Vitexin - analytical standard, ≥98% , CAS No.3681-93-4

CAS: 3681-93-4 Cat. No.: V113960 Molecular Weight: 432.38 Beilstein Registry Number: 67796 EC Number: 222-963-8

GRADE & PURITY Analytical standard, ≥98%

Synonyms

4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)- | 8-beta-D-Glucopyranosyl-apigenin | AS-55909 | DTXCID00112778 | Flavone, 8-D-glucosyl-4',5,7-trihydroxy- | Vitexin,(S) | VITEXINE | 8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

Vitexin is a naturally-occuring flavonoid and lignan compound that is identified in various plant sources. Vitexin is demonstrated to produce antioxidant effects in accord with other flavonoid compounds.
An apigenin flavone glycoside.

Specifications

Synonyms

4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-5, 7-dihydroxy-2-(4-hydroxyphenyl)- | 8-beta-D-Glucopyranosyl-apigenin | AS-55909 | DTXCID00112778 | Flavone, 8-D-glucosyl-4', 5, 7-trihydroxy- | Vitexin, (S) | VITEXINE | 8-((2S, 3R, 4R, 5S, 6R)-3, 4, 5-trihydroxy-6

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Antioxidant agent. Potent glucosidase inhibitor (IC 50 = 48 nM). HIF-1 α inhibitor. Inhibits TNF-α, IL-1β, IL-6, and IL-33 production. Shows antinociceptive, anti-inflammatory, and antioxidant effects in vivo.

Storage

Argon charged, Room temperature

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: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• InChIKey: SGEWCQFRYRRZDC-VPRICQMDSA-N
• INCHI: 1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1
• Isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• WGK Germany: 3
• Molecular Weight: 432.38
• Beilstein: 67796

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid C-glycosides
          • Level6 Flavonoid 8-C-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid C-glycosides
• Direct Parent: Flavonoid 8-C-glycosides
• Alternative Parents: 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Phenolic glycosides Hexoses Chromones C-glycosyl compounds 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives Oxanes Benzene and substituted derivatives Heteroaromatic compounds Vinylogous acids Secondary alcohols Oxacyclic compounds Dialkyl ethers Polyols Organic oxides Hydrocarbon derivatives Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-8-c-glycoside - Hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Phenolic glycoside - Hexose monosaccharide - Glycosyl compound - C-glycosyl compound - Chromone - 1-benzopyran - Benzopyran - Pyranone - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Pyran - Monosaccharide - Monocyclic benzene moiety - Benzenoid - Oxane - Heteroaromatic compound - Vinylogous acid - Secondary alcohol - Ether - Dialkyl ether - Organoheterocyclic compound - Oxacycle - Polyol - Primary alcohol - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid 8-c-glycosides. These are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
• External Descriptors: flavones - Flavones and Flavonols

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)

Discover Target: TYR

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ACHE Tclin Acetylcholinesterase (18204 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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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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RNASEL Tchem RNase L (193 Activities)

Discover Target: RNASEL

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BJ (6930 Activities)

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HepG2 (196354 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)

Discover Target: AKR1B10

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

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KOPN-8 (317 Activities)

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SEM (217 Activities)

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SUP-B15 (167 Activities)

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THLE-2 (239 Activities)

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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

Discover Target: NA

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pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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3T3-L1 (3664 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, and DMSO.
• Sensitivity: Moisture sensitive
• Molecular Weight: 432.400 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 432.106 Da
• Monoisotopic Mass: 432.106 Da
• Topological Polar Surface Area: 177.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 690.000
• 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

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3. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang.  (2022)  Multispectroscopic and computational evaluation of the binding of flavonoids with bovine serum albumin in the presence of Cu2+.  FOOD CHEMISTRY,      [PMID:35279499] [10.1016/j.foodchem.2022.132656]

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6. Hongjin Tang, Lin Huang, Dongsheng Zhao, Chunyong Sun, Ping Song.  (2020)  Interaction mechanism of flavonoids on bovine serum albumin: Insights from molecular property-binding affinity relationship.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:32480277] [10.1016/j.saa.2020.118519]

7. Jie Zhao, Lin Huang, Chunyong Sun, Dongsheng Zhao, Hongjin Tang.  (2020)  Studies on the structure-activity relationship and interaction mechanism of flavonoids and xanthine oxidase through enzyme kinetics, spectroscopy methods and molecular simulations.  FOOD CHEMISTRY,      [PMID:32330646] [10.1016/j.foodchem.2020.126807]

