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
• Article Data: 20

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

Description

4-Hydroxy-3-methoxymandelic acid, also known as Vanillylmandelic acid (VMA), is an aromatic ether that serves as a metabolite of catecholamines. It is an off-white solid and is the 3-O-methyl ether of 3,4-dihydroxymandelic acid. VMA is a significant biomarker in the diagnosis of various medical conditions, particularly neuroendocrine tumors.

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

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

Downstream Products

• 97412-19-6 diacetylvanillylmandelic acid 
• 2911-74-2 α-hydroxy-4-hydroxy-3-methoxybenzeneacetic acid methyl ester 
• 195388-21-7 4-hydroxy-3-methoxymandelic acid N-succinimidyl ester 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 121-33-5 vanillin 
• 139473-89-5 4-hydroxy-3-methoxymandelic acid (phenylmethyl) ester 
• 108260-70-4 C₁₁H₁₄O₅ 
• 153750-09-5 4-hydroxy-3-methoxyphenyl alpha acetoxyacetic acid 
• 1259373-03-9 N-(heptan-4-yl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide 
• 41093-71-4 3-methoxy-4-hydroxy mandelic acid 
• 88-14-2 2-furanoic acid 
• 52058-11-4 ethyl 4-hydroxy-3-methoxymandelate 
• 60563-13-5 ethyl homovanillate 
• 15964-80-4 2-(4-hydroxy-3-methoxyphenyl)acetic acid methyl ester 

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.

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 %.

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.