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히푸르산

Hippuric Acid

HCID 464
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
495-69-2
표준 SMILES
O=C(O)CNC(=O)c1ccccc1
InChIKey
QIAFMBKCNZACKA-UHFFFAOYSA-N
분자식
C9H9NO3
평균 분자량
179.17 g/mol
단동위원소 질량
179.05824315

개요

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.

이름 및 식별자

우선 이름
Hippuric Acid
IUPAC
2-benzamidoacetic acid
현지명
히푸르산
영어명
Hippuric acid
분자식
C9H9NO3
분자량
179.17

이름 및 동의어

Hippuric acid495-69-22-Benzamidoacetic acidN-BenzoylglycineBenzoylglycineGlycine, N-benzoyl-hippurateBenzamidoacetic acidBenzoylaminoacetic acidHippursaeurePhenylcarbonylaminoacetic acidBenzamidoessigsaeure
이름 더 보기
마뇨산히푸르산히푸릭애씨드hippuricHIPURIC ACIDBZ-GLY-OHAKOS B029712CPD-425
2-(Phenylformamido)Acetic AcidBenzoylaminoessigsaeureAcido ippuricoDTXSID9046073TE0865N2ETHIPPURICUM ACIDUMNSC-9982DTXCID7026073

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
0.3
극성 표면적
66.4 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
3
무거운 원자 수
13
형식 전하
0
복잡도
197

실험 및 물리화학적 성질

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

0.31

0.31

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

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

Solid

Collision Cross Section · 4건

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)]

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

145.9 Ų [M+H]+

물리화학적 성질

녹는점
187 · 187-191 °C (lit.)
끓는 점
311.69 °C · 311.69°C (rough estimate)
밀도
1 · 1,371 g/cm3
굴절률
1.56 · 1.5600 (estimate)
저장 조건
30 °C · Store below +30°C.
용해도
3.26 g/L · 3.26g/L
물리적 상태
결정성 분말
산도 계수 (pKa)
3.62 · 3.62(at 25℃)
색상
흰색에서 거의 흰색
수소이온지수(pH)
2.5 · 2.5-3.5 (10g/l, H2O, 20℃)(slurry)
수용성
물에 용해됩니다.
Merck
14 · 14,4716
BRN
1073987 · 1073987
안정성
안정적인. 산화제와 호환되지 않습니다.
주요 응용
임상 시험
화장품 원료 기능
헤어 컨디셔닝
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
EPA
Glycine, N-benzoyl- (495-69-2)

화학적 성질

White crystalline powder

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 3건

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 · 1건

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%)

독성 정보

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 · 1건

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 · 1건

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).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
MR8150000
HS 번호
2924299090
risk_code
22-37/38-41-36/37/38
hazard_code
Xn,Xi
safety_code
26-39-36/37-22
위험 등급
IRRITANT
기존화학 물질
KE-02753
F 고인화성물질
3-10
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

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

용도 및 제조

Uses · 2건

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
응용 분야 · 1건

용도N-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.

제조 방법 · 1건

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].

상·하류 제품 정보

상류 원료

Formyl chloride나트륨 글리신산염글리신염화벤조일티오락틱산

하류 제품

2-BENZAMIDO-3-(4-(N,N-BIS-(2-클로로에틸)아미노)페닐)프로피온산DL-이소류신(3,4-디메톡시페닐)아세트산3,4-Dihydroxyphenylacetic acidDL-3-(4-Fluorophenyl)alanine벤조산글리신 염화수소산염(Z)-N-(1-chloro-1-(2-methoxyphenyl)-3-oxo-3-(piperidin-1-yl)prop-1-en-2-yl)benzamide밥타크61/40-87

추가 설명

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

관련 반응

92건
반응 기록 만들기
HRID 4494 반응식
HRID 4494반응물로uspto-grants-1988_02
HRID 117216 반응식
HRID 117216반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 133552 반응식
HRID 133552반응물로uspto-grants-2008_06
HRID 133587 반응식
HRID 133587반응물로uspto-grants-2008_06
HRID 140002 반응식
HRID 140002반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 190629 반응식
HRID 190629반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 215258 반응식
HRID 215258반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 215939 반응식
HRID 215939반응물로uspto-grants-2012_06
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