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495-69-2 Usage

Physical and Chemical Properties

Hippuric acid is also known as "Benzoylaminoethanoic acid",its molecular formula is C9H9NO3. The molecular weight is 179.18. As colorless crystals. Melting point 187~188 ℃. It's soluble in cold water, chloroform, ether, cold ethanol, slightly soluble in amyl alcohol, soluble in hot water, hot ethanol, sodium phosphate solution, almost insoluble in benzene, carbon disulfide, petroleum ether. Naturally it occurs in herbivores (such as horses) of urine, it is also present in small amounts in human urine,it is easily hydrolyzed to benzoic acid and glycine. Hippuric acid can reduce urine pH within a certain range,which makes the bacteria living environment change, and then plays a synergistic bactericidal effect. Urinary hippuric acid is measured using pyridine-benzene chloride colorimetry. The principle is that hippuric acid reacts with benzene sulfonyl chloride in pyridine solution, and the product in ethanol solution is yellow compound, according to the color depth, quantitative analysis is processed by colorimetry. Normal urine hippuric acid content varies widely because of different varieties of diet and intake (from 0.3 to 2.5 grams per day), and there are individual differences. After Toluene goes into the body, through metabolic transformation, most of it becomes to hippuric acid and is excreted through urine. Determination of horse urine? hippuric acid content can be used as? exposure indicators to reflect the body's absorption of toluene, but it can not serve as indicators of the diagnosis. Hippuric acid can be made by reaction of benzoyl chloride with glycine in sodium hydroxide solution . It can be used for biochemical reagents and organic synthesis. Hippuric acid ammonium salt is crystal, soluble in water, soluble in ethanol; potassium salt is crystal, containing single molecule of crystal water, soluble in water, soluble in ethanol. Properties, uses, methods of synthesis of hippuric acid Information compiled by Andy of lookchem (2016-11-19).

Hippuric acid excretion test

The use of the principles of sodium benzoate going into the human body and? binding? glycine? in the liver to be non-toxic hippuric acid and being excreted with the urine,can be used to exam? liver detoxification function, which is called hippuric acid excretion test. The kidneys can not only excrete hippuric acid, it can also synthesize a small amount of? hippuric acid .It is only in normal renal function that hippuric acid test can truly reflect the liver's detoxification function using hippuric acid excretion test . A little after the subjects take breakfast, oral 6g sodium benzoate is taken. 4h after taking the drug, collect the urine, measure the urine excretion, the normal amount ofhippuric acid after 4h discharge should be> 3.0g. To avoid nausea and vomiting induced often by oral sodium benzoate? , intravenous injection 1.77g sodium benzoate can be slowly done? ,urine is collected 1h after injection, discharge amount is measured? , the? normal discharge amount should be 1h> 0.7g. When there is liver parenchymal disease, such as hepatitis, cirrhosis and liver necrosis, the liver synthesis of hippuric acid dysfunctions, which decreases production of hippuric acid? . Obstructive jaundice causes small changes. Reduced renal blood flow and renal excretion dysfunction also lead to the reducing of the amount of hippuric acid discharge . Some fruits contain benzoic acid? such as apples, bananas, etc., they should be banned when testing. Hippuric acid test has many factors and sodium benzoate can cause adverse reactions in patients, and the valuation of liver detoxification function is less precise, it has been less clinical. Reference: China Medical Encyclopedia twenty-seven DIAGNOSIS? [author:Sun Rongwu]

Uses

Different sources of media describe the Uses of 495-69-2 differently. You can refer to the following data:
1. The product is used for medicine, dyes intermediates and it is used for the production of fluorescent yellow H8GL, disperse fluorescent FFL and so on.
2. N-Benzoylglycine also known as Hippuric Acid is the glycine conjugate of benzoic acid commonly found in ruminant urine. It is synthesized in the liver and its production is greatly increased following consuption of benzoic acid. In itself it does not have a direct biological function, however p-hydroxy-hippurica acid can be used as an inhibitor of Ca2+ ATPase.
3. Hippuric acid is used as a intermediate for the manufacturing medicine and other organic compounds. Hippuric acid can be used to study cell biology, chemical biology, bioactive small molecules, amino acid derivatives, peptide synthesis, chemical synthesis and nutrition. Hippuric acid has been used to inform the metabolism and urinary excretion of procyanidins.
4. Hippuric acid can be used to study cell biology, chemical biology, bioactive small molecules, amino acid derivatives, peptide synthesis, chemical synthesis and nutrition. Hippuric acid has been used to inform the metabolism and urinary excretion of procyanidins.

