3-Hydroxyflavone - 10mM in DMSO , CAS No.577-85-5

CAS: 577-85-5 Cat. No.: H424860 Molecular Weight: 238.24 Beilstein Registry Number: 17(3/4)6428 EC Number: 209-416-9

GRADE & PURITY 10mM in DMSO

Synonyms

3-Hydroxy-2-phenyl-4H-chromen-4-one | A869585 | BDBM50187668 | NCGC00095653-02 | C01495 | MFCD00006832 | NSC 58585 | DivK1c_006927 | EU-0001678 | Flavon-3-ol | KBioSS_000808 | 3-hydroxyflavon | flavonols | 3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CI | S

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Reactant involved in: · Studies of photochemically-induced dioxygenase-type CO-release reactivity · Phase-transfer protection and deprotection of hydroxychromones · O-methylation with di-Me carbonate Reactant involved in the synthesis of biologically active molecules including: · 2-Chloropyridine derivatives for studies of antitumor agents and telomerase inhibitors · Dihydrochromenopyrazines and chromenoquinoxalines Involved in studies of its electrochemical properties using voltammetric methodologies

Specifications

Synonyms

3-Hydroxy-2-phenyl-4H-chromen-4-one | A869585 | BDBM50187668 | NCGC00095653-02 | C01495 | MFCD00006832 | NSC 58585 | DivK1c_006927 | EU-0001678 | Flavon-3-ol | KBioSS_000808 | 3-hydroxyflavon | flavonols | 3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CI | S

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
• IUPAC Name: 3-hydroxy-2-phenylchromen-4-one
• InChIKey: HVQAJTFOCKOKIN-UHFFFAOYSA-N
• INCHI: 1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
• Isomeric SMILES: C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
• WGK Germany: 3
• RTECS: LK8650000
• Molecular Weight: 238.24
• Beilstein: 17(3/4)6428
• Reaxy-Rn: 15789
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=15789&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavones
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavonols
• Alternative Parents: 3-hydroxyflavonoids Chromones Pyranones and derivatives Benzene and substituted derivatives Heteroaromatic compounds Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3-hydroxyflavone - 3-hydroxyflavonoid - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Pyranone - Monocyclic benzene moiety - Pyran - Benzenoid - Heteroaromatic compound - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
• External Descriptors: flavonols - 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(Human)

CYP1B1 Tchem Cytochrome P450 1B1 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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TOP2A Tclin DNA topoisomerase II alpha (6317 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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CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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

CA1 Tclin Carbonic anhydrase I (13240 Activities)

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

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

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FASN Tchem Fatty acid synthase (3390 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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TOP2B Tclin DNA topoisomerase II beta (959 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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

CA12 Tclin Carbonic anhydrase XII (6231 Activities)

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UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)

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CA9 Tclin Carbonic anhydrase IX (8255 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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Caco-2 (12174 Activities)

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H9 (1832 Activities)

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HCT-116 (91556 Activities)

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Monocyte (474 Activities)

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KB (17409 Activities)

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CWR22R (2180 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

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P4HB Tchem Protein disulfide-isomerase (716 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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

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

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UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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UGT1A1 Tchem UDP-glucuronosyltransferase 1-1 (448 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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UGT1A6 Tbio UDP-glucuronosyltransferase 1-6 (221 Activities)

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UGT1A7 Tbio UDP-glucuronosyltransferase 1-7 (106 Activities)

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UGT1A8 Tbio UDP-glucuronosyltransferase 1-8 (233 Activities)

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UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)

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UGT1A10 Tbio UDP-glucuronosyltransferase 1-10 (257 Activities)

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UGT2A1 UDP-glucuronosyltransferase 2A1 (59 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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UGT1A3 Tbio UDP-glucuronosyltransferase 1-3 (217 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Salmonella typhimurium (15756 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Escherichia coli (133304 Activities)

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Pichia kudriavzevii (7448 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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Candida parapsilosis (8521 Activities)

