874-24-8

Basic information

• Product Name: 3-Hydroxypicolinic acid
• Synonyms: TIMTEC-BB SBB006727;RARECHEM AL BO 0972;2-PYRIDINECARBOXYLIC ACID, 3-HYDROXY-;3-HYDROXYPYRIDINE-2-CARBOXYLIC ACID;3-HYDROXYPICOLINIC ACID;3-HPA;3-HYDROXY-2-PYRIDINECARBOXYLIC ACID;3-HYDROXYPICOLINIC ACID, MATRIX SUB-STAN CE FOR MALDI-MS
• CAS NO: 874-24-8
• Molecular Formula: C₆H₅NO₃
• Molecular Weight: 139.11
• EINECS: 212-859-0
• Product Categories: Pyridine;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Pyridine series;Organic acids;Pyridines;Analytical Chemistry;Mass Spectrometry;Matrix Materials (MALDI-TOF-MS);alcohol| carboxylic acid
• Mol File: 874-24-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 213-218 °C(lit.)
• Boiling Point: 255.04°C (rough estimate)
• Flash Point: 226.6 °C
• Appearance: White to almost white/Fine Powder
• Density: 1.4429 (rough estimate)
• Vapor Pressure: 6.34E-09mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), DMSO (Slightly)
• PKA: 1.14±0.50(Predicted)
• Water Solubility: Soluble in water (0.25g in 10ml).
• BRN: 118954
• CAS DataBase Reference: 3-Hydroxypicolinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxypicolinic acid(874-24-8)
• EPA Substance Registry System: 3-Hydroxypicolinic acid(874-24-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/22
• Safety Statements: 26-28-36/37/39-36
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 874-24-8(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Needles

Uses

3-Hydroxypicolinic acid (3-HPA) is a matrix material used in matrix-assisted laser desorption/ionization (MALDI) based mass spectroscopy (MS) for the analysis of large biomolecules and quantification of oligonucleotides.

Definition

ChEBI: A monohydroxypyridine that is picolinic acid in which the hydrogen at position 3 is replaced by a hydroxy group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of oligonucleotides.

InChI:InChI=1/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)/p-1

Upstream product

• 1849-55-4 2-Formyl-3-hydroxypyridin 
• 98-98-6 2-Picolinic acid 
• 98140-94-4 3-amino-2-picolinehydroxamic acid 
• 76045-30-2 (S)-4,5-dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid 
• 27507-15-9 ethyl 3-aminopyridine-2-carboxylate 
• 1462-86-8 3-amino-pyridine-2-carboxylic acid 
• 1121-25-1 2-methyl-3-pyridinol 
• 1121-60-4 pyridine-2-carbaldehyde 
• 56-87-1 L-lysine 
• 6602-28-4 3-hydroxypyridine N-oxide 
• 109-00-2 3-HYDROXYPYRIDINE 
• 932-35-4 3-hydroxypyridine-2-carbonitrile 

Downstream Products

• 109-00-2 3-HYDROXYPYRIDINE 
• 14764-90-0 2,6-diiodo-3-hydroxypyridine 
• 73406-50-5 ethyl 3-hydroxypyridine-2-carboxylate 
• 56879-47-1 3-hydroxypiperidine-2-carboxylic acid 
• 668-72-4 Virginiamycin S₁ 
• 208649-02-9 (+/-)-cis-3-hydroxypiperidine-2-carboxylic acid 
• 160938-52-3 N-(2,6-diisopropyl-phenyl)-3-hydroxy-picolinamide 
• 1082-59-3 3-hydroxy-pyridine-2-carboxylic acid anilide 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 85567-41-5 3-hydroxy-N-propylpyridine-2-carboxamide 
• 170689-52-8 3-benzyloxypyridine-2-carboxylic acid benzyl ester 
• 1032-85-5 3-hydroxy-N-(4-nitrobenzyl)picolinamide 
• 3373-02-2 3-Hydroxy-N-(m-nitrobenzyl)-picolinamid 
• 1084-61-3 3-Hydroxy-N-(p-tolyl)-picolinamid 

Relevant articles and documents

In vitro reconstitution of the biosynthetic pathway of 3-hydroxypicolinic acid

3-Hydroxypicolinic acid (3-HPA) is an important pyridine building block of bacterial secondary metabolites. Although the main biosynthetic pathways of these metabolites have been identified and well characterized, the enzymatic mechanism underlying the biosynthesis of 3-HPA has yet to be elucidated. In this work, we successfully reconstituted the complete biosynthetic pathway of 3-HPA in vitro. We showed that an l-lysine 2-aminotransferase, a two-component monooxygenase, and a FAD-dependent dehydrogenase are required to convert l-lysine to 3-HPA. We further demonstrated that 3-HPA does not derive from the direct hydroxylation of the picolinic acid at C-3, but from a successive process of C-3 hydroxylation of the piperideine-2-carboxylic acid and tautomerization of the produced 3-hydroxyl dihydropicolinic acid. Therefore, this study unveils the unusual assembly logic of 3-HPA and sheds light on the potential of engineering the 3-HPA pathway for generating novel pyridine-based building blocks.

Kinetics of oxidation of heterocyclic compounds by quinolinium dichromate

Quinolinium dichromate in sulfuric acid oxidized heterocyclic aldehydes (to the corresponding acids) and heterocyclic carboxylic acids (to the corresponding hydroxy-substituted acids) in acetic acidwater medium (vol. ratio, v(water)/v(acetic acid) = 50:50). The kinetic results supported a mechanistic pathway proceeding via a rate-determining decomposition of the chromate ester.

3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene

The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that the new systems were sometimes more and sometimes less effective than previously described systems in the case of stepwise and segment couplings. Applications to assembly of the model decapeptide ACP showed that HDATU was far more effective than HDTU and more effective than HATU under some conditions.