production method

Benzoyl chloride reacts with the amino acid in sodium hydroxide solution, amido sodium benzene is obtained, then it is acidized with hydrochloric acid. The amino acid is dissolved in sodium hydroxide solution, at the same time drop? benzoyl chloride and sodium hydroxide solution? below 30 ℃? , the reaction solution is always alkaline. After finishing adding, stir for 30min. Then add? hydrochloric acid to pH 2, filter? crude, use water to recrystallize , hippuric acid is obtained. Consumption of raw materials fixed: amino acid (90%) 610kg/t, benzoyl chloride (60%) 1520kg/t, caustic soda (30%) 1960kg/t, hydrochloric acid (30%) 900kg/t.

Chemical Properties

White crystalline powder

Preparation

Preparation of Hippuric acid from Glycine. Principle: The hydroxy and amino functions can be easily benzoylated using Benzoyl chloride in aqueous alkaline conditions. This reaction is known as Schotten-Baumann reaction. Reaction: Procedure: Dissolve 0.5 g of glycine in 5 ml of 10% NaOH solution in a 25 ml conical flask. Add 0.9 ml of benzoyl chloride in five portions to the solution. Stopper the flask and shake vigorously after each addition until all the benzoyl chloride is reacted. Transfer the solution to a beaker and add few grams of ice and add conc. HCl slowly with stirring until the solution is acidic to litmus paper. Filter the crystalline precipitate of the product on a Buchner funnel, wash with cold water and drain well. Place the solid in a conical flask with 10 ml CCl4 and boil gently for 10 min. Allow the mixture to cool slightly, filter under gentle suction and wash with 10-20 ml CCl4. Record the practical yield and re-crystallize it. Re-crystallization: Dissolve the crude product from boiling water (5 ml), with addition of decolorizing charcoal if necessary, filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC [using Butanal : acetic acid: water (4 : 1 : 1) as solvent or CHCl3:methanol (9 : 1) or toluene].

Definition

ChEBI: An N-acylglycine in which the acyl group is specified as benzoyl.

Purification Methods

Crystallise the acid from boiling H2O. Dry it over P2O5. Also purify it by dissolving 135-140g in 2L of boiling H2O, filtering through a steam-heated funnel and allowing to crystallise at ~20o (yield 115-122g first crop, m 186-187o). [Ingersoll & Babcock Org Synth Coll Vol II 328 1943, Beilstein 9 225, I 100.]

Check Digit Verification of cas no

The CAS Registry Mumber 495-69-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 5 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 495-69:
(5*4)+(4*9)+(3*5)+(2*6)+(1*9)=92
92 % 10 = 2
So 495-69-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)/p-1

495-69-2 Well-known Company Product Price

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  • TCI America

  • (H0143)  Hippuric Acid  >98.0%(T)

  • 495-69-2

  • 25g

  • 115.00CNY

  • Detail
  • TCI America

  • (H0143)  Hippuric Acid  >98.0%(T)

  • 495-69-2

  • 100g

  • 275.00CNY

  • Detail
  • TCI America

  • (H0143)  Hippuric Acid  >98.0%(T)

  • 495-69-2

  • 500g

  • 690.00CNY

  • Detail
  • Alfa Aesar

  • (A12690)  Hippuric acid, 98%   

  • 495-69-2

  • 100g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (A12690)  Hippuric acid, 98%   

