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6-Hydroxypyridine-3-carboxylic acid

PESTANAL®, analytical standard

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Synonym(s):
2-Hydroxy-5-pyridinecarboxylic acid, 6-Hydroxynicotinic acid
Empirical Formula (Hill Notation):
C6H5NO3
CAS Number:
5006-66-6
Molecular Weight:
139.11
Beilstein:
115991
EC Number:
225-682-9
MDL number:
MFCD00006277
UNSPSC Code:
41116107
PubChem Substance ID:
329751860
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

PESTANAL®

Assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤1.0% water

mp

>300 °C (lit.)
302-308 °C

application(s)

agriculture
environmental

format

neat

SMILES string

OC(=O)c1ccc(O)nc1

InChI

1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)

InChI key

BLHCMGRVFXRYRN-UHFFFAOYSA-N

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General description

6-Hydroxypyridine-3-carboxylic acid has aliphatic carboxylate anions.

Find more information here: Neonicotinoids

Application

It can be used as a good organic linker source for the construction of lanthanide coordination polymers. It was used in qualitative and quantitative analysis of substrates and metabolites of neonicotinoids using LC-MSD TOF, in a study performed to clone 6-chloronicotinic acid chlorohydrolase from newly isolated 6-chloronicotinic acid mineralizing Bradyrhizobiaceae strain SG-6C.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

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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Two-and three-dimensional lanthanide?organic frameworks constructed using 1-hydro-6-oxopyridine-3-carboxylate and oxalate ligands.
Liu, Cai-Ming, et al.
Dalton Transactions, 29, 5666-5672 (2009)
Yao Yang et al.
Wei sheng wu xue bao = Acta microbiologica Sinica, 48(1), 112-115 (2008-03-15)
Recently, new insecticides containing 3-chloropyridylmethyl group as a versatile building block have been developed, among which imidachloprid is a promising one. The synthesis of imidachloprid can use 6-Hydroxynicotinic acid, the first intermediate of the bacterial degradation of nicotinic acid, as
R A Ludwig
Journal of bacteriology, 165(1), 304-307 (1986-01-01)
Rhizobium sp. strain ORS571 conducts synergistic, free-living N2 fixation and nicotinate oxidation. Explicitly, ORS571 is able to fix N2 aerobically because 6-OH-nicotinate acts as an intracellular O2 sink. Because 6-OH-nicotinate oxidation is mandatory for aerobic, free-living N2 fixation and because
S Shiraishi et al.
Journal of chromatography, 338(1), 51-59 (1985-02-27)
Gas chromatography--mass spectrometry has been used to identify specific metabolites produced by Gram-negative bacteria such as Pseudomonas aeruginosa, Serratia marcescens, Klebsiella pneumoniae and Escherichia coli in a defined medium. 6-Hydroxynicotinic acid was detected in spent culture media of Pseudomonas aeruginosa
Ashish Gupta et al.
NMR in biomedicine, 18(5), 293-299 (2005-03-11)
The utility of (1)H NMR spectroscopy is suggested and demonstrated for the diagnosis of Pseudomonas aeruginosa in urinary tract infection (UTI). The specific property of P. aeruginosa of metabolizing nicotinic acid to 6-hydroxynicotinic acid (6-OHNA) is exploited. The quantity of
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