482-38-2

Basic information

• Product Name: KAEMPFERITRIN
• Synonyms: lespenefril;KAEMPFEROL-3,7-DIRHAMNOSIDE;3,7-Bis[(6-deoxy-α-L-mannopyranosyl)oxy]-4',5-dihydroxyflavone;3,7-Bis[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Kaempherol 3,7-bismannoside;Lespedin;3,7-bis[(6-deoxy-beta-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;KAEMPFERITRIN(P)
• CAS NO: 482-38-2
• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.52
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 482-38-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 202～203℃
• Boiling Point: 908.6 °C at 760 mmHg
• Flash Point: 302.8 °C
• Appearance: /
• Density: 1.70
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: -20°C
• PKA: 5.81±0.40(Predicted)
• CAS DataBase Reference: KAEMPFERITRIN(CAS DataBase Reference)
• NIST Chemistry Reference: KAEMPFERITRIN(482-38-2)
• EPA Substance Registry System: KAEMPFERITRIN(482-38-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 482-38-2(Hazardous Substances Data)

Usage

Description

Kaempferitrin is a flavonoid glycoside that has been found in B. pinnatum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 8.73 μg/ml) and is active against the bacteria S. aureus, P. aeruginosa, and S. typhi, as well as the fungi C. albicans, C. parapsilosis, and C. neoformans (MICs = 16-32 μg/ml). Kaempferitrin inhibits LPS-and IFN-γ-induced nitric oxide (NO) production in isolated mouse macrophages (IC50 = 40 μM). It decreases blood glucose levels in a rat model of alloxan-induced diabetes when administered at a dose of 100 mg/kg.

Uses

Kaempferitirin is a glycoside of Kaempferol (K100000), a plant flavonoid that exhibits antioxidant properties and is known to reduce risks of various types cancer and cardiovascular diseases. Kaempferitirin have been isolated as natural products from plants such as Hedyotis Verticilata.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Kaempferitrin (Lespenefril) is a naturally-occurring kaempferol glycoside with antimicrobial, antioxidant, and anti-inflammatory activities.

InChI:InChI=1/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1

Upstream product

• 520-18-3 kaempferol 
• 1374991-37-3 C₅₈H₅₂O₂₂ 
• 1374991-31-7 C₄₆H₃₆O₁₅ 
• 1374991-25-9 C₃₉H₃₂O₉ 
• 1374991-22-6 5,4'-di-O-acetyl-kaempferol 
• 108-73-6 3,5-dihydroxyphenol 
• 55317-02-7 2-methoxy-1-(2,4,6-trihydroxyphenyl)ethanone 
• 943827-54-1 4'-benzyloxy-5-hydroxy-3-methoxy-7-(methoxymethyloxy)flavone 
• 943827-53-0 2-methoxy-1-[2-(p-benzyloxybenzoyloxy)-4,6-bis(methoxymethyloxy)phenyl]ethanone 
• 943827-52-9 2-methoxy-1-[2-hydroxy-4,6-bis(methoxymethyloxy)phenyl]ethanone 
• 943827-56-3 4'-benzyloxy-3,7-dihydroxy-5-[((4-methylphenyl)sulfonyl)oxy]flavone 
• 943827-55-2 4'-benzyloxy-3-methoxy-7-(methoxymethyloxy)-5-[((4-methylphenyl)sulfonyl)oxy]flavone 
• 943827-57-4 4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone 

Downstream Products

• 482-39-3 kaempferol 3-rhamnoside 
• 3615-41-6 L-Rhamnose 
• 520-18-3 kaempferol 
• 5041-97-4 kaempferol-7-O-α-L-rhamnoside 
• 73-34-7 L-rhamnose 
• 7658-08-4 D-quionovose 
• 118333-31-6 (2S,3S)-3,40,5,7-tetrahydroxyflavanone 
• 99208-33-0 3,5-dihydroxy-2-(4-methoxy-phenyl)-7-α-L-rhamnopyranosyloxy-chromen-4-one 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 6014-42-2 L-rhamnose 
• 85561-92-8 kaempferol 3,7-di-O-α-L-rhamnoside peracetate 
• 111128-11-1 5-hydroxy-2-(4-methoxy-phenyl)-3,7-bis-α-L-rhamnopyranosyloxy-chromen-4-one 

Relevant articles and documents

The Gastrointestinal Tract Metabolism and Pharmacological Activities of Grosvenorine, a Major and Characteristic Flavonoid in the Fruits of Siraitia grosvenorii

Grosvenorine is the major flavonoid compound of the fruits of Siraitia grosvenorii (Swingle) C. Jeffrey, a medical plant endemic to China. In the present study, for the first time, the grosvenorine metabolism in an in vitro simulated human gastrointestinal tract (including artificial gastric juice, artificial intestinal juice and intestinal flora), as well as its pharmacological activities (including anti-complement, antibacterial and antioxidant activities), was investigated. The results showed that grosvenorine was metabolized by human intestinal flora; its four metabolites were isolated by semi-preparative HPLC and identified by NMR as kaempferitrin, afzelin, α-rhamnoisorobin, and kaempferol. Further pharmacological evaluation showed that grosvenorine exhibited good antibacterial and antioxidant activities, with its metabolites possessing more potent activities. Although grosvenorine did not present obvious anticomplement activity, its metabolites showed interesting activities. This study revealed that intestinal bacteria play an important role in the gastrointestinal metabolism of grosvenorine and significantly affect its pharmacological activities.

Synthesis of kaempferitrin

(Chemical Equation Presented) A short synthesis of Kaempferitrin (1), a 3,7-diglycosylflavone, is reported. Key features include the synthesis of a protected form of kaempferol in which all four hydroxy groups are differentiated and the first bis-glycosyl