13720-19-9

Basic information

• Product Name: Oleana-11,13(18)-diene-3β,23,28-triol
• Synonyms: Celsiogenin B;Oleana-11,13(18)-diene-3β,23,28-triol
• CAS NO: 13720-19-9
• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.70032
• Mol File: 13720-19-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oleana-11,13(18)-diene-3β,23,28-triol(CAS DataBase Reference)
• NIST Chemistry Reference: Oleana-11,13(18)-diene-3β,23,28-triol(13720-19-9)
• EPA Substance Registry System: Oleana-11,13(18)-diene-3β,23,28-triol(13720-19-9)

Safety Data

• Hazardous Substances Data: 13720-19-9(Hazardous Substances Data)

Upstream product

• 465-99-6 hedaragenin 
• 35043-82-4 3β,23,28-trihydroxy-olean-12-ene 
• 13720-18-8 Acetic acid (4aS,6aS,6bR,8aR,9R,10S,12aS,12bR)-10-acetoxy-9-acetoxymethyl-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-hexadecahydro-2H-picen-4a-ylmethyl ester 
• 57475-62-4 3β,23-dihydroxy-13β,28-epoxy-olean-11-ene 
• 5672-32-2 diacetylhederagenin 
• 80713-21-9 3β,23-diacetoxy-oleana-11,13(18)-dien-28-oic acid 
• 80713-22-0 (4aS,6aS,6bR,8aR,9R,10S,12aS)-10-Acetoxy-9-acetoxymethyl-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-hexadecahydro-2H-picene-4a-carboxylic acid methyl ester 
• 141896-30-2 mimengoside A 
• 74163-66-9 Verbascosaponin 

Relevant articles and documents

Monodesmosidic oleanene-type saponins from kidney vetch (Anthyllis vulneraria L.) with hemolytic activity

Two undescribed monodesmosidic oleanene-type saponins, namely 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-saikogenin G (1) and 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-16-deoxysaikogenin F (2), named anthylloside A and B, have been isolated from an acetone-water extract from aerial parts of kidney vetch (A. vulneraria L.). Isolation of 1 and 2 was achieved by solvent partition with EtOAc and subsequent repeated chromatographic purification. The structures of the isolated compounds were elucidated by spectrometric (HR-MS) and spectroscopic methods (1H- and 13C-NMR, UV, IR and CD), as well as GC–MS analysis of samples after 1 N HCl hydrolysis and subsequent derivatization. The configuration and conformation of both 1 and 2 were assigned by means of comprehensive 2D-NMR analyses including 1H-1H?COSY, ROESY, decoupled gHSQC, gHMBC and selective 1D-TOCSY experiments. Moreover, 1 and 2 possess significant hemolytic activity, which was assessed in a blood agar assay and compared to that of three reference saponins.

CHEMICAL MODIFICATION OF OLEANENE-OLIGOGLYCOSIDES BY MEANS OF ANODIC OXIDATION

By utilizing anodic oxidation as the key reaction, various olean-12-ene sapogenols were readily converted into olean-11-en-28,13β-olide, 11α,12α-epoxy-oleanan-28,13β-olide, and 13β,28-epoxy-olean-11-ene derivatives, respectively in high yields.Since previous protection of hydroxyl groups in the starting compounds was not required, the conversion method was directly applied to hederagenin oligoglycosides and corresponding oligoglycosides of olean-11-ene sapogenols, functionalized as above, were successfully synthesized.KEYWORDS - anodic oxidation; olean-12-ene sapogenol; olean-11-en-28,13β-olide; 11α,12α-epoxy-oleanan-28,13β-olide; 13β,28-epoxy-olean-11-ene; triterpene oligoglycoside; Sapindus mukurossi

Triterpenes, XXXIII. On the Saponin of the Flowers of Verbascum phlomoides L.

From the flowers of Verbascum phlomoides L. a saponin verbascosaponin (1), C54H90O22, was isolated containing as aglycone verbascogenin, C30H50O4, with one double bond.At acidic conditions it is transformed into the known triterpene A (2), C30H48O3, with two double bonds.Four sugar units were found in the glycoside - 2 D-glycose, 1 L-rhamnose, and 1 D-fucose.The sequence of the sugar chain was determined.