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Phloroglucinol carboxylic acid

From Wikipedia, the free encyclopedia
Phloroglucinol carboxylic acid
Chemical structure of phloroglucinol carboxylic acid
Chemical structure of phloroglucinol carboxylic acid
Names
Preferred IUPAC name
2,4,6-Trihydroxybenzoic acid
Other names
PGCA
Phloroglucinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.001.334Edit this at Wikidata
UNII
  • 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
  • C1=C(C=C(C(=C1O)C(=O)O)O)O
Properties
C7H6O5
Molar mass170.11954 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Phloroglucinol carboxylic acid, also called‘Phloroglucinic acid’ or simply‘PGCA’, is atrihydroxybenzoic acid, a type ofphenolic acid. It can be encountered in nature were it is produced byplants ormicroorganisms. Structurally, the molecule can be perceived asGallic acid in which the 2hydroxy groups at positions 3 and 5 respectively on thebenzene ring backbone have been moved “up” to positions 2 and 6, closely neighboring thecarboxylic acid functional group.Salts andesters of PGCA (e.g.potassium salt ormethyl ester) are known as Phloroglucinates.

It is produced byPseudomonas fluorescens.[1] It is acatechin degradation product excreted by the bacteriumAcinetobacter 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.
Phenolic acids (C6-C1) and their glycosides
Monohydroxybenzoic acids
Glycosides
Alkylated
Dihydroxybenzoic acids
Alkylated
Trihydroxybenzoic acids
Glycosides
Alkylated
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