  • 495-69-2

  • 500g

  • 722.0CNY

  • Detail
  • Alfa Aesar

  • (A12690)  Hippuric acid, 98%   

  • 495-69-2

  • 1000g

  • 1363.0CNY

  • Detail
  • Sigma

  • (112003)  Hippuricacid  98%

  • 495-69-2

  • 112003-5G

  • 352.17CNY

  • Detail
  • Sigma

  • (112003)  Hippuricacid  98%

  • 495-69-2

  • 112003-100G

  • 422.37CNY

  • Detail
  • Sigma

  • (112003)  Hippuricacid  98%

  • 495-69-2

  • 112003-500G

  • 1,082.25CNY

  • Detail

495-69-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name N-benzoylglycine

1.2 Other means of identification

Product number -
Other names BZ-GLY-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:495-69-2 SDS

495-69-2Synthetic route

glycine
56-40-6

glycine

2-benzoyl-4,5-dichloropyridazin-3(2H)-one
155164-66-2

2-benzoyl-4,5-dichloropyridazin-3(2H)-one

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Heating;98%
benzoyl chloride
98-88-4

benzoyl chloride

glycine
56-40-6

glycine

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sodium hydroxide In water96%
With sodium hydroxide at 15 - 20℃; for 0.5h;96%
With hydrogenchloride; sodium hydroxide95%
benzoyl chloride
98-88-4

benzoyl chloride

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With hydrogenchloride In sodium hydroxide96%
1,3-Diphenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one
82059-55-0

1,3-Diphenyl-2,5-dihydro-1H-[1,2,4]triazin-6-one

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With 2,4,6-tri-tert-butyl phenoxyl radical In water; chlorobenzene for 18h; Ambient temperature;95%
4-methoxybenzyl 2-benzamidoacetate

4-methoxybenzyl 2-benzamidoacetate

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.25h;94%
(2-hydrazinyl-2-oxoethyl)benzamide
2443-68-7

(2-hydrazinyl-2-oxoethyl)benzamide

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sodium bromate; thallium(III) nitrate trihydrate for 2.5h; Heating;92%
1-benzoyldeoxyvasicinone chloride

1-benzoyldeoxyvasicinone chloride

glycine
56-40-6

glycine

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
In benzene88.5%
(Z)-4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one
182930-16-1

(Z)-4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 0.25h; Heating;88%
glycine
56-40-6

glycine

benzyl alcohol
100-51-6

benzyl alcohol

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With oxygen; sodium hydroxide In tetrahydrofuran; water at 25℃; for 12h;87%
With oxygen; sodium hydroxide In tetrahydrofuran; water at 20℃; for 12h; Green chemistry;87%
With oxygen; sodium hydroxide In tetrahydrofuran; water at 25℃; under 760.051 Torr; for 12h;87%
N-allylbenzamide
10283-95-1

N-allylbenzamide

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
Stage #1: N-allylbenzamide With ozone In water; acetonitrile at 0℃; Inert atmosphere;
Stage #2: With sodium chlorite In water; acetonitrile at 15 - 20℃; under 760.051 Torr; Inert atmosphere;
Stage #3: With sodium hydrogen sulfate In water; acetonitrile at 35℃; for 0.166667h; Inert atmosphere;
87%
glycine
56-40-6

glycine

polymer-bound mixed benzoic dithiocarbamic anhydride

polymer-bound mixed benzoic dithiocarbamic anhydride

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
In chloroform for 1h;80%
N-(2-hydroxyethyl)-benzamide
18838-10-3

N-(2-hydroxyethyl)-benzamide

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With styrene oxide; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 90℃; for 12h; Inert atmosphere;80%
With styrene oxide In toluene at 100℃; for 4h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube;77%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); 1,1'-sulfinylbisbenzene In tetrahydrofuran at 70℃; for 2.5h; Inert atmosphere; Sealed tube; Green chemistry;88 %Chromat.
1-benzoyl-1H-benzotriazole
4231-62-3

1-benzoyl-1H-benzotriazole

glycine
56-40-6

glycine

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 25℃; for 2h;77%
methyl hippurate
1205-08-9

methyl hippurate

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); bis(tri-n-butyltin)oxide In diethyl ether at 25℃; for 8h;76%
phenyl(2-thioxothiazolidin-3-yl)methanone
70326-37-3

phenyl(2-thioxothiazolidin-3-yl)methanone

glycine
56-40-6

glycine

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
Ambient temperature;67%
N-(α-methoxybenzyliden)glycinmethylester

