3,4-Dihydroxybenzaldehyd Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
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.
Chemische Eigenschaften
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.
Physikalische Eigenschaften
Appearance: pale beige acicular crystal (in water or methylbenzene) or off-white
powder, crystal twin shape. Solubility: easily soluble in ethanol, acetone, ethyl acetate, ethyl ether, and hot water; soluble in cold water; insoluble in benzene and
chloroform. Melting point: 150–153°C. Specific optical rotation: easily oxidized to
benzoquinone and changes color, and it is instable in water.
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.
Allgemeine Beschreibung
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.
Clinical Use
Perhexiline injection containing protocatechualdehyde 100 mg/2 mL by intravenous infusion or intramuscular injection was used to treat coronary heart disease,
chest tightness, angina, and myocardial infarction.
Injection treats ischemic stroke and improves both symptoms and signs of patients.
Treating chronic hepatitis and early cirrhosis: relieving the symptoms, promoting
the recovery of liver function, and hepatosplenomegaly.
It can significantly improve the blood rheology index for patients with acute exacerbation of chronic pulmonary heart disease.
Treatment of peptic ulcer: a certain effect.
Others: it has effect on many diseases like viral myocarditis, embolism of central
retinal artery, thromboangiitis obliterans, scleredema neonatorum, scleroderma,
psoriasis, nerve deafness, and toxemia of pregnancy.
Enzyminhibitor
This aldehyde (FW = 138.12 g/mol), also known as 3,4- dihydroxybenzaldehyde and 4-formylcatechol, is soluble in water (5 g/100 mL at 20°C) and has a pKa value of 7.55 at 25°C. Protocatechualdehyde induces apoptosis in cytotoxic T cells. Target(s): aldehyde oxidase; aldose reductase; b-carotene 15,15’-monooxygenase; mandelonitrile lyase; protocatechuate 3,4-dioxygenase; protocatechuate 4,5- dioxygenase; tyrosinase, weakly inhibited, IC50 = 620 μM; and xanthine oxidase.
läuterung methode
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.]
3,4-Dihydroxybenzaldehyd Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
3-(3,4-Dihydroxyphenyl)propionsure
3',4'-(DIOCTYLOXY)BENZALDEHYDE
3',4'-(DIDECYLOXY)BENZALDEHYDE
4'-FORMYLBENZO-15-CROWN 5-ETHER
3,4-DIHYDRO-2H-1,5-BENZODIOXEPINE-7-CARBALDEHYDE
2,5-dibromo-3,4-dimethoxy-Benzaldehyde
2,3-Dihydroxybenzaldehyd
4-(DIFLUOROMETHOXY)-3-(CYCLOPROPYLMETHOXY)-BENZALDEHYDE
2,3-Dihydro-1,4-benzodioxin-6-carbaldehyd
3,4-Bis(benzyloxy)benzaldehyd
4-Difluoromethoxy-3-hydroxybenzaldehyde
