4385-56-2

Basic information

• Product Name: 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID
• Synonyms: 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID;HOMOSYRINGIC ACID;(4-Hydroxy-3,5-dimethoxyphenyl)acetic acid;Benzeneacetic acid, 4-hydroxy-3,5-dimethoxy-;4-Hydroxy-3,5-dimethoxybenzeneacetic acid;3,5-Dimethoxy-4-hydroxyphenylacetic acid 97%;2-(4-hydroxy-3,5-dimethoxyphenyl)acetic acid;RARECHEM AL BO 0593
• CAS NO: 4385-56-2
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.2
• EINECS: 224-494-4
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;C10;Carbonyl Compounds;Carboxylic Acids
• Mol File: 4385-56-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 127-131 °C(lit.)
• Boiling Point: 397.1 °C at 760 mmHg
• Flash Point: 158.7 °C
• Appearance: /
• Density: 1.299 g/cm³
• Vapor Pressure: 5.08E-07mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.29±0.10(Predicted)
• CAS DataBase Reference: 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID(4385-56-2)
• EPA Substance Registry System: 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID(4385-56-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 4385-56-2(Hazardous Substances Data)

Usage

General Description

3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID is a chemical compound with the molecular formula C10H12O5. It is a derivative of phenylacetic acid, which is commonly found in various plants and fruits. 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID is known for its antioxidant properties and potential therapeutic applications, particularly in the treatment of neurodegenerative disorders. It has also been studied for its anti-inflammatory and anticancer activities. Additionally, 3,5-DIMETHOXY-4-HYDROXYPHENYLACETIC ACID has been identified as a metabolite of the psychoactive drug mescaline, indicating its role in the body's biotransformation processes. Overall, this chemical compound has garnered interest for its potential pharmaceutical and physiological effects.

InChI:InChI=1/C10H12O5/c1-14-7-3-6(5-9(11)12)4-8(15-2)10(7)13/h3-4,13H,5H2,1-2H3,(H,11,12)

Upstream product

• 91144-18-2 syringylglyoxalic acid 
• 105105-04-2 (4-acetoxy-3,5-dimethoxy-phenyl)-acetonitrile 
• 42973-55-7 4-hydroxy-3,5-dimethoxyphenylacetonitrile 
• 358742-96-8 methyl 2-(3,5-dimethoxy-1-methyloxycarbonyl-4-oxo-2,5-cyclohexadienyl)ace 
• 99988-74-6 (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxothiazolidin-4-one 
• 99866-07-6 3-(4-hydroxy-3,5-dimethoxy-phenyl)-2-thioxo-propionic acid 
• 99856-67-4 3-(4-hydroxy-3,5-dimethoxy-phenyl)-2-hydroxyimino-propionic acid 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 39667-14-6 2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol 
• 1292298-65-7 4-(2-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxoethoxy)-4-oxobutan-1-ammonium-2,2,2-trifluoroacetate 
• 51149-28-1 2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone 
• 284043-14-7 4-tert-butoxycarbonylamino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester 
• 22802-00-2 1-(4-acetoxy-3,5-dimethoxy-phenyl)-2-diazo-ethanone 
• 861085-86-1 2-diazo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone 

Downstream Products

• 20824-45-7 4-hydroxy-3,5-dimethoxyphenethyl alcohol 
• 100118-51-2 (4-acetoxy-3,5-dimethoxy-phenyl)-acetic acid 
• 42973-69-3 2-(4-Hydroxy-3,5-dimethoxy-phenyl)-N-[2-(4-hydroxy-3,5-dimethoxy-phenyl)-ethyl]-acetamide 
• 42973-68-2 3,5-Dimethoxy-4-hydroxyphenylacetamid 
• 39500-13-5 4,4'-Diacetoxy-3,5-dimethoxybibenzyl 
• 488855-69-2 N-[3-(3,4-dimethyl-phenyl)-propyl]-2-(4-hydroxy-3,5-dimethoxy-phenyl)-acetamide 
• 35263-53-7 1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-one 
• 27065-69-6 2-(4-benzyloxy-3,5-dimethoxyphenyl)acetic acid 
• 1224591-71-2 C₁₉H₂₀N₂O₈ 
• 1426853-74-8 C₂₀H₂₂O₈ 
• 1426853-75-9 C₁₉H₂₀O₇ 
• 1426853-76-0 (E)-methyl 3-(benzo[d][1,3]dioxol-5-yl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acrylate 
• 1426853-77-1 C₁₉H₁₈O₇ 
• 1426853-72-6 C₁₉H₂₂O₆ 

Relevant articles and documents

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

2-Diazo-1-(4-hydroxyphenyl)ethanone: A versatile photochemical and synthetic reagent

α-Diazo arylketones are well-known substrates for Wolff rearrangement to phenylacetic acids through a ketene intermediate by either thermal or photochemical activation. Likewise, α-substituted p-hydroxyphenacyl (pHP) esters are substrates for photo-Favorskii rearrangements to phenylacetic acids by a different pathway that purportedly involves a cyclopropanone intermediate. In this paper, we show that the photolysis of a series of α-diazo-p- hydroxyacetophenones and p-hydroxyphenacyl (pHP) α-esters both generate the identical rearranged phenylacetates as major products. Since α-diazo-p-hydroxyacetophenone (1a, pHP N2) contains all the necessary functionalities for either Wolff or Favorskii rearrangement, we were prompted to probe this intriguing mechanistic dichotomy under conditions favorable to the photo-Favorskii rearrangement, i.e., photolysis in hydroxylic media. An investigation of the mechanism for conversion of 1a to p-hydroxyphenyl acetic acid (4a) using time-resolved infrared (TRIR) spectroscopy clearly demonstrates the formation of a ketene intermediate that is subsequently trapped by solvent or nucleophiles. The photoreaction of 1a is quenched by oxygen and sensitized by triplet sensitizers and the quantum yields for 1a-c range from 0.19 to a robust 0.25. The lifetime of the triplet, determined by Stern-Volmer quenching, is 31 ns with a rate for appearance of 4a of k = 7.1 × 10 6 s-1 in aq. acetonitrile (1:1 v:v). These studies establish that the primary rearrangement pathway for 1a involves ketene formation in accordance with the photo-Wolff rearrangement. Furthermore we have also demonstrated the synthetic utility of 1a as an esterification and etherification reagent with a variety of substituted α-diazo-p- hydroxyacetophenones, using them as synthons for efficiently coupling it to acids and phenols to produce pHP protect substrates. The Royal Society of Chemistry and Owner Societies.

Synthesis and evaluation of 4-hydroxyphenylacetic acid amides and 4-hydroxycinnamamides as antioxidants

4-Hydroxyphenylacetic acid amides and 4-hydroxycinnamamides were synthesized and their antioxidant and neuroprotective activities were evaluated. Among the prepared compounds, 6f, 6g, 8b, and 9 exhibited potent inhibition of lipid peroxidation in rat brain homogenates, and marked DPPH radical scavenging activities. Furthermore, 6f, 6g, and 9 exhibited neuroprotective action against the oxidative damage induced by the exposure of primary cultured rat cortical cells to H2O2, xanthine/xanthine oxidase, or Fe2+/ascorbic acid. Based on these results, we found that 6f was the most potent antioxidant among the compounds tested.