3-Hydroxybenzoic acid

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3-Hydroxybenzoic acid
Names

Preferred IUPAC name 3-Hydroxybenzoic acid
Other names m-Hydroxybenzoic acid meta-Hydroxybenzoic acid 3-Carboxyphenol m-Salicylic acid
Identifiers
CAS Number	99-06-9^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:30764^Y
ChEMBL	ChEMBL65369^Y
ChemSpider	7142^Y
ECHA InfoCard	100.002.478
PubChem CID	7420
UNII	2ZFW40OJ7U^Y
CompTox Dashboard (EPA)	DTXSID6021610
InChI InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)^Y Key: IJFXRHURBJZNAO-UHFFFAOYSA-N^Y
SMILES C1=CC(=CC(=C1)O)C(=O)O O=C(O)c1cc(O)ccc1
Properties
Chemical formula	C₇H₆O₃
Molar mass	138.12 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

3-Hydroxybenzoic acid is a monohydroxybenzoic acid.

Preparation

3-Hydroxybenzoic acid can be obtained by the alkali fusion of 3-sulfobenzoic acid between 210 – 220°C.^[1]

Natural occurrence

3-Hydroxybenzoic acid is a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery.

It can also be formed by a Pseudomonas species from 3-Chlorobenzoic acid.^[2]

3-Hydroxybenzoic Acid can be found in the pineapple fruit as well.

References

^ Clarke, M. F.; Owen, L. N. (1950). "434. Alicyclic glycols. Part V. 3-Hydroxymethylcyclohexanol". Journal of the Chemical Society (Resumed): 2108–2115. doi:10.1039/JR9500002108.
^ H.W. Johnston, G.G. Briggs and M. Alexander (1972). "Metabolism of 3-chlorobenzoic acid by a pseudomonad". Soil Biology and Biochemistry. 4 (2): 187–190. doi:10.1016/0038-0717(72)90010-7.

Phenolic acids (C6-C1) and their glycosides

Monohydroxybenzoic acids

Glycosides	p-Hydroxybenzoic acid glucoside
Alkylated	Methylparaben (Methyl-p-hydroxybenzoic acid)

Dihydroxybenzoic acids

2,3-Dihydroxybenzoic acid (Hypogallic acid)
2,4-Dihydroxybenzoic acid
2,5-Dihydroxybenzoic acid (Gentisic acid)
2,6-Dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid (Protocatechuic acid)
3,5-Dihydroxybenzoic acid

Alkylated	Ethyl protocatechuate Orsellinic acid

Trihydroxybenzoic acids

Glycosides	Bergenin Norbergenin Theogallin Chebulic acid
Alkylated	Ethyl gallate Eudesmic acid Methyl gallate Syringic acid

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