Kaempferol 3-O-β -rutinoside - ≥98%(HPLC) , CAS No.17650-84-9

CAS: 17650-84-9 Cat. No.: K138386 Molecular Weight: 594.52 EC Number: 685-716-7

GRADE & PURITY ≥98%(HPLC)

Synonyms

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | KAEMPFEROL 3-O-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->6)-.BETA.-D-GLUCOPYRANOSIDE) | UNII-4056D20K3H | Dimethylamine, anhydrous | UN2346 | Nicoti

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Kaempferol 3-O-β -rutinoside is a bitter tasting flavonol glycoside that was isolated from flowers of a Clematis cultivar.

Specifications

Synonyms

5, 7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | KAEMPFEROL 3-O-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->6)-.BETA.-D-GLUCOPYRANOSIDE) | UNII-4056D20K3H | Dimethylamine, anhydrous | UN2346 | Nicoti

Specifications & Purity

≥98%(HPLC)

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504763583
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763583
• Canonical Smiles: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• InChIKey: RTATXGUCZHCSNG-QHWHWDPRSA-N
• INCHI: 1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
• WGK Germany: 3
• Molecular Weight: 594.52
• Reaxy-Rn: 1696714
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1696714&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-3-O-glycosides
• Alternative Parents: 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones O-glycosyl compounds Chromones Disaccharides 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Pyranones and derivatives Oxanes Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Secondary alcohols Acetals Oxacyclic compounds Polyols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glycoside - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Disaccharide - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Oxane - Pyran - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Acetal - Polyol - Organic oxygen compound - Alcohol - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
• External Descriptors: rutinoside - disaccharide derivative - trihydroxyflavone - kaempferol O-glucoside

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TYR Tclin Tyrosinase (717 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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AKR1B1 Tclin Aldose reductase (1404 Activities)

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NQO1 Tchem Quinone reductase 1 (1746 Activities)

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N9 (414 Activities)

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PANC-1 (6144 Activities)

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SK-MEL-2 (46422 Activities)

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SK-OV-3 (52876 Activities)

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A549 (127892 Activities)

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BT-549 (31254 Activities)

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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Streptococcus mutans (2687 Activities)

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Entamoeba histolytica (2676 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Giardia intestinalis (1290 Activities)

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Influenza A virus (11224 Activities)

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3T3-L1 (3664 Activities)

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MDCK (10148 Activities)

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RAW264.7 (28094 Activities)

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C6 (2371 Activities)

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BV-2 (3710 Activities)

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C2C12 (756 Activities)

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Dyrk1a Dual specificity tyrosine-phosphorylation-regulated kinase 1A (1629 Activities)

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nanH Sialidase (337 Activities)

Discover Target: nanH

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• Molecular Weight: 594.500 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 594.158 Da
• Monoisotopic Mass: 594.158 Da
• Topological Polar Surface Area: 245.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 985.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Huiqun Fan, Mingshun Chen, Taotao Dai, Lizhen Deng, Chengmei Liu, Wei Zhou, Jun Chen.  (2023)  Phenolic compounds profile of Amomum tsaoko Crevost et Lemaire and their antioxidant and hypoglycemic potential.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2023.102508]

2. Qi Sun, Jiajin Zhu, Feiwei Cao, Fengjia Chen.  (2017)  Anti-inflammatory properties of extracts from Chimonanthus nitens Oliv. leaf.  PLoS One,  12  (7): (e0181094).  [PMID:28700722] [10.1371/journal.pone.0181094]

3. Xiaoping Zhang, Huiqing Lv, Zuguang Li, Kezhi Jiang, Maw-Rong Lee.  (2014)  HPLC/QTOF-MS/MS application to investigate phenolic constituents from Ficus pandurata H. aerial roots.  BIOMEDICAL CHROMATOGRAPHY,  29  (6): (860-868).  [PMID:25408477] [10.1002/bmc.3366]

4. Cheng-Hai Yan, Ding Wang, Ruo-Xi Mei, Lu Tan, Yi-Jiang-Cheng Li, Richard Ansah Herman, Yan Xu, Lu-Chan Gong, Jun Wang.  (2025)  High-efficiency flavonoid deglycosylation of whole cells with surface display of α-L-rhamnosidase in Escherichia coli.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.106114]

5. Yu Meng, Wenhao Zou, Tingting Guo, Lin Zhang, Pengpai Zhang, Penghua Shu.  (2025)  Optimization of ultrasound-assisted deep eutectic solvent extraction, characterization, and bioactivities of flavonoids from Cercis glabra leaves.  ULTRASONICS SONOCHEMISTRY,      [PMID:40543485] [10.1016/j.ultsonch.2025.107434]