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Cas Database

123-08-0

123-08-0

Identification

  • Product Name:p-Hydroxybenzaldehyde

  • CAS Number: 123-08-0

  • EINECS:204-599-1

  • Molecular Weight:122.123

  • Molecular Formula: C7H6O2

  • HS Code:2912.49

  • Mol File:123-08-0.mol

Synonyms:Benzaldehyde,p-hydroxy- (8CI);4-Formylphenol;4-Hydroxybenzaldehyde;NSC 2127;Parahydroxybenzaldehyde;p-Formylphenol;Benzaldehyde,4-hydroxy-;p-Oxybenzaldehyde;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes: Xi:Irritant;

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 519 Articles be found

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Brady,Jakobovits

, p. 767,769, 777 (1950)

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Selective synthesis of p-hydroxybenzaldehyde by liquid-phase catalytic oxidation of p-cresol

Rode, Chandrashekhar V.,Sonar, Mahesh V.,Nadgeri, Jayprakash M.,Chaudhari, Raghunath V.

, p. 873 - 878 (2004)

Liquid-phase oxidation of p-cresol over insoluble cobalt oxide (Co 3O4) catalyst under elevated pressure of air gave 95% selectivity to p-hydroxybenzaldehyde, an important flavoring intermediate. The selectivity to p-hydroxybenzaldehyde could be enhanced by manipulating the concentrations of p-cresol, sodium hydroxide, and catalyst and the partial pressure of oxygen in such a way that the byproducts normally encountered in this oxidation process were eliminated or minimized significantly.

Practical process for the air oxidation of cresols: Part B. evaluation of the laboratory-scale oxidation process

Barton, Benita,Logie, Catherine G.,Schoonees, Barbara M.,Zeelie, Bernard

, p. 70 - 79 (2005)

Mechanistic proposals and predictions made in a preceding paper (Part A) were evaluated by carrying out the catalytic air oxidation of p-cresol in an alternative solvent system, comprising either a mixture of ethylene glycol and acetic acid (for oxidations under acidic conditions) or ethylene glycol and water (for oxidations under basic conditions). The results obtained in these experiments confirmed that ethylene glycol acts as a nucleophile in these solvent systems, thereby stabilizing the quinomethide intermediate and resulting in highly efficient oxidations in both alkaline and acidic media. 4-Hydroxybenzaldehyde, the desired product, was thus obtained in isolated yields of up to 98% and purities >99%. The inherent draw-backs associated with alkaline methanol and aqueous acetic acid solutions were thus circumvented, and the result is a highly efficient process for the production of 4-hydroxybenzaldehyde.

Synthesis of Copolymers of N-Vinylpyrrolidone with Crotonic Acid Modified with 4-Oxybenzaldehyde

Solovskii,Borisenko,Tarabukina,Amirova

, p. 514 - 519 (2018)

Radical copolymerization of N-vinylpyrrolidone with crotonic acid in 2-propanol has afforded water-soluble products, which have been characterized in terms of composition as well as molecular and hydrodynamic parameters. The obtained copolymers have been modified with 4-oxybenzaldehyde. Structures of the products of the polymer analogous reaction, potential carriers of several bioactive substances, have been confirmed using elemental and functional analysis and spectroscopic data.

A novel practical cleavage of tert-butyl esters and carbonates using fluorinated alcohols

Choy, Jason,Jaime-Figueroa, Saul,Lara-Jaime, Teresa

, p. 2244 - 2246 (2010)

Thermolytic cleavage of t-butyl esters and t-butyl carbonates was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvent. Thus, a practical method to cleanly convert t-butyl esters and carbonates into the corresponding carboxylic acids, decarboxylated products, or alcohols in nearly quantitative yields was developed. The product is recovered by a simple solvent evaporation. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic esters.

Increased para Selectivity in the Reimer-Tiemann Reaction by Use of Polyethylene Glycol as Complexing Agent

Neumann, Ronny,Sasson, Yoel

, p. 569 - 570 (1986)

The para selectivity of the Reimer-Tiemann reaction was increased by use of polyethylene glycol in the reaction medium.The polyethylene glycol complexes the phenolate substrate masking the ortho position of the benzene nucleus increasing para selectivity without affecting the total yield.

Novel and efficient oxidation of benzyl ethers to benzaldehydes by DMSO/49% aq. HBr

Naik, Ramesh,Pasha

, p. 1723 - 1726 (2007)

Dimethylsulfoxide (DMSO) oxidizes benzyl ethers into corresponding benzaldehydes at 110°C; the reaction is accelerated by 49% aq. HBr. The conditions work well for different aryl-substituted benzyl ethers. This protocol is inert toward dialkyl ethers. Copyright Taylor & Francis Group, LLC.

