7-Azido-4-methylcoumarin - ≥98% , CAS No.95633-27-5

CAS: 95633-27-5 Cat. No.: A331202 Molecular Weight: 201.18

GRADE & PURITY ≥98%

Synonyms

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

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Product Application:

7-Azido-4-methylcoumarin is a highly sensitive and selective fluorogenic H|2|S probe. The aromatic azide moiety of AzMC is selectively reduced in the presence of H|2|S, producing the fluorescent 7-amino-4-methylcoumarin (AMC) with a concomitant increase in fluorescence with λex = 365 nm and λem = 450 nm. It is a photoaffinity labeling probe for the substrate binding site of human sulfotransferase 1A1 (SULT1A1). 7-Azido-4-methylcoumarin is a tool for monitoring the activity of pyridoxal-5'-phosphate (PLP)-dependent enzymes (e.g. cystathionine β-synthase (CBS), cystathionine γ-lyase (CGL) and tryptophan synthase (TS)) and to identify novel cystathionine β-synthase (CBS) inhibitors and activators.

Specifications

Synonyms

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

Specifications & Purity

≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Product Properties

• Excitation and Emision Ranges: λex 365 nm,λem 450 nm

Names and Identifiers

• Pubchem Sid: 504771298
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771298
• Canonical Smiles: CC1=CC(=O)OC2=C1C=CC(=C2)N=[N+]=[N-]
• IUPAC Name: 7-azido-4-methylchromen-2-one
• InChIKey: HEKDKVLIMUWRRZ-UHFFFAOYSA-N
• INCHI: 1S/C10H7N3O2/c1-6-4-10(14)15-9-5-7(12-13-11)2-3-8(6)9/h2-5H,1H3
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)N=[N+]=[N-]
• Molecular Weight: 201.18
• Reaxy-Rn: 5570484
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5570484&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarins and derivatives
• Alternative Parents: 1-benzopyrans Pyranones and derivatives Benzenoids Heteroaromatic compounds Lactones Azo imides Azo compounds Oxacyclic compounds Organopnictogen compounds Organooxygen compounds Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin - Benzopyran - 1-benzopyran - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Azo compound - Azo imide - Lactone - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Organic salt - Organic cation - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
• External Descriptors: Not available

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

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Molecular Weight: 201.180 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 201.054 Da
• Monoisotopic Mass: 201.054 Da
• Topological Polar Surface Area: 40.700 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 358.000
• 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. Chen JingQuan, Cheng WeiYi, Ren WeiYe, He LiTing, Wang Xiaoqi, Hong Xiujuan, Wang ChenLi, Wu Yajun, Bao Dandan, Wu Zhibing, Wei Yinghui, Piao Ji-Gang.  (2025)  Self-activated prodrug nanocomposites reprogramming lactic acid metabolism to initiate acidosis-endoplasmic reticulum stress cascade and potentiate immunogenic cell death for enhanced liver cancer therapy.  JOURNAL OF NANOBIOTECHNOLOGY,      [PMID:41327195] [10.1186/s12951-025-03874-1]