Hippursure
BENZOYLGLYCINE · hippurate · hippuric · HIPURIC ACID · N-BENZOYLGLYCINE · BZ-GLY-OH · AKOS B029712 · Hippursaeure
Identifikatoren & physikalische Daten
| CAS No. | 495-69-2 |
|---|---|
| Summenformel | C9H9NO3 |
| Durchschnittliche Molmasse | 179,17 g/mol |
| Monoisotopische Masse | 179,05824315 g/mol |
| SMILES | O=C(O)CNC(=O)c1ccccc1 |
| InChIKey | QIAFMBKCNZACKA-UHFFFAOYSA-N |
| PubChem CID | 464 |
| ChEMBL | CHEMBL461 |
| ChEBI | CHEBI:18089 |
| EC No. | 207-806-3 |
| DTXSID | DTXSID9046073 |
| Lokaler Name | Hippursure |
Chemische & physikalische Eigenschaften
| XLogP | 0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,4 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 197 |
| LogP (Verteilungskoeffizient) | 0.31 |
| Löslichkeit | 3.75 mg/mL3.26g/lSoluble in water. |
| Schmelzpunkt | 187 - 191 °C187-191 °C (lit.) |
| Dampfdruck | 0.00000076 [mmHg] |
| Physical Description | Solid[Merck Index] White crystalline powder[Alfa Aesar MSDS] |
| Collision Cross Section | 139.72 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]142 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]149.6 Ų [M+Na]+ [CCS Type: DT146.82 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]148.23 Ų [M-H]- [CCS Type: DT154.06 Ų [M+Na]+ [CCS Type: DT149.9 Ų [M+Na]+147.7 Ų [M-H]-153.1 Ų [M+Na]+145.9 Ų [M+H]+142.4 Ų [M-H]- |
| Siedepunkt | 311.69°C (rough estimate) |
| Dichte | 1,371 g/cm3 |
| Brechungsindex | 1.5600 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 3.62(at 25℃) |
| Farbe | White to almost white |
| pH | 2.5-3.5 (10g/l, H2O, 20℃)(slurry) |
| Merck | 14,4716 |
| BRN | 1073987 |
| Stabilität | Stable. Incompatible with oxidizing agents. |
| Hauptanwendungen | clinical testing |
| Kosmetik-Inhaltsstoffe Funktionen | 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 (Verteilungskoeffizient) | 0.771 |
| CAS Datenbank | 495-69-2(CAS DataBase Reference) |
| EPA chemische Informationen | Glycine, N-benzoyl- (495-69-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.2% (3 of 58) of reports.DangerH302 (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 exposureRespiratory 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. |
|---|---|
| Regulatorische Informationen | Chemical: Glycine, N-benzoyl-Status: Active Update: 03-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19668Glycine, N-benzoyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | The glycine conjugate of benzoic acid and a human metabolite of tolueneHas 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 Categories | Acute Tox. 4 (93.1%)Skin Irrit. 2 (94.8%)Eye Dam. 1 (93.1%)STOT SE 3 (93.1%) |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| Gesundheitliche Auswirkungen | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| Expositionspfade | Endogenous, Ingestion, Dermal (contact) |
| Toxizitätsübersicht | 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 | 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29242990 |
| RTECS-Nr. | MR8150000 |
| R-Sätze (R) | 22-37/38-41-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-39-36/37-22 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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].