639-14-5

Basic information

• Product Name: (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid
• Synonyms: (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid;Astrantiagenin D;GYPSOPHILASAPONIN;GITHAGENINE;3β-Hydroxy-23-oxoolean-12-en-28-oic acid;3-Hydroxy-23-oxo-olean-12-en-28-oic acid, (3-beta,4-alpha)- (9ci);Albsapogenin;Einecs 211-353-7
• CAS NO: 639-14-5
• Molecular Formula: C₃₀H₄₆O₄
• Molecular Weight: 470.68384
• EINECS: 211-353-7
• Mol File: 639-14-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 274-276°
• Boiling Point: 492.11°C (rough estimate)
• Appearance: /
• Density: 0.9967 (rough estimate)
• Refractive Index: 1.4800 (estimate)
• CAS DataBase Reference: (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid(639-14-5)
• EPA Substance Registry System: (3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid(639-14-5)

Safety Data

• Hazardous Substances Data: 639-14-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23.

Upstream product

• 1207550-40-0 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->4)-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 1207550-42-2 3-O-β-D-galactopyranosyl-(1->3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 465-99-6 hedaragenin 
• 1028100-35-7 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-(6-O-acetyl)-β-D-glucopyranosyl-(1->3)-[β-D-xylopyranosyl-(1->4)]-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1028100-34-6 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1028100-33-5 3-O-β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside 
• 1028100-31-3 gypsogenin 28-O-α-D-galactopyranosyl’-(1→6)-β-D-glucopyranosyl-(1 →6)[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosylester 
• 96552-97-5 C₄₉H₇₆O₁₉ 
• 32448-19-4 28-Hydroxy-23,28-dioxoolean-12-en-3β-yl β-D-Glucopyranoside 

Downstream Products

• 582-16-1 2,7-dimethylnaphthalene 
• 108368-99-6 6-Hydroxy-1.2.5-trimethyl-naphthalin 
• 486-34-0 1,2,7-trimethylnaphthalene 
• 1679-02-3 2,9-dimethyl-picene 
• 1616947-29-5 benzyl 3-hydroxy-23-oxoolean-12-en-28-oate 
• 1616947-39-7 benzyl 3-(acetyloxy)-23-oxoolean-12-en-28-oate 
• 641-91-8 1,2,5-trimethylnaphthalene 
• 466-02-4 hedragonic acid 
• 465-99-6 hedaragenin 

Relevant articles and documents

New triterpenoidal saponins from Gypsophila repens

Six new triterpene glycosides, repensosides A-F (1-6, resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D- and 2D-NMR spectroscopic experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.

Interconversion of hederagenin and gypsogenin and accessing 4-epi-hedragonic acid

Gypsogenin (1) and hederagenin (2) were isolated by extracting the powdered roots of Saponaria officinalis and the pericarp of Sapindus saponaria, respectively. While the gypsophila derived saponin can be obtained easily and in large quantities as a technical product, the plant material from Sapindus saponaria is difficult to obtain in Europe and the North-Americas, whereas in Latin America it is readily available (unlike the gypsophila saponin). In order to achieve a better accessibility of both aglycones, gypsogenin (1) and hederagenin (2), a simple synthesis for their interconversion was developed. Modification of the reaction conditions led to the first synthesis of 4-epi-hedragonic acid (3).

New triterpenoid saponins from the roots of Gypsophila perfoliata Linn.

Nine new triterpenoid saponins (1-9) have been isolated from the roots of Gypsophila perfoliata Linn. Their structures were established on the basis of extensive NMR (1H, 13C, HSQC and HMBC) and ESIMS studies.