63-36-5

Basic information

• Product Name: 2-Hydroxybenzoic acid ion(1-)
• Synonyms: 2-hydroxybenzoate;2-hydroxy-benzoic acid, deprotonated form;salicylate mono-anion;hydroxybenzoate
• CAS NO: 63-36-5
• Molecular Formula: C₇H₅O₃-
• Molecular Weight: 137.115
• Mol File: 63-36-5.mol

Chemical Properties

• Boiling Point: 336.3°Cat760mmHg
• Flash Point: 144.5°C
• Density: g/cm³
• CAS DataBase Reference: 2-Hydroxybenzoic acid ion(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxybenzoic acid ion(1-)(63-36-5)
• EPA Substance Registry System: 2-Hydroxybenzoic acid ion(1-)(63-36-5)

Safety Data

• Hazardous Substances Data: 63-36-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A monohydroxybenzoate that is the conjugate base of salicylic acid.

Upstream product

• 87059-79-8 ω-formyl-2'-hydroxyacetophenone 
• 59223-01-7 α-formyl-2-hydroxydeoxybenzoin 
• 26163-37-1 N,N'-dimethylpiperidazine 
• 69-72-7 salicylic acid 
• 6415-12-9 tetramethylhydrazine 
• 23337-93-1 N,N'-diethyl-N,N'-dimethyl-hydrazine 
• 4267-00-9 tetraethyl-hydrazine 
• 60678-69-5 tetrapropyl-hydrazine 
• 60678-72-0 N-Isopropyl-N'-methyl-hydrazin 
• 49840-64-4 N,N',N'-Triisopropyl-N-methyl-hydrazine 
• 21849-74-1 1,1-Diethyl-2,2-dimethylhydrazin 
• 68970-05-8 N,N'-Diisobutyl-N,N'-dimethyl-hydrazine 
• 63892-83-1 (4aR,6aS)-5,6-Dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10-dodecahydro-benzo[c]cinnoline 
• 50-78-2 aspirin 

Downstream Products

• 71749-77-4 (C₆H₅)B(OH)C₆H₄(O)(COO)^(1-) 
• 71749-76-3 NO₂(C₆H₄)B(OH)C₆H₄(O)(COO)^(1-) 
• 55205-94-2 iron(II)-salicylate 
• 120-80-9 benzene-1,2-diol 
• 124-38-9 carbon dioxide 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 69-72-7 salicylic acid 

Relevant articles and documents

Excited-state proton-coupled electron transfer within ion pairs

The use of light to drive proton-coupled electron transfer (PCET) reactions has received growing interest, with recent focus on the direct use of excited states in PCET reactions (ES-PCET). Electrostatic ion pairs provide a scaffold to reduce reaction orders and have facilitated many discoveries in electron-transfer chemistry. Their use, however, has not translated to PCET. Herein, we show that ion pairs, formed solely through electrostatic interactions, provide a general, facile means to study an ES-PCET mechanism. These ion pairs formed readily between salicylate anions and tetracationic ruthenium complexes in acetonitrile solution. Upon light excitation, quenching of the ruthenium excited state occurred through ES-PCET oxidation of salicylate within the ion pair. Transient absorption spectroscopy identified the reduced ruthenium complex and oxidized salicylate radical as the primary photoproducts of this reaction. The reduced reaction order due to ion pairing allowed the first-order PCET rate constants to be directly measured through nanosecond photoluminescence spectroscopy. These PCET rate constants saturated at larger driving forces consistent with approaching the Marcus barrierless region. Surprisingly, a proton-transfer tautomer of salicylate, with the proton localized on the carboxylate functional group, was present in acetonitrile. A pre-equilibrium model based on this tautomerization provided non-adiabatic electron-transfer rate constants that were well described by Marcus theory. Electrostatic ion pairs were critical to our ability to investigate this PCET mechanism without the need to covalently link the donor and acceptor or introduce specific hydrogen bonding sites that could compete in alternate PCET pathways.

Conversion of Anthranilate Synthase into Isochorismate Synthase: Implications for the Evolution of Chorismate-Utilizing Enzymes

Chorismate-utilizing enzymes play a vital role in the biosynthesis of metabolites in plants as well as free-living and infectious microorganisms. Among these enzymes are the homologous primary metabolic anthranilate synthase (AS) and secondary metabolic i

Synthesis and chemical and biological comparison of nitroxyl- and nitric oxide-releasing diazeniumdiolate-based aspirin derivatives

