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Protocatechualdehyde

Description
Protocatechualdehyde
Protocatechualdehyde structure
CAS No.
139-85-5
Chemical Name:
Protocatechualdehyde
Synonyms
Nc 033;NSC 22961;AURORA 17180;PROTOPINE(RG);rancinamyciniv;Catechaldehyde;Rancinamycin IV;4-Formylcatechol;AKOS BBS-00003254;Protocatechualdehyd
CBNumber:
CB7784165
Molecular Formula:
C7H6O3
Formula Weight:
138.12
MOL File:
139-85-5.mol

Protocatechualdehyde Properties

Melting point:
150-157 °C(lit.)
Boiling point:
213.5°C (rough estimate)
Density 
1.2667 (rough estimate)
refractive index 
1.4600 (estimate)
storage temp. 
Store below +30°C.
solubility 
6.3g/l
form 
Crystalline Powder
pka
pK (25°) 7.55
color 
slightly brown
Water Solubility 
50 g/L (20 ºC)
Sensitive 
Air Sensitive
Merck 
14,7893
BRN 
774381
Stability:
Stable. Incompatible with strong bases, strong oxidizing agents.
CAS DataBase Reference
139-85-5(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
4PVP2HCH4T
NIST Chemistry Reference
3,4-Dihydroxybenzaldehyde(139-85-5)
EPA Substance Registry System
Benzaldehyde, 3,4-dihydroxy- (139-85-5)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P280a-P304+P340-P405-P501a-P261-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes  Xi
Risk Statements  36/37/38-22
Safety Statements  26-36-37/39
WGK Germany  3
RTECS  UL0380000
9
Hazard Note  Irritant/Air Sensitive
HS Code  29124900

Protocatechualdehyde price More Price(60)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.20475 3,4-Dihydroxybenzaldehyde for synthesis 139-85-5 25 g $104.52 2021-12-16 Buy
Sigma-Aldrich 37520 3,4-Dihydroxybenzaldehyde purum, ≥97.0% (HPLC) 139-85-5 25g $193 2021-12-16 Buy
Sigma-Aldrich 8.20475 3,4-Dihydroxybenzaldehyde for synthesis 139-85-5 100 g $253.45 2021-12-16 Buy
Sigma-Aldrich 37520 3,4-Dihydroxybenzaldehyde purum, ≥97.0% (HPLC) 139-85-5 100g $464 2021-12-16 Buy
TCI Chemical D0566 3,4-Dihydroxybenzaldehyde >98.0%(GC)(T) 139-85-5 25g $19 2021-12-16 Buy

Protocatechualdehyde Chemical Properties,Uses,Production

Description

Is a phenolic aldehyde crystalline compound with the molecular formula C7H6O3. The compound is released from cork stoppers into wine. Also known as procatechuic aldehyde, 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.

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

brown powder

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

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

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 2037, 1962 DOI: 10.1021/jo01053a030

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.]

Protocatechualdehyde Preparation Products And Raw materials

Raw materials

Preparation Products


Protocatechualdehyde Suppliers

Global( 653)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 15418 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679
86-0551-65418697 info@tnjchem.com China 3000 55
Anqing Chico Pharmaceutical Co., Ltd.
15380796838
chloewu@chicopharm.cn CHINA 341 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29953 58
NINGBO INNO PHARMCHEM CO., LTD.
13867897135
sales@nbinno.com CHINA 925 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2940 58
Chengdu Biopurify Phytochemicals Ltd.
18482058008 18080483897
maggie@biopurify.com China 2712 58

View Lastest Price from Protocatechualdehyde manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-01-27 Protocatechualdehyde
139-85-5
US $100.00 / KG 1KG 99.9% 1000kg/month Shanxi Lianxu New Material Co., LTD
2022-01-25 3,4-dihydroxybenzaldehyde
139-85-5
US $10.00 / KG 1Kg/Bag 99% 20 Tons Hebei Zhanyao Biotechnology Co. Ltd
2021-11-17 3,4-Dihydroxybenzaldehyde 139-85-5
139-85-5
US $30.00 / g 1g ≥98% 1000.00 kgs NanJing Spring & Autumn Biological Engineering CO., LTD.

Protocatechualdehyde Spectrum


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