3,4-ジヒドロキシフェニル酢酸

Dopac

HCID 547CAS 102-32-9

基本情報

標準SMILES
O=C(O)Cc1ccc(O)c(O)c1
InChIKey
CFFZDZCDUFSOFZ-UHFFFAOYSA-N
分子式
C8H8O4
平均分子量
168.15 g/mol
単同位体質量
168.04225874

概要

(3,4-dihydroxyphenyl)acetic acid is a dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine. It has a role as a human metabolite. It is a member of catechols and a dihydroxyphenylacetic acid. It is functionally related to a phenylacetic acid. It is a conjugate acid of a (3,4-dihydroxyphenyl)acetate.

名称と識別子

優先名称
Dopac
IUPAC
2-(3,4-dihydroxyphenyl)acetic acid
現地名
3,4-ジヒドロキシフェニル酢酸
英語名
3,4-Dihydroxyphenylacetic acid
分子式
C8H8O4
分子量
168.15

名称と別名

3,4-Dihydroxyphenylacetic acid102-32-9Dopac2-(3,4-DIHYDROXYPHENYL)ACETIC ACIDHomoprotocatechuic acidDopacetic acidBenzeneacetic acid, 3,4-dihydroxy-Acetic acid, (3,4-dihydroxyphenyl)-BA 2773KEX5N0R4N5NSC-73191DTXSID9074430
名称をさらに表示
3,4-ジヒドロキシフェニル酢酸カテコール-p-酢酸(3,4-ジヒドロキシフェニル)酢酸ドーパ酢酸ジヒドロキシフェニル酢酸4-カルボキシメチルカテコール2-(3,4-ジヒドロキシフェニル)酢酸4-カルボキシメチルピロカテコール3,4-ジヒドロキシベンゼン酢酸ドーパセト酸[3,4-ジヒドロキシフェニル]酢酸ホモプロトカテク酸カテコール-4-酢酸ピロカテコール-4-酢酸3,4‐ジヒドロキシフェニル酢酸N,N-DIMETHYL-P-PHENYLENEDIAMINE SULFATE3,4-DihydroxyphenyLba2773dopaceticacid
HMDB013363,4 Dihydroxyphenylacetic AcidRefChem:486240DTXCID3032676203-024-13,4-Dihydroxybenzeneacetic acidDihydroxyphenylacetic acid(3,4-DIHYDROXYPHENYL)ACETIC ACID

データベース識別子

CAS
102-32-9
PubChem CID
547
DTXSID
DTXSID9074430
ChEMBL
CHEMBL1284
ChEBI
CHEBI:41941
UNII
KEX5N0R4N5
EC Number
203-024-1
Nikkaji
J804D

物性

構造計算による物性

XLogP
0.5
極性表面積
77.8 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
2
重原子数
12

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 件

0.98

0.98

Solubility4 mg/mL
Melting Point168 °C
Vapor Pressure0.00000082 [mmHg]

物理化学的性質

融点
127 · 127-130 °C (lit.)
沸点
257.07 °C · 257.07°C (rough estimate)
比重(密度)
1.3037 · 1.3037 (rough estimate)
屈折率
1.509 · 1.5090 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
50 mg/mL、透明、ほぼ無色 · 水:可溶50mg/mL、透明、ほぼ無色

化学的性質

化学的特性beige to light brown crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): 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 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

F
10-23
wgk
3
rtecs
AH0590000
hs_code
29182900
risk_code
36/37/38
hazard_code
Xi

化学と産業

薬理情報

Metabolism/Metabolites3,4-dihydroxyphenylacetic acid has known human metabolites that include 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, and Protocatehuic acid.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysAlkaptonuria

用途と製造

UsesA deaminated metabolite of LEVODOPA. [ChemIDplus]
応用分野 · 4 件

用途有機合成原料、DOPACの検出定量。

説明3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.wikipedia

使用3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).

一般的な説明3,4-dihydroxyphenylacetic acid (DOPAC) is a normal constituent of rat brain tissue. A mass fragmentographic method for determination of DOPAC in rat brain tissue has been described. It is major metabolite of dopamine (DA). The voltammetric reduction of DOPAC has been studied at a glassy carbon electrode modified with single-wall carbon nanotubes (SWNTs). Semi-automatic fluorometric assay technique for DOPAC has been reported.

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