cas 55-10-7, 4-Hydroxy-3-methoxymandelic acid

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Design, synthesis, and evaluation of phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents
In this paper, we designed and synthesized a series of novel phenylpiperazine-phenylacetate derivatives as rapid recovery hypnotic agents. The best compound 10 had relatively high affinity for the GABAA receptor and low affinity for thirteen other off-target receptors. In three animal models (mice, rats, and rabbits), compound 10 exerted potent hypnotic effects (HD50 = 5.2 mg/kg in rabbits), comparable duration of the loss of righting reflex (LORR), and significant shorter recovery time (time to walk) than propanidid. Furthermore, compound 10 (TI = 18.1) showed higher safety profile than propanidid (TI = 14.7) in rabbits. Above results suggested that compound 10 may have predictable and rapid recovery profile in anesthesia.
Qi, Zhaoyang,Li, Ziying,Zhu, Mo,Zhang, Xiaohua,Zhang, Guisen,Zhuang, Tao,Chen, Yin,Huang, Ling
(2021/12/20)

An efficient environmentally friendly CuFe2O4/SiO2catalyst for vanillyl mandelic acid oxidation in water under atmospheric pressure and a mechanism study
With the aim of the green production of vanillin, a highly efficient environmentally friendly oxidation system was introduced to oxidize vanillyl mandelic acid (VMA) with a porous CuFe2O4/SiO2 component nano-catalyst in aqueous solution under atmospheric pressure. The N2 adsorption-desorption pattern indicated that CuFe2O4/SiO2 possessed a much higher specific surface area (49.98 m2 g-1) than that of CuFe2O4 (5.02 m2 g-1), which further indicated that the SiO2 substrate restrained the aggregation of CuFe2O4 nanoparticles. The conversion for VMA and selectivity for vanillin reached 98% and 96%, respectively, under atmospheric pressure. The excellent catalytic performance was attributed to the synergistic effect of the catalytic capacity of CuFe2O4 and the adsorption capacity for the reactant of SiO2. Simultaneously, the effect of different reaction conditions for catalyst activity and selectivity were investigated. Furthermore, the probable mechanism of VMA oxidation was investigated by in situ ATR-FTIR, H2-TPR, XPS and 1H NMR. More importantly, the decarboxylation was verified to proceed in basic conditions rather than in conventional acidic conditions. This journal is
Mao, Haifang,Wang, Hongzhao,Meng, Tao,Wang, Chaoyang,Hu, Xiaojun,Xiao, Zuobing,Liu, Jibo
p. 982 - 992
(2021/01/25)

Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids
The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine-diphosphate-dependent (ThDP) oxalyl-CoA decarboxylase (OXC)/2-hydroxyacyl-CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl-CoA thioester substrates through the release of the C1-unit formyl-CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C1-extensions of various aldehydes to yield the corresponding 2-hydroxyacyl-CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl-CoA synthetase and a 2-hydroxyacyl-CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable (S)-α-hydroxy acids with enantiomeric excess up to 99 %.
Burgener, Simon,Cortina, Ni?a Socorro,Erb, Tobias J.
supporting information
p. 5526 - 5530
(2020/02/20)

Method for preparing 3-methoxy-4-hydroxymandelic acid
The invention belongs to the technical field of the condensation reaction of glyoxylic acid and phenols, and provides a method for preparing 3-methoxy-4-hydroxymandelic acid. The method comprises thefollowing steps: in the presence of a catalyst, a phenolic compound and a glyoxylic acid aqueous solution are contacted in an alkaline solution for the condensation reaction to produce 3-methoxy-4-hydroxymandelic acid, wherein the catalyst is selected from a metal-Salen complex which contain a ligand with a quaternary ammonium salt cation, or a catalytic system of a metal-Salen complex as a main catalyst and an organic base containing a cation as a co-catalyst. According to the method, the aldehyde group can be activated, the activity of the condensation reaction is improved, the selectivity of the p-condensation product is improved, and the yield of the p-product, namely 3-methoxy-4-hydroxymandelic acid, is improved.
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Paragraph 0081-0145

(2019/07/16)

Phenylacetic acid ester compound and use thereof
The invention relates to a phenylacetate compound as shown in a general formula (I) and a pharmaceutical composition containing the phenylacetate compound, as well as application in anesthesia and sedation.
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Paragraph 0059-0064

(2019/03/02)

Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells
With raising prevalence of obesity, the regulation of human body fat is increasingly relevant. The modulation of fatty acid uptake by enterocytes represents a promising target for body weight maintenance. Recent results demonstrated that the trigeminal active compounds capsaicin, nonivamide, and trans-pellitorine dose-dependently reduce fatty acid uptake in differentiated Caco-2 cells as a model for the intestinal barrier. However, non-pungent alternatives have not been investigated and structural determinants for the modulation of intestinal fatty acid uptake have not been identified so far. Thus, based on the previous results, we synthesized 23 homovanillic acid esters in addition to the naturally occurring capsiate and screened them for their potential to reduce intestinal fatty acid uptake using the fluorescent fatty acid analog Bodipy-C12 in differentiated Caco-2 cells as an enterocyte model. Whereas pre-incubation with 100 μM capsiate did not change fatty acid uptake by Caco-2 enterocytes, a maximum inhibition of ?47% was reached using 100 μM 1-methylpentyl-2-(4-hydroxy-3-methoxy-phenyl)acetate. Structural analysis of the 24 structural analogues tested in the present study revealed that a branched fatty acid side chain, independent of the chain length, is one of the most important structural motifs associated with inhibition of fatty acid uptake in Caco-2 enterocytes. The results of the present study may serve as an important basis for designing potent dietary inhibitors of fatty acid uptake.
Lieder, Barbara,Hans, Joachim,Hentschel, Fabia,Geissler, Katrin,Ley, Jakob
(2019/10/14)

METHOD FOR PRODUCING AN AROMA SUBSTANCE
A method of preparing a compound of formula (IV) where R1 is alkyl of 1 to 4 carbon atoms, comprises reacting cyclohexene with hydrogen peroxide and an alcohol R1OH in the presence of a catalyst comprising a zeolite of framework structure MWW, wherein the framework of the zeolite comprises silicon, titanium, boron, oxygen and hydrogen.
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(2017/10/17)

A vanillin clean production method
The invention discloses a clean production method of oxidizing 3-methoxy-4-hydroxy mandelic acid for joint production of vanillin and superfine silver powder under an alkaline condition by adopting silver nitrate. The clean production method comprises the following steps: adding a silver nitrate solution, a 3-methoxy-4-hydroxy mandelic acid solution and a sodium hydroxide solution in a parallel flow manner into a reactor, reacting to generate a 3-methoxy-4-hydroxy acetophenone sodium solution and superfine silver powder, filtering and separating the generated silver powder, washing with deionized water and ethyl alcohol sequentially, and drying to obtain the superfine silver powder, wherein the reduction yield of the silver powder is 99.4 per cent to 100 per cent; acidizing filter liquor after the silver powder is separated, performing decarboxylation on 3-methoxy-4-hydroxy benzoylformic acid to generate the vanillin, using methylbenzene to extract the vanillin therein, recycling the methylbenzene solvent, and performing recrystallization on residues in an ethanol aqueous solution to obtain the vanillin, wherein the oxidation yield of the methoxy-4-hydroxy mandelic acid is 95.7 per cent to 98.5 per cent. The silver nitrate is taken as an oxidizing agent to prepare the vanillin, so that the oxidation yield is improved, and the oxidation reaction time is shortened. Two practical fine chemical products can be produced simultaneously, the raw materials can be sufficiently utilized, the generation of waste materials is reduced, the production cost is reduced, and the technological process is safe and environment-friendly.
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Paragraph 0035

(2017/09/12)

Method for producing alkoxy-hydroxybenzaldehyde that is substantially free of alkyl-alkoxy-hydroxybenzaldehyde
The invention relates to a method for producing at least one alkoxy-hydroxybenzaldehyde (AHBA) from at least one hydroxyphenol (HP), said method being characterised in that it comprises the formation of at least one alkoxyphenol (AP) and alkyl-alkoxyphenol (AAP) and the separation (S) of AP from AAP, said separation (S) being carried out prior to obtaining AHBA.
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(2015/07/27)

Improved synthesis of 3-methoxy-4-hydroxymandelic acid by glyoxalic acid method
The most important industrial process for the synthesis of vanillin is performed in two steps involving an condensation reaction of glyoxalic acid with guaiacol followed by an oxidative decarboxylation of the intermediary 3-methoxy-4-hydroxymandelic acid
Niu, Dong-Fang,Li, Hui-Cheng,Zhang, Xin-Sheng
p. 8174 - 8177
(2013/09/02)

Synthesis of racemic mandelic acids with the composite phase transfer catalyst β-cyclodextrin-[bmim]PF6
Ionic liquids were employed as a part of composite phase transfer catalyst to synthesise mandelic acid, and it is found that [bmim]PF6 coupled with β-cyclodextrin is the most effective catalyst, which was also applicable to other reactions used to synthesise mandelic acid derivatives. Reaction conditions were optimized and the products were characterised by 1H NMR and IR.
Yang, Ben-Yong,Yang, De-Hong
experimental part
p. 484 - 485
(2011/11/29)

