(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]ox

Introduction：Basic information about (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]ox, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one Basic information

• Product Name: (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one
• Synonyms: (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one;(+)-(2R,3R)-Dihydrokaempferol 3-O-alpha-L-rhamnoside;(2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside;Dihydrokaempferol 3-O-alpha-L-rhamnopyranoside;Dihydrokaempferol 3-rhamnoside;Engelitin;AroMadendrin 3-rhaMnoside;3-((6-Deoxy-alpha-L-Mannopyranosyl)oxy)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one(2R-trans)
• CAS: 572-31-6
• MF: C21H22O10
• MW: 434.39
• EINECS: 300-009-2
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 572-31-6.mol

(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one Chemical Properties

• Melting point: 176-177℃
• Boiling point: 763.4±60.0 °C(Predicted)
• density: 1.66
• storage temp.: -20°C
• solubility: DMSO:93.0(Max Conc. mg/mL);214.09(Max Conc. mM)
• pka: 7.37±0.60(Predicted)
• form: powder
• color: White
• Optical Rotation: [α]/D -13 to -17°, c =0.5 in pyridine
• InChIKey: VQUPQWGKORWZII-WDPYGAQVSA-N
• SMILES: O1[C@H]([C@@H]([C@@H]([C@H]([C@@H]1C)O)O)O)O[C@@H]2[C@H](Oc4c(c(cc(c4)O)O)C2=O)c3ccc(cc3)O

Safety Information

• WGK Germany: WGK 3
• HS Code: 29389090
• Storage Class: 11 - Combustible Solids

(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one Usage And Synthesis

Chemical Properties

Off-white crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Smilax glabra.

Uses

Engeletin is a polyphenol compound used as an anti-oxidant.

Biological Activity

New MCE product August 2018. Engeletin is a flavanonol glycoside present in the skin of white grapes and white wine th at exhibits anti-inflammatory activities. It inhibits LPS induced cytokines production in mouse J774A.1 macrophages. Also, engeletin attenuates LPS-induced endometritis in mice through inhibiting NF-KB activation, and inhibits inflammatory response in LPS-induced acute lung injury (ALI).

in vivo

Engeletin (25, 50, 100 mg/kg, i.p.) markedly reduces LPS-increased myeloperoxidase activity in mice, activates NF-κB-pathway activation, decreases the production of inflammatory mediators (iNOS and COX-2), and suppresses the expression of TLR4-signaling downstream molecules such as MyD88, IRAK1, TRAF6, and TAK1 proteins^[1].

IC 50

NF-κB