79595-97-4

Basic information

• Product Name: norbergenin
• Synonyms: norbergenin;(2R)-3,4,4aα,10bβ-Tetrahydro-3β,4α,8,9,10-pentahydroxy-2α-(hydroxymethyl)pyrano[3,2-c][2]benzopyran-6(2H)-one
• CAS NO: 79595-97-4
• Molecular Formula: C₁₃H₁₄O₉
• Molecular Weight: 314.245
• Mol File: 79595-97-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 705.9°Cat760mmHg
• Flash Point: 271.9°C
• Appearance: /
• Density: 1.799g/cm³
• Vapor Pressure: 6.47E-21mmHg at 25°C
• Refractive Index: 1.716
• CAS DataBase Reference: norbergenin(CAS DataBase Reference)
• NIST Chemistry Reference: norbergenin(79595-97-4)
• EPA Substance Registry System: norbergenin(79595-97-4)

Safety Data

• Hazardous Substances Data: 79595-97-4(Hazardous Substances Data)

Usage

General Description

Norbergenin is a chemical compound found in the plant Schisandra chinensis, commonly known as the Chinese magnolia vine. It belongs to the class of lignans, which are natural compounds known for their potentially beneficial effects on human health. Research has suggested that norbergenin may possess antioxidant, anti-inflammatory, and neuroprotective properties. Additionally, it has been investigated for its potential to inhibit the growth of cancer cells. Due to these potential health benefits, norbergenin is being studied for its therapeutic properties and has attracted the interest of the pharmaceutical and nutraceutical industries.

InChI:InChI=1/C13H14O9/c14-2-5-8(17)10(19)12-11(21-5)6-3(13(20)22-12)1-4(15)7(16)9(6)18/h1,5,8,10-12,14-19H,2H2/t5-,8-,10+,11+,12-/m0/s1

Upstream product

• 477-90-7 bergenin 
• 477-90-7 bergenin 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 571146-93-5 (2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one 
• 646999-29-3 (6aR,7S,7aS,11aR,12aS)-1,2,3-Tris-benzyloxy-7-hydroxy-9-(4-methoxy-phenyl)-6a,7,7a,11,11a,12a-hexahydro-6,8,10,12-tetraoxa-benzo[a]anthracen-5-one 
• 646998-81-4 Hexanoic acid (2R,3S,4S,4aR,10bS)-8,9,10-tris-benzyloxy-3,4-dihydroxy-6-oxo-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromen-2-ylmethyl ester 
• 646999-66-8 Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester 

Relevant articles and documents

Hypervalent iodine-mediated oxygenative phenol dearomatization reactions

Both λ3- and λ5-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have shown evident signs of success. Moreover, the use of stabilized IBX (i.e., SIBX) in our methodology for O-demethylation of 2-methoxyphenols, which relies on the same key oxygenating dearomatization event, is reported here to be much more efficacious than that of IBX itself in the chemoselective one-step conversion of homovanillyl alcohol into hydroxytyrosol, and bergenin into norbergenin.

ISOLATION OF NORBERGENIN FROM SAXIFRAGA STOLONIFERA

Key Word Index - Saxifraga stolonifera; Saxifragaceae; desmethylbergenin; norbergenin; bergenin; tri-O-methyl-norbergenin. Norbergenin, a C-glucoside, was isolated from Saxifraga stolonifera and its structure assigned as 2β-D-glucopyranosylgallic acid δ-lactone.