基本情報
- 標準SMILES
O=C(O)CNC(=O)c1ccccc1- InChIKey
QIAFMBKCNZACKA-UHFFFAOYSA-N- 分子式
- C9H9NO3
- 平均分子量
- 179.17 g/mol
- 単同位体質量
- 179.05824315
名称と識別子
- 優先名称
- Hippuric Acid
- IUPAC
- 2-benzamidoacetic acid
- 現地名
- 馬尿酸
- 英語名
- Hippuric acid
- 分子式
- C9H9NO3
- 分子量
- 179.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
495-69-2- PubChem CID
- 464
- DTXSID
DTXSID9046073- ChEMBL
CHEMBL461- ChEBI
CHEBI:18089- UNII
- TE0865N2ET
- EC Number
- 207-806-3
- Nikkaji
- J1.562H
物性
構造計算による物性
- XLogP
- 0.3
- 極性表面積
- 66.4 Ų
- 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
実験および物理化学的性質
Physical Description
Solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
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]-
物理化学的性質
- 融点
- 187 · 187-191 °C (lit.)
- 沸点
- 311.69 °C · 311.69°C (rough estimate)
- 比重(密度)
- 1 · 1,371 g/cm3
- 屈折率
- 1.56 · 1.5600 (estimate)
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 3.26 g/リットル · 3.26g/リットル
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 3.62 · 3.62(at 25℃)
- 色
- 白~ほぼ白
- PH
- 2.5 · 2.5-3.5 (10g/l, H2O, 20℃)(slurry)
- 水溶解度
- 水に溶ける。
- Merck
- 14 · 14,4716
- BRN
- 1073987 · 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
- 0.771 · 0.771
- CAS データベース
- 495 · 495-69-2(CAS DataBase Reference)
- EPAの化学物質情報
- Glycine, N-benzoyl- (495-69-2)
化学的性質
化学的特性White crystalline powder
安全と法規制
GHS分類
GHS Classification
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.
危険有害性情報
Regulatory Information
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
Hazards Summary
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]
毒性情報
Toxicity Summary
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.
法規制情報
Regulatory Information
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
安全データ
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MR8150000
- hs_code
- 29242990
- risk_code
- 22-37/38-41-36/37/38
- 化審法
- (3)-1391
- hazard_code
- Xn,Xi
- safety_code
- 26-39-36/37-22
- hazard_class
- IRRITANT
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
用途と製造
Uses
Found in the urine of herbivorous animals and humans; [Merck Index]
Naturally produced by the body (endogenous).
応用分野
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.
調製方法
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: An N-acylglycine in which the acyl group is specified as benzoyl.
関連反応
関連ノート
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