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C85409

Sigma-Aldrich

Coumalic acid

97%

Synonym(s):

2-Oxo-2H-pyran-5-carboxylic acid, 2-Pyrone-5-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C6H4O4
CAS Number:
500-05-0
Molecular Weight:
140.09
Beilstein:
119747
EC Number:
207-899-0
MDL number:
MFCD00006644
UNSPSC Code:
12352100
PubChem Substance ID:
24893071
NACRES:
NA.22

Assay

97%

form

powder

bp

218 °C/120 mmHg (lit.)

mp

203-205 °C (dec.) (lit.)

SMILES string

OC(=O)C1=COC(=O)C=C1

InChI

1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9)

InChI key

ORGPJDKNYMVLFL-UHFFFAOYSA-N

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General description

Decarboxylates to α-pyrone, a Diels-Alder diene.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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V Günzler et al.
The Biochemical journal, 242(1), 163-169 (1987-02-15)
From the structure-activity relationships of known competitive inhibitors, coumalic acid (2-oxo-1,2H-pyran-5-carboxylic acid) was deduced to be a potential syncatalytic inhibitor for chick-embryo prolyl 4-hydroxylase. The compound caused time-dependent inactivation, the reaction rate being first-order. The inactivation constant was 0.094 min-1
A Merriweather et al.
Molecular and biochemical parasitology, 116(2), 185-197 (2001-08-28)
The cuticle of parasitic nematodes consists primarily of a network of collagen molecules. The enzyme responsible for collagen maturation is prolyl 4-hydroxylase, making this enzyme a central activity in cuticle biosynthesis and a potentially important chemotherapeutic target. Adult and embryonic
Weijun Chen et al.
International journal of food sciences and nutrition, 63(2), 236-241 (2011-09-29)
The oxidative modification of human low density lipoprotein (LDL) plays a significant role in atherosclerosis. In this study, the inhibiting activity of areca inflorescence extracts (AIEs) on LDL oxidation was investigated by an in vitro study with Trolox as the
Yongxia Li et al.
Phytopathology, 110(4), 805-812 (2020-03-03)
Poplar canker, mainly caused by Botryosphaeria species, is a serious disease that has resulted in the reduced productivity and death of poplar worldwide. Different Populus species have varied resistance levels to poplar canker; however, whether phenolic compounds in poplar are
Michio Ohi et al.
Bioscience, biotechnology, and biochemistry, 67(1), 170-173 (2003-03-07)
Some chemicals were examined for their effects on the germination of resting spores of the clubroot pathogen Plasmodiophora brassicae, and on the control of clubroots in Chinese cabbage. Caffeic acid, coumalic acid, and corilagin stimulated the germination of Plasmodiophora spores
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