53155-25-2

Basic information

• Product Name: euscaphic acid
• Synonyms: euscaphic acid;Acuminatic acid;Euscapic acid;Euscophic acid;Jacarandic acid
• CAS NO: 53155-25-2
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.704
• EINECS: 200-258-5
• Product Categories: Triterpenoids
• Mol File: 53155-25-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 262-264 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 602.7 °C at 760 mmHg
• Flash Point: 332.3 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 4.86E-17mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Pyridine (Slightly)
• PKA: 4.47±0.70(Predicted)
• CAS DataBase Reference: euscaphic acid(CAS DataBase Reference)
• NIST Chemistry Reference: euscaphic acid(53155-25-2)
• EPA Substance Registry System: euscaphic acid(53155-25-2)

Safety Data

• Hazardous Substances Data: 53155-25-2(Hazardous Substances Data)

Usage

Description

Euscaphic acid, a natural product derived from Folium Eriobotryae, is known for its hypoglycemic and anti-inflammatory properties. It possesses the ability to downregulate NF-κB activations and inhibit LPS-induced inflammatory responses, making it a potential candidate for various therapeutic applications.

Uses

Used in Pharmaceutical Industry:
Euscaphic acid is used as a hypoglycemic agent for managing blood sugar levels due to its natural ability to lower glucose levels in the body.
Used in Anti-Inflammatory Applications:
Euscaphic acid is used as an anti-inflammatory agent for reducing inflammation and modulating the immune response. Its capacity to downregulate NF-κB activations and inhibit LPS-induced inflammatory responses makes it a promising candidate for treating various inflammatory conditions.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, given its anti-inflammatory properties and potential to modulate immune responses, Euscaphic acid could potentially be investigated for its use in cancer prevention or treatment, particularly in the context of inflammation-related cancers.

InChI:InChI=1/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20?,21-,22+,23-,26+,27-,28-,29-,30+/m1/s1

Upstream product

• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 
• 95298-47-8 2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester 
• 1309589-79-4 2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester 
• 121064-78-6 3-O-trans-p-coumaroyltormentic acid 

Downstream Products

• 13850-14-1 (2R,3R,19R)-2,3-bis(acetyloxy)-19-hydroxyurs-12-en-28-carboxylic acid 
• 13850-15-2 methyl 2α,3β,19-trihydroxyurs-12-en-28-oate 
• 13849-91-7 polnolic acid 
• 1412898-52-2 (2R,19R)-methyl 2-acetyloxy-19-hydroxy-3-oxours-12-en-28-carboxylate 
• 97094-23-0 (2R,3R,19R)-3-acetyloxy-2,19-dihydroxyurs-12-en-28-carboxylic acid 
• 97094-22-9 (2R,3R,19R)-2-acetyloxy-3,19-dihydroxyurs-12-en-28-carboxylic acid 
• 63478-78-4 methyl 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oate 
• 14539-80-1 Diacetyl-tormentsaeure-methylester 
• 52936-89-7 methyl 2α,3α,19-trihydroxyurs-12-en-28-oate 
• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 

Relevant articles and documents

Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis

Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl3-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.

Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina

A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 μM), 28-O-β-d- glucopyranosyl pomolic acid (IC50 = 9.5 μM), rosamutin (IC 50 = 35.5 μM), and kaji-ichigoside F1 (IC50 = 14.1 μM), inhibited d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN.

Retrovirus protease inhibitors

A compound composition and method of treating a retrovirus infection are disclosed. In particular, isolated triterpenes have been shown to have significant inhibitory activity against HIV-1.