26153-38-8

Basic information

• Product Name: 3,5-Dihydroxybenzaldehyde
• Synonyms: 3,5-DIHYDROXYBENZALDEHYDE;ALPHA-RESORCYLIC ALDEHYDE;3,5-DIHYDOXYBENZAL DEHYDE;3,5-Dihydroxybenzaldehyde,98%;3,5-2-hydroxybenzaldehyde;5-Formylresorcinol, 5-Formylbenzene-1,3-diol;3,5-Dihydroxybenzaldehyde 98%
• CAS NO: 26153-38-8
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• EINECS: 247-479-4
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C7;Carbonyl Compounds;benzaldehyde series
• Mol File: 26153-38-8.mol

Chemical Properties

• Melting Point: 153-158 °C(lit.)
• Boiling Point: 324.291 °C at 760 mmHg
• Flash Point: 164.138 °C
• Appearance: White to tan to gray/Crystalline Powder
• Density: 1.409 g/cm³
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in ethanol and diethyl ether.
• PKA: 8.73±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 1930147
• CAS DataBase Reference: 3,5-Dihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dihydroxybenzaldehyde(26153-38-8)
• EPA Substance Registry System: 3,5-Dihydroxybenzaldehyde(26153-38-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 26153-38-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3,5-Dihydroxybenzaldehyde is used as a building block for the synthesis of 3,5-dihydroxyphenylglycine (3,5-DHPG), which is an important intermediate in the pharmaceutical industry. It is also used in the synthesis of Terbutaline, a significant bronchodilator.
Used in Chemical Synthesis:
3,5-Dihydroxybenzaldehyde is utilized in the synthesis of various complex structures, such as fulgide, 5-bis(undeca-4,6-diynyloxy)benzaldehyde, 3,5-didodecyloxybenzaldehyde, and 1′-methyl-1′,5′-dihydro-2′-(3,5-bis(undeca-4,6-diynyloxy)phenyl)-1H-pyrrolo[3′,4′:1,9](C60-Ih)[5,6]fullerene (F2D).
Used in Condensation Reactions:
3,5-Dihydroxybenzaldehyde has been reported to be used in the condensation of isopropyl ethers of p-hydroxyphenyl acetic acid, leading to the formation of new compounds with potential applications.
Used in Synthesis of Antileishmanial and Antioxidant Agents:
It has been employed in the synthesis of 2,4-dimethylbenzoylhydrazones, which exhibit antileishmanial and antioxidant activities, making it a valuable compound in the development of therapeutic agents against Leishmania infections and oxidative stress-related conditions.

InChI:InChI=1/C7H6O3/c8-4-5-1-6(9)3-7(10)2-5/h1-4,9-10H

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 35354-29-1 3,5-diacetoxybenzoic acid 
• 861532-85-6 3,5-bis-methoxycarbonyloxy-benzoyl chloride 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 65877-43-2 4'-methoxy-stilbene-3,5,3'-triol 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 856077-23-1 3,5-bis-methoxycarbonyloxy-benzaldehyde 
• 39192-49-9 3,5-diacetoxybenzoyl chloride 
• 102-61-4 3,5-dihydroxystilbene 

Downstream Products

• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 446033-33-6 3,5-bis(3,3-dimethyl-1-butyloxy)benzaldehyde 
• 1026787-12-1 3,5-bis(2-methoxyethoxy)benzaldehyde 
• 352287-15-1 (E)-(S)-3-{4-[3-(3,5-bis-cyclopentyloxy-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester 
• 352287-02-6 (E)-(S)-3-{4-[3-(3,5-diisopropoxy-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester 
• 937175-41-2 C₁₅H₂₂O₃ 
• 937175-34-3 C₁₇H₂₄O₄ 
• 352287-17-3 (E)-(S)-3-(4-{3-[3,5-bis-(2,2,2-trifluoro-ethoxy)-phenyl]-allyloxy}-phenyl)-2-ethoxy-propionic acid ethyl ester 
• 937175-40-1 (E)-3-[3,5-bis-(2,2,2-trifluoro-ethoxy)-phenyl]-prop-2-en-1-ol 
• 937175-33-2 (E)-3-[3,5-bis-(2,2,2-trifluoro-ethoxy)-phenyl]-acrylic acid ethyl ester 
• 352287-79-7 C₂₆H₃₄O₆ 
• 192710-87-5 (E)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 

