3-Hydroxybenzoic acid: Difference between revisions

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{{Short description|A type of benzoic acid}}
{{Short description|Overview of 3-Hydroxybenzoic acid}}
{{Chembox
| ImageFile = 3-hydroxybenzoic_acid.svg
| ImageSize = 200px
| ImageAlt = Skeletal formula of 3-hydroxybenzoic acid
| IUPACName = 3-Hydroxybenzoic acid
| OtherNames = m-Hydroxybenzoic acid
| Section1 = {{Chembox Identifiers
  | CASNo = 99-06-9
  | PubChem = 7428
  | ChemSpiderID = 7153
  | UNII = 0YIW783RG1
  | ChEBI = 30747
  | ChEMBL = 1231
  | SMILES = OC(=O)C1=CC(=CC=C1)O
  | InChI = 1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
  | InChIKey = IWYDHOAUDWTVEP-UHFFFAOYSA-N
}}
}}


'''3-Hydroxybenzoic acid''' is an [[organic compound]] with the formula C_H_O_. It is a type of [[benzoic acid]] substituted with a [[hydroxyl group]] at the meta position. This compound is a [[monohydroxybenzoic acid]] and is one of the three isomers of [[hydroxybenzoic acid]].
== 3-Hydroxybenzoic acid ==
[[File:3-hydroxybenzoic_acid.svg|thumb|right|Chemical structure of 3-Hydroxybenzoic acid]]
3-Hydroxybenzoic acid is an organic compound with the formula C_H_O_. It is one of the three isomeric [[hydroxybenzoic acids]], the others being [[2-hydroxybenzoic acid]] (salicylic acid) and [[4-hydroxybenzoic acid]]. This compound is a [[phenolic acid]] and is characterized by a hydroxyl group (-OH) attached to the benzene ring of [[benzoic acid]] at the third position.


==Structure and properties==
== Chemical Properties ==
3-Hydroxybenzoic acid consists of a [[benzene ring]] with a [[carboxylic acid]] group (COOH) and a hydroxyl group (OH) attached to it. The hydroxyl group is located at the third position relative to the carboxyl group, hence the name "3-hydroxy". This structure imparts certain chemical properties, such as the ability to form [[hydrogen bonds]], which influence its solubility and reactivity.
3-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water but more soluble in organic solvents such as ethanol and ether. It exhibits typical properties of phenolic acids, including the ability to form esters and salts. The presence of the hydroxyl group influences its acidity, making it more acidic than benzoic acid itself.


==Synthesis==
== Biological Significance ==
3-Hydroxybenzoic acid can be synthesized through various methods, including the [[Kolbe-Schmitt reaction]], which involves the carboxylation of [[phenol]]s. Another method involves the oxidation of [[m-cresol]] using oxidizing agents such as [[potassium permanganate]].
In biological systems, 3-hydroxybenzoic acid can be found as a metabolite in the degradation of aromatic compounds. It is involved in various [[biochemical pathways]] and can be produced by certain [[microorganisms]] as part of their metabolic processes. This compound is also studied for its potential [[antioxidant]] properties and its role in plant defense mechanisms.


==Applications==
== Synthesis ==
This compound is used in the synthesis of various [[pharmaceuticals]], [[dyes]], and [[polymers]]. It serves as an intermediate in the production of [[salicylic acid]] derivatives and is also used in the manufacture of certain [[cosmetics]] and [[preservatives]].
3-Hydroxybenzoic acid can be synthesized through several methods, including the [[Kolbe-Schmitt reaction]], which involves the carboxylation of phenolates. Another method involves the hydroxylation of benzoic acid using oxidizing agents. These synthetic routes are important for producing the compound in laboratory settings for research and industrial applications.


==Biological significance==
== Applications ==
3-Hydroxybenzoic acid is found in some [[plants]] and is a part of the [[phenolic acid]] family, which plays a role in plant defense mechanisms. It is also studied for its potential [[antioxidant]] properties and its role in [[metabolic pathways]] in [[microorganisms]].
This compound is used in the synthesis of various [[pharmaceuticals]], [[dyes]], and [[polymers]]. Its derivatives are explored for their potential use in [[medicine]] due to their biological activity. Additionally, 3-hydroxybenzoic acid is used as a precursor in the synthesis of more complex organic compounds.


==Related compounds==
== Related Compounds ==
* [[2-Hydroxybenzoic acid]]
* [[4-Hydroxybenzoic acid]]
* [[Benzoic acid]]
* [[Salicylic acid]]
* [[Salicylic acid]]
* [[4-Hydroxybenzoic acid]]
* [[2-Hydroxybenzoic acid]]


==Related pages==
== Related Pages ==
* [[Benzoic acid]]
* [[Phenolic acid]]
* [[Phenolic compounds]]
* [[Organic chemistry]]
* [[Carboxylic acids]]
* [[Biochemistry]]


[[Category:Organic compounds]]
[[Category:Phenolic acids]]
[[Category:Benzoic acids]]
[[Category:Benzoic acids]]
[[Category:Phenolic acids]]
[[Category:Hydroxy acids]]

Latest revision as of 05:15, 16 February 2025

Overview of 3-Hydroxybenzoic acid


3-Hydroxybenzoic acid[edit]

Chemical structure of 3-Hydroxybenzoic acid

3-Hydroxybenzoic acid is an organic compound with the formula C_H_O_. It is one of the three isomeric hydroxybenzoic acids, the others being 2-hydroxybenzoic acid (salicylic acid) and 4-hydroxybenzoic acid. This compound is a phenolic acid and is characterized by a hydroxyl group (-OH) attached to the benzene ring of benzoic acid at the third position.

Chemical Properties[edit]

3-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water but more soluble in organic solvents such as ethanol and ether. It exhibits typical properties of phenolic acids, including the ability to form esters and salts. The presence of the hydroxyl group influences its acidity, making it more acidic than benzoic acid itself.

Biological Significance[edit]

In biological systems, 3-hydroxybenzoic acid can be found as a metabolite in the degradation of aromatic compounds. It is involved in various biochemical pathways and can be produced by certain microorganisms as part of their metabolic processes. This compound is also studied for its potential antioxidant properties and its role in plant defense mechanisms.

Synthesis[edit]

3-Hydroxybenzoic acid can be synthesized through several methods, including the Kolbe-Schmitt reaction, which involves the carboxylation of phenolates. Another method involves the hydroxylation of benzoic acid using oxidizing agents. These synthetic routes are important for producing the compound in laboratory settings for research and industrial applications.

Applications[edit]

This compound is used in the synthesis of various pharmaceuticals, dyes, and polymers. Its derivatives are explored for their potential use in medicine due to their biological activity. Additionally, 3-hydroxybenzoic acid is used as a precursor in the synthesis of more complex organic compounds.

Related Compounds[edit]

Related Pages[edit]