoisolariciresinol diglucoside is used as a functional ingredient for its potential health benefits. Flaxseed, being the richest source of SDG, is often incorporated into various food products to enhance their nutritional value and provide consumers with a natural source of health-promoting compounds.
Used in Cardiovascular Disease (CVD) Prevention:
SDG is used as a preventive agent for cardiovascular diseases due to its ability to reduce lipid and glucose concentration, lower blood pressure, and decrease oxidative stress and inflammation. These properties contribute to the overall cardioprotective effects of SDG, making it a valuable addition to the diet for individuals at risk of developing CVD.
Used in Metabolic Syndrome Management:
SDG is used as a therapeutic agent for managing metabolic syndrome, a cluster of conditions that increase the risk of heart disease, stroke, and type 2 diabetes. The compound's ability to regulate lipid and glucose levels, as well as its anti-inflammatory and antioxidant properties, make it a promising candidate for the prevention and management of metabolic syndrome.

InChI:InChI=1/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1

Upstream product

• 1456548-37-0 C₈₈H₇₈O₂₄ 
• 1456548-38-1 C₈₈H₇₈O₂₄ 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE

Provided is a synthesis process for (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside.

Synthesis and antioxidant evaluation of (S,S)- and (R,R)- secoisolariciresinol diglucosides (SDGs)

Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R,R)-SDG-2 exhibited potent antioxidant properties (EC50 = 292.17 ± 27.71 μM and 331.94 ± 21.21 μM, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50 = 275.24 ± 13.15 μM). These values are significantly lower than those of ascorbic acid (EC50 = 1129.32 ± 88.79 μM) and α-tocopherol (EC50 = 944.62 ± 148.00 μM). Compounds (S,S)-SDG-1 and (R,R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68 ± 0.27; synthetic (S,S)-SDG-1: 2.09 ± 0.16; synthetic (R,R)-SDG-2: 1.96 ± 0.27], peroxyl [natural (S,S)-SDG-1: 2.55 ± 0.11; synthetic (S,S)-SDG-1: 2.20 ± 0.10; synthetic (R,R)-SDG-2: 3.03 ± 0.04] and DPPH [natural (S,S)-SDG-1: EC50 = 83.94 ± 2.80 μM; synthetic (S,S)-SDG-1: EC50 = 157.54 ± 21.30 μM; synthetic (R,R)-SDG-2: EC50 = 123.63 ± 8.67 μM] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S,S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use.