PTEROIC ACID Chemical Properties

Melting point:

>400℃

Boiling point:

610.0±65.0 °C(Predicted)

Density 

1.69

storage temp. 

2-8°C

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

powder

pka

4.65±0.10(Predicted)

color 

Light Yellow to Brown

InChI

InChI=1S/C14H12N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,6,16H,5H2,(H,22,23)(H3,15,17,19,20,21)

InChIKey

JOAQINSXLLMRCV-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(NCC2=CN=C3C(=N2)C(=O)NC(N)=N3)C=C1

Safety Information

WGK Germany 

3

HS Code 

2933599590

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

PTEROIC ACID Usage And Synthesis

Uses

Pteroic Acid is a constituent as well as a degradation product of Folid Acid (F680300) formed via anzymatic hydrolysis. has been shown to activate the glutamylation of methotrexate by folylpolyglutama te synthetase.

Uses

Pteroic Acid (Methotrexate EP Impurity D N-Desmethyl Impurity) is a constituent as well as a degradation product of Folic Acid (F680300) formed via enzymatic hydrolysis. has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase.

Definition

ChEBI: 4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoic acid is a pteroic acid. It is functionally related to a 2-aminopteridin-4-ol. It is a conjugate base of a 2-amino-6-{[(4-carboxyphenyl)amino]methyl}-4-hydroxypteridin-1-ium. It is a conjugate acid of a 4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoate. It is a tautomer of a 4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoic acid and a 4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoic acid.

General Description

Folic Acid Impurity D is an impurity of the water-soluble B-vitamin, folic acid. Folic Acid is generally used in the treatment of certain types of anemia.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Synthesis

Pteroic acid can be prepared by a variety of conventional methods, said methods including synthesis, microbial degradation of folic acid, enzymatic degradation of folic acid, hydrolysis of folic acid and other conventional methods. Generally, pteroic acid prepared by these methods can often be contaminated with significant amounts of folic acid. For example, pterionic acid prepared by enzymatic degradation may contain 25% folic acid. Thus, effective methods are needed to remove folic acid contaminants as well as other impurities originating from the preparation of pteroic acid. Vitamin-drug concoctions, including concoctions of pteroic acid, may be prepared using synthetic methods. In some cases, those synthetic methods can also result in the formation of by-products, impurities, or other contaminants.

Enzyme inhibitor

This metabolite (FWfree-acid = 312.29 g/mol; CAS 119-24-4), also known as 4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoic acid, is a structural component of folates. Pteroic acid is a growth factor for a number of Enterococci. Pteroic acid is a yellow powder that is slightly soluble in aqueous NaOH. The lmax values in 0.1 M NaOH are 255, 275, and 365 nm (e = 26300, 23400, and 8900 M–1cm–1, respectively). Target(s): arylamine N-acetyltransferase; dihydrofolate reductase; dihydrofolate synthetase, weakly inhibited; dihydropteroate synthase; glutamate carboxypeptidase; and xanthine oxidase.

Purification Methods

Crystallise it from dilute HCl. Dry it in vacuo. Hygroscopic IRRITANT. [Nair et al. J Org Chem 46 3152 1981, Beilstein 26 III/IV 3942.]

PTEROIC ACID(119-24-4)Related Product Information

• (2S)-2-[[4-[Bis[(2-aMino-4-oxo-1,4-dihydropteridin-6-yl)Methyl]aMino]benzoyl]aMino]pentanedioic Acid
• 2-Amino-7-(chloromethyl)pteridin-4(1H)-one
• 2-Amino-4-hydroxy-1H-pteridine
• Erinacine A Erinacin A
• 5-formyl-5,6,7,8-tetrahydropteroic acid
• 2-Amino-6-(chloromethyl)-4(3H)-pteridinone
• Folitixorin (Mixture of DiastereoMers)
• N-(4-aminobenzoyl)- D-Glutamic acid
• Folic acid
• 5-Methyl Tetrahedropteroic Acid (Mixture of DiastereoMers)
• Folic Acid Impurity C
• N-(p-Aminobenzoyl)glutamic acid
• folic acid
• 5-Methyltetrahydrofolic acid
• 10-Formylfolic Acid
• Folinic acid
• 6-HYDROXY-2,4,5-TRIAMINOPYRIMIDINE
• L-Tetrahydrofolic Acid