Total synthesis of the proposed structures of gladiosides I and II

Hussain, Nazar,Delar, Emmanilo,Piochon, Marianne,Groleau, Marie-Christine,Tebbji, Faiza,Sellam, Adnane,Déziel, Eric,Gauthier, Charles

, (2021)

Burkholderia gladioli is a Gram-negative bacterium that biosynthesizes a cocktail of potent antimicrobial compounds, including the antifungal phenolic glycoside sinapigladioside. Herein, we report the total synthesis of the proposed structures of gladiosides I and II, two structurally related phenolic glycosides previously isolated from B. gladioli OR1 cultures. Importantly, the physical and analytical data of the synthetic compounds were in significant discrepancies with the natural products suggesting a misassignment of the originally proposed structures. Furthermore, we have uncovered an acid-catalyzed fragmentation mechanism converting the α,β-unsaturated methyl carbamate-containing gladioside II into the aldehyde-containing gladioside I. Our results lay the foundation for the expeditious synthesis of derivatives of these Burkholderia-derived phenolic glycosides, which would enable to decipher their biological roles and potential pharmacological properties.

Aqueous selective photocatalytic oxidation of salicyl alcohol by TiO2 catalysts: Influence of some physico-chemical features

Yurdakal, Sedat,Bellardita, Marianna,Pibiri, Ivana,Palmisano, Leonardo,Loddo, Vittorio

, p. 16 - 24 (2021)

Partial photocatalytic oxidation of salicyl alcohol (2-hydroxybenzyl alcohol) to salicylaldehyde in water was investigated under environmental friendly conditions in the presence of home-prepared and commercial TiO2 (Merck and Aeroxide P25) samples under UVA irradiation. The photocatalysts were characterized by using BET, XRD, SEM and/or TEM techniques. The effects of crystallinity degree, pH (3–11) and presence of a hole trap (ethanol) on the photocatalytic activity and product selectivity were investigated. 4-Hydroxybenzyl alcohol was also used to study the influence of the position of the substituent group in the aromatic ring. High alcohols conversion and product selectivity values were obtained at pH = 11 by using well crystallized TiO2 samples. The conversion values significantly decreased by increasing the hole trap concentration, whereas the selectivity values increased slightly. The selectivity towards the corresponding aldehyde after 30% of alcohol conversion was significantly higher for 4-HBA (48%) than for 2-HBA (32%), due to the role of the para position of the substituent group. In order to clarify the different selectivity of the products, various experiments have been also performed starting from the products; these results indicate that the selectivity is also strongly dependent on the stability of the formed products under the experimental conditions used. By concluding, this article reports that the conversion and selectivity values for the studied reaction depend both on the TiO2 type and on the substrate.

Iron-Catalyzed Synthesis of the Hexahydrocyclopenta[c]furan Core and Concise Total Synthesis of Polyflavanostilbene B

Wang, Xujie,Liu, Fu,Yun, Juping,Feng, Ziming,Jiang, Jianshuang,Yang, Yanan,Zhang, Peicheng

, p. 10127 - 10131 (2018)

The first synthesis of polyflavanostilbene B (1), which has seven contiguous stereocenters including two quaternary carbon centers, from abundant polymeric (?)-epicatechin gallate on a gram scale in three steps without the use of protecting groups is reported. The key transformations of this strategy include a regioselective and stereoselective substitution of resveratrol to give the 4-derivative of (?)-epicatechin 3-gallate and an iron-catalyzed cyclization reaction. The possible radical cyclization mechanism in the formation of the hexahydrocyclopenta[c]furan core is also discussed.

Oxidation of p-cresol to p-hydroxybenzaldehyde with molecular oxygen in the presence of CuMn-oxide heterogeneous catalyst

Wang, Feng,Yang, Guanyu,Zhang, Wei,Wu, Wenhai,Xu, Jie

, p. 633 - 638 (2004)

A high-yield synthesis of p-hydroxybenzaldehyde from p-cresol and molecular oxygen was achieved over a CuMn-oxide supported carbon catalyst. The reaction parameters such as pressure, stirring speed, reaction temperature, solvent, and the amount of sodium hydroxide in the reaction media were optimized. As a result, a high conversion of p-cresol (99%) and a high selectivity to p-hydroxybenzaldehyde (96%) were realized at the same time. Catalyst separation and recycling tests clearly showed that the reaction proceeded on the heterogeneous catalyst but not on dissolved species.

Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging

Fási, Laura,Di Meo, Florent,Kuo, Ching-Ying,Stojkovic Buric, Sonja,Martins, Ana,Kúsz, Norbert,Béni, Zoltán,Dékány, Miklós,Balogh, Gy?rgy Tibor,Pesic, Milica,Wang, Hui-Chun,Trouillas, Patrick,Hunyadi, Attila

, p. 1657 - 1668 (2019)

Cancer cells generally possess higher levels of reactive oxygen species than normal cells, and this can serve as a possible therapeutic target. In this proof-of-concept study, an antioxidant-inspired drug discovery strategy was evaluated using a hydroxycinnamic acid derivative. The processing of oxidized mixtures of p-coumaric acid methyl ester (pcm) revealed a new antitumor lead, graviquinone. Graviquinone bypassed ABCB1-mediated resistance, induced DNA damage in lung carcinoma cells but exerted DNA protective activity in normal keratinocytes, and modulated DNA damage response in MCF-7 cells. The cytotoxic effect of pcm in MCF-7 cells was potentiated under H2O2-induced oxidative stress, and the formation of graviquinone was confirmed by Fenton's reaction on pcm. In silico density functional theory calculations suggested graviquinone as a kinetic product of pcm-scavenging ?OH radicals. Our results demonstrate the pharmacological value of an in situ-formed, oxidative stress-related metabolite of an antioxidant. This might be of particular importance for designing new strategies for antioxidant-based drug discovery.

Highly active nanostructured Co3O4 catalyst with tunable selectivity for liquid phase air oxidation of p-cresol

Kshirsagar, Vikas S.,Vijayanand, Subramanian,Potdar, Hari S.,Joy, Pattayil A.,Patil, Kashinath R.,Rode, Chandrashekhar V.

, p. 310 - 311 (2008)

This is a first report of highly efficient heterogeneous nanostructured Co3O4 catalyst (6-8 nm) having high surface area (95 m2/g) developed for selective liquid phase air oxidation of p7-cresol under atmospheric pressure conditions. Copyright

Enzymatic oxidative coupling of hydroxyphenylglycine derivatives

Guo, Zhi-Wei,Machiya, Koji,Ma, You-An,Sih, Charles J.

, p. 5679 - 5682 (1998)

In contrast to N-protected tyrosine derivatives, N-protected hydroxy-D- phenylglycine derivatives underwent decarboxylation to give 4- hydroxybenzaldehyde under the normal incubation conditions. When both the carboxyl and amino groups of hydroxy-D-phenylglycine are blocked, the C-C and C-O coupling products were obtained in 48% and 32% yields respectively. No racemization of the chiral center was observed for all the substrates examined.

Reduced Graphene Oxide Composite with Oxidizable Manganese/Cobalt Mixed Oxide for p-Cresol Oxidation by Using Molecular Oxygen

Jha, Ajay,Patil, Sagar H.,Solanki, Bhanu P.,Ribeiro, Ana P. C.,Castro, Carlos A. N.,Patil, Kashinath R.,Coronas, Alberto,Rode, Chandrashekhar V.

, p. 1164 - 1169 (2015)

A composite of graphene oxide (GO) with mixed oxide (MnCo) was prepared by using a solvothermal method. During the synthesis, both the reduction of GO and growth of metal oxides took place simultaneously. The as-prepared composite material was highly selective for the liquid-phase oxidation of p-cresol to form p-hydroxybenzaldehyde in 71% yield within 1 h. The composite material was characterised by SEM, X-ray photoelectron spectroscopy, high-resolution TEM and cyclic voltammetry (CV). A CV study revealed that the increase in the redox potential of the mixed oxide after being supported on GO, led to its higher activity of the catalyst for the oxidation reaction. The stability of the catalyst under the reaction conditions was studied by its successful reuse in three cycles.

Specific Catalysis by α-Cyclodextrin on the Dichlorocarbene Attack at Phenolate

Komiyama, Makoto,Hirai, Hidefumi

, p. 2053 - 2056 (1981)

A selsctive attack of dichlorocarbene at the para-position of the phenolate has been achieved by using α-cyclodextrin and the reaction mechanism has been studied by the 13C-NMR and 1H-NMR spectroscopy.The attack of the carbene at the para-position of phenolate (82percent) is dominant over the attack at the ortho-position (18percent) in the presence of 0.15 mol dm-3 of α-cyclodextrin, which is in contrast with the predominance of the ortho-attack (59percent) over the para-attack (41percent) in the absence of α-cyclodextrin.

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Amakasu,T.,Sato,K.

, p. 1428 - 1432 (1967)

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FORMATION OF p-HYDROXYBENZOIC ACID FROM p-COUMARIC ACID BY CELL FREE EXTRACT OF LITHOSPERMUM ERYTHRORHIZON CELL CULTURES

Yazaki, Kazufumi,Heide, Lutz,Tabata, Mamoru

, p. 2233 - 2236 (1991)

The enzymatic formation of p-hydroxybenzoic acid from p-coumaric acid has been detected in cell free extracts of Lithospermum erythrorhizon cell cultures.In the absence of NAD, p-hydroxybenzaldehyde is formed instead of p-hydroxybenzoic acid.The reaction is specific to p-coumaric acid.In addition, a p-hydroxybenzaldehyde dehydrogenase activity is also found.The results suggest that the reaction mechanism is non-oxidative.Key Word Index - Lithospermum erythrorhizon; Boraginaceae; cell culture;biosynthesis; p-hydroxybenzoic acid; p-coumaric acid; p-hydroxybenzaldehyde; shikonin.