N-(α-methoxybenzyliden)glycinmethylester

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 4h;66%
4-guanidinophenyl N-benzoylglycinate
288608-40-2

4-guanidinophenyl N-benzoylglycinate

H-Ala-Ala-Lys-Ala-Gly-OH

H-Ala-Ala-Lys-Ala-Gly-OH

A

Hippuric Acid
495-69-2

Hippuric Acid

B

Bz-Gly-Ala-Ala-Lys-Ala-Gly-OH

Bz-Gly-Ala-Ala-Lys-Ala-Gly-OH

C

Bz-Gly-Ala-Ala-Lys-OH

Bz-Gly-Ala-Ala-Lys-OH

Conditions
ConditionsYield
With sodium chloride; calcium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; mutant trypsin D189E In methanol; water at 25℃; for 0.5h; pH=8.0; Product distribution; Further Variations:; Reaction partners; Catalysts; reaction time;A n/a
B 65%
C n/a
With HEPES buffer; sodium chloride; calcium chloride; K60E,D189S,D194N mutant trypsin In water; N,N-dimethyl-formamide pH=8.0; Kinetics; Further Variations:; Catalysts; Reaction partners; Enzymatic reaction;
With HEPES buffer; sodium chloride; calcium chloride; K60E,D189S,D194N mutant trypsin In water; N,N-dimethyl-formamide at 25℃; pH=8.0; Kinetics; Further Variations:; Catalysts; Reaction partners; Enzymatic reaction;
methanol
67-56-1

methanol

(3-Oxo-1,5-diphenyl-2,6,7-trioxa-4-aza-bicyclo[3.2.0]hept-4-yl)-acetic acid

(3-Oxo-1,5-diphenyl-2,6,7-trioxa-4-aza-bicyclo[3.2.0]hept-4-yl)-acetic acid

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
Heating;A n/a
B 60%
formaldehyd
50-00-0

formaldehyd

carbon monoxide
201230-82-2

carbon monoxide

benzamide
55-21-0

benzamide

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide In various solvent(s) at 120℃; under 45003.6 Torr; for 12h;60%
With sulfuric acid; palladium; lithium bromide In 1-methyl-pyrrolidin-2-one at 120℃; under 45004.5 Torr; for 16h; Inert atmosphere; Autoclave;30%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

sodium glycinate
856946-93-5

sodium glycinate

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
In ethylene glycol at 114 - 127℃; for 5h; Conversion of starting material;58%
iodobenzene
591-50-4

iodobenzene

glycine
56-40-6

glycine

Mo(CO)6

Mo(CO)6

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate In tetrahydrofuran at 100℃; for 0.25h; mocrowaver irradiation;50%
<<(Hydroxyimino)phenylmethyl>amino>essigsaeure
5319-69-7

<<(Hydroxyimino)phenylmethyl>amino>essigsaeure

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In 1,4-dioxane at 0℃; for 1h;45%
3-Phenyl-4H-1,2,4-oxadiazin-6(5H)-on
93769-18-7

3-Phenyl-4H-1,2,4-oxadiazin-6(5H)-on

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In 1,4-dioxane at 0℃; for 1h;40%
N-(3,3-diphenylpropyl)benzamide
100938-80-5

N-(3,3-diphenylpropyl)benzamide

A

Hippuric Acid
495-69-2

Hippuric Acid

B

benzophenone
119-61-9

benzophenone

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 60℃; for 6h; Sealed tube;A 31%
B 38%
iodobenzene
591-50-4

iodobenzene

glycine
56-40-6

glycine

CO

CO

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With triethylamine; palladium diacetate In N,N-dimethyl-formamide at 60℃; under 760 Torr; for 30h;25%
dibenzyl disulphide
150-60-7

dibenzyl disulphide

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
Ausscheidung im Rattenharn nach Verfuetterung;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

