4-Hydroxycoumarin - ≥98% , CAS No.1076-38-6

CAS: 1076-38-6 Cat. No.: H107607 Molecular Weight: 162.14 Beilstein Registry Number: 17488 EC Number: 214-060-2

GRADE & PURITY ≥98%

Synonyms

4-Hydroxy coumarin | 4-Monohydroxycoumarin | AM84328 | Tox21_113421 | 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98% | NSC11889 | NSC-11889 | SCHEMBL131312 | WARFARIN SODIUM IMPURITY B [EP IMPURITY] | 2-Hydroxy-4H-1-benzopyran-4-one | 4-HYDROXY-1-BENZOPY

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

4-Hydroxy coumarin | 4-Monohydroxycoumarin | AM84328 | Tox21_113421 | 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98% | NSC11889 | NSC-11889 | SCHEMBL131312 | WARFARIN SODIUM IMPURITY B [EP IMPURITY] | 2-Hydroxy-4H-1-benzopyran-4-one | 4-HYDROXY-1-BENZOPY

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488201698
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488201698
• Canonical Smiles: C1=CC=C2C(=C1)C(=CC(=O)O2)O
• IUPAC Name: 4-hydroxychromen-2-one
• InChIKey: VXIXUWQIVKSKSA-UHFFFAOYSA-N
• INCHI: 1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CC(=O)O2)O
• WGK Germany: 3
• RTECS: DJ3100000
• Alternate CAS: 22105-09-5,1076-38-6
• NSC Number: 11889
• MeSH Entry Terms: 4-hydroxycoumarin;4-OH coumarin
• Molecular Weight: 162.14
• Beilstein: 17488
• Reaxy-Rn: 129768
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=129768&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 4-hydroxycoumarins
• Alternative Parents: 1-benzopyrans Pyranones and derivatives Benzenoids Vinylogous acids Heteroaromatic compounds Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4-hydroxycoumarin - Benzopyran - 1-benzopyran - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Vinylogous acid - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
• External Descriptors: hydroxycoumarin

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)

CA9 Tclin Carbonic anhydrase 9 (1 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ALDH2 Tclin Aldehyde dehydrogenase (509 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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CSNK2A1 Tchem Casein kinase II alpha (3512 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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SORD Tchem Sorbitol dehydrogenase (133 Activities)

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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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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL3 (228 Activities)

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SK-MEL-5 (47095 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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U-937 (7138 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus fumigatus (16427 Activities)

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Dermatophagoides pteronyssinus (58 Activities)

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Trypanosoma cruzi (99888 Activities)

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Rattus norvegicus (775804 Activities)

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Botrytis cinerea (4183 Activities)

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B16-F10 (4610 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Mbp Myelin basic protein (42 Activities)

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Maob Monoamine oxidase (439 Activities)

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Colletotrichum acutatum (300 Activities)

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Diaporthe ampelina (88 Activities)

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Phomopsis obscurans (86 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 213℃
• Molecular Weight: 162.140 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.032 Da
• Monoisotopic Mass: 162.032 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 232.000
• 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. Kuang Yi, Xia Yunlong, Wang Xing, Rao Qingqing, Yang Shengxiang.  (2022)  Magnetic Surface Molecularly Imprinted Polymer for Selective Adsorption of 4-Hydroxycoumarin.  Frontiers in Chemistry,      [PMID:35464201] [10.3389/fchem.2022.862777]

2. Yunchang Fan, Dongxu Cai, Xin Wang, Lei Yang.  (2018)  Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition.  MOLECULES,  23  (9): (2154).  [PMID:30150588] [10.3390/molecules23092154]

3. Yusheng Yuan, Liu Yang, Shaopu Liu, Jidong Yang, Hui Zhang, Jingjing Yan, Xiaoli Hu.  (2017)  Enzyme-catalyzed Michael addition for the synthesis of warfarin and its determination via fluorescence quenching of l-tryptophan.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:28095360] [10.1016/j.saa.2017.01.014]

4. Bang-Hua Xie, Zhi Guan, Yan-Hong He.  (2012)  Promiscuous enzyme-catalyzed Michael addition: synthesis of warfarin and derivatives.  JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY,  87  (12): (1709-1714).  [PMID:] [10.1002/jctb.3830]

5. Ruiling Zhuo, Xiaokang Zhang, Yong Chen, Mengyang Xing, Shiping Tian, Boqiang Li.  (2024)  3-hydroxycoumarin effectively inhibits development and pathogenicity by targeting Pempk proteins of Penicillium expansum.  POSTHARVEST BIOLOGY AND TECHNOLOGY,      [PMID:] [10.1016/j.postharvbio.2024.112987]

6. Jiaxiang Liu, Wenqi Song, Huizhe Niu, Ying Lu, Haiyan Yang, Wentao Li, Yu-zhen Zhao, Zongcheng Miao.  (2024)  Superior Circularly Polarized Luminescence Brightness Achieved with Chiral Heteroleptic Nine-Coordinate Coumarin-Based Tb3+ Complexes.  INORGANIC CHEMISTRY,      [PMID:39270127] [10.1021/acs.inorgchem.4c02007]

7. Jiaxiang Liu, Yanan Guo, Qian Zhang, Huizhe Niu, Da Li, Zhenhao Xu, Wentao Li, Yuzhen Zhao, Zongcheng Miao.  (2025)  Circularly polarized yellow luminescence using novel chiral binary coumarin-based Dy3+ complexes.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2025.113156]

8. Si-Yue Ma, Lin-Li Yang, Jing-Sha Yang, Ya Xiao, Guo-Qing Wang, Hong-Wu Liu, Yue Ding, Xiang Zhou, Li-Wei Liu, Zhi-Bing Wu, Song Yang.  (2025)  New coumarin–cinnamic acid hybrids: potent FtsZ inhibitors as alternatives to bactericides for controlling bacterial infection.  PEST MANAGEMENT SCIENCE,      [PMID:41034602] [10.1002/ps.70272]