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N-(4-Aminobenzoyl)-L-glutamic acid

N-(4-Aminobenzoyl)-L-glutamic acid structure

CAS No:
4271-30-1
Formula:
C12H14N2O5
Chemical Name:
N-(4-Aminobenzoyl)-L-glutamic acid
Synonyms:
L-Glutamic acid,N-(4-aminobenzoyl)-;Glutamic acid,N-(p-aminobenzoyl)-,L-;Glutamic acid,N-(p-aminobenzoyl)-;N-(4-Aminobenzoyl)-L-glutamic acid;N-(p-Aminobenzoyl)-L-glutamic acid;(p-Aminobenzoyl)glutamic acid;(p-Aminobenzoyl)-L-glutamic acid;N-(p-Aminobenzoyl)glutamic acid;N-(p-Aminobenzoyl)-L(+)-glutamic acid;(4-Aminobenzoyl)-L-glutamic acid;NSC 71042;(2S)-2-[(4-Aminobenzoyl)amino]pentanedioic acid;(S)-2-(4-Aminobenzamido)pentanedioicacid
Categories:
Biochemical Engineering > Amino Acids and Derivatives

Description

Light Tan Waxy Solid

N-(4-aminobenzoyl)-L-glutamic acid is a dipeptide resulting from the formal condensation of the carboxylic acid group of 4-aminobenzoic acid with the amino group of L-glutamic acid. It is a dicarboxylic acid, a dipeptide, a substituted aniline and a N-acyl-L-alpha-amino acid. It is a conjugate acid of a N-(4-aminobenzoyl)-L-glutamate.

N-(4-Aminobenzoyl)-L-glutamic acid Basic Attributes

Molecular Weight：

266.25

Exact Mass：

266.25

EC Number：

224-261-7

UNII：

9BKY99A8HJ

DSSTox ID：

DTXSID80227354

HScode：

2924299090

Characteristics

PSA：

130

XLogP3：

Appearance：

Beige crystalline powder

Density：

1.4±0.1 g/cm3

Melting Point：

173 °C

Boiling Point：

607.1°C at 760 mmHg

Flash Point：

321.0±31.5 °C

Refractive Index：

1.618

Storage Conditions：

−20°C

Specific rotation：

-15 º (c=2% in 0.1N HCl)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36/37/39

Precautionary statement(s)：

P261, P264, P270, P272, P280, P285, P301+P312, P302+P352, P304+P341, P321, P330, P333+P313, P342+P311, P363, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4-aminobenzoylglutamic acid

N-(4-Aminobenzoyl)-L-glutamic acid Use and Manufacturing

Methods of Manufacturing

P-nitrobenzoyl chloride is condensed with glutamic acid and then reduced with ammonium sulfide. The process is as follows: (1) Condensation Put water, magnesium oxide and glutamic acid into the reaction tank, adjust the pH to 8-9, stir to make All materials are dissolved. The temperature was lowered to 20°C, and the benzene solution of p-nitrobenzoyl chloride was slowly added dropwise, the temperature was controlled not to exceed 30°C, the pH was not lower than 7.5, and the reaction solution changed from white to purple to fading. After the addition, continue to stir for 1-2h. Stand still and layer, take the lower aqueous solution and filter. The upper benzene solution is washed with a small amount of water. The water wash and the filtrate are combined. Adjust the pH to 3-3.5 with hydrochloric acid. Set aside to precipitate p-nitrobenzoic acid and filter. pH=1, stirring vigorously, and then standing for 24h to precipitate crystals. Filter to obtain N-p-nitrobenzoylglutamic acid, melting point 110-112℃. The yield was 73%. (2) After reduction, mix water and N-p-nitrobenzoylglutamic acid, add ammonium sulfide, stir to dissolve, slowly heat and boil to evaporate to 1/3 of the volume of solution pH 6-7, stop heating, Add activated carbon to decolorize and filter. The filtrate was naturally cooled to room temperature, adjusted to pH3-3.5 with hydrochloric acid, and allowed to stand for 24h. Crystals were precipitated, filtered, and the filter cake was washed with water and dried to obtain N-p-aminobenzoyl-L-glutamic acid, melting point 170-172°C , Yield 58%.

Uses

Marker in folate metabolism studies.

Computed Properties

Molecular Weight:266.25
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:266.09027155
Monoisotopic Mass:266.09027155
Topological Polar Surface Area:130
Heavy Atom Count:19
Complexity:350
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ammonium sulfide

Ammonium sulfide ((NH4)2(S5))

Folic acid

4-Nitrobenzoic acid

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Guide of N-(4-Aminobenzoyl)-L-glutamic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
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N-(4-Aminobenzoyl)-L-glutamic acid

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