4-ヒドロキシフェニル酢酸

Hydroxyphenylacetic acid

HCID 127CAS 156-38-7

基本情報

標準SMILES
O=C(O)Cc1ccc(O)cc1
InChIKey
XQXPVVBIMDBYFF-UHFFFAOYSA-N
分子式
C8H8O3
平均分子量
152.15 g/mol
単同位体質量
152.04734412

概要

4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a mouse metabolite, a plant metabolite, a fungal metabolite and a human metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.

名称と識別子

優先名称
Hydroxyphenylacetic acid
IUPAC
2-(4-hydroxyphenyl)acetic acid
現地名
4-ヒドロキシフェニル酢酸
英語名
4-Hydroxyphenylacetic acid
分子式
C8H8O3
分子量
152.15

名称と別名

4-hydroxyphenylacetic acid156-38-7p-hydroxyphenylacetic acid(4-Hydroxyphenyl)acetic acid4-Hydroxybenzeneacetic acidbenzeneacetic acid, 4-hydroxy-(p-Hydroxyphenyl)acetic acid4-CarboxymethylphenolParahydroxy phenylacetic acidAcetic acid, (p-hydroxyphenyl)-3J9SHG0RCNNSC-25066
名称をさらに表示
4-ヒドロキシフェニル酢酸2-(4-ヒドロキシフェニル)酢酸p-ヒドロキシベンゼン酢酸p-ヒドロキシフェニル酢酸4-ヒドロキシベンゼン酢酸(4-ヒドロキシフェニル)酢酸ヒドロキシフェニル酢酸(p-ヒドロキシフェニル)酢酸P‐ヒドロキシフェニル酢酸4-ヒドロキシフェニル酢酸, 99%2-(4-hydroxyphenyl)acetic acidPHPA4-Hydroxyphenylacetic4-hydrophenylacetic acid4-hydroxybenzeneaceticacidNSC 27460
NSC-27460DTXSID5059745CHEBI:18101para-hydroxyphenylacetic acidRefChem:524062DTXCID6035023205-851-3Hydroxyphenylacetic acid

データベース識別子

CAS
156-38-7
PubChem CID
127
DTXSID
DTXSID5059745
ChEMBL
CHEMBL1772
ChEBI
CHEBI:18101
UNII
3J9SHG0RCN
EC Number
205-851-3
Nikkaji
J5.873D

物性

構造計算による物性

XLogP
0.8
極性表面積
57.5 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
2
重原子数
11

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials PropertiesFusion temperature
LogP · 2 件

0.75

1.26

Solubility60.7 mg/mL
Melting Point148 - 150 °C
Vapor Pressure0.0000555 [mmHg]

物理化学的性質

融点
148 · 148-151 °C(lit.)
沸点
234.6 °C · 234.6°C (rough estimate)
比重(密度)
1.2143 · 1.2143 (rough estimate)
蒸気圧
0.007 Pa · 0.007Pa at 25℃
屈折率
1.4945 · 1.4945 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
化学的性質 · 1 件

化学的特性4-Hydroxyphenylacetic acid is a white to cream or light tan crystalline powder. sublimation. Insoluble in cold water, soluble in hot water, ether, ethanol, ethyl acetate. In the case of ferric chloride, it is a purple-green precipitate. It is used as a pharmaceutical raw material for the synthesis of cephalosporin antibiotics, antipyretic analgesics.

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (97%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 233 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: Benzeneacetic acid, 4-hydroxy-

Status: Cease Manufacture Update: 01-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22446

(4-Hydroxyphenyl)-acetic acid: 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 SummaryIntraperitoneal LD50 (mouse) = 3,500 mg/kg; [RTECS] An irritant; [Alfa Aesar MSDS] See Phenylacetic acid.
Hazard Classes and CategoriesSkin Irrit. 2 (97%)

安全データ

wgk
3
tsca
TSCA listed
rtecs
AI2680000
hs_code
29182990
risk_code
36/37/38
化審法
(9)-1022

化学と産業

薬理情報

Metabolism/Metabolites4-hydroxyphenylacetic acid has known human metabolites that include 2-Phenylacetic acid.
MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Tissue LocationsBladder
Cellular LocationsCytoplasm
Metabolite PathwaysAlkaptonuria

用途と製造

General Manufacturing InformationBenzeneacetic acid, 4-hydroxy-: ACTIVE

応用分野

用途有機合成原料。酵素、糖及びホルモンの定量。

使用A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development.

調製方法 · 2 件

製造方法4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid. 4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.

純化方法Crystallise the acid from water or Et2O/pet ether. The p-bromophenacyl ester has m 117o (from EtOH). [Beilstein 10 II 112, 10 III 430, 10 IV 543.]

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
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爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
補足説明 · 1 件

定義ChEBI: 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It derives from an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.

関連反応

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