N-(thiobenzoyl)glycine
2584-64-7

N-(thiobenzoyl)glycine

A

Hippuric Acid
495-69-2

Hippuric Acid

B

thiobenzoic acid
98-91-9

thiobenzoic acid

α-hydroxyhippuric acid
19791-95-8, 19791-97-0, 16555-77-4

α-hydroxyhippuric acid

A

Hippuric Acid
495-69-2

Hippuric Acid

B

bis-benzoylamino-acetic acid
72761-72-9

bis-benzoylamino-acetic acid

C

benzamide
55-21-0

benzamide

Conditions
ConditionsYield
at 150 - 160℃;
ethyl hippurate
1499-53-2

ethyl hippurate

Hippuric Acid
495-69-2

Hippuric Acid

Conditions
ConditionsYield
With sodium hydroxide
With lithium hydroxide In ethanol
Hippuric Acid
495-69-2

Hippuric Acid

salicylaldehyde
90-02-8

salicylaldehyde

3-benzamidocoumarin
2549-08-8

3-benzamidocoumarin

Conditions
ConditionsYield
With PPA at 90 - 100℃; for 1.66667h;100%
With zinc(II) chloride for 0.75h; Heating;82%
With sodium acetate; acetic anhydride Heating;60%
Hippuric Acid
495-69-2

Hippuric Acid

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

4-[(E)-(3,4-dimethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one
25349-38-6

4-[(E)-(3,4-dimethoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one

Conditions
ConditionsYield
With sodium acetate for 0.0833333h; microwave irradiation;100%
Stage #1: Hippuric Acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran at 75℃; for 0.233333h;
90%
clinoptilolite for 0.2h; Product distribution; Further Variations:; Catalysts; Temperatures; reaction times, with or without microwave irradiation; microwave irradiation;81%
Hippuric Acid
495-69-2

Hippuric Acid

3-benzyloxy-4-methoxybenzaldehyde
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

4-(3-benzyloxy-4-methoxybenzylidene)-2-phenyl-5-oxazolone

4-(3-benzyloxy-4-methoxybenzylidene)-2-phenyl-5-oxazolone

Conditions
ConditionsYield
With sodium acetate for 0.0833333h; microwave irradiation;100%
With sodium acetate; acetic anhydride for 2.5h;
Hippuric Acid
495-69-2

Hippuric Acid

3-azido-4-methoxybenzaldehyde

3-azido-4-methoxybenzaldehyde

4-[1-(3-Azido-4-methoxy-phenyl)-meth-(E)-ylidene]-2-phenyl-4H-oxazol-5-one

4-[1-(3-Azido-4-methoxy-phenyl)-meth-(E)-ylidene]-2-phenyl-4H-oxazol-5-one

Conditions
ConditionsYield
With sodium acetate for 0.0833333h; microwave irradiation;100%
Hippuric Acid
495-69-2

Hippuric Acid

4-methoxy-3-nitrobenzaldehyde
31680-08-7

4-methoxy-3-nitrobenzaldehyde

2-Phenyl-4-(3-nitro-4-methoxy-benzyliden)-4H-(1,3)-oxazol-5-on
904-42-7

2-Phenyl-4-(3-nitro-4-methoxy-benzyliden)-4H-(1,3)-oxazol-5-on

Conditions
ConditionsYield
With sodium acetate for 0.0833333h; microwave irradiation;100%
Hippuric Acid
495-69-2

Hippuric Acid

(R)-6-methylamino-2-methylheptene
1620401-56-0

(R)-6-methylamino-2-methylheptene

(R)-isometheptene hippurate

(R)-isometheptene hippurate

Conditions
ConditionsYield
In acetone at -20℃; Solvent; Temperature;100%
Hippuric Acid
495-69-2

Hippuric Acid

isonipecotic acid methyl ester
2971-79-1

isonipecotic acid methyl ester

methyl 1-(2-benzamidoacetyl)piperidine-4-carboxylate

methyl 1-(2-benzamidoacetyl)piperidine-4-carboxylate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; Reagent/catalyst;100%
Hippuric Acid
495-69-2

Hippuric Acid

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

2-phenyl-4,5-oxazoledione

2-phenyl-4,5-oxazoledione

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water99.7%
Hippuric Acid
495-69-2

