1678-71-3

Basic information

• Product Name: Benzeneacetic acid, a,2-dihydroxy-
• Synonyms: Mandelicacid, o-hydroxy- (6CI,7CI,8CI); NSC 126698; o-Hydroxymandelic acid
• CAS NO: 1678-71-3
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.1467
• Mol File: 1678-71-3.mol

Chemical Properties

• Boiling Point: 397.5°Cat760mmHg
• Flash Point: 208.4°C
• Density: 1.48g/cm³
• CAS DataBase Reference: Benzeneacetic acid, a,2-dihydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a,2-dihydroxy-(1678-71-3)
• EPA Substance Registry System: Benzeneacetic acid, a,2-dihydroxy-(1678-71-3)

Safety Data

• Hazardous Substances Data: 1678-71-3(Hazardous Substances Data)

Upstream product

• 408507-52-8 2-amino-DL-mandelic acid 
• 611-71-2 MANDELIC ACID 
• 34073-50-2 3-diazo-2,3-dihydro-2-benzofuranone 
• 118-93-4 o-hydroxyacetophenone 
• 298-12-4 Glyoxilic acid 
• 108-95-2 phenol 
• 17392-15-3 2-hydroxy-3(2H)-benzofuranone 
• 484-38-8 isatic acid 
• 34073-47-7 C₁₅H₁₂N₂O₄S 
• 22303-62-4 3-hydroxy-3H-benzofuran-2-one 
• 17392-16-4 (2-hydroxyphenyl)oxoacetic acid 

Downstream Products

• 235792-38-8 methyl 2-hydroxymandelate 
• 614-75-5 2-Hydroxyphenylacetic acid 

Relevant articles and documents

Kinetics and mechanism of hydrolysis of 3-diazobenzofuran-2-one and its hydrolysis product (3-hydroxybenzofuran-2-one)

Rates of acid-catalyzed hydrolysis of 3-diazobenzofuran-2-one, measured in concentrated aqueous perchloric acid and hydrochloric acid solutions, were found to correlate well with the Cox-Yates Xo excess acidity function, giving kH+ = 1.66 × 10-4 M-1 s-1, m? = 0.86 and kH+/kD+ = 2.04. The normal direction (kH/kD > 1) of this isotope effect indicates that hydrolysis occurs by rate-determining protonation of the substrate on its diazo-carbon atom. It was found previously that the next higher homolog of the present substrate, 4-diazoisochroman-3-one, also undergoes hydrolysis by this reaction mechanism but with a rate constant 15 times greater than that for the present substrate; this difference in reactivity can be understood in terms of the various resonance forms that contribute to the structures of these substrates. The product of the present hydrolysis reaction is 3-hydroxybenzofuran-2-one, which itself quickly undergoes subsequent acid-catalyzed hydrolysis to 2-hydroxymandelic acid. The acidity dependence of this subsequent hydrolysis is much shallower than that of the diazo compound precursor, and rates of reaction correlate as well with [H+] as with Xo. This is due in part to incursion of a nonproductive protonation on the hydroxy group of 3-hydroxybenzofuran-2-one that impedes hydrolysis and produces saturation of acid catalysis. Rates of hydrolysis of the hydroxy compound were also measured in dilute HClO4 and NaOH solutions as well as in CH3CO2H, H2PO4-, (CH2OH)3CNH3-, and NH4- buffers, and the rate profile constructed from these data showed the presence of uncatalyzed and hydroxide ion-catalyzed reactions. This hydroxide-ion catalysis became saturated at [NaOH] ? 0.05 M, implying occurrence of yet another nonproductive substrate ionization.

QUINONE METHIDE ANALOG SIGNAL AMPLIFICATION

Disclosed herein are novel quinone methide analog precursors and embodiments of a method and a kit of using the same for detecting one or more targets in a biological sample. The method of detection comprises contacting the sample with a detection probe, then contacting the sample with a labeling conjugate that comprises an enzyme. The enzyme interacts with a quinone methide analog precursor comprising a detectable label, forming a reactive quinone methide analog, which binds to the biological sample proximally to or directly on the target. The detectable label is then detected. In some embodiments, multiple targets can be detected by multiple quinone methide analog precursors interacting with different enzymes without the need for an enzyme deactivation step.

Photoreactions of 3-Diazo-3H-benzofuran-2-one; Dimerization and Hydrolysis of Its Primary Photoproduct, A Quinonoid Cumulenone: A Study by Time-Resolved Optical and Infrared Spectroscopy

