482-39-3

Basic information

• Product Name: KAEMPFEROL 3-O-GLUCORHAMNOSIDE
• Synonyms: AFZELIN;KAEMPFEROL 3-O-GLUCORHAMNOSIDE;KAEMPFEROL 3-O-RHAMNOSIDE;2-(4-Hydroxyphenyl)-4-oxo-5,7-dihydroxy-4H-1-benzopyran-3-yl α-L-rhamnopyranoside;3-(α-L-Rhamnopyranosyloxy)-5,7,4'-trihydroxyflavone;3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Kaempferol 3-rhamnoside;KaeMpferin
• CAS NO: 482-39-3
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.38
• Mol File: 482-39-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 172-174 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 765.6 °C at 760 mmHg
• Flash Point: 272.3 °C
• Appearance: /
• Density: 1.7 g/cm³
• Vapor Pressure: 1.19E-24mmHg at 25°C
• Refractive Index: 1.748
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 6.20±0.40(Predicted)
• CAS DataBase Reference: KAEMPFEROL 3-O-GLUCORHAMNOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: KAEMPFEROL 3-O-GLUCORHAMNOSIDE(482-39-3)
• EPA Substance Registry System: KAEMPFEROL 3-O-GLUCORHAMNOSIDE(482-39-3)

Safety Data

• Hazardous Substances Data: 482-39-3(Hazardous Substances Data)

Usage

Uses

Kaempferol 3-O-α-L-Rhamnoside is found in Cornus macrophylla and has shown to have antibacterial activity against Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals.

Definition

ChEBI: A glycosyloxyflavone that is kaempferol attached to a alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage.

InChI:InChI=1/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1

Upstream product

• 942942-49-6 4',5,7-tri-O-benzyl-kaempferol 3-O-(2''-O-benzyl-α-L-rhamnopyranoside) 
• 520-18-3 kaempferol 
• 1266714-86-6 kaempferol-3-O-(3,4-di-O-acetyl-α-L-rhamnopyranoside) 
• 71801-95-1 kaempferol 3-α-rhamnopyranoside-7-β-xylopyranoside 
• 132536-65-3 kaempferol 3-α-rhamnopyranoside-4'-β-xylopyranoside 
• 482-38-2 kaempferitrin 
• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 247244-65-1 L-aculose 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 916069-03-9 3-((2S,5R,6S)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 916069-02-8 3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 23405-70-1 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 

Downstream Products

• 520-18-3 kaempferol 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 6014-42-2 L-rhamnose 
• 72165-31-2 Peracetylated-SL₀₁₀₁ 

Relevant articles and documents

A regiospecific rhamnosyltransferase from: Epimedium pseudowushanense catalyzes the 3- O -rhamnosylation of prenylflavonols

Epimedium is used in traditional Chinese medicine and contains flavonol glycosides that exhibit multiple biological activities. These bioactive flavonol glycosides usually have a rhamnose moiety at the 3-OH position of prenylflavonols, such as icariin (9), baohuoside I (1a) and baohuoside II (2a). However, to date, no rhamnosyltransferase has been reported to catalyze the 3-O-rhamnosylation of prenylflavonols. In this article, a flavonol rhamnosyltransferase, EpPF3RT, was identified from E. pseudowushanense B. L. Guo. The recombinant enzyme regiospecifically transfers a rhamnose moiety to 8-prenylkaempferol (1) and anhydroicaritin (2) at the 3-OH position to form baohuoside II (1a) and baohuoside I (2a) in vitro. In addition, a UDP-rhamnose synthase gene, EpRhS, from E. pseudowushanense was functionally characterized and used to produce the UDP-rhamnose sugar donor. Furthermore, an engineered Escherichia coli strain containing EpPF3RT and EpRhS was established to produce baohuoside II (1a) from whole cells. These studies indicate the significant potential of an enzymatic approach for the rhamnosylation of bioactive flavonoids in Epimedium plants and will provide a promising alternative for producing bioactive rhamnosylated flavonoids combined with other genes/enzymes by synthetic biology.

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.

Changes in flavonoid content and tyrosinase inhibitory activity in kenaf leaf extract after far-infrared treatment

The tyrosinase inhibitory activity of ethanolic extract of kenaf (Hibiscus cannabinus L.) leaf was evaluated before and after subjecting it to far-infrared (FIR) irradiation. The main component of the extract was analyzed as kaempferitrin (kaempferol-3,7-O-α-dirhamnoside). Prior to FIR irradiation, no inhibitory activity of the extract was detected in a tyrosinase assay. However, after FIR irradiation for 1 h at 60 °C, significant tyrosinase inhibitory activity (IC50 = 3500 ppm) was observed in it. In HPLC analysis, derhamnosylation products (kaempferol, afzelin, and α-rhamnoisorobin) were detected. The inhibitory activity may be due to the existence of derhamnosylation products. This study demonstrated that FIR irradiation can be used as a convenient tool for deglycosylation of flavonoid glycoside.