Hippuric Acid

methanol
67-56-1

methanol

methyl hippurate
1205-08-9

methyl hippurate

Conditions
ConditionsYield
With tetrachloromethane at 20℃; for 2.5h; UV-irradiation;99%
With ammonium cerium(IV) nitrate at 20℃; for 36h;97%
With tert.-butylnitrite at 40℃; for 48h;95%
Hippuric Acid
495-69-2

Hippuric Acid

benzaldehyde
100-52-7

benzaldehyde

(4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one
17606-70-1

(4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one

Conditions
ConditionsYield
With potassium acetate In acetic anhydride Heating;99%
With acetic anhydride; palladium diacetate for 0.0666667h; microwave irradiation;98%
With copper diacetate; acetic anhydride at 48 - 50℃; for 0.0833333h; Product distribution; Further Variations:; Reagents; Temperatures; microwave irradiation;97%
Hippuric Acid
495-69-2

Hippuric Acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(4Z)-4-(4-methoxybenzylidene)-2-phenyl-oxazolin-5-one
57427-78-8

(4Z)-4-(4-methoxybenzylidene)-2-phenyl-oxazolin-5-one

Conditions
ConditionsYield
With calcium acetate; acetic anhydride at 74 - 76℃; for 0.05h; microwave irradiation;99%
With 1-butyl-3-methylimidazolium phosphotungstate; acetic anhydride at 80℃; for 0.25h; Erlenmeyer azlactone synthesis;93%
Stage #1: Hippuric Acid With 1,3,5-trichloro-2,4,6-triazine; sodium carbonate; triphenylphosphine In tetrahydrofuran for 0.0166667h;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran
92%
Hippuric Acid
495-69-2

Hippuric Acid

N-methylbenzamide
88070-48-8

N-methylbenzamide

Conditions
ConditionsYield
In acetone for 3h; Ambient temperature; Irradiation;99%
In acetone for 1h; Irradiation;97%
Hippuric Acid
495-69-2

Hippuric Acid

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

(4Z)-4-(3-nitrobenzylidene)-2-phenyloxazol-5(4H)-one
15601-45-3, 66949-11-9, 123990-32-9

(4Z)-4-(3-nitrobenzylidene)-2-phenyloxazol-5(4H)-one

Conditions
ConditionsYield
With calcium acetate; acetic anhydride at 45 - 47℃; for 0.0666667h; microwave irradiation;99%
With acetic anhydride; palladium diacetate for 0.1h; microwave irradiation;96%
Stage #1: Hippuric Acid With triethylamine sulfate at 80℃; for 0.0833333h; Green chemistry;
Stage #2: 3-nitro-benzaldehyde at 100℃; for 0.383333h; Reagent/catalyst; Green chemistry; stereoselective reaction;
95%
Hippuric Acid
495-69-2

Hippuric Acid

2-(4-methoxyphenylmethylene)malononitrile
2826-26-8

2-(4-methoxyphenylmethylene)malononitrile

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
5429-22-1

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

Conditions
ConditionsYield
With sodium acetate; acetic anhydride for 0.05h; Heating;99%
Hippuric Acid
495-69-2

Hippuric Acid

2-(4-methylbenzylidene)malononitrile
2826-25-7

2-(4-methylbenzylidene)malononitrile

4-(4-methylbenzylidene)-2-phenyloxazol-5-one
82309-33-9

4-(4-methylbenzylidene)-2-phenyloxazol-5-one

Conditions
ConditionsYield
With sodium acetate; acetic anhydride for 0.05h; Heating;99%
Hippuric Acid
495-69-2

Hippuric Acid

4-phenylhydrazono-2-phenyl-4H-oxazol-5-one
54506-04-6

4-phenylhydrazono-2-phenyl-4H-oxazol-5-one

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; aniline; sodium nitrite In water98.8%
Multi-step reaction with 2 steps
1.1: 0.5 h / 60 °C
2.1: hydrogenchloride; sodium nitrite / water / 0.17 h / 0 - 5 °C
2.2: 2 h / 0 - 10 °C
View Scheme
Hippuric Acid
495-69-2

Hippuric Acid

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline
143230-70-0

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenylhydrazone]

