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C4261

Sigma-Aldrich

Coumarin

≥99% (HPLC)

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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/REAXYS Number:
383644
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

vapor pressure

0.01 mmHg ( 47 °C)

Quality Level

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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1 of 4

This Item
Y0000438PHL800178.22316
Coumarin ≥99% (HPLC)

C4261

Coumarin

Coumarin European Pharmacopoeia (EP) Reference Standard

Y0000438

Coumarin

Coumarin phyproof® Reference Substance

PHL80017

Coumarin

Coumarin for synthesis

8.22316

Coumarin

mp

68-73 °C (lit.)

mp

68-73 °C (lit.)

mp

68-73 °C (lit.)

mp

68-71 °C

bp

298 °C (lit.)

bp

298 °C (lit.)

bp

298 °C (lit.)

bp

-

vapor pressure

0.01 mmHg ( 47 °C)

vapor pressure

0.01 mmHg ( 47 °C)

vapor pressure

0.01 mmHg ( 47 °C)

vapor pressure

1.3 hPa ( 106 °C)

form

powder

form

-

form

flakes

form

crystals

Gene Information

rat ... Maoa(29253), Maob(25750)

Gene Information

-

Gene Information

-

Gene Information

-

Application

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

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

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

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

flash_point_f

323.6 °F - closed cup

flash_point_c

162 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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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
María E Riveiro et al.
Bioorganic & medicinal chemistry, 17(18), 6547-6559 (2009-09-01)
The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro
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
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

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