Novel synthesis of Ag decorated TiO2 anchored on zeolites derived from coal fly ash for the photodegradation of bisphenol-A

Hlekelele, Lerato,Franklyn, Paul J.,Dziike, Farai,Durbach, Shane H.

, p. 1902 - 1912 (2018)

The disposal of millions of tons of coal fly ash (CFA) threatens the environment, hence means to reuse CFA are highly sought after. In this study, CFA was reused to make materials which were tested for water purification. Zeolitic material (CFA-Zeo) was derived from CFA by a 2-step alkali-fusion hydrothermal method and then composited with TiO2 nanoparticles using a novel resin-gel technique. CFA-Zeo loadings were 15 and 30 wt% in the resulting TiO2/CFA-Zeo composites. These composites were then loaded with 1 wt% Ag nanoparticles by a deposition-precipitation technique using NaOH and urea. CFA-Zeo rods (morphology confirmed by TEM) were confirmed by PXRD to be sodium aluminum silicate hydrate. TEM analyses of the CFA-Zeo rods in the composites revealed them to be completely coated with TiO2 nanoparticles that had Ag nanoparticles on their surfaces. The photoluminescence emission peak of TiO2 was found to be significantly higher than that of TiO2/CFA-Zeo composites, with the TiO2/CFA-Zeo composites that were loaded with Ag having even lower emission intensities. UV-vis DRS spectra showed that CFA-Zeo had no effect on the band gap of TiO2, while composites that contained Ag had a wide absorption band in the visible region. The photocatalytic efficiency of these materials was then determined using bisphenol-A (BPA) as a model compound under both UV and visible light. Except for the 30 wt% TiO2/CFA-Zeo composites without Ag, all of the composites had superior photoactivity to uncomposited TiO2 under both UV and visible light. On the other hand, composites with Ag nanoparticles showed the best photoactivities. The superior photoactivities of these composites under UV-light were mainly attributed to the separation of charge carriers, whereas under visible light it was attributed to the ability of silver to harvest visible light through surface plasmon resonance (SPR).

Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase

Williams, David E.,Steino, Anne,De Voogd, Nicole J.,Mauk, A. Grant,Andersen, Raymond J.

, p. 1451 - 1458 (2012)

Two new merohexaprenoids, halicloic acids A (1) and B (2), have been isolated from the marine sponge Haliclona (Halichoclona) sp. collected in the Philippines. The glycolic acids 1 and 2 slowly decomposed during acquisition of NMR data to aldehydes 3 and 4, respectively, via an oxidative decarboxylation. Halicloic acid B (2) has the new rearranged "haliclane" meroterpenoid carbon skeleton. The halicloic acids 1 and 2 are indoleamine 2,3-dioxygenase inhibitors that are significantly more active than the decomposition products 3 and 4.

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Kratzl,Billek

, p. 845,854 (1954)

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Selective oxidation of aromatic hydrocarbons by potassium and phosphorous-modified iron oxide-silica nanocomposite

Masoudian, Shahla,Monfared, Hassan Hosseini

, p. 37 - 43 (2012)

Supported iron catalysts are active for hydrocarbon oxidation with H 2O2, but the hydrogen peroxide dismutation is a shortcoming that may constrain their applications. Herein, we attempted to address this problem using potassium and phosphate-doped iron oxide-silica nanocomposite (KPFeSi) synthesized via sol-gel methods. The promoted silica-iron oxide nanocomposite has been characterized by elemental analyses, FTIR, X-ray powder diffraction (XRD), scanning electron microscopy (SEM) and Brunauer-Emmett-Teller (BET) surface-size determination. The synthesized KPFeSi was an active catalyst in the low-temperature liquid phase oxidation of various alkyl aromatics with hydrogen peroxide in conversions of 31-78%. Furthermore, the direct oxidation of benzene into phenol using hydrogen peroxide has been achieved in the absence of any acid with this KPFeSi compound. Springer Science+Business Media B.V. 2011.

