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Product Name:
3,4-Dihydroxybenzaldehyde
CAS No:
139-85-5
Usage:
ADF
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Product Introduction

3,4-Dihydroxybenzaldehyde (CAS 139-85-5)
Synonym: Protocatechuic aldehyde
Application: An apoptosis inducer of human leukemia cells
CAS Number: 139-85-5
Purity:        ≥98%
Molecular Weight: 138.12
Molecular Formula: C7H6O3

Technical Information

Physical State: Solid
Storage: Store at 4° C
Melting Point: 150-159° C
Boiling Point: ~295.4° C at 760 mmHg (Predicted)
Density: ~1.4 g/cm3 (Predicted)

Safety and Reference Information
PubChem CID: 8768
SMILES: OC1=CC=C(C=O)C=C1O


3,4-Dihydroxybenzaldehyde (CAS 139-85-5), its cas register number is 139-85-5. It also can be called Protocatechualdehyde; Rancinamycin IV; and 4-Formyl-1,2-dihydroxybenzene. It is hazardous, so the first aid measures and others should be known. In addition, 3,4-Dihydroxybenzaldehyde (CAS 139-85-5) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.  3,4-Dihydroxybenzaldehyde (CAS 139-85-5) is an important pharmaceutical intermediate, and can be used for synthesis of antibiotics and anti-inflammatory drugs.

Physical properties about 3,4-Dihydroxybenzaldehyde (CAS 139-85-5) are:
(1)ACD/LogP: 0.934;
(2)ACD/LogD (pH 5.5): 0.93;
(3)ACD/LogD (pH 7.4): 0.72;
(4)ACD/BCF (pH 5.5): 2.99;
(5)ACD/BCF (pH 7.4): 1.84;
(6)ACD/KOC (pH 5.5): 76.12;
(7)ACD/KOC (pH 7.4): 46.86;
(8)#H bond acceptors: 3;
(9)#H bond donors: 2;
(10)Index of Refraction: 1.674 ;
(11)Molar Refractivity: 36.769 cm3;
(12)Molar Volume: 97.959 cm3;
(13)Polarizability: 14.576 10-24cm3;
(14)Surface Tension: 69.0270004272461 dyne/cm;
(15)Density: 1.41 g/cm3;
(16)Flash Point: 146.695 °C;
(17)Enthalpy of Vaporization: 55.655 kJ/mol;
(18)Boiling Point: 295.418 °C at 760 mmHg;
(19)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Wear suitable gloves and eye/face protection;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H;
(2)InChIKey=IBGBGRVKPALMCQ-UHFFFAOYSA-N;
(3)Smilesc1(cc(c(O)cc1)O)C=O

The toxicity data is as follows:

Organism
Test Type
Route
Reported Dose (Normalized Dose)
Effect
Source
mouse
LD50
intraperitoneal
205mg/kg (205mg/kg)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Annales Pharmaceutiques Francaises. Vol. 15, Pg. 461, 1957.
mouse
LD50
intravenous
56mg/kg (56mg/kg)

U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07875,

Electrocatalysis of NADH Oxidation with Electropolymerized Films of 3,4-Dihydroxybenzaldehyde(cas 139-85-5)
The oxidation of 3,4-Dihydroxybenzaldehyde(cas 139-85-5) (3,4-DHB) on glassy carbon electrodes gives rise to stable redox-active electropolymerized films containing a quinone moiety. The redox response of the films is that anticipated for a surface-immobilized redox couple, and the pH dependence of the redox activity of these films is 60 mV/pH unit, which is very close to the anticipated Nernstian dependence of 59 mV/pH unit. We have characterized the dependence of the growth of these films on the solution concentration of 3,4-DHB, the potential for deposition, the time of deposition, and the pH. In addition, we have measured their permeability and apparent diffusion coefficient (D-app) of these films. These films exhibit potent and persistent electrocatalytic behavior toward NADH oxidation. In a now injection analysis determination, the limit of detection is estimated to be in the submicromolar regime.

3,4-Dihydroxybenzaldehyde(cas 139-85-5) purified from the barley seeds (Hordeum vulgare) inhibits oxidative DNA damage and apoptosis via its antioxidant activity
Barley is a major crop worldwide. It has been reported that barley seeds have an effect on scavenging ROS. However, little has been known about the functional role of the barley on the inhibition of DNA damage and apoptosis by ROS. In this study, we purified 3,4-Dihydroxybenzaldehyde(cas 139-85-5) from the barley with silica gel column chromatography and HPLC and then identified it by GC/MS. And we firstly investigated the inhibitory effects of 3,4-Dihydroxybenzaldehyde(cas 139-85-5) purified from the barley on oxidative DNA damage and apoptosis induced by H 2O 2, the major mediator of oxidative stress and a potent mutagen. In antioxidant activity assay such as DPPH radical and hydroxyl radical scavenging assay, Fe 2+ chelating assay, and intracellular ROS scavenging assay by DCF-DA, 3,4-Dihydroxybenzaldehyde(cas 139-85-5) was found to scavenge DPPH radical, hydroxyl radical and intracellular ROS. Also it chelated Fe 2+. In in vitro oxidative DNA damage assay and the expression level of phospho-H2A.X, it inhibited oxidative DNA damage and its treatment decreased the expression level of phospho-H2A.X. And in oxidative cell death and apoptosis assay via MTT assay and Hoechst 33342 staining, respectively, the treatment of 3,4-Dihydroxybenzaldehyde(cas 139-85-5) attenuated H 2O 2-induced cell death and apoptosis. These results suggest that the barley may exert the inhibitory effect on H 2O 2-induced tumor development by blocking H 2O 2-induced oxidative DNA damage, cell death and apoptosis.

Mechanistic study of electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-Dihydroxybenzaldehyde(cas 139-85-5) in the presence of 3-hydroxy-1H-phenalene-1-one

The mechanism of the electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-Dihydroxybenzaldehyde(cas 139-85-5) in the presence of 3-hydroxy-1H-phenalene-1-one as a nucleophile has been studied in water/acetonitrile (80/20 v/v) solution using cyclic voltammetry and controlled-potential coulometry methods. The results indicate that the quinones derived from oxidation of 2,5-dihydroxybenzoic acid and 3,4-Dihydroxybenzaldehyde(cas 139-85-5) participate in Michael addition reactions with 3-hydroxy-1H-phenalene-1-one and via ECE and ECEC mechanisms convert to the different products, with good yield under controlled potential conditions, at carbon electrode.

SYNTHESIS OF 3,4-Dihydroxybenzaldehyde(cas 139-85-5)
A process for the preparation of 3,4 dihydroxybenzaldehyde from p hydroxybenaldehyde, bromine and potassium hydroxide was studied, which comprises the steps of bromation and hydrolysis. The effects of amount of reactants, temperature, pressure, catalyst and the concentration of KOH were investigated. The hydrolysis conditions were determined as follows: molar ratio of KOH to 3 bromo 4 hydroxybenzaldehyde 3∶1, reaction temperature 150 ℃, reaction pressure 0.4 MPa, reaction time 0.5 h, amount of catalyst 4% (based on the mass of 3 bromo 4 hydroxybenzaldehyde). 3,4 Dihydroxybenzaldehyde was given in over 53% yield.