17353-03-6

Basic information

• Product Name: 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one
• Synonyms: 2''-O-Rhamnopyranosylpopulnin;7-[(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3,4',5-trihydroxyflavone;7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;7-((2-o-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one;Einecs 241-377-3;Kaemp-7-neohesperidoside;KAEMPFEROL-7-NEOHESPERIDOSIDE(RG);3,4′,5,7-Tetrahydroxyflavone 7-[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside]
• CAS NO: 17353-03-6
• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.5181
• EINECS: 241-377-3
• Mol File: 17353-03-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 258～260℃
• Boiling Point: 934.7°Cat760mmHg
• Flash Point: 310.4°C
• Appearance: /
• Density: 1.76g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.744
• Storage Temp.: ?20°C
• CAS DataBase Reference: 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one(17353-03-6)
• EPA Substance Registry System: 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one(17353-03-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 17353-03-6(Hazardous Substances Data)

Usage

Description

7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one, also known as Kaempferol 7-O-Neohesperidoside, is a flavonoid glycoside that was isolated from the seeds of the Litchi chinensis fruit. It is a complex organic compound with a unique chemical structure, characterized by the presence of multiple hydroxyl groups and glycosidic linkages.

Uses

1. Used in Antiviral Applications:
7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one is used as an antiviral agent for treating infections caused by influenza viruses. Its antiviral properties are attributed to its ability to inhibit viral replication and reduce the severity of symptoms associated with influenza infections.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one can be used as a key ingredient in the development of new drugs targeting various diseases, including viral infections and other inflammatory conditions. Its unique chemical structure and biological activities make it a promising candidate for drug discovery and development.
3. Used in Functional Foods and Nutraceuticals:
7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one can also be utilized in the development of functional foods and nutraceuticals, given its potential health benefits and natural origin. It can be incorporated into dietary supplements, fortified foods, and beverages to enhance their nutritional value and provide additional health-promoting properties.
4. Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one can be used as an active ingredient in skincare products, hair care products, and oral care products. Its antioxidant and anti-inflammatory properties may contribute to improved skin health, hair health, and oral health, making it a valuable addition to a wide range of personal care products.

Biochem/physiol Actions

Kaempferol 7-O-neohesperidoside was shown to have anti-proliferative effects on a variety of human cancer cell lines in vitro.

InChI:InChI=1/C27H30O15/c1-9-17(31)20(34)23(37)26(38-9)42-25-21(35)18(32)15(8-28)41-27(25)39-12-6-13(30)16-14(7-12)40-24(22(36)19(16)33)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-21,23,25-32,34-37H,8H2,1H3

Upstream product

• 10236-47-2 naringin 

Downstream Products

• 1219698-84-6 C₃₆H₃₆O₁₉ 
• 1219698-85-7 C₃₆H₃₆O₁₉ 

Relevant articles and documents

STRUCTURAL ASPECTS OF ANTHOCYANIN-FLAVONOID COMPLEX FORMATION AND ITS ROLE IN PLANT COLOR

Key Word Index - Anthocyanin; flavonoid glycosides; synthesis; complex formation; plant color; spectral properties. The complex formation of flavonoids with anthocyanins, resulting in increase in both absorbance and in a bathochromic shift of the visible absorption maximum of the latter, is based mainly on hydrogen bond formation between the carbonyl group of the anthocyanin anhydrobase and aromatic hydroxyl groups of the complex-forming flavonoids.The larger the number of hydroxyl groups in the flavonoid molecule, the strongr the complex formation.The presence of a 3-hydroxyl group in the flavonoid molecule has little effect on the complex-forming ability.The nature of the sugar substituent of the complex-forming flavonoid compound has no influence on the reaction.The 5-hydroxyl group of flavonoids is strongly bound by intramolecular hydrogen bond to the 4-carbonyl and does not participate in the complex formation.The most important hydroxyl group in the flavonoid molecule is one in the 7-position.Unsaturation at C2-C3 in the heterocyclic ring is an important factor for complex formation.Aromatic hydroxyl groups in the flavonoid system alone cannot account for all the complex-forming ability, suggesting additional involvment by electrostatic forces and configurational or steric effects.