Phloroglucinol carboxylic acid

Phloroglucinol carboxylic acid
	Chemical structure of phloroglucinol carboxylic acid
Names
	Preferred IUPAC name 2,4,6-Trihydroxybenzoic acid
	Other names PGCA; Phloroglucinic acid
Identifiers
CAS Number	83-30-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:165217;
ChemSpider	59891 ;
ECHA InfoCard	100.001.334
PubChem CID	66520;
UNII	3NC0UQ5EMR ;
CompTox Dashboard (EPA)	DTXSID1058890 ;
	InChI InChI=1S/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12) Key: IBHWREHFNDMRPR-UHFFFAOYSA-N ; InChI=1/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12) Key: IBHWREHFNDMRPR-UHFFFAOYAP;
	SMILES C1=C(C=C(C(=C1O)C(=O)O)O)O;
Properties
Chemical formula	C7H6O5
Molar mass	170.11954 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phloroglucinol carboxylic acid, also called ‘Phloroglucinic acid’ or simply ‘PGCA’, is a trihydroxybenzoic acid, a type of phenolic acid. It can be encountered in nature were it is produced by plants or microorganisms. Structurally, the molecule can be perceived as Gallic acid in which the 2 hydroxy groups at positions 3 and 5 respectively on the benzene ring backbone have been moved “up” to positions 2 and 6, closely neighboring the carboxylic acid functional group. Salts and esters of PGCA (e.g. potassium salt or methyl ester) are known as Phloroglucinates.

It is produced by Pseudomonas fluorescens.^[1] It is a catechin degradation product excreted by the bacterium Acinetobacter calcoaceticus, a species of bacteria part of the human body normal flora, grown on catechin as sole source of carbon.^[2] It is also found in wine.^[3]

References

^ Biosynthesis of Phloroglucinol. Jihane Achkar, Mo Xian, Huimin Zhao and J. W. Frost, J. AM. CHEM. SOC., 2005, volume 127, pages 5332-5333, doi:10.1021/ja042340g
^ M. Arunachalam, N. Mohan, R. Sugadev, P. Chellappan and A. Mahadevan: Degradation of (+)-catechin by Acinetobacter calcoaceticus MTC 127, Biochimica et Biophysica Acta (BBA), Volume 1621, Issue 3, 11 June 2003, pages 261–265, doi:10.1016/S0304-4165(03)00077-1.
^ C. García Barroso, R. Cela Torrijos and J. A. Pérez-Bustamante: HPLC separation of benzoic and hydroxycinnamic acids in wines, Chromatographia, Volume 17, Number 5, pages 249–252, doi:10.1007/BF02263033.

[1] Biosynthesis of Phloroglucinol. Jihane Achkar, Mo Xian, Huimin Zhao and J. W. Frost, J. AM. CHEM. SOC., 2005, volume 127, pages 5332-5333, doi:10.1021/ja042340g

[2] M. Arunachalam, N. Mohan, R. Sugadev, P. Chellappan and A. Mahadevan: Degradation of (+)-catechin by Acinetobacter calcoaceticus MTC 127, Biochimica et Biophysica Acta (BBA), Volume 1621, Issue 3, 11 June 2003, pages 261–265, doi:10.1016/S0304-4165(03)00077-1.

[3] C. García Barroso, R. Cela Torrijos and J. A. Pérez-Bustamante: HPLC separation of benzoic and hydroxycinnamic acids in wines, Chromatographia, Volume 17, Number 5, pages 249–252, doi:10.1007/BF02263033.

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