N-(p-Aminobenzoyl)glutamic acid

Product Name: N-(p-Aminobenzoyl)glutamic acid
CAS No.: 4271-30-1
Chemical Name: N-(p-Aminobenzoyl)glutamic acid
Synonyms: N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID;Methotrexate EP Impurity K;(2S)-2-(4-Aminobenzamido)pentanedioic Acid;(2S)-2-[(4-Aminobenzoyl)amino]pentanedioic Acid;NSC 71042;H-4-ABZ-GLU-OH;Folic acid iMpurity A;Methotrexate Impurity K;Folic Acid EP Impurity A;P-aminobenzoyl glutamate
CBNumber: CB2193546
Molecular Formula: C12H14N2O5
Formula Weight: 266.25
MOL File: 4271-30-1.mol

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N-(p-Aminobenzoyl)glutamic acid Property

Melting point:: ~175 °C (dec.)
alpha: -15 º (c=2% in 0.1N HCl)
Boiling point:: 409.45°C (rough estimate)
Density: 1.2846 (rough estimate)
refractive index: 1.6660 (estimate)
storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility: Aqueous Base (Sparingly), Aqueous Acid (Sparingly), DMSO (Sparingly)
form: Solid
pka: 3.50±0.10(Predicted)
color: White to Light
Merck: 14,426
BRN: 2816320
Stability:: Hygroscopic
InChIKey: GADGMZDHLQLZRI-VIFPVBQESA-N
CAS DataBase Reference: 4271-30-1(CAS DataBase Reference)

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Safety

Risk Statements: 36/37/38
Safety Statements: 26-36/37/39
WGK Germany: 3
HS Code: 2924296000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: Y0001242
Product name: Folic acid impurity A
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 25 mg
Price: $225
Updated: 2025/07/31

Sigma-Aldrich

Product number: A0879
Product name: N-(4-Aminobenzoyl)-L-glutamic acid
Purity: ≥98% (TLC)
Packaging: 5g
Price: $502
Updated: 2025/07/31

Sigma-Aldrich

Product number: 1019870
Product name: N-(4-Aminobenzoyl)-L-glutamic acid
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 50mg
Price: $392
Updated: 2025/07/31

TCI Chemical

Product number: A0442
Product name: N-(4-Aminobenzoyl)-L-glutamic Acid
Purity: >97.0%(T)
Packaging: 1g
Price: $97
Updated: 2025/07/31

TCI Chemical

Product number: A0442
Product name: N-(4-Aminobenzoyl)-L-glutamic Acid
Purity: >97.0%(T)
Packaging: 5g
Price: $315
Updated: 2025/07/31

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N-(p-Aminobenzoyl)glutamic acid Chemical Properties,Usage,Production

Chemical Properties

Light Tan Waxy Solid

Uses

Marker in folate metabolism studies.

Uses

Major metabolite of 5-Methyltetrahydrofolic Acid

Definition

ChEBI: A dipeptide resulting from the formal condensation of the carboxylic acid group of 4-aminobenzoic acid with the amino group of L-glutamic acid.

Biological Activity

N-p-Aminobenzoyl)-L-glutamic acid is a folate catabolite th at can be metabolized by bacterial p-aminobenzoate auxotrophs possessing the enzyme p-aminobenzoyl-glutamate hydrolase.

Synthesis

6758-40-3

4271-30-1

General procedure for the synthesis of N-(4-aminobenzoyl)-L-glutamic acid from N-p-nitrobenzoylglutamic acid: 27.23 g (0.1 mol) of N-nitrobenzoyl-L-glutamic acid and 118 g of methanol were added to a reaction vessel, and stirred until complete dissolution. Subsequently, 0.59 g of 10% Pd/C catalyst was added and 18.92 g (0.3 mol) of ammonium formate was added slowly. The reaction mixture was stirred at room temperature and kept for 30 minutes. After completion of the reaction, the Pd/C catalyst was recovered by filtration. The filtrate was adjusted to pH=3 with hydrochloric acid in methanol and left to stand for 30 min before filtering the precipitated crystals. The crystals were washed with a small amount of methanol and dried to give 25.75 g of N-(4-aminobenzoyl)-L-glutamic acid, with 99.88% purity by HPLC, 96.58% yield, and 95.64% total yield as nitrobenzoic acid.

Purification Methods

Crystallise the acid from H2O. Also purify it by dissolving 2.7g in H2O (130mL), adding aqueous NaOH to pH 5.5 and adding portionwise a solution of 0.5M CuSO4 to complete precipitation of the Cu salt. This salt is filtered off, suspended in H2O and H2S is bubbled through to precipitate CuS, filter, evaporate and recrystallise the residue from H2O. It has max (H2O) at 273nm. [Backer & Houtman Recl Trav Chim Pays-Bas 70 738, 743 1951, Beilstein 14 IV 1153.]