Photochromism of the synthetic 4′,7-dihydroxyflavylium chloride

Figueiredo, Paulo,Lima, Jo?o C.,Santos, Helena,Wigand, Marie-Claude,Brouillard, Raymond,Ma?anita, António L.,Pina, Fernando

, p. 1249 - 1254 (1994)

The synthetic compound 4′,7-dihydroxyflavylium chloride shows an interesting photochromic effect at moderately acidic pH values. Pale yellow solutions of this compound, equilibrated in the dark at pH 3.4, become bright yellow upon irradiation with 313-nm light. Switching off the light, gives back the initial pale yellow solution. Photochemical methods, 1H NMR, and molecular orbital calculations were used to elucidate this photochromic behavior. In solutions equilibrated in the dark (pH 5.7), the existence of two main species in equilibrium is demonstrated: the colored flavylium cation and the colorless trans-chalcone. Freshly prepared solutions of this compound at pH 6.2 reveal the existence of another colored form, the quinonoidal base, which reacts thermally to yield trans-chalcone. An analogous reaction takes place in freshly prepared solutions at pH 3.4: the flavylium cation is partially converted into trans-chalcone. The extent of such conversion is pH dependent and nearly complete at pH 6.2. Irradiation of transchalcone at the wavelength of 313 nm partially gives back the initial colored form, with concomitant formation of small amounts of photodegradation products. The turnover of the photochromic reaction is greater at pH 3.4 than at pH 6.2. The photochromism is explained on the basis of a trans-cis photoisomerization. In fact the relative stability of the two chalcone isomers is reversed in the excited state, as predicted from molecular orbital calculations.

Metal incorporated Horseradish Peroxidase (HRP) catalyzed oxidation of resveratrol: Selective dimerization or decomposition

Li, Chang,Xu, Xiaofei,Lu, Jing,Wang, Lin,Pan, Yuanjiang

, p. 22976 - 22980 (2013)

Horseradish Peroxidase (HRP) is a commercially available and prevalently used peroxidase with no specific substrate binding domain. However, after being incorporated with different metal cations, new catalytic functions were found in biomimetic oxidation of resveratrol. Based on the results of screening, Ca, Cu, Fe and Mn incorporated enzymes showed distinctive effects, either decomposition or dimerization products were observed.

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Hodgson,Jenkinson

, p. 469,470 (1929)

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BIOSYNTHESIS OF TUBERIN AND XANTHOCILLIN FROM TYROSINE

Herbert, Richard B.,Mann, Jonathan

, p. 4263 - 4266 (1984)

(2S)-Tyrosine (5) is incorporated stereospecifically into tuberin (1) with retention of the 3-pro-S proton and incomplete retention of the 2-S proton; a parallel pathway to the xanthocillin (4) is apparent with stereospecific retention of the 3-pro-R proton of tyrosine; results of experiments with threo- and erythro-3-hydroxytyrosine in relation to tuberin biosynthesis are reported.

A highly stable zeotype mesoporous zirconium metal-organic framework with ultralarge pores

Feng, Dawei,Wang, Kecheng,Liu, Tian-Fu,Park, Jihye,Wei, Zhangwen,Bosch, Mathieu,Zhou, Hong-Cai,Su, Jie,Zou, Xiaodong,Yakovenko, Andrey

, p. 149 - 154 (2015)

Through topological rationalization, a zeotype mesoporous Zr-containing metal-organic framework (MOF), namely PCN-777, has been designed and synthesized. PCN-777 exhibits the largest cage size of 3.8 nm and the highest pore volume of 2.8 cm3 g-1among reported Zr-MOFs. Moreover, PCN-777 shows excellent stability in aqueous environments, which makes it an ideal candidate as a support to incorporate different functional moieties. Through facile internal surface modification, the interaction between PCN- 777 and different guests can be varied to realize efficient immobilization.

Copper and manganese: Two concordant partners in the catalytic oxidation of p-cresol to p-hydroxybenzaldehyde

Wang, Feng,Yang, Guan-Yu,Zhang, Wei,Wu, Wen-Hai,Xu, Jie

, p. 1172 - 1173 (2003)

Copper and manganese were found to be two concordant partners in the synthesis of p-hydroxybenzaldehyde from p-cresol; under mild conditions, this research realised 95.6% selectivity for p-hydroxybenzaldehyde at 98.5% conversion of p-cresol.

PHOTOCATALYTIC OXIDATION OF p-CRESOL IN AQUEOUS TITANUM DIOXIDE SUSPENSION

Brezova, Vlasta,Brandsteterova, Eva,Ceppan, Michal,Pies, Juraj

, p. 1285 - 1293 (1993)

The reaction products of the photocatalytic oxidation of p-cresol were characterized by high performance liquid chromatography.The influence of p-cresol concentration as well as the presence of dioxygen and hydrogen peroxide on the rate of photocatalytic oxidation was studied.The p-cresol concentration in the irradiated systems was determined by spectroscopic method using α-nitroso-β-naphthol or by the Principal Component Regression method (in the samples with hydrogen peroxide added).The reaction pathway of the photocatalytic oxidation of p-cresol in TiO2 was suggested.

