Homovanillic Acid (HCID 1738)

概要

Homovanillic acid is a monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. It has a role as a mouse metabolite and a human metabolite. It is a member of guaiacols and a monocarboxylic acid. It is functionally related to a (3,4-dihydroxyphenyl)acetic acid. It is a conjugate acid of a homovanillate.

名称と識別子

優先名称: Homovanillic Acid
IUPAC: 2-(4-hydroxy-3-methoxyphenyl)acetic acid
現地名: 4-ヒドロキシ-3-メトキシフェニル酢酸
英語名: Homovanillic acid
分子式: C9H10O4
分子量: 182.17

名称と別名

Homovanillic acid306-08-14-Hydroxy-3-methoxyphenylacetic acid2-(4-hydroxy-3-methoxyphenyl)acetic acidBenzeneacetic acid, 4-hydroxy-3-methoxy-Vanillacetic acid3-Methoxy-4-hydroxyphenylacetic acid4-Hydroxy-3-methoxybenzeneacetic acid(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACIDAcetic acid, (4-hydroxy-3-methoxyphenyl)-X77S6GMS36DTXSID5059791

名称をさらに表示

4-ヒドロキシ-3-メトキシフェニル酢酸3-メトキシ-4-ヒドロキシベンゼン酢酸3-メトキシ-4-ヒドロキシフェニル酢酸4-ヒドロキシ-3-メトキシベンゼン-1-酢酸4-ヒドロキシ-3-メトキシベンゼン酢酸グアイアシル酢酸(4-ヒドロキシ-3-メトキシフェニル)酢酸ホモバニリン酸(3-メトキシ-4-ヒドロキシフェニル)酢酸ホモバニリン酸, 98+%HVAHomovanilic acidJACS-306-08-1homovanillicaciVanilacetic acidHOMOVANIUIC ACID

HMDB00118NSC-16682CHEBI:545959Acid, Homovanillic3 Methoxy 4 Hydroxyphenylacetic Acid4 Hydroxy 3 Methoxyphenylacetic AcidAcid, 3-Methoxy-4-HydroxyphenylaceticAcid, 4-Hydroxy-3-Methoxyphenylacetic

データベース識別子

CAS: 306-08-1
PubChem CID: 1738
DTXSID: DTXSID5059791
ChEMBL: CHEMBL1562
ChEBI: CHEBI:545959
UNII: X77S6GMS36
EC Number: 206-176-7
Nikkaji: J61.262F

物性

構造計算による物性

XLogP: 0.4
極性表面積: 66.8 Å²
水素結合供与体数: 2
水素結合受容体数: 4
回転可能結合数: 3
重原子数: 13
形式電荷: 0
複雑度: 180

実験および物理化学的性質

Chemical ClassesBiological Agents -> Other Biomolecules

LogP0.33

Solubility17 mg/mL

Melting Point138 - 140 °C

Vapor Pressure0.00000823 [mmHg]

Physical Description · 2 件

White solid; [Merck Index] White to pale brown crystalline powder; [Alfa Aesar MSDS]

Solid

物理化学的性質

融点: 142 · 142-145 °C(lit.)
沸点: 235.56 °C · 235.56°C (rough estimate)
比重(密度): 1.1634 · 1.1634 (rough estimate)
屈折率: 1.4209 · 1.4209 (estimate)
貯蔵温度: Keep in dark place,Inert atmosphere,Room temperature
溶解性: DMSO（微量）、メタノール（微量、加温）
酸解離定数(Pka): 4.39 · 4.39±0.10(Predicted)
外見: 結晶性粉末
色: 白からベージュ
水溶解度: 溶ける
Merck: 14 · 14,4740
BRN: 2213447 · 2213447
安定性: 吸湿性
主な用途: 医薬品
InChI: 1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChIKey: QRMZSPFSDQBLIX-UHFFFAOYSA-N
SMILES: COc1cc(CC(O)=O)ccc1O
LogP: 0.33 · 0.330
CAS データベース: 306 · 306-08-1(CAS DataBase Reference)
NISTの化学物質情報: 4 · Benzeneacetic acid, 4-hydroxy-3-methoxy-(306-08-1)
EPAの化学物質情報: Homovanillic acid (306-08-1)

化学的性質

化学的特性white to beige 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 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationBenzeneacetic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

F: 10-23
wgk: 3
tsca: TSCA listed
hs_code: 29189900
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
hazard_class: IRRITANT
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Tissue LocationsBrain

Cellular LocationsCytoplasm

Metabolite PathwaysAlkaptonuria

用途と製造

UsesA metabolite present in human urine; [Merck Index]

General Manufacturing InformationBenzeneacetic acid, 4-hydroxy-3-methoxy-: ACTIVE

応用分野 · 3 件

用途有機合成原料、ホモバニリン酸の試験研究用。

説明Homovanillic acid (HVA) is a dopamine metabolite. It is formed via deamination of dopamine by monoamine oxidase (MAO) to produce 3,4-dihydroxyphenylacetic acid (DOPAC; ) followed by DOPAC metabolism by catechol-O-methyltransferase (COMT). HVA undergoes hydrogen peroxide-dependent oxidation in the presence of horseradish peroxidase to form a fluorescent dimer that displays excitation/emission maxima of 312/420 nm, respectively. It has been used to quantify hydrogen peroxide production in macrophages and neutrophils.

使用Fluorimetric reagent and major catecholamine metaboliteHomovanillic acid is used as a reagent in the determination of oxidative enzymes. It is associated with dopamine levels in the brain. Its presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

上流・下流製品情報

上流原料

グアイアコールパラジウム水酸化ナトリウムグリオキシル酸硫酸水素 2-Methoxy-4-[(methylamino)methyl]phenol Benzeneacetic acid, α,4-dihydroxy-3-methoxy-, (αS)-4-ベンジルオキシ-3-メトキシフェニル酢酸酢酸4-シアノメチル-2-メトキシフェニル 4-ヒドロキシ-3-メトキシフェニル酢酸エチル 2-ブロモ-1-(4-ヒドロキシ-3-メトキシフェニル)エタノン

下流製品

N-ブチルホルムアミド 6-O,7-セコ-5,6-ジデオキシ-6,7-ジデヒドロ-20-O-[(4-ヒドロキシ-3-メトキシフェニル)アセチル]-21-デフェニル-21-ベンジルダフネトキシン 4-ヒドロキシ-3-メトキシベンゾニトリル Benzeneacetic acid, 3,4-dihydroxy-5-methoxy-

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補足説明

定義ChEBI: A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.

4-ヒドロキシ-3-メトキシフェニル酢酸

基本情報

概要