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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O3
Molecular Weight 138.121
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTOCATECHUALDEHYDE

SMILES

c1cc(c(cc1C=O)O)O

InChI

InChIKey=IBGBGRVKPALMCQ-UHFFFAOYSA-N
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H

HIDE SMILES / InChI

Molecular Formula C7H6O3
Molecular Weight 138.121
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

PubMed

TitleDatePubMed
Redox reaction between amino-(3,4-dihydroxyphenyl)methyl phosphonic acid and dopaquinone is responsible for the apparent inhibitory effect on tyrosinase.
2002 Aug
Peroxynitrite scavenging activities of aromatic compounds isolated from Konnyaku, Amorphophallus konjac K.Koch.
2002 Jun
Modulation of ornithine decarboxylase activity and mitogen-activated protein kinases in protocatechualdehyde-induced apoptosis of CTLL-2 cells.
2002 Nov-Dec
[Medicinal resources of Salvia yunnanensis].
2002 Sep
Simultaneous determination and pharmacokinetic studies on (3,4-Dihydroxyphenyl)-lactic acid and protocatechuic aldehyde in rat serum after oral administration of Radix Salviae miltiorrhizae extract.
2003 Jul
[Determination of danshensu in rat serum after oral administer compound Salvia recipe].
2003 Jun
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
Synthesis and antioxidant activity of 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-benzenediol, a metabolite of Sphaerophysa salsula.
2003 Nov
Characterization of acylated flavonoid-O-glycosides and methoxylated flavonoids from Tagetes maxima by liquid chromatography coupled to electrospray ionization tandem mass spectrometry.
2004
O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase.
2004 Apr
Anti-oxidative compounds in barley tea.
2004 Dec
Purification, crystallization and preliminary X-ray crystallographic analysis of hydroxycinnamoyl-coenzyme A hydratase-lyase (HCHL), a crotonase homologue active in phenylpropanoid metabolism.
2004 Dec
Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid.
2004 Dec 29
Comparative study of electron mediators used in the electrochemical oxidation of NADH.
2004 May 15
Protective effects of Danshensu from the aqueous extract of Salvia miltiorrhiza (Danshen) against homocysteine-induced endothelial dysfunction.
2004 Nov 12
[Effect of danshensu, protocatechualdehyde and danshen injection on calcium ion concentration in cytoplasm of human erythrocytes].
2004 Oct
Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus.
2005 Dec
[Analysis of four components in Fufang Danshen Tablets by high performance liquid chromatography with electrochemical and ultraviolet detections].
2005 Nov
[Study of chemical constituents in active parts of Mentha spicata III].
2006 Apr
Comparison of protocatechuic aldchyde in Radix Salvia miltiorrhiza and corresponding pharmacological sera from normal and fibrotic rats by high performance liquid chromatography.
2006 Apr 14
Determination of four water-soluble compounds in Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system.
2006 Apr 3
[Determination of danshensu and protocatechuic aldehyde in Guanxinning injection powder by RP-HPLC].
2006 Aug
Improved quality control method for Danshen products--consideration of both hydrophilic and lipophilic active components.
2006 Jun 7
Fibronectin is essential for hepatitis B virus propagation in vitro: may be a potential cellular target?
2006 Jun 9
Polyphenolic constituents of Actaea racemosa.
2006 Mar
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
Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis.
2006 Nov 1
[Qualitative fingerprint and quantitative determination of caffeic acid in compound dandelion enema].
2006 Oct
[Determination of danshensu and protocatechuic aldehyde in Guanxinning injections by reversed-phase high performance liquid chromatography].
2006 Sep
[Studies on in vitro culture of adventitious root in Salvia miltiorrhiza].
2006 Sep
Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis.
2006 Sep 15
Protocatechuic aldehyde inhibits hepatitis B virus replication both in vitro and in vivo.
2007 Apr
Simultaneous determination of seven active components of Fufang Danshen tablet by high performance liquid chromatography.
2007 Jan
Hydrolytic kinetics of lithospermic acid B extracted from roots of Salvia miltiorrhiza.
2007 Jan 17
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
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 Jul
Phytotoxic effects of 21 plant secondary metabolites on Arabidopsis thaliana germination and root growth.
2007 Jul
Preparation and preliminary biological evaluation of a novel 109Pd labeled porphyrin derivative for possible use in targeted tumor therapy.
2007 Mar
Isolation and characterization of two phenolic compounds from the stem bark of Musanga cecropioides R. Brown (Moraceae).
2007 Mar-Apr
Synthesis of L-threo-3,4-dihydroxyphenylserine (L-threo-DOPS) with thermostabilized low-specific L-threonine aldolase from Streptomyces coelicolor A3(2).
2007 May
Dehydrogenase based reagentless biosensor for monitoring phenylketonuria.
2007 May 15
Simultaneous determination and pharmacokinetic study of water-soluble and lipid-soluble components of danshen in rat plasma using HPLC-UV method.
2007 Nov
[Study on chemical constituents of Orobanche coerulescens].
2007 Oct
[Separation of water-soluble active components in Salvia miltiorrhiza bge. f. alba using capillary zone electrophoresis].
2007 Sep
[Studies on polyphenolic chemical constitutents from root of Salvia yunnansis].
2007 Sep
[Inhibition effects of constituents of Radix Salviae Miltiorrhizae on proliferation and procollagen transcription of dermal fibroblasts in systemic sclerosis].
2007 Sep 11
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
Determination of fifteen bioactive components in Radix et Rhizoma Salviae Miltiorrhizae by high-performance liquid chromatography with ultraviolet and mass spectrometric detection.
2008 Feb
Dynamics of phenolic acids and lignin accumulation in metal-treated Matricaria chamomilla roots.
2008 Mar
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 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:22:45 UTC 2021
Edited
by admin
on Sat Jun 26 11:22:45 UTC 2021
Record UNII
4PVP2HCH4T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROTOCATECHUALDEHYDE
MI  
Systematic Name English
3,4-DIHYDROXYBENZALDEHYDE
Systematic Name English
4-FORMYL-1,2-DIHYDROXYBENZENE
Systematic Name English
PROTOCATECHUICALDEHYDE [INCI]
Common Name English
NSC-22961
Code English
GM-W03
Brand Name English
BENZALDEHYDE, 3,4-DIHYDROXY-
Systematic Name English
PROTOCATECHUALDEHYDE [MI]
Common Name English
PROTOCATECHUIC ALDEHYDE
Common Name English
DIHYDROXYBENZALDEHYDE, 3,4-
Systematic Name English
PROTOCATECHUICALDEHYDE
INCI  
INCI  
Official Name English
Code System Code Type Description
DRUG BANK
DB11268
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
CAS
139-85-5
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
MERCK INDEX
M9272
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY Merck Index
MESH
C005581
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
PUBCHEM
8768
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
WIKIPEDIA
PROTOCATECHUIC ALDEHYDE
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
RXCUI
1362689
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
205-377-7
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
FDA UNII
4PVP2HCH4T
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
EPA CompTox
139-85-5
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
DRUG CENTRAL
4612
Created by admin on Sat Jun 26 11:22:45 UTC 2021 , Edited by admin on Sat Jun 26 11:22:45 UTC 2021
PRIMARY
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ACTIVE MOIETY