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
| Molecular Formula | C7H6O3 |
| Molecular Weight | 138.1207 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| A highly sensitive spectrophotometric determination of micro amounts of vanadium(V) in environmental and alloy samples by using 3,4-dihydroxybenzaldehydeisonicotinoylhydrazone (3,4-DHBINH). | 2008-09 |
|
| Dynamics of phenolic acids and lignin accumulation in metal-treated Matricaria chamomilla roots. | 2008-03 |
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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. | 2008-02 |
|
| Ameliorating effects of compounds derived from Salvia miltiorrhiza root extract on microcirculatory disturbance and target organ injury by ischemia and reperfusion. | 2008-02 |
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| Effect of phenolic aldehydes and flavonoids on growth and inactivation of Oenococcus oeni and Lactobacillus hilgardii. | 2008-02 |
|
| Determination of fifteen bioactive components in Radix et Rhizoma Salviae Miltiorrhizae by high-performance liquid chromatography with ultraviolet and mass spectrometric detection. | 2008-02 |
|
| Simultaneous determination and pharmacokinetic study of water-soluble and lipid-soluble components of danshen in rat plasma using HPLC-UV method. | 2007-11 |
|
| [Study on chemical constituents of Orobanche coerulescens]. | 2007-10 |
|
| Characterization of ligV essential for catabolism of vanillin by Sphingomonas paucimobilis SYK-6. | 2007-10 |
|
| Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. | 2007-10 |
|
| [Inhibition effects of constituents of Radix Salviae Miltiorrhizae on proliferation and procollagen transcription of dermal fibroblasts in systemic sclerosis]. | 2007-09-11 |
|
| Liquid chromatography-tandem mass spectrometry analysis of protocatechuic aldehyde and its phase I and II metabolites in rat. | 2007-09-01 |
|
| [Separation of water-soluble active components in Salvia miltiorrhiza bge. f. alba using capillary zone electrophoresis]. | 2007-09 |
|
| [Studies on polyphenolic chemical constitutents from root of Salvia yunnansis]. | 2007-09 |
|
| Improved quality evaluation of Radix Salvia miltiorrhiza through simultaneous quantification of seven major active components by high-performance liquid chromatography and principal component analysis. | 2007-09 |
|
| 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. | 2007-08-27 |
|
| Isolation and characterization of two phenolic compounds from the stem bark of Musanga cecropioides R. Brown (Moraceae). | 2007-08-02 |
|
| Study on the mechanisms of an extract of Salvia miltiorrhiza on the regulation of permeability of endothelial cells exposed to tumour necrosis factor-alpha. | 2007-07 |
|
| Phytotoxic effects of 21 plant secondary metabolites on Arabidopsis thaliana germination and root growth. | 2007-07 |
|
| [Studies on HPLC-fingerprint of Rhizoma Fagopyri Dibotoryis]. | 2007-06 |
|
| The effect of the major components of Salvia Miltiorrhiza Bunge on bone marrow cells. | 2007-05-22 |
|
| Dehydrogenase based reagentless biosensor for monitoring phenylketonuria. | 2007-05-15 |
|
| Synthesis of L-threo-3,4-dihydroxyphenylserine (L-threo-DOPS) with thermostabilized low-specific L-threonine aldolase from Streptomyces coelicolor A3(2). | 2007-05 |
|
| [Identification of jizhi syrup using HPLC fingerprint]. | 2007-04 |
|
| Protocatechuic aldehyde inhibits hepatitis B virus replication both in vitro and in vivo. | 2007-04 |
|
| [Pharmacokinetic interactions between the main components in the extracts of Salvia miltiorrhiza Bge. in rat]. | 2007-03 |
|
| Preparation and preliminary biological evaluation of a novel 109Pd labeled porphyrin derivative for possible use in targeted tumor therapy. | 2007-03 |
|
| 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. | 2007-01-26 |
|
| Hydrolytic kinetics of lithospermic acid B extracted from roots of Salvia miltiorrhiza. | 2007-01-17 |
|
| Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia. | 2007-01 |
|
| Simultaneous determination of seven active components of Fufang Danshen tablet by high performance liquid chromatography. | 2007-01 |
|
| Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis. | 2006-11-01 |
|
| [Qualitative fingerprint and quantitative determination of caffeic acid in compound dandelion enema]. | 2006-10 |
|
| Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis. | 2006-09-15 |
|
| [Determination of danshensu and protocatechuic aldehyde in Guanxinning injections by reversed-phase high performance liquid chromatography]. | 2006-09 |
|
| [Studies on in vitro culture of adventitious root in Salvia miltiorrhiza]. | 2006-09 |
|
| [Determination of danshensu and protocatechuic aldehyde in Guanxinning injection powder by RP-HPLC]. | 2006-08 |
|
| Fibronectin is essential for hepatitis B virus propagation in vitro: may be a potential cellular target? | 2006-06-09 |
|
| Improved quality control method for Danshen products--consideration of both hydrophilic and lipophilic active components. | 2006-06-07 |
|
| 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. | 2006-05-26 |
|
| Synthesis, physico-chemical and DNA interaction studies of homo- and hetero-trinuclear complexes. | 2006-05-01 |
|
| Comparison of protocatechuic aldchyde in Radix Salvia miltiorrhiza and corresponding pharmacological sera from normal and fibrotic rats by high performance liquid chromatography. | 2006-04-14 |
|
| Simultaneous quantification of six major phenolic acids in the roots of Salvia miltiorrhiza and four related traditional Chinese medicinal preparations by HPLC-DAD method. | 2006-04-11 |
|
| Determination of four water-soluble compounds in Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system. | 2006-04-03 |
|
| [Study of chemical constituents in active parts of Mentha spicata III]. | 2006-04 |
|
| Polyphenolic constituents of Actaea racemosa. | 2006-03 |
|
| Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus. | 2005-12 |
|
| [Analysis of four components in Fufang Danshen Tablets by high performance liquid chromatography with electrochemical and ultraviolet detections]. | 2005-11 |
|
| Aqueous extract of Salvia miltiorrhiza attenuates increased endothelial permeability induced by tumor necrosis factor-alpha. | 2005-10 |
|
| [Effects of mineral cations on the accumulation of tanshinone II A and protocatechuic aldehyde in the adventitious root culture of Salvia niltiorrhiza]. | 2005-06 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:22:13 GMT 2025
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on
Mon Mar 31 19:22:13 GMT 2025
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| Record UNII |
4PVP2HCH4T
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| Record Status |
Validated (UNII)
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| Record Version |
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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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