Structural modifications of nonsteroidal anti-inflammatory drugs (NSAIDs) have successfully reduced the side effect of gastrointestinal ulceration without affecting anti-inflammatory activity, but they may increase the risk of myocardial infarction with chronic use. The fact that nitroxyl (HNO) reduces platelet aggregation, preconditions against myocardial infarction, and enhances contractility led us to synthesize a diazeniumdiolate-based HNO-releasing aspirin and to compare it to an NO-releasing analogue. Here, the decomposition mechanisms are described for these compounds. In addition to protection against stomach ulceration, these prodrugs exhibited significantly enhanced cytotoxcity compared to either aspirin or the parent diazeniumdiolate toward nonsmall cell lung carcinoma cells (A549), but they were not appreciably toxic toward endothelial cells (HUVECs). The HNO-NSAID prodrug inhibited cylcooxgenase-2 and glyceraldehyde 3-phosphate dehydrogenase activity and triggered significant sarcomere shortening on murine ventricular myocytes compared to control. Together, these anti-inflammatory, antineoplasic, and contractile properties suggest the potential of HNO-NSAIDs in the treatment of inflammation, cancer, or heart failure.

Entropic and enthalpic components of catalysis in the mutase and lyase activities of pseudomonas aeruginosa PchB

The isochorismate-pyruvate lyase from Pseudomonas aeruginosa (PchB) catalyzes two pericyclic reactions, demonstrating the eponymous activity and also chorismate mutase activity. The thermodynamic parameters for these enzyme-catalyzed activities, as well a

PH dependence of catalysis by pseudomonas aeruginosa isochorismate - Pyruvate lyase: Implications for transition state stabilization and the role of lysine 42

An isochorismate - pyruvate lyase with adventitious chorismate mutase activity from Pseudomonas aerugionsa (PchB) achieves catalysis of both pericyclic reactions in part by the stabilization of reactive conformations and in part by electrostatic transitio

Nueleophile specificity in anthranilate synthase, aminodeoxychorismate synthase, isochorismate synthase, and salicylate synthase

Anthranilate synthase (AS), aminodeoxychorismate synthase (ADCS), isochorismate synthase (IS), and salicylate synthase (SS) are structurally homologous chorismate-utilizing enzymes that carry out the first committed step in the formation of tryptophan, fo

Inhibition of chorismate-utilising enzymes by 2-amino-4-carboxypyridine and 4-carboxypyridone and 5-carboxypyridone analogues

Several 2-amino-4-carboxypyridine, 4- and 5-carboxypyridone-based compounds were prepared and tested against three members of the chorismate-utilising enzyme family, anthranilate synthase, isochorismate synthase and salicylate synthase. Most compounds exhibited low micromolar inhibition of these three enzymes. The most potent inhibitor was a 4-carboxypyridone analogue bearing a lactate side chain on the pyridyl nitrogen which exhibited inhibition constants of 5, 91 and 54 μM against anthranilate synthase, isochorismate synthase and salicylate synthase respectively. The Royal Society of Chemistry 2010.

Isochorismate pyruvate lyase: A pericyclic reaction mechanism?

Isochorismate pyruvate lyase (IPL) catalyzes the cleavage of isochorismate to give salicylate and pyruvate, a key step in bacterial siderophore biosynthesis. We investigated the enzyme from Pseudomonas aeruginosa using isochorismate selectively deuterated

Effects of organic salts on the rate of intramolecular general base-catalyzed piperidinolysis of ionized phenyl salicylate in the presence of cationic micelles

Pseudo-first-order rate constants (kobs), obtained for the cleavage of ionized phenyl salicylate (PS-) at constant [NaOH], [MeCN], [CTABr]T (total concentration of cetyltrimethylammonium bromide), [Pip]T (total

Binding of sodium salicylate by β-cyclodextrin or 2,6-di-o-methyl-β- cyclodextrin in aqueous solution

Speed of sound and conductivity experiments have been done at 298.15 K to study the encapsulation process of sodium salicylate (NASA) by β- cyclodextrin (β-CD) and 2,6-di-O-methyl-β-cyclodextrin (DIMEB) in aqueous solutions. Since the concentration of the salicyclic form (HSA), coming from the hydrolysis of SA-, is negligible at biological pH, the binding process studied in this work is that of the SA- species. The stoichiometries of the complexes DIMEB: SA- and β-CD:SA- have been found to be 1:1, as usually determined for most CD:drug complexes. Their association constants and their ionic molar conductivities at infinite dilution have been obtained by fitting the experimental conductivity data with a nonlinear regression method (NLR). For that purpose, a model based on that of Gelb and co-workers has been used. From the values of K(β-CD:SA-) = (105 ± 15) M-1 and K(DIMEB:SA-) = (140 ± 20) M-1 obtained, the bioavailability of the salicylate drug in the complexed form has been discussed.