References

[1] Patent: CN105439895, 2016, A. Location in patent: Paragraph 0029; 0030
[2] Chirality, 2010, vol. 22, # 2, p. 252 - 257
[3] Journal of the Chemical Society, 1949, p. 1401,1404
[4] Yakugaku Zasshi, 1949, vol. 69, p. 457
[5] Chem.Abstr., 1950, p. 3442

N-(p-Aminobenzoyl)glutamic acid Preparation Products And Raw materials

Raw materials

4-Nitrobenzoyl chloride P-NITROBENZOYL-L-GLUTAMIC ACID Purple 4-Nitrobenzoic acid Ammonium sulfide

Preparation Products

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Shaanxi Dideu New Materials Co. Ltd

Product: N-(p-Aminobenzoyl)glutamic acid 4271-30-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-04-24

WUHAN FORTUNA CHEMICAL CO., LTD

Product: N-(p-Aminobenzoyl)glutamic acid 4271-30-1
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 1000KGS
Release date: 2021-11-08

Hebei Chuanghai Biotechnology Co., Ltd

Product: N-(p-Aminobenzoyl)glutamic acid 4271-30-1
Price: US $30.00-10.00/KG
Min. Order: 50KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-24

4271-30-1, N-(p-Aminobenzoyl)glutamic acidRelated Search:

Benzoyl peroxide TEA-LAUROYL GLUTAMATE N-Formylmorpholine P-AMINOBENZAMIDE GLUTAMIC ACID L-Glutamic acid L-Tetrahydrofolic Acid FOLIC ACID IMP. A (EP): N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID MM(CRM STANDARD),FOLIC ACID IMP. A (EP): N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID MM(CRM STANDARD) 4-Aminobenzoic acid p-Aminobenzamide Glutamic acid 2-Amino-7-(chloromethyl)pteridin-4(1H)-one Levomefolate calcium 6-hydroxymethylpterin Folic Acid Impurity C (2S)-2-[[4-[Bis[(2-aMino-4-oxo-1,4-dihydropteridin-6-yl)Methyl]aMino]benzoyl]aMino]pentanedioic Acid Folitixorin (Mixture of DiastereoMers) 2-Amino-4-hydroxy-1H-pteridine N-(4-aminobenzoyl)- D-Glutamic acid

H-4-ABZ-GLU-OH

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P-AMINOBENZOYL-L-GLUTAMIC ACID

P-AMINO BENZAMIDE GLUTAMIC ACID

N-(4-AMINOBENZOYL)-L-GLUTAMIC ACID

N-(4-Aminobenzoyl)-L-Glutaminic Acid

L-Glutamic acid, N-(4-aminobenzoyl)-

N-(p-Aminobenzoyl)glutamic acid

2-[(4-aminobenzoyl)amino]glutaric acid

2-[(4-azanylphenyl)carbonylamino]pentanedioic acid

4-AMINOBENZOYLGLUTAMIC ACID

4-AMINOBENZOIC GLUTAMIC ACID

4-aminobenzoyl－L-glutamic acid

NSC 71042

(S)-2-(4-AMinobenzaMido)pentanedioic acid

Folic acid iMpurity A

Folic acid iMpurity A N-(4-AMinobenzoyl)-L-glutaMic acid

N-(P-Aminobenzoyl)-L-glutamic acidN-(P-Aminobenzoyl)-L-(+)glutamicacid EuE

N-(4-aminobenzoyl)-L-Glutamic acid (Folic Acid Imp A)

4-Aminobenzoylglutamic Acid (50 mg)

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Calcium Levofolinate Impurity 1(Calcium Levofolinate EP Impurity A)

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Folinic Acid Impurity A (Methotrexate Impurity K)

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N-4-Aminobenzoyl-L-glutaminsure

Folinic Acid Impurity A (4-Aminobenzoyl Glutamic Acid)

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Folic Acid EP Impurity A

Folic Acid Impurity 1（Folic Acid EP Impurity A）

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N-(p-Aminobenzoyl)glutamic acid USP/EP/BP

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Para amino-benzoyl glutamate

Folic Acid EP Impurity A (Methotrexate EP Impurity K)

Methotrexate EP Impurity K (Folic Acid EP Impurity A)

N-(4-Aminobenzoyl)-L-glutamic acid, ≥98% (TLC)

Folic acid Impurity AQ: What is Folic acid Impurity A Q: What is the CAS Number of Folic acid Impurity A Q: What is the storage condition of Folic acid Impurity A

4-Aminobenzoylglutamic Acid (F0M031)

(2S)-2-(4-Aminobenzamido)pentanedioic Acid

(2S)-2-[(4-Aminobenzoyl)amino]pentanedioic Acid

4-Aminobenzoylglutamic Acid (1019870)

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N-(p-Aminobenzoyl)glutamicaci

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