257930-74-8

Basic information

• Product Name: (8S,8'S)-(-)-secoisolariciresinol diglucoside
• CAS NO: 257930-74-8
• Molecular Weight: 686.708
• Mol File: 257930-74-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 989.2±65.0 °C(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (8S,8'S)-(-)-secoisolariciresinol diglucoside(CAS DataBase Reference)
• NIST Chemistry Reference: (8S,8'S)-(-)-secoisolariciresinol diglucoside(257930-74-8)
• EPA Substance Registry System: (8S,8'S)-(-)-secoisolariciresinol diglucoside(257930-74-8)

Safety Data

• Hazardous Substances Data: 257930-74-8(Hazardous Substances Data)

Usage

General Description

(8S,8'S)-(-)-secoisolariciresinol diglucoside is a phytoestrogenic lignan found in various plants, suchjson as flaxseed, sesame, and whole grains. The compound has gained attention for its potential health benefits, particularly in relation to its estrogen-like effects and its potential in preventing chronic diseases. Studies have shown that secoisolariciresinol diglucoside may have protective effects against cardiovascular diseases, breast cancer, and menopausal symptoms, and it also exhibits antioxidant and anti-inflammatory properties. Additionally, the compound has been investigated for its potential role in bone health and as a promising ingredient in functional foods and nutraceuticals. Overall, (8S,8'S)-(-)-secoisolariciresinol diglucoside shows promise as a natural compound with various health-promoting properties.

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.