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Candida tropicalis (8381 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Rattus norvegicus (775804 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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Stenotrophomonas maltophilia (1743 Activities)

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3T3-L1 (3664 Activities)

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B16 (5829 Activities)

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CCRF S-180 (1031 Activities)

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L1210 (27553 Activities)

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P388 (20296 Activities)

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Lewis lung carcinoma cell line (1243 Activities)

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fabG 3-oxoacyl-acyl-carrier protein reductase (70 Activities)

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fabI Enoyl-acyl-carrier protein reductase (415 Activities)

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Lipe Hormone-sensitive lipase (209 Activities)

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CALM Calmodulin (71 Activities)

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Aorta (2975 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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HSP40, subfamily A, putative (505 Activities)

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Ntrk2 BDNF/NT-3 growth factors receptor (124 Activities)

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E6 Protein E6 (25 Activities)

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gyrB DNA gyrase (2092 Activities)

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Thoracic aorta (838 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: air sensitive
• Melt Point(°C): 171-172°C
• Molecular Weight: 238.240 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 238.063 Da
• Monoisotopic Mass: 238.063 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 366.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Qian-Qian Huang.  (2021)  A novel nickel complex with 3-Hydroxyflavone: Synthesis, CrystalStructure and reactivity towards O2 of Ni4(C15O3H9)4(CH3O)4(H2O)4.  INORGANIC CHEMISTRY COMMUNICATIONS,      [PMID:] [10.1016/j.inoche.2021.108795]

2. Xiaojun He, Wei Xiong, LileiZhang, Chuchu Xu, Jinyi Fan, Yuna Qian, Jinsheng Wen, Feng Ding, Jianliang Shen.  (2019)  ESIPT-based ratiometric fluorescent probe for highly selective and sensitive sensing and bioimaging of group IIIA ions in living cancer cells and zebrafish.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2019.108059]

3. Li-Feng Li, Meng-Di Wang, Chen-Yang Zhang, Meng-Yao Jin, Hua-Lei Chen, Huan Luo, Tian-Yu Hou, Zhi-Jun Zhang, He Li.  (2025)  Influence of hydroxyl substitution on the inhibition of flavonoids in advanced glycation end-products formation in glucose-lysine-arginine Maillard reaction models.  FOOD RESEARCH INTERNATIONAL,      [PMID:40086959] [10.1016/j.foodres.2025.116068]

4. Qinli Ye, Miaomiao Wu, Qian Xu, Shuwen Zeng, Tao Jiang, Wei Xiong, Songyin Fu, Muhammad Danang Birowosuto, Chenjie Gu.  (2024)  Porous carbon film/WO3-x nanosheets based SERS substrate combined with deep learning technique for molecule detection.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:38309005] [10.1016/j.saa.2024.123962]

5. Haolin Zhang, Jingjing Zhang, Hui Cao, Petra Högger, Randolph Arroo, Mohamed A. Farag, Avi Shpigelman, Jianbo Xiao, Chunlin Li.  (2025)  Amination of Flavonoids Possessing a Pyrogallol Group in Cell Culture Medium at 37°C.  Food Frontiers,  6  (2): (1058-1078).  [PMID:] [10.1002/fft2.70002]

6. Boying Wang, Jin Liu, Wenfei Shen, Yao Wang, Jun Li, Yan Zhang, Qiao Wang, Christopher D. Snow, Matt J. Kipper, Soo Wohn Lee, Laurence A. Belfiore, Jianguo Tang.  (2025)  Multilevel Information Encoding of Metal Ion-Induced Fluorescent Nanoaggregates and Full-Color Electrohydrodynamic Printing.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.5c00886]

7. Changhai Sun, Mengxin Xiao, Biyue Cui, Shiyuan Sun, Shushuang Shen, Shuting Zhang, Xinran Zhang, Liting Mu.  (2026)  Study on the Correlation Between Anthoxanthins Compounds' Reverse-Phase Chromatographic Behavior and Their Solubility.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2026.145944]