PTEROIC ACID

Base Information

• Chemical Name: PTEROIC ACID
• CAS No.: 119-24-4
• Molecular Formula: C14H12 N6 O3
• Molecular Weight: 312.288
• Hs Code.: 2933990090
• Mol file: 119-24-4.mol

Synonyms:Benzoicacid, 4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]- (9CI); Benzoicacid, p-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]- (6CI); Pteroicacid (7CI,8CI); NSC 14972; p-[(2-Amino-4-hydroxy-6-pteridylmethyl)amino]benzoicacid

Chemical Property of PTEROIC ACID

Chemical Property:

• Vapor Pressure: 2.61E-18mmHg at 25°C
• Melting Point: >400℃
• Boiling Point: 659.8°Cat760mmHg
• PKA: 4.65±0.10(Predicted)
• Flash Point: 352.9°C
• PSA: 147.14000
• Density: 1.69g/cm³
• LogP: 1.67210
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Pteroic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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. 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.

Technology Process of PTEROIC ACID

There total 32 articles about PTEROIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.7%

folate (65165-92-6) → pteroic acid (119-24-4)

Guidance literature:

With hydrogenchloride; carboxypeptidase G; Tris buffer; zinc(II) chloride; for 120h; Ambient temperature;

DOI:10.1021/jm00085a010

Reference yield: 68.0%

pyrofolic acid (223378-69-6) → folate (65165-92-6) + pteroic acid (119-24-4)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja971568j

Reference yield: 52.0%

N10-(trifluoroacetyl)pyrofolic acid (223378-68-5) → folate (65165-92-6) + pteroic acid (119-24-4)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja971568j

upstream raw materials:

2,5,6-triamino-3,4-dihydro-4-pyrimidinone

2,3-dibromopropanal

4-amino-benzoic acid

1,1,3-tribromoacetone

Downstream raw materials:

10-formyl-pteroic acid

5-formyl-5,6,7,8-tetrahydro-pteroic acid

10,N²-diacetyl-pteroic acid

5,6,7,8-tetrahydro-pteroic acid

Refernces

Chemical Conversion of Folic Acid to Pteroic Acid

10.1021/jo00331a016

The study presents a chemical method for converting folic acid to pteroic acid, a valuable intermediate for synthesizing folic acid analogues and derivatives. The process involves treating folic acid with acetic anhydride to form a mixture of acetylated azlactones, which are then cleaved with mild base to yield mainly acetylated pteroic acids. Further treatment with hot base removes the acetyl groups, resulting in pteroic acid with a yield of 55-60% contaminated with folic acid. The study also discusses various side reactions and byproducts, including the formation of a pyrazine derivative from the hydrolysis of the glutamic acid moiety and the opening of the pyrimidine ring. The authors detail the experimental procedures, including HPLC analysis, UV absorption spectra, mass spectrometry, and proton NMR spectra, and provide a method for separating folic and pteroic acids using column chromatography. The research was supported by a grant from the National Cancer Institute, National Institutes of Health.