8. Xiaoqin Wang, Wencong Jia, Guoyin Lai, Lijuan Wang, María del Mar Contreras, Daomao Yang.  (2020)  Extraction for profiling free and bound phenolic compounds in tea seed oil by deep eutectic solvents.  JOURNAL OF FOOD SCIENCE,  85  (5): (1450-1461).  [PMID:32249418] [10.1111/1750-3841.15019]

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10. Lingyi Liu, Meirong Pang, Ying Zhang.  (2015)  Lipase-catalyzed regioselective synthesis of flavone C-glucosides esters and high-efficiency oil-soluble antioxidant of bamboo leaves (eAOB-o).  EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY,  117  (10): (1636-1646).  [PMID:] [10.1002/ejlt.201400541]

11. Yan Yu, Yan-Ping Liu, Jin-Fen Zheng, Xi-Jin Yang, Qi-Ju Shao, Dan Wang, Luo-Wei Wang, Fu-Zhen Li, Lan Yu, Rong-Xiang Chen.  (2025)  Comprehensive profiling of antioxidants in Zanthoxylum bungeanum leaves using two-dimensional liquid chromatography and regional comparisons.  INTERNATIONAL JOURNAL OF FOOD PROPERTIES,      [PMID:] [10.1080/10942912.2025.2479629]

12. Jingyu Gao, Longli Xie, Yu Peng, Mo Li, Jingming Li, Yuanying Ni, Xin Wen.  (2024)  Deep Eutectic Solvents as New Extraction Media for Flavonoids in Mung Bean.  Foods,  13  (5): (777).  [PMID:38472890] [10.3390/foods13050777]

13. wenwen Li, Zeyuan Deng, Shuang Xiao, qian Du, Mengru Zhang, Hailing Song, Caidong Zhao, Liufeng Zheng.  (2024)  Protective effect of vitexin against high fat-induced vascular endothelial inflammation through inhibiting trimethylamine N-oxide-mediated RNA m6A modification.  Food & Function,      [PMID:38855818] [10.1039/D3FO04743A]

14. Jiaying Liu, Yuanfan Chen, Jing Zhang, Yun Zheng, Yun An, Chenglai Xia, Yonger Chen, Song Huang, Shaozhen Hou, Dong Deng.  (2024)  Vitexin alleviates MNNG-induced chronic atrophic gastritis via inhibiting NLRP3 inflammasome.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:39716512] [10.1016/j.jep.2024.119272]

15. Qiuxiao Yang, Dingding Shi, Yanling Ren, Chao Yang, Hongxia Qu, Yueming Jiang, Taotao Li.  (2024)  Vitexin is a potential postharvest treatment for ameliorating litchi fruit pericarp browning by regulating autophagy.  POSTHARVEST BIOLOGY AND TECHNOLOGY,      [PMID:] [10.1016/j.postharvbio.2024.113061]

16. Qinghua Ni, Qiao Chen, Haixia Xu, Wenjun Wang, Zhongping Yin, Qing-Feng Zhang.  (2025)  γ-Cyclodextrin metal-organic framework enhanced the bioavailability of vitexin in rats by increasing solubility and inhibiting re-crystallization.  NEW JOURNAL OF CHEMISTRY,      [PMID:] [10.1039/D5NJ00704F]

17. Danyang Liu, Hao Zhou, Changwei Zhang, Zhiwen Qi, Xianghui Kong, Chengzhang Wang.  (2025)  Synthesis and characterization of magnetic molecularly imprinted polymers and application to the direct extraction of flavonoids from bamboo leaves.  Advances in Bamboo Science,      [PMID:] [10.1016/j.bamboo.2025.100197]

18. Xinghua Yu, Yujun Zhang, Lingan Zeng, Haiyan Chen, Xuemei Dong, Tianfu Zhang, Ben Zhong Tang, Fei Sun.  (2025)  Ferritin-Nanocaged Aggregation-Induced Emission Drug Vitexin Inhibits Ferroptosis to Treat Asthenozoospermia.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202522020]

19. Shi Shen, Jingbo Wang, Qin Zhuo, Xi Chen, Tingting Liu, Shuang-Qing Zhang.  (2018)  Quantitative and Discriminative Evaluation of Contents of Phenolic and Flavonoid and Antioxidant Competence for Chinese Honeys from Different Botanical Origins.  MOLECULES,  23  (5): (1110).  [PMID:29738446] [10.3390/molecules23051110]

20. 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]

21. Chen Ru, Cheng Si-Min, Wang Hao-Chuan, Kun-Dong, Sun Hui-Li, Sun Meng-Mei, Gao Bo, Wu Wen-Ning.  (2025)  Vitexin Alleviates Kainic Acid-Induced Seizure Through Inhibiting P2X7R/NLRP3 Signaling Pathway.  INFLAMMATION,      [PMID:40586851] [10.1007/s10753-025-02324-2]