馬尿酸
馬尿酸 · ベンゾイルグリシン · ベンゾイルアミノ酢酸 · (ベンゾイルアミノ)酢酸 · [N-ベンゾイルアミノ]酢酸 · 2-(ベンゾイルアミノ)酢酸 · N-ベンゾイルグリシン · Ｎベンゾイルグリシン（尿酸）
識別子と物理属性
| CAS No. | 495-69-2 |
|---|---|
| 分子式 | C9H9NO3 |
| 平均分子量 | 179.17 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 馬尿酸 |
化学・物理的性質
| XLogP | 0.3 |
|---|---|
| 極性表面積 | 66.4 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 3 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 197 |
| LogP（分配係数） | 0.31 |
| 溶解度 | 3.75 mg/mL3.26g/リットル水に溶ける。 |
| 融点 | 187 - 191 °C187-191 °C (lit.) |
| 蒸気圧 | 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]- |
| 沸点 | 311.69°C (rough estimate) |
| 密度 | 1,371 g/cm3 |
| 屈折率 | 1.5600 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 3.62(at 25℃) |
| 色 | 白～ほぼ白 |
| pH | 2.5-3.5 (10g/l, H2O, 20℃)(slurry) |
| Merck | 14,4716 |
| BRN | 1073987 |
| 安定性 | 安定。酸化剤と相容れない。 |
| 主な用途 | 臨床検査 |
| 化粧品成分の機能 | ヘアコンディショニング |
| 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（分配係数） | 0.771 |
| CAS データベース | 495-69-2(CAS DataBase Reference) |
| EPAの化学物質情報 | Glycine, N-benzoyl- (495-69-2) |
化学的特性
White crystalline powder
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 有害性の概要 | 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. |
| 健康影響 | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| 暴露経路 | Endogenous, Ingestion, Dermal (contact) |
| 毒性の概要 | 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 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | MR8150000 |
| 税関コード | 29242990 |
| 危険文句（R） | 22-37/38-41-36/37/38 |
| 化審法 | (3)-1391 |
| 危険表示 | Xn,Xi |
| 安全措置（S） | 26-39-36/37-22 |
| 危険等級 | IRRITANT |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
尿中に排泄される安息香酸の解毒産物。Nα-ベンゾイルグリシンNα-benzoylglycineともいう。最初、ウマの尿中に発見されたのでこの名でよばれるが、ヒトの尿中にも少量排泄(はいせつ)される。N -ベンゾイルグリシンともいう。化学式 C6H5CONHCH2COOH 。草食動物の尿中に見出される物質で，馬尿から初めて取出されたのでこの名がある。針状晶で，分解点 187℃。グリシンから容易に合成される。肝臓で安息香酸の解毒作用により生成し，尿中に排泄される。ブリタニカ国際大百科事典 小項目事典 ブリタニカ
用途
有機合成原料、馬尿酸の定量用。
使用
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.
製法・合成法
製造方法
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].
純化方法
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.]