3,4-Dihydroxybenzaldehyd
3,4-DIHYDROXYBENZALDEHYDE · PROTOCATECHUIC ALDEHYDE · Benzaldehyde, 3,4-dihydroxy- · 3,4－Dihydroxybenzyl aldehyde · Catechaldehyde · Nc 033 · NSC 22961 · AURORA 17180
Identifikatoren & physikalische Daten
| CAS No. | 139-85-5 |
|---|---|
| Summenformel | C7H6O3 |
| Durchschnittliche Molmasse | 138,12 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | 3,4-Dihydroxybenzaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 124 |
| Stoffklassen | Other Classes -> Benzaldehydes |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 0.82 |
| Aromastoffe | EU Flavoring substances |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Dampfdruck | 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] |
| Schmelzpunkt | 150-157 °C(lit.) |
| Siedepunkt | 213.5°C (rough estimate) |
| Dichte | 1.2667 (rough estimate) |
| Brechungsindex | 1.4600 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 6.3g/l50 g/L (20 ºC) |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pK (25°) 7.55 |
| Farbe | slightly brown |
| Geruch | at 100.00 %. dry medicinal bitter almond |
| Geruchsart | medicinal |
| Merck | 14,7893 |
| BRN | 774381 |
| Stabilität | Stable. Incompatible with strong bases, strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | BLEACHINGANTIOXIDANTSKIN CONDITIONING |
| 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 (Verteilungskoeffizient) | 1.090 |
| CAS Datenbank | 139-85-5(CAS DataBase Reference) |
| NIST chemische Informationen | 3,4-Dihydroxybenzaldehyde(139-85-5) |
| EPA chemische Informationen | Benzaldehyde, 3,4-dihydroxy- (139-85-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Gefahrenübersicht | 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%) |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| F | 9 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29124900 |
| RTECS-Nr. | UL0380000 |
| R-Sätze (R) | 36/37/38-22 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant/Air Sensitive |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
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.
History
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
Verwenden
3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells.