4-HYDROXYCOUMARIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H6O3
Molecular Weight	162.1421
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(=O)OC2=C1C=CC=C2

InChI

InChIKey=VXIXUWQIVKSKSA-UHFFFAOYSA-N

InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H

HIDE SMILES / InChI

Molecular Formula	C9H6O3
Molecular Weight	162.1421
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Synthesis and biological evaluation of coumarin derivatives as inhibitors of Mycobacterium bovis (BCG).	2012-12	22943459
3-Acetyl-4-hy-droxy-6,7-dimethyl-2H-chromen-2-one.	2010-11-13	21589432
Molecular Basis for Drug Resistance in HIV-1 Protease.	2010-11	21994628
Synthesis of functionalized chromenes from Meldrum's acid, 4-hydroxycoumarin, and ketones or aldehydes.	2010-11	20615198
Warfarin: an environment-dependent switchable molecular probe.	2010-10-30	21031478
Regulators of the proteasome pathway, Uch37 and Rpn13, play distinct roles in mouse development.	2010-10-27	21048919
Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants.	2010-09	20211681
2,2,4-Trimethyl-7-nitro-2,3-dihydro-1H-1,5-benzodiazepin-5-ium perchlorate.	2010-06-26	21588044
Genetic variations in human glutathione transferase enzymes: significance for pharmacology and toxicology.	2010-06-13	20981235
Design of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents.	2010-06-11	20657442
Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives.	2010-05-15	20435480
Inhibition of human DHODH by 4-hydroxycoumarins, fenamic acids, and N-(alkylcarbonyl)anthranilic acids identified by structure-guided fragment selection.	2010-04-06	20183850
Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model.	2010-04	19690859
Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-diones in water.	2010-02	19836289
A novel 4-hydroxycoumarin biosynthetic pathway.	2010-01	19757094
Synthesis of 3-amino-4-hydroxy coumarin and dihydroxy-phenyl coumarins as novel anticoagulants.	2010	21125812
(4R)-Ethyl 4-(4-chloro-phen-yl)-2-hydr-oxy-5-oxo-2,3,4,5-tetra-hydro-pyrano[3,2-c]chromene-2-carboxyl-ate.	2009-12-19	21580101
Synthesis and insecticidal activity of new 4-hydroxy-2H-1-benzopyran-2-one derivatives.	2009-12	19430739
Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1).	2009-11-26	19877692
4,4-Dimethyl-2-tosyl-1,2,3,3a,4,11b-hexa-hydro-11H-pyrrolo[3,4-c]pyrano[5,6-c]chromen-11-one 0.125-hydrate.	2009-10-31	21578517
Diastereoselective synthesis of trans-2,3-dihydrofurans with pyridinium ylide assisted tandem reaction.	2009-10-02	19739607
Formation of coumarines during the degradation of alkyl substituted aromatic oil components by the yeast Trichosporon asahii.	2009-10	19536538
HPLC method for simultaneous determination of impurities and degradation products in zonisamide.	2009-09	20502570
Study on the inhibitory mechanism and binding mode of the hydroxycoumarin compound NSC158393 to HIV-1 integrase by molecular modeling.	2009-09	19382173
Ethyl 2-hydr-oxy-5-oxo-4-phenyl-2,3,4,5-tetra-hydro-pyrano[3,2-c]chromene-2-carboxyl-ate.	2009-07-25	21583645
Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives.	2009-07	18725173
4-Hydr-oxy-3-[(2E)-3-(3,4,5-trimethoxy-phen-yl)prop-2-eno-yl]-2H-chromen-2-one.	2009-06-20	21582916
Synthesis and studies of new 2-(coumarin-4-yloxy)-4,6-(substituted)-S-triazine derivatives as potential anti-HIV agents.	2009-05	19415671
Reactions of 3-benzoyl-7-dimethylamino-4-hydroxycoumarin and their potential applications in solution- and solid-phase synthesis.	2009-05	19184500
Evaluation of alternatives to warfarin as probes for Sudlow site I of human serum albumin: characterization by high-performance affinity chromatography.	2009-04-17	18926542
Synthesis and molecular descriptor characterization of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents.	2009-04-14	19384281
Redox active donor-substituted punicin derivatives.	2009-04-07	19300831
3-Anilinothio-carbonyl-4-hydroxy-chromen-2-one.	2009-03-31	21582638
Design and microwave-assisted synthesis of naphtho[2,3-f]quinoline derivatives and their luminescent properties.	2009-03-09	19115830
Biosynthesis of biphenyls and benzophenones--evolution of benzoic acid-specific type III polyketide synthases in plants.	2009-03-02	19699497
Systems pharmacology and genome medicine: a future perspective.	2009-01-22	19348698
Pharmacogenomics of anticoagulants: steps toward personal dosage.	2009-01-21	19348697
Electrochemical synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives.	2008-11	18981606
Coumarin, anthroquinone and stilbene derivatives with anticholinesterase activity.	2008-08-02	18669022
The synthesis and antimicrobial activity of some 4-hydroxycoumarin derivatives.	2008-08	18816263
Synthesis and antimicrobial evaluation of some novel 2-aminothiazole derivatives of 4-hydroxy-chromene-2-one.	2008-08	18623301
2-Amino-4'-bromo-2',5-dioxo-4H,5H-pyrano[3,2-c]chromene-4-spiro-3'(2'H)-1'H-indole-3-carbonitrile N,N-dimethyl-formamide solvate.	2008-05-30	21202670
3D-QSAR investigation of synthetic antioxidant chromone derivatives by molecular field analysis.	2008-03	19325746
Comparison of the effect of 4-hydroxycoumarin and umbelliferone on the phase transition of dipalmitoylphosphatidylcholine (DPPC) bilayers.	2007-06-22	18799825
Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida).	2006-05-17	19127719
Biotin-avidin amplified enzyme-linked immunosorbent assay for determination of isoflavone daidzein.	2005-02-15	18969844
Genetic polymorphism in the human UGT1A6 (planar phenol) UDP-glucuronosyltransferase: pharmacological implications.	1997-12	9429234
Coumarin-based inhibitors of HIV integrase.	1997-01-17	9003523
Competitive inhibition of HIV-1 protease by 4-hydroxy-benzopyran-2-ones and by 4-hydroxy-6-phenylpyran-2-ones.	1994-05-16	8185622
Inhibitory effect of coumarins on HIV-1 replication and cell-mediated or cell-free viral transmission.	1993-08	7905238

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:39:02 GMT 2025` Edited by `admin` on `Mon Mar 31 19:39:02 GMT 2025`
Record UNII	X954ZLL2RD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-HYDROXYCOUMARIN

Systematic Name

English

NSC-11889

Preferred Name

English

4-HYDROXYCHROMEN-2-ONE

Systematic Name

English

2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-

Systematic Name

English

4-HYDROXYCOUMARIN [USP IMPURITY]

Common Name

English

4-HYDROXY-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

BENZOTETRONIC ACID

Common Name

English

WARFARIN SODIUM IMPURITY B [EP IMPURITY]

Common Name

English

4-COUMARINOL

Systematic Name

English

COUMARIN, 4-HYDROXY-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

214-060-2