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Sigma-Aldrich

7-Azido-4-Methylcoumarin

97%

Synonym(s):

4-Methyl-7-azidocoumarin, 7-Azido-4-methyl-2H-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H7N3O2
CAS Number:
95633-27-5
Molecular Weight:
201.18
MDL number:
MFCD16652405
UNSPSC Code:
12352125
PubChem Substance ID:
329768736
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder

mp

117.8 °C

SMILES string

CC1=CC(=O)Oc2cc(ccc12)N=[N+]=[N-]

InChI

1S/C10H7N3O2/c1-6-4-10(14)15-9-5-7(12-13-11)2-3-8(6)9/h2-5H,1H3

InChI key

HEKDKVLIMUWRRZ-UHFFFAOYSA-N

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Application

7-Azido-4-methylcoumarin (AzMC) is a fluorogenic probe useful for the detection of hydrogen sulfide (H2S). The aromatic azide moiety is selectively reduced in the presence of H2S, producing the fluorescent 7-amino-4-methylcoumarin (AMC) with a concomitant increase in fluorescence with λex = 365nm and λem = 450nm. The probe can be used both to monitor enzymatic production of H2S in vitro and also to visualize H2S in cells. The probe is highly sensitive and selective for H2S, providing a linear detection range in vitro between 200nm – 100μM H2S with 10μM probe, and reacting selectively with H2S in the presence of mM concentrations of cysteine, homocysteine, glutathionine and many other common biological analytes.

Caution: Use of this product with DTT, TCEP and/or biological thiols >25mM should be avoided for maximum efficiency.

AzMC is readily soluble in DMSO.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Megan K Thorson et al.
Angewandte Chemie (International ed. in English), 52(17), 4641-4644 (2013-03-21)
Buzzing with activity: A hydrogen sulfide selective fluorogenic probe, 7-azido-4-methylcoumarin (AzMC), serves as a highly sensitive assay for cystathionine β-synthase activity, and is suitable for the high-throughput discovery of novel enzyme inhibitors.
Bifeng Chen et al.
The Analyst, 138(3), 946-951 (2012-12-18)
A coumarin-based fluorescence chemoprobe was developed and evaluated for the selective and sensitive detection of hydrogen sulfide in degassed PBS buffers and fetal bovine serum. Fluorescence detection of hydrogen sulfide in living cells was also successfully achieved using two-photon confocal
Rebecca A Ellwood et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(9) (2021-02-26)
Duchenne muscular dystrophy (DMD) is an X-linked recessive disorder characterized by progressive muscle degeneration and weakness due to mutations in the dystrophin gene. The symptoms of DMD share similarities with those of accelerated aging. Recently, hydrogen sulfide (H2S) supplementation has
Ghulam Mohammad et al.
Investigative ophthalmology & visual science, 61(14), 35-35 (2020-12-30)
Hyperglycemia damages the retinal mitochondria, and the mitochondrial damage plays a central role in the development of diabetic retinopathy. Patients with diabetes also have higher homocysteine levels, and abnormalities in homocysteine metabolism result in decreased levels of hydrogen sulfide (H2S)
Karim Zuhra et al.
Cells, 8(8) (2019-08-07)
Hydrogen sulfide (H2S) is an endogenously produced signaling molecule. The enzymes 3-mercaptopyruvate sulfurtransferase (MST), partly localized in mitochondria, and the inner mitochondrial membrane-associated sulfide:quinone oxidoreductase (SQR), besides being respectively involved in the synthesis and catabolism of H2S, generate sulfane sulfur

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