139-85-5 Usage
Description
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.
Chemical Properties
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.
Physical properties
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
Uses
Different sources of media describe the Uses of 139-85-5 differently. You can refer to the following data:
1. 3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells.
2. 3,4-Dihydroxybenzaldehyde may be used for the surface modification of nanocrystalline TiO2 particles. Electrodeposited layer of 3,4-dihydroxybenzaldehyde may be used as effective redox mediator during oxidation of NADH at graphene. It may be used in the preparation of new diSchiff base ligands, which forms di-, tri- and tetranuclear Co(II) and Cu(II) complexes.
Synthesis Reference(s)
The Journal of Organic Chemistry, 27, p. 2037, 1962 DOI: 10.1021/jo01053a030
General Description
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.
Pharmacology
Protection of?Myocardial Cells and?Myocardial Ischemia
Reducing Ca2+ concentration in adult erythrocyte cytosolic to protect the myocardium, dilating the coronary arteriae, promoting collateral circulation, increasing
myocardial oxygen supply coronary blood flow, improving collateral circulation
without increasing the ventricular and myocardial oxygen consumption, decreasing
heart rate, inhibiting myocardial contractility, expanding peripheral vascular, and
ultimately reducing cardiac load and myocardial oxygen consumption. Used for the
treatment of coronary heart disease and angina pectoris.
Effects on?Atherosclerosis
Protocatechualdehyde improves atherosclerosis from the effect of inhibition of
inflammation, apoptosis, and leukocyte chemotaxis.
Antithrombotic Effects
1. Platelet aggregation inhibition: Administration of protocatechualdehyde in?vitro
and in?vivo has apparently effect on inhibiting platelet aggregation induced by
ADP.?Protocatechualdehyde 0.625, 1.25, and 2.5?mg/ml can decrease the degree
and slow down the rate of platelet aggregation and promote the aggregation of
platelet.
2. Improving microcirculation: Protocatechualdehyde can increase the blood flow
of microcirculation, accelerate the flow of blood to improve the oxygen supply
of cells, and reduce the number of normal red cells to spiny red cells and the
abnormal shape of spiny red cells.
Antioxidation Effects
Protocatechualdehyde contains phenolic hydroxyl in ortho-position, which is material base for its antioxidation. It has good activities for scavenging free radical. So it
treats cardiovascular and cerebrovascular diseases induced by active oxygen.
Protection of?Nerve Cells and?Cerebral Ischemia Injury
Protection of cerebral ischemia injury might be concerned with reducing the production of TXA2?in brain tissue, inhibiting the release of excitatory amino acids in
brain tissue, and improving the microcirculation of brain tissue.
Repair of?Damaged Venous Valve and?Treatment of?Phlebeurysm
Protocatechualdehyde reduced the fibrosis of tissues and organs effectively, dissolved fibrin, promoted the regeneration of fibrotic cells, and repaired damaged
venous valves to prevent flowing back of blood and cure phlebeurysm effectively.
Other Effects
Protecting the liver and promoting repair and regeneration of liver tissue; antifibrosis of liver and promoting the healing of fracture and wounds; antibacterial,
anti-inflammatory, antiviral, anti-sepsis, and preventing pigmentation.
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.
Enzyme inhibitor
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.
Purification Methods
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 139-85-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 9 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 139-85:
(5*1)+(4*3)+(3*9)+(2*8)+(1*5)=65
65 % 10 = 5
So 139-85-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
139-85-5Relevant articles and documents
Electrochemically exfoliated graphene for nanosensor applications
Sivasankar,Senthilkumar,Vivekananth,Kalaivani,Sivakumar
, p. 7097 - 7104 (2019)
Water dispersible graphene layer are the excellent nano materials used for wide range of electronic applications. High quality graphene was synthesized by an eco-friendly, easy and cost effective electrochemical exfoliation method. In this work, graphite rod was used both as an anode and cathode for the production of graphene. Potassium sulphate (K2SO4) was used as an intercalating agent. Electrochemically exfoliated graphene (EEG) was coated on glassy carbon electrode (GCE) and evaluated towards the electrochemical oxidation of vanillin and L-phenylalanine. The fabricated electrode was able to detect vanillin and L-Phenylalanine as low as 0.2 μM with signal to noise ratio of 3. A significant increase in the current was observed for the graphene coated electrode for both vanillin and L-phenylalanine when compared to bare Glassy electrode. The finding clearly demonstrated the higher detection capability, selectivity and reproducibility of EEG.
Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety
Varró, Gábor,Pogrányi, Balázs,Grün, Alajos,Simon, András,Heged?s, László,Kádas, István
, p. 2265 - 2285 (2018)
Abstract: Some new trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% ee) were achieved by applying (8S,9S)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic trans-dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold. Graphical abstract: [Figure not available: see fulltext.].
On the difference in decomposition of taxifolin and luteolin vs. fisetin and quercetin in aqueous media
Sokolová, Romana,Rame?ová, ?árka,Kocábová, Jana,Kolivo?ka, Viliam,Degano, Ilaria,Pitzalis, Emanuela
, p. 1375 - 1383 (2016)
Abstract: The decomposition of flavonols quercetin and fisetin, flavone luteolin and flavanone taxifolin was studied in slightly alkaline solution under ambient conditions. The study was based on spectrophotometry and high-pressure liquid chromatography. Products formed by atmospheric oxygen oxidation and hydrolysis were identified by HPLC–DAD and HPLC–ESI-MS/MS. Only small differences in the chemical structure of flavonoids resulted in extremely variable oxidation pathways and products. Oxidation of flavonols led to the formation of both a benzofuranone derivative and several open structures. On the contrary, the benzofuranone derivative was not found as a product of taxifolin and luteolin oxidative decomposition. These compounds were oxidized to their hydroxylated derivatives and typical open structures. Quercetin was not identified as a possible oxidation product of taxifolin. Graphical Abstract: [Figure not available: see fulltext.]
Efficient demethylation of aromatic methyl ethers with HCl in water
Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
supporting information, p. 1995 - 2009 (2021/03/26)
A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.
Herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl
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, (2021/06/21)
The invention discloses a herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl. The herbicide is prepared from the following raw materials in parts by weight: 1-15 parts of haloxyfop-R-methyl, 1-15 parts of flumetsulam, 1-37 parts of halosulfuron-methyl, 1-2 parts of a modified antioxidant, 10-12 parts of borax, 6-8 parts of a surfactant, 10-12 parts of triethanolamine, 10-12 parts of vegetable oil and 40-42 parts of deionized water. After the haloxyfop-R-methyl, the flumetsulam and the halosulfuron-methyl are mixed, the effects are complementary, the weeding spectrum is wider, the weeding activity is high, the weeding effect is more excellent. In addition, the modified antioxidant is added into the herbicide formula, so that the composite herbicide has the effects of resisting oxidation aging and ultraviolet aging, effective components are prevented from decomposing and losing efficacy in the presence of light, the pesticide effect is kept lasting, and the application prospect and popularization value are remarkably improved.
A synthetic preparation method for small carbags hydrochloric acid
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Paragraph 0191-0193, (2021/12/08)
The present invention belongs to the field of organic chemistry, relates to a method of synthesizing berberine hydrochloride, comprising: S1: with 5-halo-o-quinoastearaldehyde and piperine ethylamine to obtain N- [2-(3,4-dimethoxyphenyl-5-yl) ethyl] -1- (5-halo-2,3-dimethoxybenzyl) methylimide; S2: to obtain 2- (3,4-diimoxyphenyl) -N- (5-bromo-2,3-dimethoxybenzyl) ethylamine; S3: to obtain 2-(3,4-dimethoxyphenyl) -N- (5-bromo-2 S4: to obtain 12-halogenated berberine derivative; S5: to obtain berberine. The present invention is free from the application of the by-product o-vanillin synthesis of o-resveratal raw material constraints, synthesis of 5- substitute o-resveratal and piperine ethylamine, and the use of the two preparation of berberine hydrochloride, with raw materials readily available, mild reaction conditions, easy to operate, high chemical yield, low cost and other advantages.