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenylhydrazone]

Conditions
ConditionsYield
With hydrogenchloride; acetic anhydride; acetic acid; sodium nitrite In water98.5%
Hippuric Acid
495-69-2

Hippuric Acid

aminosulfonic acid
5329-14-6

aminosulfonic acid

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline
143230-70-0

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3,-pentafluoropropoxymethyl)-phenylhydrazone]
143230-69-7

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3,-pentafluoropropoxymethyl)-phenylhydrazone]

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water98.1%
Hippuric Acid
495-69-2

Hippuric Acid

2-phenylazlactone
1199-01-5

2-phenylazlactone

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.75h; Inert atmosphere;98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.75h; Inert atmosphere;98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.75h; Inert atmosphere;91%
Hippuric Acid
495-69-2

Hippuric Acid

2-(Trimethylsilyl)ethanol
2916-68-9

2-(Trimethylsilyl)ethanol

2-(Trimethylsilyl)-ethyl N-benzoylglycinate
85538-32-5

2-(Trimethylsilyl)-ethyl N-benzoylglycinate

Conditions
ConditionsYield
With chloro-trimethyl-silane In tetrahydrofuran at 66℃; for 36h;98%
Hippuric Acid
495-69-2

Hippuric Acid

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

4-(3'-nitrobenzylidene)-2-phenyl-4-oxazolone
15601-45-3, 66949-11-9, 123990-32-9

4-(3'-nitrobenzylidene)-2-phenyl-4-oxazolone

Conditions
ConditionsYield
With acetic anhydride; 5-sulfosalicylic Acid In water at 20℃; for 0.533333h; Green chemistry;98%
With titanium(IV) dioxide; acetic anhydride In ethanol at 120℃; for 0.416667h;96%
With acetic anhydride; 4-aminobenzene sulfonic acid In water at 20℃; for 0.75h; Green chemistry;96%
Hippuric Acid
495-69-2

Hippuric Acid

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one
57427-96-0

4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one

Conditions
ConditionsYield
With 1,1',1''-(2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene)tris(4-(4-nitrobenzyl)pyridine-1-ium) bromide; acetic acid at 20℃; for 0.0666667h; Catalytic behavior; Reagent/catalyst; Erlenmeyer-Plochl-Bergmann;98%
With acetic anhydride In ethanol at 20℃; for 5h; Solvent; Temperature; Green chemistry;89%
Stage #1: Hippuric Acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 4-nitrobenzaldehdye In tetrahydrofuran at 75℃; for 0.283333h;
86%
Hippuric Acid
495-69-2

Hippuric Acid

(E)-1-(N,N-dimethylamino)-1-penten-3-one
6137-82-2, 38664-62-9

(E)-1-(N,N-dimethylamino)-1-penten-3-one

N-(6-ethyl-2-oxo-2H-pyran-3-yl)benzamide

N-(6-ethyl-2-oxo-2H-pyran-3-yl)benzamide

Conditions
ConditionsYield
for 0.133333h; microwave irradiation;98%
Hippuric Acid
495-69-2

Hippuric Acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(Z)-4-(4-methylbenzylidene)-2-phenyloxazol-5(4H)-one
57427-79-9, 57427-88-0, 82309-33-9

(Z)-4-(4-methylbenzylidene)-2-phenyloxazol-5(4H)-one

Conditions
ConditionsYield
With acetic anhydride; palladium diacetate for 0.05h; microwave irradiation;98%
Hippuric Acid
495-69-2

Hippuric Acid

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(4-bromobenzylidene)-2-phenyl-5(4H)oxazolone
20345-16-8

4-(4-bromobenzylidene)-2-phenyl-5(4H)oxazolone

Conditions
ConditionsYield
With iron(III) oxide; acetic anhydride at 25 - 30℃; for 0.166667h; Erlenmeyer-Plochl-Bergmann; Sonication; Irradiation;98%
With potassium phosphate; acetic anhydride In 1,2-dichloro-ethane at 20 - 80℃; for 3h; Erlenmeyer reaction; Inert atmosphere;93%
With sodium acetate; acetic anhydride at 60℃; for 0.5h; Erlenmeyer-Plochl azlactone and amino acid synthesis; Neat (no solvent);92%
Hippuric Acid
495-69-2

