Isovanillin (HCID 12127)

概要

Isovanillin is a member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase. It has a role as a HIV protease inhibitor, an antifungal agent, an antidiarrhoeal drug, an EC 1.2.3.1 (aldehyde oxidase) inhibitor, an animal metabolite and a plant metabolite. It is a member of benzaldehydes, a monomethoxybenzene and a member of phenols.

名称と識別子

優先名称: Isovanillin
IUPAC: 3-hydroxy-4-methoxybenzaldehyde
現地名: イソバニリン
英語名: Isovanillin
分子式: C8H8O3
分子量: 152.15

名称と別名

3-Hydroxy-4-methoxybenzaldehydeISOVANILLIN621-59-0Isovanilline5-Formylguaiacol3-Hydroxy-p-anisaldehydeBenzaldehyde, 3-hydroxy-4-methoxy-iso-Vanillin4A9N90H9X6NSC-82996RefChem:792444210-694-9

名称をさらに表示

イソバニリン5-ホルミルグアイヤコール3-ヒドロキシ-4-メトキシベンズアルデヒド3-ヒドロキシ-4-メトキシベンゼンカルボアルデヒド3-ヒドロキシ-p-アニスアルデヒド4-メトキシ-5-ヒドロキシベンズアルデヒド4-メトキシ-3-ヒドロキシベンズアルデヒド3-ヒドロキシ-4-メトキシベンズアルデヒドイソバニリン3‐ヒドロキシ‐4‐メトキシベンズアルデヒドイソバニリン MATRIX SUBSTANCE FOR MALDI-MS,≥99.5% (HPLC)3-ヒドロキシ-4-メトキシ(1,2,3,4,5,6-13C6)ベンズアルデヒドm-ヒドロキシ-p-メトキシベンズアルデヒド(13C6)イソバニリンISOVANILINsovanillin3-Hydroxy-4-methoxyBenzaldehyde,3-hydroxy-4-methoxy-C8H8O3NSC 82996lsovanillin

Isovanicaline3-Hydroxy-4-methoxy-benzaldehydep-Anisaldehyde, 3-hydroxy-Oxy-3 methoxy-4 benzaldehyde3-hydroxy-4-anisaldehyde4-Methoxy-3-hydroxybenzaldehydeisovanilineMFCD00003369

データベース識別子

CAS: 621-59-0
PubChem CID: 12127
DTXSID: DTXSID7049423
ChEMBL: CHEMBL275563
ChEBI: CHEBI:193161
UNII: 4A9N90H9X6
EC Number: 210-694-9
Nikkaji: J57.879G

物性

構造計算による物性

XLogP: 1
極性表面積: 46.5 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 135

実験および物理化学的性質

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Food AdditivesFood

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点: 113 · 113-116 °C
沸点: 179 °C15 · 179 °C15 mm Hg(lit.)
比重(密度): 1.2 · 1.20
蒸気圧: 0 Pa · 0Pa at 20℃
屈折率: 1.4945 · 1.4945 (estimate)
闪点: 179 °C/15mm · 179°C/15mm
貯蔵温度: Keep in dark place,Sealed in dry,Room Temperature
溶解性: アセトン、メタノールに可溶。
酸解離定数(Pka): 1 · pK1:8.889 (25°C)
外見: 結晶性
色: ほんのり茶色
水溶解度: 2.27 g/L · 2.27g/L at 20℃
BRN: 1073021 · 1073021
InChI: 1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3
InChIKey: JVTZFYYHCGSXJV-UHFFFAOYSA-N
SMILES: COc1ccc(C=O)cc1O
LogP: 0.95 at · 0.95 at 20℃
CAS データベース: 621 · 621-59-0(CAS DataBase Reference)
NISTの化学物質情報: 3 · Benzaldehyde, 3-hydroxy-4-methoxy-(621-59-0)
EPAの化学物質情報: 3 · Benzaldehyde, 3-hydroxy-4-methoxy- (621-59-0)

化学的性質

化学的特性Light Tan Cyrstalline Solid

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 13.3% (8 of 60) of reports.

Warning

H315 (86.7%): 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 60 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 InformationStatus: Active Update: 28-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22519

Hazard Classes and CategoriesSkin Irrit. 2 (86.7%)

安全データ

wgk: 3
tsca: TSCA listed
rtecs: CU6540000
hs_code: 29124900
risk_code: 36/37/38
化審法: (3)-1200
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36/37-36
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

用途と製造

General Manufacturing InformationBenzaldehyde, 3-hydroxy-4-methoxy-: ACTIVE

応用分野 · 2 件

使用3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.

一般的な説明3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.

調製方法 · 2 件

製造方法Synthesis of isovanillin: 4-Hydroxybenzaldehyde is used as raw material, firstly react with bromine to obtain 3-bromo-4-hydroxybenzaldehyde, then react with methyl iodide to obtain 3-bromo-4-methoxybenzaldehyde, and then hydrolyzed under the action of sodium hydroxide and cuprous chloride to produce isovanillin. The yield was 64.1%.

純化方法Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.]