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417327

Sigma-Aldrich

4-Hydroxy-6,7-dimethylcoumarin

98%

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About This Item

Empirical Formula (Hill Notation):
C11H12O4
CAS Number:
Molecular Weight:
208.21
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

98%

mp

248-251 °C (lit.)

SMILES string

Cc1cc2OC(=O)C=C(O)c2cc1C

InChI

1S/C11H10O3/c1-6-3-8-9(12)5-11(13)14-10(8)4-7(6)2/h3-5,12H,1-2H3

InChI key

AYHZQBMBPNZPEY-UHFFFAOYSA-N

Application

4-Hydroxy-6,7-dimethylcoumarin was used to investigate its biological activity against bacteria and fungi.[1] It may be used for the following syntheses:
  • 6,7-dimethyl-4-[(oxiran-2-yl)methoxy]-2H-1-benzopyran-2-one[2]
  • 2H-pyrans[3]
  • 3-acetyl-4-hydroxy-6,7-dimethyl-2H-chromen-2-one[4]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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3-Acetyl-4-hydroxy-6, 7-dimethyl-2H-chromen-2-one.
Asad M, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 66(12), 3129-3130 (2010)
Carlos L Céspedes et al.
Journal of agricultural and food chemistry, 54(10), 3521-3527 (2006-05-17)
Mexican tarragon (Tagetes lucida Cv. Asteraceae: Campanulatae) is an important, nutritious plant and an effective herbal medicine. Seven coumarins, 7,8-dihydroxycoumarin (4), umbelliferone (7-hydroxycoumarin) (5), scoparone (6,7-dimethoxycoumarin) (7), esculetin (6,7-dihydroxycoumarin) (11), 6-hydroxy-7-methoxycoumarin (12), herniarin (7-methoxycoumarin) (13), and scopoletin (6-methoxy-7-hydroxycoumarin) (14), and
Yeh-Long Chen et al.
Bioorganic & medicinal chemistry, 13(20), 5710-5716 (2005-07-05)
Certain coumarin alpha-methylene-gamma-butyrolactones were synthesized and evaluated for antiproliferative and vasorelaxing activities. These compounds were synthesized via alkylation of hydroxycoumarins 2a-f followed by oxidation and the Reformatsky-type condensation. The results of this study are as follows (1) for the vasorelaxing
Iodine-Catalyzed One-Pot Synthesis of 2H-Pyrans by Domino Knoevenagel/6p-Electrocylization.
Jung EJ, et al.
Bull. Korean Chem. Soc., 30, 2833-2836 (2009)

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