14162-53-9

Basic information

• Product Name: Oleanolic acid beta-D-glucopyranosyl ester
• Synonyms: Oleanolic acid β-D-glucopyranosyl ester;(3β)-3-Hydroxy-olean-12-en-28-oic acid b-D-glucoPyranosyl ester;OLEANOLIC ACID BETA-D-GLUCOPYRANOSYL ESTER;(3beta)-3-Hydroxy-olean-12-en-28-oic acid beta-D-glucopyranosyl ester;(3beta)-3-Hydroxy-olean-12-en-28-oic acid b-D-glucoPyranosyl ester;3β-Hydroxy-5α-olean-12-en-28-oic acid β-D-glucopyranosyl ester;3β-Hydroxyolean-12-en-28-oic acid β-D-glucopyranosyl ester;3β-Hydroxyoleana-12-ene-28-oic acid 28-β-D-glucopyranosyl ester
• CAS NO: 14162-53-9
• Molecular Formula: C₃₆H₅₈O₈
• Molecular Weight: 618.84
• Product Categories: Pentacyclic triterpenes
• Mol File: 14162-53-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oleanolic acid beta-D-glucopyranosyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Oleanolic acid beta-D-glucopyranosyl ester(14162-53-9)
• EPA Substance Registry System: Oleanolic acid beta-D-glucopyranosyl ester(14162-53-9)

Safety Data

• Hazardous Substances Data: 14162-53-9(Hazardous Substances Data)

Usage

Description

Oleanolic acid beta-D-glucopyranosyl ester, also known as (3beta)-3-Hydroxy-olean-12-en-28-oic acid beta-D-glucopyranosylester, is a chemical compound derived from oleanolic acid, a naturally occurring triterpenoid. It is characterized by the presence of a glucopyranosyl ester group, which contributes to its unique properties and potential applications.

Uses

Used in Pharmaceutical Research:
Oleanolic acid beta-D-glucopyranosyl ester is used as a research chemical compound for various pharmaceutical applications. Its unique structure and properties make it a valuable tool in the development of new drugs and therapies, particularly in the areas of cancer treatment and other diseases.
Used in Drug Delivery Systems:
Similar to gallotannin, oleanolic acid beta-D-glucopyranosyl ester can be employed in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating this compound into novel drug delivery platforms, such as organic and metallic nanoparticles, researchers can improve the delivery and efficacy of associated drugs, potentially leading to better treatment options for various diseases.
Used in Anticancer Applications:
While the provided materials do not explicitly mention the anticancer properties of oleanolic acid beta-D-glucopyranosyl ester, it is worth noting that oleanolic acid itself has been studied for its potential anticancer effects. As a derivative of oleanolic acid, this compound may also hold promise in the development of anticancer agents. Further research would be necessary to explore its potential in modulating oncological signaling pathways and enhancing chemo-sensitivity in resistant cases.

Upstream product

• 508-02-1 Oleanolic acid 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 676530-80-6 oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester 
• 50-99-7 D-glucose 
• 17990-42-0 Oleanonsaeure 
• 99633-21-3 RB-4 
• 99633-18-8 rotundinoside B 

Downstream Products

• 4339-72-4 3-O-acetyloleanolic acid 
• 498-07-7 levoglucosan 
• 50-99-7 D-glucose 
• 508-02-1 Oleanolic acid 

Relevant articles and documents

Synthesis of Bisdesmosidic Oleanolic Acid Saponins via a Glycosylation-Deprotection Sequence under Continuous Microfluidic/Batch Conditions

We report the first synthesis of a series of bisdesmosidic oleanolic acid saponins using microflow reactor Comet X-01 via a continuous flow glycosylation-batch deprotection sequence. The main results of this study can be summarized as follows: (1) The microfluidic glycosylation of oleanolic acid at C-28 was achieved in quantitative yield and was applied to the synthesis of six C-28-monoglycosidic saponins. (2) The microfluidic glycosylation of oleanolic acid at C-3 was achieved in good yield without orthoester byproduct formation and was applied to the synthesis of three bisdesmosidic saponins. (3) The continuous synthesis of saponins via a microfluidic glycosylation-batch deprotection sequence was achieved in four steps involving two purifications. Thus, the continuous microfluidic glycosylation-deprotection process is expected to be suitable for the preparation of a library of bisdesmosidic oleanolic acid saponins for in vivo pharmacological studies.

New approaches to the structural modification of olean-type pentacylic triterpenes via microbial oxidation and glycosylation

Microbial transformation of 4 olean-type pentacyclic triterpenes (OPTs), 3-oxo oleanolic acid (1), 3-acetyl oleanolic acid (2), oleanolic acid (3), and esculentoside A (4) was studied. After the screening of 12 strains of microbes, preparative biotransformation by two strains of Streptomyces griseus ATCC 13273 and Aspergillus ochraceus CICC 40330 resulted in the isolation of 10 metabolites. The microbial catalyzed high efficient regio-selective methyl oxidation and glycosylation were discovered, which could be provided as an alternative method to expand the structural diversity of OPTs. All the structures of the metabolites were elucidated unambiguously by ESI-MS, 1H NMR, 13C NMR, and 2D-NMR spectroscopy.

USE OF URSOLIC ACID SAPONIN,OLEANOLIC ACID SAPONIN IN PREPARATION OF INCREASING LEUCOCYTES AND/OR PLATELET MEDICINE

The invention provides the use of ursolic acid saponin and oleanolic acid saponin of formula (I) in preparing medicaments for increasing leucocytes and/or platelets. The invention also provides a pharmaceutical composition containing the same compound. The invention utilizes the cheap and accessible ursolic acid and oleanolic acid which are widely present in natural plants as raw materials, introduces monosaccharyls or oligosaccharyls by structural modification. It is proved by pharmacological tests that the compound of formula (I) have an activity of obviously increasing leucocytes and/or platelets.