Light-induced deazotization of 3-diazo-3H-benzofuran-2-one (1) in solution is accompanied by facile (CO)-O bond cleavage yielding 6-(oxoethenylidene)-2,4-cyclohexadien-1-one (3), which appears with a rise time of 28 ps. The expected Wolff-rearrangement product, 7-oxabicyclo[4.2.0]octa-1,3,5-trien-8-ylidenemethanone (4), is not formed. The efficient light-induced formation of the quinonoid cumulenone 3 opens the way to determine the reactivity of a cumulenone in solution. The reaction kinetics of 3 were monitored by nanosecond flash photolysis with optical (λ max ≈ 460 nm) as well as Raman (1526 cm-1) and IR detection (2050 cm-1). Remarkably, the reactivity of 3 is that expected from its valence isomer, the cyclic carbene 3H-benzofuran-2-one-3-ylidene, 2. In aqueous solution, acid-catalyzed addition of water forms the lactone 3-hydroxy-3H-benzofuran-2-one (5). The reaction is initiated by protonation of the cumulenone on its β-carbon atom. In hexane, cumulenone 3 dimerizes to isoxindigo ((E)-[3,3′ ]bibenzofuranylidene-2,2′-dione, 7), coumestan (6H-benzofuro[3,2-c][1]benzopyran-6-one, 8), and a small amount of dibenzonaphthyrone ([1]benzopyrano[4,3-][1]benzopyran-5,11-dione, 9) at a nearly diffusion-controlled rate. Ab initio calculations (G3) are consistent with the observed data. Carbene 2 is predicted to have a singlet ground state, which undergoes very facile, strongly exothermic (irreversible) ring opening to the cumulenone 3. The calculated barrier to formation of 4 (Wolff-rearrangement) is prohibitive. DFT calculations indicate that protonation of 3 on the β-carbon is accompanied by cyclization to the protonated carbene 2H +, and that dimerization of 3 to 7 and 9 takes place in a single step with negligible activation energy.

Method of preparing 2- and 4-hydroxymandelic acid

The invention relates to a method of preparing 2- and 4-hydroxymandelic acid by condensing glyoxylic acid with phenol. The glyoxylic acid is reacted with phenol, after which the formed reaction mixture or the phenol, the 2- and 4-hydroxymandelic acid respectively are elution-separated in a column comprising an anion exchange resin, wherein first the excess phenol is separated, followed by the separation of the 4-hydroxymandelic acid and finally the 2-hydroxymandelic acid, both in the form of acid and salt, depending on the eluent used.

Separation of 2- and 4-hydroxymandelic acid

Hydroxyalkylation of phenol with glyoxylic acid, catalyzed by AlIII, results, under neutral aqueous conditions, in ortho-rich mixtures of hydroxymandelic acids. Para-rich mixtures of hydroxymandelic acids are obtained by ZnII catalysis under slightly alkaline conditions. A new separation method of these mixtures into the pure alkali salts of 2- and 4-hydroxymandelic acid is presented. Formation of a complex between the alkali ion and three co-operating oxygen atoms of 2-hydroxymandelate explains the excellent solubility of the ortho isomer in acetone, enabling extraction of this isomer selectively from mixtures of alkali salts of 2- and 4-hydroxymandelic acid.

Metal ion catalysis in the hydroxyalkylation of phenol with glyoxylic acid

The hydroxyalkylation reaction of phenol with glyoxylic acid in aqueous medium is found to be homogeneously catalyzed by various metal ions.Catalysis with MII ions results in a reaction product with an ortho/para ratio of 0.2 to 1.1, whereas catalysis using higher valent cations, because of their ability to form mixed complexes with phenol and glyoxylic acid, affords a reaction product with an ortho/para ratio 1.3 to 28.The catalyzed Cannizzaro reaction of glyoxylic acid was observed as a side-reaction.Addition of a suitable inert ligand, e. g. oxalic acid or NTA, is shown to decrease the ortho/para ratio and suppress the Cannizzaro reaction.The coordination of glyoxylic acid and its hydrate with several cations has been studied by NMR techniques and a mechanism of the catalyzed hydroxyalkylation and Cannizzaro reaction is proposed.

Oxidation of Mandelic Acid by Fenton's Reagent

Mandelic acid forms a stable 1:1 complex with Fe2+ at pH 1-3.Its oxidation by H2O2 and S2O82- has been investigated in the hope of detecting intramolecular oxidation-reduction of any intermediate FeIV species, rather than the usual hydroxyl radical process.Products are benzaldehyde and hydroxymandelic acids, consistent with either, but added hydroxyl radical traps - acetone or crotonic acid - are able to intercept only about half of the reaction.However, they reduce yields of benzaldehyde but not hydroxymandelic acids, and it is concluded that the balance of the reaction involves cage reactions of newly formed hydroxyl radicals rather than a high-valence iron species.

7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids

Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.

7-(D-α-Hydroxy-2-arylacetamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo-[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids and derivatives

7-(D-α-Hydroxy-2-arylacetamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids and derivatives containing blocking groups on the α-hydroxy group and their nontoxic, pharmaceutically acceptable salts are valuable as antibacterial agents and are particularly valuable as therapeutic agents in poultry and in animals, including man, in the treatment of infectious diseases caused by many Gram-positive and Gram-negative bacteria. A preferred compound is 7-(D-mandelamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acid.

7-(D-α-Hydroxy-2-arylacetamido)-3-(tetrazolo-[4,5-b]pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acids

7-(D-α-Hydroxy-2-arylacetamido)-3-(tetrazolo-[4,5-b]pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acids and their nontoxic, pharmaceutically acceptable salts are valuable as antibacterial agents and are particularly valuable as therapeutic agents in poultry and animals, including man, in the treatment of infectious diseases caused by many Gram-positive and Gram-negative bacteria.