Bergenin

Title: Bergenin
CAS Registry Number: 477-90-7
CAS Name: 3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano[3,2-c][2]benzopyran-6(2H)-one
Additional Names: 4-methoxy-2-[tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl]-a-resorcylic acid d-lactone; bergenit; vakerin; ardisic acid B; cuscutin; peltophorin
Molecular Formula: C14H16O9
Molecular Weight: 328.27
Percent Composition: C 51.22%, H 4.91%, O 43.86%
Literature References: From root of Saxifraga (Bergenia) crassifolia L., and from rhizome of S. sibirica L. Saxifragaceae: Morelle, Compt. Rend. 93, 646 (1881); Ber. 14, 2694 (1881); Ssadikow, Guthner, Biochem. Z. 190, 340 (1927); Tschitschibabin et al., Ann. 469, 93 (1929). Identity with vakerin: Carruthers et al., Chem. Ind. (London) 1957, 76. Identity with ardisic acid B: Hung, Chu, C.A. 52, 15827h (1958). Identity with cuscutin: Jain, Mishra, Indian J. Chem. 1, 499 (1963). Identity with peltophorin: Joshi, Kamat, Naturwissenschaften 56, 89 (1969). Structure: Posternak, Dürr, Helv. Chim. Acta 41, 1159 (1958); Fujise et al., Bull. Chem. Soc. Jpn. 32, 97 (1959). Synthesis and structure: Hay, Haynes, J. Chem. Soc. 1958, 2231. Biosynthesis: Wenkert, Chem. Ind. (London) 1959, 906.
Properties: Crystals from methanol, mp 238°. uv max: 275, 220 nm (log e 3.92, 4.42). [a]D18 -37.7° (c = 1.96 in ethanol); [a]D24 -45.3° (c = 0.51 for anhydr in water). Freely sol in water; sol in alcohol.
Melting point: mp 238°
Optical Rotation: [a]D18 -37.7° (c = 1.96 in ethanol); [a]D24 -45.3° (c = 0.51 for anhydr in water)
Absorption maximum: uv max: 275, 220 nm (log e 3.92, 4.42)
Derivative Type: Monohydrate
Properties: Crystals from water, mp 140°. Slightly sol in water, freely in alcohol.
Melting point: mp 140°
Status: This monograph has been retired and is no longer subject to revision or update.
Bermoprofen Berninamycin Beryllium Acetate Beryllium Acetylacetonate Beryllium Borohydride

Bergenin
Chemical structure of bergenin
Identifiers
CAS number 477-90-7 (anhydrous) N=, 5956-63-8 (unspecified hydrate)
PubChem 66065
ChemSpider 59455 YesY
UNII L84RBE4IDC YesY
ChEMBL CHEMBL273019 YesY
Jmol-3D images Image 1
Properties
Molecular formula C14H16O9
Molar mass 328.27 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bergenin alias Cuscutin is trihydroxybenzoic acid glycoside. It is the C-glycoside of 4-O-methyl gallic acid. It possesses an O-demethylated derivative called norbergenin. These are chemical compounds and drugs of Ayurveda, commonly known as Paashaanbhed. It shows a potent immunomodulatory effect.[1]

Bergenin can be isolated from Bergenia species like Bergenia ciliata and Bergenia ligulata,[2] from rhizomes of Bergenia stracheyi. It is also found in the stem bark of Dryobalanops aromatica,[3] in Ardisia elliptica and in Mallotus japonicus.[4]