Relevant articles and documents

Synthesis of 3, 5 - dihydroxy benzaldehyde method (by machine translation)

The invention discloses a method for synthesizing 3, 5 - dihydroxy benzaldehyde of the method, the synthetic route is: first 3, 5 - dihydroxy benzoic acid sodium borohydride, dimethyl sulfate, boric acid under the action of the three methyl ester intermediate B obtained, then intermediate B in chromium trioxide and sulfuric acid to obtain compound under the action of the C, i.e. 3, 5 - dihydroxy benzaldehyde; reaction is: The invention of mild synthetic conditions, the reaction yield is high, and the process of the method is simple, the raw material is cheap, simple and convenient operation, is extremely suitable for industrial production, has a very wide range of industrial application and market value. (by machine translation)

Synthesis technology of 3,5-dihydroxy benzaldehyde

The invention belongs to the technical field of synthesis of fine chemical intermediates, and particularly relates to a synthesis technology of 3,5-dihydroxy benzaldehyde. The synthesis technology ofthe 3,5-dihydroxy benzaldehyde comprises the steps of (1) adding an electrophilic activator and a reaction medium into a reaction kettle, stirring and cooling a mixture, adding an oxidizing agent dropwise, adding a 3,5-dihydroxybenzyl alcohol solution dropwise, and adding triethylamine; (2) placing reactant into ice hydrochloric acid, separating liquid, using an extraction agent for extraction, washing, drying and filtering an organic layer, conducting rotary evaporateion on filter liquor to extract a solvent, and obtaining a crude product; and (3) dissolving the crude product in the step (2)in acetone, adding a mixture into normal hexane, which is stirred at a proper speed, dropwise, filtering the mixture to obtain one part of product, freezing filter liquor to obtain the other part of products, and drying the product to obtain the product. The electrophilic activator is oxalyl chloride or thionyl chloride. The oxidizing agent is dimethyl sulfoxide. The reaction medium is dichloromethane or tetrahydrofuran. The extraction agent is diethyl ether or dichloromethane. The synthesis technology of the 3,5-dihydroxy benzaldehyde has the characters of being simple to operate, environmentally friendly, low in cost and high in yield.

Medicinal composition containing resveratrol and being capable of inhibiting drug-resisting staphylococcus aureus

The invention belongs to the field of pharmacy, and relates to compound 3, 4',5-trihydroxy-diphenyl (resveratrol) and applications of the compound 3, 4',5-trihydroxy-diphenyl (resveratrol) in preparing sensitivity enhancing medicines of methicillin-resistant staphylococcus aureus capable of resisting fluoroquinolones. The compound 3, 4',5- trihydroxy-diphenyl (resveratrol) is wide in distribution,at present, resveratrol has been found in plants of at least 21 families, 31 categories and 72 kinds, wherein the contents in grape, polygonum cuspidatum and peanut are relatively high, and no obvious toxic and side effects exist. The antibacterial test shows that the compound has the pharmacological activity of improving the sensitivity of the multidrug-resisting staphylococcus aureus for norfloxacin, especially aiming at the methicillin-resistant staphylococcus aureus SA1199B containing fluoroquinolones-resisting gene NorA, the MIC value of norfloxacin can be reduced by 16 times after the compound and norfloxacin are mixed for use, and further, the composition can be used for preparing antibiotic synergistic medicines.