Hippuric Acid

1,1-dicyano-2-methyl-3-ethoxycarbonyl-1-propene
52903-67-0

1,1-dicyano-2-methyl-3-ethoxycarbonyl-1-propene

ethyl 3-(5-oxo-2-phenyloxazol-4(5H)-ylidene)butanoate
96138-48-6

ethyl 3-(5-oxo-2-phenyloxazol-4(5H)-ylidene)butanoate

Conditions
ConditionsYield
With sodium acetate; acetic anhydride for 1h; Heating;98%
Hippuric Acid
495-69-2

Hippuric Acid

4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

(Z/E)-4-(4-chlorobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one
15601-44-2

(Z/E)-4-(4-chlorobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one

Conditions
ConditionsYield
With sodium acetate; acetic anhydride for 0.05h; Heating;98%
Hippuric Acid
495-69-2

Hippuric Acid

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

Benzoylglycylglycine methyl ester
51514-00-2

Benzoylglycylglycine methyl ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 4h; Ionic liquid; Green chemistry;98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethylene glycol at 20℃; for 4h; Solvent; Green chemistry;95%
Hippuric Acid
495-69-2

Hippuric Acid

aminosulfonic acid
5329-14-6

aminosulfonic acid

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline
143230-70-0

4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)aniline

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenylhydrazone]

2-phenyl-4,5-oxazoledione 4-[4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenylhydrazone]

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water97.95%
With hydrogenchloride; sodium acetate; acetic anhydride; acetic acid; sodium nitrite In water97.1%

495-69-2Relevant articles and documents

A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester

Nizovtsev, Alexey V.,Bovin, Nicolai V.

supporting information, p. 4428 - 4432 (2021/08/20)

A new convenient synthetic route to 2-aminopropane-1,2,3-tricarboxylic acid is described. The first two stages of the threestep synthesis are performed in a one-pot procedure and include the cyclization of hippuric acid with DCC followed by treatment with methyl bromoacetate to yield an alkylated oxazolone. Its hydrolysis with HCl provides 2-aminopropane-1,2,3-tricarboxylic acid as its HCl salt. Esterification of the resulting acid with methanol in the presence of thionyl chloride leads selectively to its symmetrical diester.

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

Gu, Xiaoke,Zhang, Yinpeng,Zou, Yueting,Li, Xin,Guan, Mingyu,Zhou, Qingqing,Qiu, Jingying

, (2020/12/09)

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

Design, synthesis and anti-inflammatory/analgesic evaluation of novel di-substituted urea derivatives bearing diaryl-1,2,4-triazole with dual COX-2/sEH inhibitory activities

Abdelazeem, Ahmed H.,El-Din, Asmaa G. Safi,Arab, Hany H.,El-Saadi, Mohammed T.,El-Moghazy, Samir M.,Amin, Noha H.

, (2021/05/19)

Herein, two novel series of diaryl-1,2,4-triazole hybrid to amide conjugates (5a-e) or urea conjugates (10a-f) have been synthesized followed by in vitro evaluation against cyclooxygenase-2/soluble epoxide hydrolase (COX-2/sEH) enzymes using ELISA enzyme assays. In vivo analgesic and anti-inflammatory activities for the new compounds have been carried out using the reported animal protocols. The preliminary results revealed that compounds 10e and 10c were the most active compounds against both COX-2/sEH enzymes (COX-2 IC50 = 1.98 μM and 2.13 μM; sEH = 1.09 and 1.23 nM, respectively). Moreover, the in vivo screening assays confirmed their superiority compared to the other derivatives by exhibiting higher anti-inflammatory and analgesic activity (91.27 and 89.32% edema inhibition; 55.97–50.00% writhing inhibition, respectively) than celecoxib (88.30% edema inhibition; 13.43% writhing inhibition). Collectively, compounds 10e and 10c can be considered as promising dual COX-2/sEH inhibitors with expected less cardiovascular adverse effects affording good anti-inflammatory and analgesic leads for further optimization.

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