-

Tsuji,Ohno

, p. 3969 (1965)

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Mechanism of the redox reaction of the aequorea green fluorescent protein (GFP)

Kojima, Satoshi,Hirano, Takashi,Niwa, Haruki,Ohashi, Mamoru,Inouye, Satoshi,Tsuji, Frederick I.

, p. 2875 - 2878 (1997)

A model compound, 4-(4-hydroxypheny])methylideneimidazol-5 undergoes a reversible redox reaction identical to that of the Aequorea green fluorescent protein (GFP), strongly suggesting that the GFP chromophore is derived via the autoxidation of a nonfluorescent dihydro precursor in dihydro-GFP.

Synthesis and antioxidant properties of a new lipophilic ascorbic acid analogue

Cotelle, Philippe,Cotelle, Nicole,Teissier, Elisabeth,Vezin, Herve

, p. 1087 - 1093 (2003)

4-(4-Hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-2-hydroxyfurane-2-one 1 was prepared by an acidic dimerisation of 4-hydroxyphenylpyruvic acid and some of its antioxidant and spectroscopic properties have been measured and compared to that of ascorbic acid. 1 is as good an antioxidant as ascorbic acid in the DPPH (2,2-diphenyl-1-picryl hydrazyl radical) test and the inhibition of hydroxyl radical and a powerful inhibitor of the Cu2+ or AAPH (2,2′-azobis-(2-amidinopropane) dihydrochloride) induced oxidation of human LDL. 1 gives a stable radical characterised by its ESR spectrum similarly to ascorbic acid but in lower concentration and with a different reactivity towards nitroxides. Theoretical calculations allow us to propose the structure for the radical formed from 1, to explain its lower stability than ascorbyl radical and to evaluate the lipophilicity of 1.

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Omura,Matsuura

, p. 1516 (1969)

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Template-guided selection of RNA ligands using imine-based dynamic combinatorial chemistry

Umuhire Juru, Aline,Cai, Zhengguo,Jan, Adina,Hargrove, Amanda E.

, p. 3555 - 3558 (2020)

This study establishes the applicability of imine-based dynamic combinatorial chemistry to discover non-covalent ligands for RNA targets. We elucidate properties underlying the reactivity of arylamines and demonstrate target-guided amplification of tight

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

Panzella, Lucia,De Lucia, Maria,Amalfitano, Carmine,Pezzella, Alessandro,Evidente, Antonio,Napolitano, Alessandra,D'Ischia, Marco

, p. 4246 - 4254 (2006)

In 0.1 M phosphate buffer, pH 3.0, and at 37 °C, resveratrol ((E)-3,4′,5-trihydroxystilbene, 1a), an antioxidant and cancer chemopreventive phytoalexin, reacted smoothly at 25 μM or 1 mM concentration with excess nitrite ions (NO2-) to give a complex pattern of products, including two novel regioisomeric α-nitro (3a) and 3′-nitro (4) derivatives along with some (E)-3,4′,5-trihydroxy-2, 3′-dinitrostilbene (5), four oxidative breakdown products, 4-hydroxybenzaldehyde, 4-hydroxy-3-nitrobenzaldehyde, 3,5- dihydroxyphenylnitromethane, and 3,5-dihydroxybenzaldehyde, two dimers, the resveratrol (E)-dehydrodimer 6 and restrytisol B (7), and the partially cleaved dimer 2. The same products were formed in the absence of oxygen. 1H, 15N HMBC and LC/MS analysis of the crude mixture obtained by reaction of 1a with Na15NO2 suggested the presence of 3,4′,5,β-tetrahydroxy-α-nitro-α,β-dihydrostilbene (8) as unstable intermediate which escaped isolation. Under similar conditions, the structurally related catecholic stilbene piceatannol ((E)-3,3′,4, 5′-tetrahydroxystilbene, 1b) gave, besides (E)-3,3′,4,5′- tetrahydroxy-β-nitrostilbene (3b), 3,4-dihydroxybenzaldehyde and small amounts of 3,5-dihydroxybenzaldehyde. Mechanistic experiments were consistent with the initial generation of the phenoxyl radical of 1a at 4′-OH, which may undergo free radical coupling with NO2 at the α- or 3′-position, to give eventually nitrated derivatives and/or oxidative double bond fission products, or self-coupling, to give dimers. The oxygen-independent, NO2--mediated oxidative fission of the double bond under mild, physiologically relevant conditions is unprecedented in stilbene chemistry and is proposed to involve breakdown of hydroxynitro(so) intermediates of the type 8.

The Enzyme-catalysed Electrochemical Conversion of p-Cresol into p-Hydroxybenzaldehyde

Hill, H. Allen O.,Oliver, B. Nigel,Page, David J.,Hopper, David J.

