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, a glycoside of Kaempferol, is a flavonoid found in various plants, including B. pinnatum and Hedyotis Verticilata. It is recognized for its antioxidant properties and is known to reduce the risks of various types of cancer and cardiovascular diseases. This substance is a primary reference substance with assigned absolute purity, and its exact value can be found on the certificate provided by PhytoLab GmbH & Co. KG.

Uses

Used in Pharmaceutical Applications:
Kaempferitrin is used as a pharmaceutical agent for its diverse biological activities. It exhibits antioxidant properties, which contribute to the reduction of risks associated with various types of cancer and cardiovascular diseases.
Used in Antimicrobial Applications:
Kaempferitrin is used as an antimicrobial agent for its activity against bacteria such as S. aureus, P. aeruginosa, and S. typhi, as well as fungi including C. albicans, C. parapsilosis, and C. neoformans.
Used in Anti-inflammatory Applications:
Kaempferitrin is used as an anti-inflammatory agent, as it inhibits LPS-and IFN-γ-induced nitric oxide (NO) production in isolated mouse macrophages.
Used in Diabetes Management:
Kaempferitrin is used in managing diabetes, as it has been shown to decrease blood glucose levels in a rat model of alloxan-induced diabetes when administered at a dose of 100 mg/kg.
Used in the Food Industry:
Kaempferitrin is used as a natural antioxidant in the food industry to enhance the shelf life and quality of various products.
Used in the Cosmetic Industry:
Kaempferitrin is used in the cosmetic industry for its antioxidant and anti-inflammatory properties, which can contribute to the development of skincare products with potential benefits for skin health and appearance.

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

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

Downstream Products

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

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