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Hippuric Acid

HCID 464
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
495-69-2
Standard SMILES
O=C(O)CNC(=O)c1ccccc1
InChIKey
QIAFMBKCNZACKA-UHFFFAOYSA-N
Molecular formula
C9H9NO3
Average molar mass
179.17 g/mol
Monoisotopic mass
179.05824315

Overview

N-benzoylglycine is an N-acylglycine in which the acyl group is specified as benzoyl. It has a role as a uremic toxin and a human blood serum metabolite. It is a conjugate acid of a N-benzoylglycinate.

Names & identifiers

Preferred name
Hippuric Acid
IUPAC
2-benzamidoacetic acid
English name
Hippuric acid
Molecular formula
C9H9NO3
Molecular weight
179.17

Names & synonyms

Hippuric acid495-69-22-Benzamidoacetic acidN-BenzoylglycineBenzoylglycineGlycine, N-benzoyl-hippurateBenzamidoacetic acidBenzoylaminoacetic acidHippursaeurePhenylcarbonylaminoacetic acidBenzamidoessigsaeure
Show more names
hippuricHIPURIC ACIDBZ-GLY-OHAKOS B029712CPD-425
2-(Phenylformamido)Acetic AcidBenzoylaminoessigsaeureAcido ippuricoDTXSID9046073TE0865N2ETHIPPURICUM ACIDUMNSC-9982DTXCID7026073

Database identifiers

CAS
495-69-2
PubChem CID
464
DTXSID
DTXSID9046073
ChEMBL
CHEMBL461
ChEBI
CHEBI:18089
UNII
TE0865N2ET
EC Number
207-806-3
Nikkaji
J1.562H

Properties

Computed structural properties

XLogP
0.3
Topological polar surface area
66.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
13
Formal charge
0
Complexity
197

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Metabolite of Fluoxetine, Lisdexamfetamine
CosmeticsHair conditioning
SpringerMaterials PropertiesCrystal structure
LogP · 2 items

0.31

0.31

Solubility3.75 mg/mL
Melting Point187 - 191 °C
Vapor Pressure0.00000076 [mmHg]
Physical Description · 2 items

Solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]

Solid

Collision Cross Section · 4 items

139.72 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 5.2% (3 of 58) of reports.

Danger

H302 (93.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 58 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Glycine, N-benzoyl-

REACH registered substance: Hippuric acid (EC: 207-806-3)

Glycine, N-benzoyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 item

The glycine conjugate of benzoic acid and a human metabolite of toluene; Has been measured in urine as an indicator of occupational exposure to toluene (in the absence of xylene and styrene exposure); [NIOSH Manual of Analytical Methods] May cause irritation; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (93.1%)

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Chemistry & industry

Pharmacology

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsKidney
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 2 items

Found in the urine of herbivorous animals and humans; [Merck Index]

Naturally produced by the body (endogenous).

Use ClassificationCosmetics -> Hair conditioning
General Manufacturing InformationGlycine, N-benzoyl-: ACTIVE
Applications · 3 items

UsesThe product is used for medicine, dyes intermediates and it is used for the production of fluorescent yellow H8GL, disperse fluorescent FFL and so on.

UsesHippuric 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.

UsesN-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.

Related reactions

92 records
New reaction record
HRID 4494 reaction equation
HRID 4494As reactantuspto-grants-1988_02
HRID 117216 reaction equation
HRID 117216As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 133552 reaction equation
HRID 133552As reactantuspto-grants-2008_06
HRID 133587 reaction equation
HRID 133587As reactantuspto-grants-2008_06
HRID 140002 reaction equation
HRID 140002As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 190629 reaction equation
HRID 190629As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 215258 reaction equation
HRID 215258As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 215939 reaction equation
HRID 215939As reactantuspto-grants-2012_06
Page 1 of 12

Compound notes

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More actions
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142 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

154.06 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

145.9 Ų [M+H]+

Physicochemical properties

Melting point
187 · 187-191 °C (lit.)
Boiling point
311.69 °C · 311.69°C (rough estimate)
Density
1 · 1,371 g/cm3
bulk density
630 kg/m3 · 630kg/m3
refractive index
1.56 · 1.5600 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
3.26 g/l · 3.26g/l
form
Crystalline Powder
pka
3.62 · 3.62(at 25℃)
color
White to almost white
PH
2.5 · 2.5-3.5 (10g/l, H2O, 20℃)(slurry)
Water Solubility
Soluble in water.
Merck
14 · 14,4716
BRN
1073987 · 1073987
Stability
Stable. Incompatible with oxidizing agents.
Major Application
clinical testing
Cosmetics Ingredients Functions
HAIR CONDITIONING
InChI
1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
InChIKey
QIAFMBKCNZACKA-UHFFFAOYSA-N
SMILES
OC(=O)CNC(=O)c1ccccc1
LogP
0.771 · 0.771
CAS DataBase Reference
495 · 495-69-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
865 N2ET · TE0865N2ET
EPA Substance Registry System
Glycine, N-benzoyl- (495-69-2)
UNSPSC Code
41116107 · 41116107
NACRES
25 · NA.25
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H315-H318-H335-H319
Precautionary statements
280 a-P304+P340-P405-P501a-P264-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280-P305+P351+P338 · P280a-P304+P340-P405-P501a-P264-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280-P305+P351+P338
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-37/38-41-36/37/38
Safety Statements
26 · 26-39-36/37-22
WGK Germany
3 · 3
RTECS
8150000 · MR8150000
F
3 · 3-10
TSCA
TSCA listed
HazardClass
IRRITANT
HS Code
2924299090 · 2924299090
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as hippuric acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

Signs and Symptoms · 1 item

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F
3-10
wgk
3
tsca
TSCA listed
rtecs
MR8150000
hs_code
2924299090
risk_code
22-37/38-41-36/37/38
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
Xn,Xi
safety_code
26-39-36/37-22
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H318-H335-H319
REACH Registrations
Active
Precautionary statements
P280a-P304+P340-P405-P501a-P264-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280-P305+P351+P338
Preparation methods · 1 item

PreparationPreparation 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].

Upstream & downstream products

Upstream raw materials

Formyl chlorideSodium glycinateGlycineBenzoyl chloride2-Mercaptopropionic acid

Downstream products

2-Benzamido-3-(4-(N,N-bis-(2-chloroethyl)amino)phenyl)propionic acidDL-Isoleucine(3,4-Dimethoxyphenyl)acetic acid3,4-Dihydroxyphenylacetic acidDL-3-(4-Fluorophenyl)alanineBenzoic acidGlycine hydrochloride(Z)-N-(1-chloro-1-(2-methoxyphenyl)-3-oxo-3-(piperidin-1-yl)prop-1-en-2-yl)benzamideBUTTPARK 61\40-87

Additional notes

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