Merck
All Photos(4)

C4261

Sigma-Aldrich

Coumarin

≥99% (HPLC)

Synonym(s):
1,2-Benzopyrone, 1-Benzopyran-2-one, 2H-Chromen-2-one
Empirical Formula (Hill Notation):
C9H6O2
CAS Number:
Molecular Weight:
146.14
Beilstein:
383644
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

vapor pressure

0.01 mmHg ( 47 °C)

assay

≥99% (HPLC)

form

powder

bp

298 °C (lit.)

mp

68-73 °C (lit.)

SMILES string

O=C1Oc2ccccc2C=C1

InChI

1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H

InChI key

ZYGHJZDHTFUPRJ-UHFFFAOYSA-N

Gene Information

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Application

Coumarin is useful as a precursor molecule for the preparation or synthesis of coumarin-based anticoagulates, antiiflammatory agents and antioxidation superoxide scavengers.

Packaging

50, 100, 500 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C4261.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Skin Sens. 1

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 1

Flash Point(F)

323.6 °F - closed cup

Flash Point(C)

162 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Shigehiro Sumiya et al.
The journal of physical chemistry. A, 117(7), 1474-1482 (2013-01-25)
A coumarin-amide-dipicolylamine linkage (L) was synthesized and used as a fluorescent receptor for metal cations in water. The receptor dissolved in water with neutral pH shows almost no fluorescence due to the photoinduced electron transfer (PET) from the amide and
Shota Morimoto et al.
Chemical communications (Cambridge, England), 49(18), 1811-1813 (2013-01-26)
A photo-switchable fluorescent flagging approach has been developed to identify photoaffinity-labeled peptides in target protein. Upon photochemical release of the ligand, the protein was newly modified with a coumarin in place of the previously attached biotin. It allowed us to
Donglei Yu et al.
Medicinal research reviews, 23(3), 322-345 (2003-03-21)
Numerous plant-derived compounds have been evaluated for inhibitory effects against HIV replication, and some coumarins have been found to inhibit different stages in the HIV replication cycle. This review article describes recent progress in the discovery, structure modification, and structure-activity
Klaus Abraham et al.
Molecular nutrition & food research, 54(2), 228-239 (2009-12-22)
Coumarin is a secondary phytochemical with hepatotoxic and carcinogenic properties. For the carcinogenic effect, a genotoxic mechanism was considered possible, but was discounted by the European Food Safety Authority in 2004 based on new evidence. This allowed the derivation of
Fabrizio Carta et al.
Bioorganic & medicinal chemistry, 20(7), 2266-2273 (2012-03-02)
A series of coumarins incorporating tert-butyl-dimethylsilyloxy- or allyoxy- moieties in positions 4-, 6 or 7 of the heterocyclic ring have been synthesized and then converted to the corresponding 2-thioxo-coumarins. Other derivatives incorporating hydroxyethyloxy-, tosylethoxy- and 2-fluroethyloxy- moieties in position 7

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