55-10-7

Basic information

• Product Name: 4-Hydroxy-3-methoxymandelic acid
• Synonyms: alpha,4-dihydroxy-3-methoxy-benzeneaceticaci;HYDROXY-3-METHOXYMANDELIC ACID, D,L-4-;DL-4-HYDROXY-3-METHOXYMANDELIC ACID;DL-3-METHOXY-4-HYDROXYMANDELIC ACID;DL-VANILLOMANDELIC ACID;ALPHA,4-DIHYDROXY-3-METHOXYBENZENEACETIC ACID;(+/-)-4-HYDROXY-3-METHOXYMANDELIC ACID;4-HYDROXY-3-METHOXYMANDELIC ACID
• CAS NO: 55-10-7
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.17
• EINECS: 200-224-0
• Product Categories: Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 55-10-7.mol

Chemical Properties

• Melting Point: 132-134 °C (dec.)(lit.)
• Boiling Point: 255.48°C (rough estimate)
• Flash Point: 173.7 °C
• Appearance: white to off-white/powder
• Density: 1.2539 (rough estimate)
• Vapor Pressure: 7.5E-08mmHg at 25°C
• Refractive Index: 1.4570 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: ~50 mg/mL
• PKA: 3.42±0.10(Predicted)
• Water Solubility: freely soluble
• Merck: 14,9933
• BRN: 2213227
• CAS DataBase Reference: 4-Hydroxy-3-methoxymandelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3-methoxymandelic acid(55-10-7)
• EPA Substance Registry System: 4-Hydroxy-3-methoxymandelic acid(55-10-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 55-10-7(Hazardous Substances Data)

Usage

Uses

Used in Medical Diagnostics:
4-Hydroxy-3-methoxymandelic acid is used as a biomarker for the detection and monitoring of neuroendocrine tumors, such as pheochromocytoma and neuroblastoma. Its elevated levels in urine or blood samples can indicate the presence of these tumors, aiding in early diagnosis and treatment planning.
Used in Research:
In the field of research, 4-Hydroxy-3-methoxymandelic acid is used as a valuable tool for studying the metabolism of catecholamines and the underlying mechanisms of various diseases. It helps researchers understand the role of catecholamines in the development and progression of neuroendocrine tumors and other related conditions.
Used in Pharmaceutical Development:
4-Hydroxy-3-methoxymandelic acid is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure makes it a promising candidate for the development of new drugs targeting neuroendocrine tumors and other catecholamine-related disorders.
Used in Environmental Monitoring:
In environmental science, 4-Hydroxy-3-methoxymandelic acid can be used as an indicator of the presence of certain pollutants or contaminants in the environment. Its detection in soil, water, or air samples can provide valuable information about the sources and pathways of these pollutants, enabling the development of effective mitigation strategies.

Biochem/physiol Actions

Epinephrine and norepineprine metabolite.

InChI:InChI=1/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)

Upstream product

• 52058-11-4 ethyl 4-hydroxy-3-methoxymandelate 
• 90-05-1 2-methoxy-phenol 
• 298-12-4 Glyoxilic acid 
• 67-66-3 chloroform 
• 121-33-5 vanillin 
• 2706-75-4 sodium glyoxylate 
• 120-80-9 benzene-1,2-diol 
• 2979-24-0 2-methoxycyclohexanol 
• 62-76-0 sodium oxalate 
• 110-83-8 cyclohexene 

Downstream Products

• 97412-19-6 diacetylvanillylmandelic acid 
• 2911-74-2 α-hydroxy-4-hydroxy-3-methoxybenzeneacetic acid methyl ester 
• 88-14-2 2-furanoic acid 
• 52058-11-4 ethyl 4-hydroxy-3-methoxymandelate 
• 121-33-5 vanillin 
• 195388-21-7 4-hydroxy-3-methoxymandelic acid N-succinimidyl ester 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 2034-60-8 1-(4-hydroxy-3-methoxy-phenyl)-propane-1,2-dione 
• 854671-16-2 1-acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-3-chloro-acetone 
• 854676-35-0 1-acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-3-diazo-acetone 
• 854668-61-4 1,3-diacetoxy-1-(4-acetoxy-3-methoxy-phenyl)-acetone 
• 139473-89-5 4-hydroxy-3-methoxymandelic acid (phenylmethyl) ester 
• 306-08-1 Homovanillic acid 
• 1148126-54-8 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetate 

Relevant articles and documents

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.

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

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 %.

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.

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.

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.

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.

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.

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.

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