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Pteroic acid

Pteroic acid structure

CAS No:
119-24-4
Formula:
C14H12N6O3
Chemical Name:
Pteroic acid
Synonyms:
Benzoic acid,4-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]-;Pteroic acid;Benzoic acid,4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]-;Benzoic acid,p-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]-;4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoic acid;p-[(2-Amino-4-hydroxy-6-pteridylmethyl)amino]benzoic acid;NSC 14972;Pyrofolic acid;33448-71-4;34794-86-0
Categories:
Analytical Chemistry > Standard

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Pteroic acid Basic Attributes

Molecular Weight：

312.28

Exact Mass：

312.28

HScode：

2933990090

Characteristics

PSA：

143

XLogP3：

-0.3

Density：

1.7±0.1 g/cm3

Melting Point：

>400 °C

Boiling Point：

659.8°C at 760 mmHg

Flash Point：

352.9ºC

Refractive Index：

1.803

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

Pteroic acid Use and Manufacturing

Methods of Manufacturing

royl azide was synthesized by methods described previously, 2 as summarized below. Folic acid (10 g, 20.9 mmol) was dissolved in THF (100 mL). The resulting solution was stirred for 10 min and then cooled to 0 C. Trifloroacetic anhydride (16 mL, 113 mmol) was added slowly and with stirring over 30 min. The reaction mixture was allowed to warm to 25 C and stirred overnight. The reaction mixture was then concentrated under reduced pressure to a thick dark viscous liquid that was dripped into benzene (150 mL). The precipitate was filtered, washed with ether, and dried under reduced pressure. THF (32 mL) was added to the solid along with ice (6.4 g), and this mixure was stirred for 4 h. The mixture was poured into ether, and the precipitate was collected by filtration, washed with ether, and dried under reduced pressure. The dried solid was then dissolved in DMSO (165 mL) and stirred at 25 C in a water bath. Hydrazine (4.9 mL, 156 mmol) was added slowly, and the reaction mixture was stirred for 8 h. MeOH (300 mL) was added to precipitate the hydrazide, which was collected by filtration and washed with MeOH (3 x 50 mL) and ether (3 x 50 mL), and dried under reduced pressure. The hydrazide was dissolved in TFA at -10 C containing KSCN (63 mg, 0.648 mmol). tBuONO (1.72 mL, 14.8 mmol) was added slowly, and the reaction mixture was stirred for 4 h at -10 C. The reaction mixture was allowed to warm to 25 C, NaN3 (432 mg, 6.6 mmol) was added, and the resulting solution was stirred for 10 min before isopropanol (150 mL) was added slowly to precipitate the pteroyl azide, which was collected by centrifugation and washed with water (3 x 50 mL), acetonitrile (50 mL), and ether (2 x 50 mL). The product was dried under high vacuum to give pteroyl azide (2.84 g, 8.4 mmol) in a yield of 40% from folic acid.

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 folylpolyglutamate synthetase.

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