Photochemical and photocatalytic degradation of trans-resveratrol

Photochemical and photocatalytic degradation of the emerging pollutant trans-resveratrol has been studied under different irradiation wavelengths and using different TiO2 catalysts. trans-Resveratrol was more easily degraded when irradiated usi

Radical-induced oxidation of trans-resveratrol

trans-Resveratrol (RVT) (3,5,4′-trihydroxystilbene), a polyphenolic constituent of red wine, is thought to be beneficial in reducing the incidence of cardiovascular diseases, partly via its antioxidant properties. However, the mechanism of action by which trans-resveratrol displays its antioxidant effect has not been totally unravelled. This study aimed at establishing a comprehensive scheme of the reaction mechanisms of the direct scavenging of HO and O2- radicals generated by water gamma radiolysis. Aerated aqueous solutions of trans-RVT (from 10 to 100 μmol L-1) were irradiated with increasing radiation doses (from 25 to 400 Gy) and further analyzed by UV-visible absorption spectrophotometry for detection of trans-RVT oxidation products. Separation and quantification of RVT and its four oxidation products previously identified by mass spectrometry, i.e., piceatannol (PCT), 3,5-dihydroxybenzoic acid (3,5-DHBA), 3,5-dihydroxybenzaldehyde (3,5-DHB) and para-hydroxybenzaldehyde (PHB), were performed by HPLC/UV-visible spectrophotometry. Determination of the radiolytic yields of trans-RVT consumption and oxidation product formation has allowed us to establish balance between trans-RVT disappearance and the sum of oxidation products formation. Under our conditions, O2- radicals seemed to poorly initiate oxidation of trans-RVT, whereas the latter, whatever its initial concentration, quantitatively reacted with HO radicals, via a dismutation mechanism. Two reaction pathways involving HO-induced trans-RVT primary radicals have been proposed to explain the formation of the oxidation end-products of trans-RVT.

Chemistry of trans-resveratrol with singlet oxygen: [2 + 2] addition, [4 + 2] addition, and formation of the phytoalexin moracin M

Resveratrol (1) reacts with singlet oxygen by two major pathways: A [2 + 2] cycloaddition forming a transient dioxetane that cleaves into the corresponding aldehydes and a [4 + 2] cycloaddition forming an endoperoxide that, upon heating, undergoes a rearrangement to moracin M. The rate constant by which singlet oxygen is removed by 1 (kT) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 ×106 M -1 sec-1 in CD3OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of kT.

Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions

trans-Resveratrol (3,5,4′-trihydroxystilbene) is a natural polyphenolic compound that exhibits antioxidant properties. Our study aimed at studying the HO*-induced oxidation of resveratrol (100 μmol.L-1) in aerated aqueous solutions. Gamma radiolysis of water was used to generate HO*/O2- free radicals (I=10 Gy.min-1, dose=400 Gy). Oxidation products were identified by direct infusion mass spectrometry and high-performance liquid chromatography/mass spectrometry. For each product, structural elucidation was based on simple mass spectra, fragmentation spectra and deuterium/hydrogen exchange spectra; the comparison with mass spectra of synthetic products provided valuable information allowing the complete identification of the oxidation products. Four products resulting from the direct attack of HO. radicals towards resveratrol were identified respectively as piceatannol (trans-3,5,3′,4′-tetrahydroxystilbene), 3,5-dihydroxybenzoic acid, 3,5-dihydroxybenzaldehyde and 4-hydroxybenzaldehyde.

Electroluminescence from a new distyrylbenzene based triazine dendrimer

We have synthesised a new distyrylbenzene cored dendrimer which utilises triazine rings to link the surface groups. It was found that methoxy surface groups were sufficient to give the dendrimer good solubility and good quality thin films could be prepared by spin-coating from solution. The dendrimer was luminescent both in solution and the solid state with the emission occurring from the core. The photoluminescence quantum yield was determined to be 31±3% in the solid state. The dendrimer was incorporated into a single layer light-emitting diode (ITO/dendrimer/Ca) and was found to emit blue light with an external quantum efficiency of 0.003%.