, p. 1469 - 1471 (1985)

The electrochemical oxidation of p-cresol was effected enzymically, using either a blue copper protein, azurin, or ferroceneboronic acid as the mediator of the anodic reaction, giving p-hydroxybenzaldehyde as the only product.

Absolute structures of C-glucosides of resveratrol oligomers from Shorea uliginosa

Ito, Tetsuro,Abe, Naohito,Oyama, Masayoshi,Iinuma, Munekazu

, p. 2516 - 2520 (2009)

Two C-glucosides of resveratrol dimers (uliginoside A (1) and hemsleyanoloside B (2)) consisting of enantiomeric aglycones and two C-glucosides of resveratrol trimers (uliginosides B (3) and C (4)) consisting of diastereomeric aglycones were isolated from

Assignment of resonance Raman spectrum of photoactive yellow protein in its long-lived blue-shifted intermediate

Unno, Masashi,Kumauchi, Masato,Sasaki, Jun,Tokunaga, Fumio,Yamauchi, Seigo

, p. 2837 - 2845 (2003)

Photoactive yellow protein (PYP) is a bacterial photoreceptor containing a 4-hydroxycinnamyl chromophore. We report the resonance Raman spectra for the long-lived blue-shifted intermediate of PYP whose chromophore is isotopically labeled with 13C at the carbonyl carbon atom or at the ring carbon atoms. Spectra have been also measured with PYP in D2O where the phenolic hydroxyl group of the chromophore is deuterated. All of the observed Raman bands are assigned on the basis of the observed isotope shifts and normal mode calculations using a density functional theory. The complete assignment provides a satisfactory framework for future investigations of the photocycle mechanism in PYP by vibrational spectroscopy.

A highly photosensitive covalent organic framework with pyrene skeleton as metal-free catalyst for arylboronic acid hydroxylation

Chen, Ying,Huo, Jianqiang,Zhang, Yubao

, (2022/03/16)

Covalent organic frameworks (COFs) have been widely utilized in metal-free photocatalytic synthesis base on their excellent properties such as super conjugation, porosity and stability. In this work, we synthesized a new COF material using 1,3,6,8-Tetrakis (p-formylphenyl)pyrene (TFPPy) and 2,2′-Dimethylbenzidine (DMBZ) as basic units through Schiff base condensation reaction. The new COF (TF-DM COF) was applied as metal-free catalyst for hydroxylation of arylboronic acids. The results indicated that the extended π conjugation of COFs enhanced the absorption of visible light, and the large porosity (BET surface area: 113.782 m2g?1) accelerated the reaction rate. Good recyclability enables it with multiple applications, which result in a great reducing of the cost. This study reports that TF-DM COF has a broad application prospect as a new generation of metal-free photocatalysts for organic conversions.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana

supporting information, p. 1629 - 1632 (2021/02/09)

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Photocatalytic Reductive C-O Bond Cleavage of Alkyl Aryl Ethers by Using Carbazole Catalysts with Cesium Carbonate

Yabuta, Tatsushi,Hayashi, Masahiko,Matsubara, Ryosuke

, p. 2545 - 2555 (2021/02/01)

Methods to activate the relatively stable ether C-O bonds and convert them to other functional groups are desirable. One-electron reduction of ethers is a potentially promising route to cleave the C-O bond. However, owing to the highly negative redox potential of alkyl aryl ethers (Ered -2.6 V vs SCE), this mode of ether C-O bond activation is challenging. Herein, we report the visible-light-induced photocatalytic cleavage of the alkyl aryl ether C-O bond using a carbazole-based organic photocatalyst (PC). Both benzylic and non-benzylic aryl ethers underwent C-O bond cleavage to form the corresponding phenol products. Addition of Cs2CO3 was beneficial, especially in reactions using a N-H carbazole PC. The reaction was proposed to occur via single-electron transfer (SET) from the excited-state carbazole to the substrate ether. Interaction of the N-H carbazole PC with Cs2CO3 via hydrogen bonding exists, which enables a deprotonation-assisted electron-transfer mechanism to operate. In addition, the Lewis acidic Cs cation interacts with the substrate alkyl aryl ether to activate it as an electron acceptor. The high reducing ability of the carbazole combined with the beneficial effects of Cs2CO3 made this otherwise formidable SET event possible.

Biocatalytic Cross-Coupling of Aryl Halides with a Genetically Engineered Photosensitizer Artificial Dehalogenase

Fu, Yu,Huang, Jian,Wu, Yuzhou,Liu, Xiaohong,Zhong, Fangrui,Wang, Jiangyun

supporting information, p. 617 - 622 (2021/02/03)

Devising artificial photoenzymes for abiological bond-forming reactions is of high synthetic value but also a tremendous challenge. Disclosed herein is the first photobiocatalytic cross-coupling of aryl halides enabled by a designer artificial dehalogenase, which features a genetically encoded benzophenone chromophore and site-specifically modified synthetic NiII(bpy) cofactor with tunable proximity to streamline the dual catalysis. Transient absorption studies suggest the likelihood of energy transfer activation in the elementary organometallic event. This design strategy is viable to significantly expand the catalytic repertoire of artificial photoenzymes for useful organic transformations.

