20188-85-6

Basic information

• Product Name: Ombuoside
• Synonyms: 3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-3',5-dihydroxy-4',7-dimethoxyflavone;3-[6-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy]-3',5-dihydroxy-4',7-dimethoxyflavone;Ombuin-3beta-rutinoside
• CAS NO: 20188-85-6
• Molecular Formula: C₂₉H₃₄O₁₆
• Molecular Weight: 638.572
• Product Categories: Miscellaneous Natural Products
• Mol File: 20188-85-6.mol

Chemical Properties

• Boiling Point: 946°Cat760mmHg
• Flash Point: 308°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: Ombuoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ombuoside(20188-85-6)
• EPA Substance Registry System: Ombuoside(20188-85-6)

Safety Data

• Hazardous Substances Data: 20188-85-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ombuoside is used as an antimicrobial agent for its ability to combat several strains of Gram-positive and Gram-negative bacteria, as well as the yeast Candida albicans. Its effectiveness against these microorganisms makes it a valuable asset in the development of new drugs and treatments for infections.
Used in Cosmetic Industry:
Ombuoside can be used as a natural preservative in cosmetic products due to its antimicrobial properties. This can help maintain the shelf life and safety of the products while reducing the need for synthetic preservatives.
Used in Food Industry:
In the food industry, Ombuoside can be utilized as a natural preservative to extend the shelf life of perishable items and inhibit the growth of harmful bacteria and fungi. This can contribute to improved food safety and quality.
Used in Agricultural Industry:
Ombuoside can be employed as a biopesticide or antimicrobial agent in agriculture to protect crops from bacterial and fungal infections. This can lead to increased crop yields and reduced reliance on chemical pesticides.
Overall, Ombuoside's antimicrobial activity makes it a versatile compound with potential applications across various industries, from pharmaceuticals to cosmetics, food, and agriculture.

InChI:InChI=1/C29H34O16/c1-10-19(32)22(35)24(37)28(42-10)41-9-17-20(33)23(36)25(38)29(44-17)45-27-21(34)18-14(31)7-12(39-2)8-16(18)43-26(27)11-4-5-13(30)15(6-11)40-3/h4-8,10,17,19-20,22-25,28-33,35-38H,9H2,1-3H3/t10-,17+,19-,20+,22+,23-,24+,25+,28+,29-/m0/s1

Upstream product

• 77-78-1 dimethyl sulfate 
• 153-18-4 rutin 
• 186581-53-3 diazomethane 

Downstream Products

• 492-61-5 β-D-glucose 
• 6014-42-2 L-rhamnose 
• 529-40-8 ombuin 
• 20188-86-7 5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-7-methoxy-3-[O²,O³,O⁴-triacetyl-O⁶-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chromen-4-one 

Relevant articles and documents

Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3′,4′,7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression.

Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity

The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).