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IV · 4-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
識別子と物理属性
| CAS No. | 139-85-5 |
|---|---|
| 分子式 | C7H6O3 |
| 平均分子量 | 138.12 g/mol |
| 単同位体質量 | 138.03169405 g/mol |
| SMILES | O=Cc1ccc(O)c(O)c1 |
| InChIKey | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
| PubChem CID | 8768 |
| ChEMBL | CHEMBL222021 |
| ChEBI | CHEBI:50205 |
| EC No. | 205-377-7 |
| DTXSID | DTXSID4074512 |
| 現地名 | 3,4-ジヒドロキシベンズアルデヒド |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 57.5 |
| 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 |
| 形式電荷 | 0 |
| 複雑度 | 124 |
| 物質分類 | Other Classes -> Benzaldehydes |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 0.82 |
| 香味料 | EU Flavoring substances |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 蒸気圧 | 0.000116 [mmHg] |
| Physical Description | Solid[Merck Index] Light brown powder[Alfa Aesar MSDS] |
| Collision Cross Section | 126.83 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 融点 | 150-157 °C(lit.) |
| 沸点 | 213.5°C (rough estimate) |
| 密度 | 1.2667 (rough estimate) |
| 屈折率 | 1.4600 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 6.3g/リットル50g/L(20℃) |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | pK (25°) 7.55 |
| 色 | やや茶色 |
| 臭い | 100.00%で。乾燥薬用ビターアーモンド |
| においのタイプ | 薬用 |
| Merck | 14,7893 |
| BRN | 774381 |
| 安定性 | 安定。強塩基、強酸化剤とは相容れない。 |
| 化粧品成分の機能 | 漂白抗酸化物質スキンコンディショニング |
| InChI | 1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H |
| InChIKey | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
| SMILES | Oc1ccc(C=O)cc1O |
| LogP（分配係数） | 1.090 |
| CAS データベース | 139-85-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 3,4-Dihydroxybenzaldehyde(139-85-5) |
| EPAの化学物質情報 | Benzaldehyde, 3,4-dihydroxy- (139-85-5) |
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.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 62.7% (89 of 142) of all reports.WarningH315 (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. |
|---|---|
| 規制情報 | 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/343503,4-Dihydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Causes 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 Categories | Skin Irrit. 2 (34.5%) |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| F | 9 |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | UL0380000 |
| 税関コード | 29124900 |
| 危険文句（R） | 36/37/38-22 |
| 化審法 | (3)-1198 |
| 危険表示 | Xi |
| hazard_note | Irritant/Air Sensitive |
| 安全措置（S） | 26-36-37/39 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.
製法・合成法
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.]