Preparation method of P-hydroxybenzaldehyde

-

Paragraph 0066-0069; 0071-0073; 0075-0076; 0078-0079; ..., (2021/07/17)

The invention relates to a preparation method of p-hydroxybenzaldehyde, which comprises the steps of (1) by taking aluminum salt and/or zinc salt as a catalyst, carrying out condensation reaction on phenol and glyoxylic acid under an alkaline condition to obtain 4-hydroxymandelic acid; and (2) oxidizing 4-hydroxymandelic acid serving as a raw material with copper ferrite serving as a catalyst to obtain p-hydroxybenzaldehyde. Compared with the prior art, the method has the advantages of easily available raw materials, mild reaction conditions, high yield and the like.

Process route upstream and downstream products

Process route

4-(1,3-dithiolan-2-yl)phenol
22068-49-1

4-(1,3-dithiolan-2-yl)phenol

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

4-[1,3]dithiolan-2-yl-2-nitro-phenol

4-[1,3]dithiolan-2-yl-2-nitro-phenol

Conditions
Conditions Yield
With bismuth(III) nitrate; water; In benzene; at 20 ℃; for 8h; Product distribution;
methyl p-hydroxycinnamate
3943-97-3,19367-38-5,61240-27-5

methyl p-hydroxycinnamate

3‐nitro‐p‐coumaric acid methyl ester
90729-87-6

3‐nitro‐p‐coumaric acid methyl ester

C<sub>10</sub>H<sub>11</sub>ClO<sub>4</sub>

C10H11ClO4

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

Conditions
Conditions Yield
With hydrogenchloride; water; dihydrogen peroxide; sodium hydroxide; sodium nitrite; In aq. buffer;
para-xylene
106-42-3

para-xylene

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

terephthalaldehyde,
623-27-8

terephthalaldehyde,

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

Conditions
Conditions Yield
With oxygen; WO(x); α -alumina; mixture of; at 560 ℃; Product distribution / selectivity; Gas phase;
55.1%
With oxygen; W12Rb0.02O(x); α -alumina; mixture of; at 580 ℃; Product distribution / selectivity; Gas phase;
55.6%
With oxygen; at 560 ℃; Product distribution / selectivity; Gas phase;
55.1%
With oxygen; at 580 ℃; Product distribution / selectivity; Gas phase;
55.6%
trans-4-Hydroxystilbene
6554-98-9

trans-4-Hydroxystilbene

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

Conditions
Conditions Yield
With oxygen; CoSMDPT; In methanol; 1,2-dichloro-ethane; at 25 ℃; for 5h;
42%
48%
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

Conditions
Conditions Yield
With air; potassium carbonate; at 20 ℃; for 12h;
99%
11%
2-((E)-benzylidene)-6-((E)-4-methoxybenzylidene)cyclohexan-1-one
57083-26-8

2-((E)-benzylidene)-6-((E)-4-methoxybenzylidene)cyclohexan-1-one

E-2-(4-methoxybenzylidene)cyclohexanone
5765-29-7,37722-53-5

E-2-(4-methoxybenzylidene)cyclohexanone

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
Conditions Yield
In water; at 220 ℃; for 4h; Title compound not separated from byproducts.; microwave irradiation;
benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

salicylic alcohol
90-01-7

salicylic alcohol

3-Hydroxybenzyl alcohol
620-24-6

3-Hydroxybenzyl alcohol

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

salicylaldehyde
90-02-8

salicylaldehyde

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With water; oxygen; at 24.84 ℃; for 5h; under 760.051 Torr; Sonication; Irradiation;
benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

salicylaldehyde
90-02-8

salicylaldehyde

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With oxygen; titanium(IV) oxide; In water; Irradiation;
Hexadecanoic acid 4-formyl-phenyl ester
99052-98-9

Hexadecanoic acid 4-formyl-phenyl ester

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

Conditions
Conditions Yield
With sodium hydrogencarbonate; sodium carbonate; In water; dimethyl sulfoxide; at 45 ℃; Rate constant; effect of DMSO ratio;
1-butylpyridinium bromide
874-80-6

1-butylpyridinium bromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

p-butoxybenzaldehyde
5736-88-9

p-butoxybenzaldehyde

Conditions
Conditions Yield
at 100 ℃; Microwave irradiation; Neat (no solvent);
72%
12%

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