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 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:165217

ChemSpider |

* 59891 N

ECHA InfoCard | 100.001.334

PubChem CID

* 66520

UNII |

* 3NC0UQ5EMR Y

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) N

Key: IBHWREHFNDMRPR-UHFFFAOYSA-N 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).

N verify (what is YN ?)

Infobox references

Chemical compound

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

[edit]

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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Phenolic acids (C6-C1) and their glycosides

Monohydroxybenzoic acids|

* 3-Hydroxybenzoic acid
* 4-Hydroxybenzoic acid
* Salicylic acid (2-Hydroxybenzoic acid)

| 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|

* Gallic acid
* Phloroglucinol carboxylic acid

| Glycosides|

* Bergenin
* Norbergenin
* Theogallin
* Chebulic acid

|

Alkylated|

* Ethyl gallate
* Eudesmic acid
* Methyl gallate
* Syringic acid

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