Wogonoside - analytical standard, ≥98% , CAS No.51059-44-0

CAS: 51059-44-0 Cat. No.: W111385 Molecular Weight: 460.4 EC Number: 803-881-7 PubChem CID: 3084961

GRADE & PURITY Analytical standard, ≥98%

Synonyms

5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid | WOGONIN 7-O-.BETA.-D-GLUCURONIDE | AKOS015897144 | ETX4944Z3R | ACon1_000851 | DTXCID10121553 | Wogonin 7-O-glucuronide | 5,7-dihydroxy-8-methoxyflavone 7-O-beta-D-glucu

Storage

Protected from light,Desiccated

Shipped In

Normal

Specifications

Synonyms

5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid | WOGONIN 7-O-.BETA.-D-GLUCURONIDE | AKOS015897144 | ETX4944Z3R | ACon1_000851 | DTXCID10121553 | Wogonin 7-O-glucuronide | 5, 7-dihydroxy-8-methoxyflavone 7-O-beta-D-glucu

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Glycosides of wogonin . Induces cell cycle arrest at G1 phase. Promotes differentiation. Shows antiproliferative and antiangiogenic effects in vivo. Orally active.

Storage

Protected from light, Desiccated

Shipped In

Normal

Grade

Analytical standard

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)OC4C(C(C(C(O4)C(=O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
• InChIKey: LNOHXHDWGCMVCO-NTKSAMNMSA-N
• INCHI: 1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1
• Isomeric SMILES: COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O
• PubChem CID: 3084961
• Molecular Weight: 460.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid O-glucuronides
            • Level7 Flavonoid-7-O-glucuronides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides - Flavonoid O-glucuronides
• Direct Parent: Flavonoid-7-O-glucuronides
• Alternative Parents: Flavonoid-7-O-glycosides 8-O-methylated flavonoids 5-hydroxyflavonoids Flavones Phenolic glycosides O-glucuronides O-glycosyl compounds Chromones Anisoles 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives Alkyl aryl ethers Beta hydroxy acids and derivatives Oxanes Monosaccharides Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Secondary alcohols Monocarboxylic acids and derivatives Oxacyclic compounds Acetals Polyols Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glucuronide - Flavonoid-7-o-glycoside - 8-methoxyflavonoid-skeleton - 5-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Phenolic glycoside - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Anisole - Pyranone - Alkyl aryl ether - Beta-hydroxy acid - 1-hydroxy-2-unsubstituted benzenoid - Pyran - Oxane - Monocyclic benzene moiety - Benzenoid - Hydroxy acid - Monosaccharide - Heteroaromatic compound - Vinylogous acid - Secondary alcohol - Oxacycle - Ether - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Polyol - Organoheterocyclic compound - Acetal - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Alcohol - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
• External Descriptors: monosaccharide derivative - beta-D-glucosiduronic acid - monomethoxyflavone - glycosyloxyflavone - monohydroxyflavone

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(non-human)

Trypsin (394 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive.
• Molecular Weight: 460.400 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 460.101 Da
• Monoisotopic Mass: 460.101 Da
• Topological Polar Surface Area: 172.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 763.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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. Xiaoli Guo, Tingze Ren, Hongbo Li, Qingxin Lu, Xin Di.  (2024)  Antioxidant activity and mechanism exploration for microwave-assisted extraction of flavonoids from Scutellariae Radix using natural deep eutectic solvent.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.110300]

2. Zhang Jiaming, Chu Jiangnan, Wu Zhengwei.  (2025)  Cold atmospheric plasma pretreatment on the extraction of bioactive compounds from Scutellaria baicalensis Georgi.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1093/ijfood/vvaf041]

3. Yanhui Zhang, Hongbo Li, Xiaoqin Hai, Xiaoli Guo, Xin Di.  (2024)  Designing green and recyclable switchable supramolecular deep eutectic solvents for efficient extraction of flavonoids from Scutellariae Radix and mechanism exploration.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38879980] [10.1016/j.chroma.2024.465084]

4. Ruyi Zhu, Yaling Zhang, Weitai He, Yanan Sun, Xin Zhao, Yaping Yan, Qian Zhang.  (2024)  Wogonoside alleviates microglia-mediated neuroinflammation via TLR4/MyD88/NF-κB signaling axis after spinal cord injury.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:38636801] [10.1016/j.ejphar.2024.176566]

5. Stoyan Dirimanov, Petra Högger.  (2019)  Screening of Inhibitory Effects of Polyphenols on Akt-Phosphorylation in Endothelial Cells and Determination of Structure-Activity Features.  Biomolecules,  9  (6): (219).  [PMID:31195734] [10.3390/biom9060219]

6. Hui Cao, Xiaojuan Liu, Nataša Poklar Ulrih, Pradeep K. Sengupta, Jianbo Xiao.  (2018)  Plasma protein binding of dietary polyphenols to human serum albumin: A high performance affinity chromatography approach.  FOOD CHEMISTRY,      [PMID:30174044] [10.1016/j.foodchem.2018.07.111]

7. Fuyun Chi, Wenshuang Wang, Shanshan Zhai, Man Zhang, Yuanyuan Hou, Gang Bai.  (2025)  Self-assembled baicalein-2,4-decadienal nanomedicine synergistically inhibits PGE2 expression and elicits anti-inflammatory responses.  Chinese Herbal Medicines,      [PMID:] [10.1016/j.chmed.2025.10.001]