Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H6O3 |
| Molecular Weight | 138.1207 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=O)C=C1O
InChI
InChIKey=IBGBGRVKPALMCQ-UHFFFAOYSA-N
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
Protocatechualdehyde (protocatechuic aldehyde) is a naturally occurring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza. There is evidence for anticancer activity of protocatechualdehyde in human colorectal cancer and breast cancer. Protocatechualdehyde leads to the inhibition of cell growth and the promotion of apoptosis through HDAC2-mediated cyclin D1 suppression in human colorectal cancer cells. In human breast cancer cells, protocatechualdehyde downregulates β-catenin and cyclin D1 through activating proteosomal degradation. The risk or severity of bleeding can be increased as a result of interaction of protocatechualdehyde with many drugs an dietary supplements (89 compounds reported).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Voltammetric biosensors for the determination of formate and glucose-6-phosphate based on the measurement of dehydrogenase-generated NADH and NADPH. | 2001 May |
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| Separation and determination of protocatechuic aldehyde and protocatechuic acid in Salivia miltorrhrza by capillary electrophoresis with amperometric detection. | 2001 Sep |
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| New insights into the acid-promoted reaction of caffeic acid and its esters with nitrite: decarboxylation drives chain nitrosation pathways toward novel oxime derivatives and oxidation/fragmentation products thereof. | 2002 Feb 8 |
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| Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits. | 2002 Sep |
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| [Determination of danshensu in rat serum after oral administer compound Salvia recipe]. | 2003 Jun |
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| 6,7-dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain. | 2003 Jun 2 |
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| Synthesis and antioxidant activity of 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-benzenediol, a metabolite of Sphaerophysa salsula. | 2003 Nov |
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| Characterization of acylated flavonoid-O-glycosides and methoxylated flavonoids from Tagetes maxima by liquid chromatography coupled to electrospray ionization tandem mass spectrometry. | 2004 |
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| Inhibition of tyrosinase by protocatechuic aldehyde. | 2004 |
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| O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase. | 2004 Apr |
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| Anti-oxidative compounds in barley tea. | 2004 Dec |
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| Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. | 2004 May |
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| Comparative study of electron mediators used in the electrochemical oxidation of NADH. | 2004 May 15 |
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| [Effect of danshensu, protocatechualdehyde and danshen injection on calcium ion concentration in cytoplasm of human erythrocytes]. | 2004 Oct |
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| Contribution of aldehyde oxidase, xanthine oxidase, and aldehyde dehydrogenase on the oxidation of aromatic aldehydes. | 2004 Oct |
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| A comparison between the use of a redox mediator in solution and of surface modified electrodes in the electrocatalytic oxidation of nicotinamide adenine dinucleotide. | 2004 Sep |
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| Enzymatic oxidation of vanillin, isovanillin and protocatechuic aldehyde with freshly prepared Guinea pig liver slices. | 2005 |
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| Biotransformation of benzaldehyde-type and acetophenone-type derivatives by Pharbitis nil hairy roots. | 2005 Apr |
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| Electrocatalytic oxidation of NADH at single-wall carbon-nanotube-paste electrodes: kinetic considerations for use of a redox mediator in solution and dissolved in the paste. | 2005 Apr |
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| On-line chemiluminescence determination protocatechuic aldehyde and protocatechuic acid in pharmaceutical preparations by capillary electrophoresis. | 2005 Apr 1 |
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| [Studies on the chemical constituents in herb of Ranunculus sceleratus]. | 2005 Jan |
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| Simultaneous determination of five marker constituents in traditional Chinese medicinal preparation Le-Mai granule by high performance liquid chromatography. | 2005 Mar 9 |
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| Quantitative analysis of the marker compounds in Salvia miltiorrihiza root and its phytomedicinal preparations. | 2005 May |
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| [Analysis of four components in Fufang Danshen Tablets by high performance liquid chromatography with electrochemical and ultraviolet detections]. | 2005 Nov |
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| Aqueous extract of Salvia miltiorrhiza attenuates increased endothelial permeability induced by tumor necrosis factor-alpha. | 2005 Oct |
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| Simultaneous quantification of six major phenolic acids in the roots of Salvia miltiorrhiza and four related traditional Chinese medicinal preparations by HPLC-DAD method. | 2006 Apr 11 |
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| Determination of four water-soluble compounds in Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system. | 2006 Apr 3 |
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| Improved quality control method for Danshen products--consideration of both hydrophilic and lipophilic active components. | 2006 Jun 7 |
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| Polyphenolic constituents of Actaea racemosa. | 2006 Mar |
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| Acid-promoted reaction of the stilbene antioxidant resveratrol with nitrite ions: mild phenolic oxidation at the 4'-hydroxystiryl sector triggering nitration, dimerization, and aldehyde-forming routes. | 2006 May 26 |
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| Effect of protocatechualdehyde on receptor for advanced glycation end products and TGF-beta1 expression in human lens epithelial cells cultured under diabetic conditions and on lens opacity in streptozotocin-diabetic rats. | 2007 Aug 27 |
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| Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia. | 2007 Jan |
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| One-step separation and purification of 3,4-dihydroxyphenyllactic acid, salvianolic acid B and protocatechualdehyde from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography. | 2007 Jan 26 |
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| Dehydrogenase based reagentless biosensor for monitoring phenylketonuria. | 2007 May 15 |
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| Simultaneous determination and pharmacokinetic study of water-soluble and lipid-soluble components of danshen in rat plasma using HPLC-UV method. | 2007 Nov |
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| [Study on chemical constituents of Orobanche coerulescens]. | 2007 Oct |
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| Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. | 2007 Oct |
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| [Separation of water-soluble active components in Salvia miltiorrhiza bge. f. alba using capillary zone electrophoresis]. | 2007 Sep |
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| Improved quality evaluation of Radix Salvia miltiorrhiza through simultaneous quantification of seven major active components by high-performance liquid chromatography and principal component analysis. | 2007 Sep |
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| Liquid chromatography-tandem mass spectrometry analysis of protocatechuic aldehyde and its phase I and II metabolites in rat. | 2007 Sep 1 |
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| One-step purification of 3,4-dihydroxyphenyllactic acid, salvianolic acid B, and protocatechualdehyde from Salvia miltiorrhiza Bunge by isocratic stepwise hydrogen bond adsorption chromatography on cross-linked 12% agarose. | 2008 Feb |
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| Ameliorating effects of compounds derived from Salvia miltiorrhiza root extract on microcirculatory disturbance and target organ injury by ischemia and reperfusion. | 2008 Feb |
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| Determination of fifteen bioactive components in Radix et Rhizoma Salviae Miltiorrhizae by high-performance liquid chromatography with ultraviolet and mass spectrometric detection. | 2008 Feb |
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| Dynamics of phenolic acids and lignin accumulation in metal-treated Matricaria chamomilla roots. | 2008 Mar |
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DB11268
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139-85-5
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m9272
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50205
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C005581
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8768
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PROTOCATECHUIC ALDEHYDE
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1362689
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4PVP2HCH4T
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22961
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205-377-7
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4PVP2HCH4T
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DTXSID4074512
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4612
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ACTIVE MOIETY