METHOD FOR PREPARING OPTIONALLY SUBSTITUTED P-HYDROXYMANDELIC COMPOUNDS AND DERIVATIVES THEREOF
The invention relates to a method for preparing optionally substituted P-hydroxymandelic compounds and derivatives thereof. The method for preparing the mandelic compounds of the invention comprises condensing in water, in the presence of an alkaline agent, an aromatic compound bearing at least one hydroxyl group and having a free para position, with glycoxylic acid, wherein said method is characterised in that said reaction is carried out in a piston-flow reactor.
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Page/Page column 5

(2011/02/15)

Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene
The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon α-methylation and α-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (>1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date.
Appendino, Giovanni,Ech-Chahad, Abdellah,Minassi, Alberto,De Petrocellis, Luciano,Marzo, Vincenzo Di
scheme or table
p. 97 - 99
(2010/04/06)

Synthesis of mandelic acid derived phthalimides as a new class of antiinflammatory and antimicrobial agents
In the present study, a new series of 2-(1,3-dioxo-2,3-dihydro-1H-2- isoindolyl) ethyl 2-hydroxy-2-(substituted phenyl) acetates 6a-e have been synthesized from the combination of N-(2-hydroxy ethyl) phthalimide 5 and substituted mandelic acids 2a-e which resulted in both anti-inflammatory and antimicrobial activity. These compounds have been characterized by IR, 1H NMR, mass spectral and elemental analysis. Among the compounds tested for anti-inflammatory activity, compound 6b and 6c showed significant activity and compound 6d showed potent antibacterial and antifungal activity. The anti-inflammatory activity has been determined by carrageenan induced acute paw oedema in rats. The results are discussed in the text. The in vitro antibacterial and antifungal activity of the compounds have been evaluated by paper disc diffusion method. The minimum inhibitory concentrations (MIC) of the compounds have also been determined by agar streak dilution method.
Varala, Ravi,Kotra, Vijay,Alam, M. Mujahid,Kumar, N. Ramesh,Ganapaty,Adapa, Srinivas R.
p. 1243 - 1248
(2008/12/23)

Method for preparing p-hydroxymandelic compounds optionally substituted
The invention concerns a method for preparing p-hydroxymandelic compounds optionally substituted and their derivatives. More particularly, it concerns a method for preparing p-hydroxymandelic acid and methoxy-3 p-hydroxymandelic acid and their derivatives. The invention concerns a method for preparing p-hydroxymandelic compounds optionally substituted and their derivatives, which consists in condensing in water, in the presence of an alkaline agent, an aromatic compound bearing at least a hydroxyl group and whereof the position in para is free, with glyoxylic acid, said method being characterised in that the reaction is carried out in the presence of an efficient amount of a compound bearing at least two carboxylic functions.
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Page column 10

(2008/06/13)

Competitive immunoassay (Cat-EIA), a helpful technique for catalytic antibody detection. Part II
The Cat-EIA procedure, described in part I, was successfully applied to the screening of 5 different catalytic activities on a given set of 11 mAbs. The precautions required to devoid false-positive identification (preceding paper), were taken into account. Two catalytic activities were thus detected, including a newly thioacetal hydrolysis.
Taran,Renard,Creminon,Valleix,Frobert,Pradelles,Grassi,Mioskowski
p. 1891 - 1894
(2007/10/03)

Competitive immunoassay (Cat-EIA), a helpful technique for catalytic antibody detection. Part I
A competitive immunoassay procedure for the screening of catalytic antibodies is reported. This screening approach (Cat-EIA) is a modification of the well-known Cat-ELISA technique avoiding the substrate modification step. It has been developed for a bimolecular reaction and has been tested on a high number of hybridoma clones. The current study explores for the first time the utility and feasibility of this method for the early detection of catalytic antibodies.
Taran,Renard,Creminon,Valleix,Frobert,Pradelles,Grassi,Mioskowski
p. 1887 - 1890
(2007/10/03)

3-methoxy-4-hydroxyphenylglycol fluorescence polarization immunoassay
The present invention is directed to a fluoroescence polarization immunoassay for determining the 3-methoxy-4-hydroxyphenylglycol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer.
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(2008/06/13)

Process for preparing aromatic hydroxyaldehydes
Aromatic hydroxy aldehydes are prepared by the simultaneous oxidation and decarboxylation of hydroxy aryl glycolic acids by reacting same with oxidizing agents in aqueous-acid medium.
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(2008/06/13)

IMPROVED PROCEDURE FOR SYNTHESIS OF DL-4-HYDROXY-3-METHOXYMANDELIC ACID (DL- ″VANILLYL″ -MANDELIC ACID, VMA).
The procedure involves slow additon of an ice-cold, aqueous solution of glyoxylic acid to an ice-cold alkaline solution of guaiacol, with efficient mechanical stirring. This one-step condensation procedure provides VMA in 68-75 percent yield.
Fatiadi,Schaffer
p. 411 - 412
(2007/10/06)