Hippuric Acid

HCID 464CAS 495-69-2

Basic information

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

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-Benzamidoacetic acidBenzoylaminoacetic acidhippurateHippursaeurePhenylcarbonylaminoacetic 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

Experimental & physicochemical properties

LogP0.31
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)]

142 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];149.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

146.82 Ų [M+H]+ [CCS Type: DT; Method: stepped-field];148.23 Ų [M-H]- [CCS Type: DT; Method: stepped-field];154.06 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

149.9 Ų [M+Na]+;147.7 Ų [M-H]-;153.1 Ų [M+Na]+;145.9 Ų [M+H]+;142.4 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.

Safety & regulation

GHS classification

GHS Classification · 6 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];H315 (94.8%): Causes skin irritation [Warning Skin corrosion/irritation];H318 (93.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H335 (93.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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.;Reported as not meeting GHS hazard criteria per 3 of 58 reports by companies.;There are 7 notifications provided by 55 of 58 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: Glycine, N-benzoyl-

Status: Active Update: 03-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19668

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%);Skin Irrit. 2 (94.8%);Eye Dam. 1 (93.1%);STOT SE 3 (93.1%)

Toxicology

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

Regulatory information

Regulatory Information · 3 items

Chemical: Glycine, N-benzoyl-

Status: Active Update: 03-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19668

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

Safety data

F
3-10
wgk
3
tsca
TSCA listed
rtecs
MR8150000
hs_code
29242990
risk_code
22-37/38-41-36/37/38

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;Liver;Placenta;Prostate
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.

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].

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州滢科生物科技有限公司62896201 13806138270
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

Additional notes

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

Related reactions

92 records

Linked notes

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