3,4-ジヒドロキシベンズアルデヒド

3,4-Dihydroxybenzaldehyde

HCID 8768CAS 139-85-5

基本情報

標準SMILES
O=Cc1ccc(O)c(O)c1
InChIKey
IBGBGRVKPALMCQ-UHFFFAOYSA-N
分子式
C7H6O3
平均分子量
138.12 g/mol
単同位体質量
138.03169405

概要

3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.

名称と識別子

優先名称
3,4-Dihydroxybenzaldehyde
IUPAC
3,4-dihydroxybenzaldehyde
現地名
3,4-ジヒドロキシベンズアルデヒド
英語名
Protocatechualdehyde
分子式
C7H6O3
分子量
138.12

名称と別名

3,4-DihydroxybenzaldehydeProtocatechualdehyde139-85-5PROTOCATECHUIC ALDEHYDERancinamycin IV4-Formyl-1,2-dihydroxybenzene3,4-Dihydroxybenzenecarbonal4PVP2HCH4TDTXSID4074512CHEBI:50205NSC-22961GM-W03
名称をさらに表示
3,4-ジヒドロキシベンズアルデヒドプロトカテクアルデヒドランシナマイシンIV4-ホルミルカテコール4-ホルミル-1,2-ベンゼンジオールプロトカテキュアルデヒドジヒドロキシベンズアルデヒドプロトカテチュアルデヒド3,4‐ジヒドロキシベンズアルデヒド3,4-ジヒドロキシベンゼン-1-カルボアルデヒドカテクアルデヒド3,4-Dihydroxybenzyl aldehydeNc 033NSC 22961AURORA 17180PROTOPINE(RG)rancinamyciniv
RefChem:45419DTXCID1034507O HUI WHITE EXTREME CELLIGHT205-377-7Benzaldehyde, 3,4-dihydroxy-catechaldehyde3,4-dihydroxy-benzaldehydeMFCD00003370

データベース識別子

CAS
139-85-5
PubChem CID
8768
DTXSID
DTXSID4074512
ChEMBL
CHEMBL222021
ChEBI
CHEBI:50205
UNII
4PVP2HCH4T
EC Number
205-377-7
Nikkaji
J5.647B、J822.910D

物性

構造計算による物性

XLogP
1.3
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
1
重原子数
10

実験および物理化学的性質

Chemical ClassesOther Classes -> Benzaldehydes
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.82
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.000116 [mmHg]

物理化学的性質

融点
150 · 150-157 °C(lit.)
沸点
213.5 °C · 213.5°C (rough estimate)
比重(密度)
1.2667 · 1.2667 (rough estimate)
屈折率
1.46 · 1.4600 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
6.3 g/リットル · 6.3g/リットル
化学的性質 · 1 件

化学的特性Protocatechualdehyde is a phenolic aldehyde crystalline compound with the molecular formula C7H6O3. The compound is released from cork stoppers into wine. protocatechualdehyde can be found in barley, grapevine, green Cavendish, and root of herb S. miltiorrhiza. The compound contains pro-apoptotic and antiproliferative properties against human breast cancer cells as well as colorectal cancer cells by reducing the expression of cyclin D1 and β-catenin.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 62.7% (89 of 142) of all reports.

Warning

H315 (34.5%): 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 142 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzaldehyde, 3,4-dihydroxy-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 13-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34350

3,4-Dihydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses convulsions and respiratory stimulation in intraperitoneal lethal-dose studies of mice (LD50 = 205 mg/kg); [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (34.5%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin

安全データ

F
9
wgk
3
rtecs
UL0380000
hs_code
29124900
risk_code
36/37/38-22
化審法
(3)-1198

化学と産業

薬理情報

MeSH Pharmacological ClassificationAgents that prevent BLOOD CLOTTING.

用途と製造

UsesPresent in wheat grains and other plants; [ChemIDplus]
応用分野 · 5 件

用途有機合成原料、酸化防止剤原料、たん白質染料。

説明Protocatechualdehyde is extracted from roots of the common traditional Chinese medicine Salvia miltiorrhiza Bge, which was harvested in autumn for better quality. Take root and remove stems, leaves and fibrous roots, then dry it. Most of them are wide, and they are mainly cultivated in recent years. South Salvia and Gansu Salvia are also widely used. Besides, there are a variety of sibling plant roots used as Salvia miltiorrhiza in Yunnan. Now, the existence of protocatechualdehyde has been found in variety of herbs, for example, in the leaf of Stenoloma Chusanum (L.) Ching and Ilex chinensis Sims.

来歴In the 1940s, the research was conducted overseas to obtain protocatechualdehyde form herbs. In 1972, the chemical group of Chinese herbal medicine in Nanjing College of Pharmacy systematically studied chemical composition in purple flower holly leaf and separated six monomers including protocatechualdehyde. Then they compared the effect of protocatechualdehyde, Salvia miltiorrhiza injection and hairy holly root injection, in which protocatechualdehyde is the most effective in increasing coronary sinus flow. Further experiments examined that protocatechualdehyde can increase coronary flow and improve coronary circulation, so it was called after perhexiline. Further clinical observation indicated that protocatechualdehyde has effect on coronary heart disease. The graduates of Nanjing College of Pharmacy in 1975 extracted, separated, isolated, and identified protocatechualdehyde in Salviamiltiorrhiza during the internship in Nanjing Municipal Hospital and studied its distribution, excretion, and toxicity in animals for clinical rational drug usage

使用3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells.

一般的な説明3,4-Dihydroxybenzaldehyde has been recognized as one of the antifungal compound extracted from the outer skin of green Cavendish bananas. It can be synthesized from catechol via Fries rearrangement.

調製方法

純化方法Crystallise the aldehyde from water or toluene and dry it in a vacuum desiccator over KOH pellets or shredded wax respectively. [Beilstein 8 IV 1762.]

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

補足説明

定義本品は、次の化学式で表される有機化合物である。

関連反応

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