Phloroglucinic acid

Structural formula
General
Surname	Phloroglucinic acid
other names	2,4,6-trihydroxybenzoic acid
Molecular formula	C 7 H 6 O 5
Brief description	crystalline solid
External identifiers / databases
EC number	201-467-5
ECHA InfoCard	100.001.334
PubChem	66520
ChemSpider	59891
Wikidata	Q374897
properties
Molar mass	170.12 g mol −1
Physical state	firmly
Melting point	100 ° C (decomposition); 205 ° C (monohydrate);
pK s value	1.68 (25 ° C)
solubility	slightly soluble in water, soluble in ethanol , very readily soluble in diethyl ether , insoluble in benzene
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phloroglucinic acid (2,4,6-trihydroxybenzoic acid) is an aromatic compound that is derived from both benzoic acid and phloroglucinol (1,3,5-trihydroxybenzene). The structure consists of a benzene ring with an attached carboxy group (-COOH) and three hydroxyl groups (-OH) as substituents . It belongs to the group of trihydroxybenzoic acids .

If cultures of Acinetobacter calcoaceticus grow on (+) - catechin as the only carbon source, they break it down to phloroglucinic acid and excrete it. A. calcoaceticus is part of the human intestinal flora.

Phloroglucinic acid has also been found in wine .

literature

Emil Baur, P. Giger: Kinetik der Phloroglucincarbonsäure , Helvetica Chimica Acta , March 15, 1943, Volume 26, Issue 2, pp. 450-453, doi: 10.1002 / hlca.19430260208 .

Individual evidence

↑ ^a ^b ^c David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-502.
↑ ^a ^b ^c data sheet 2,4,6-Trihydroxybenzoic acid monohydrate from Sigma-Aldrich , accessed on May 18, 2012 ( PDF ).
^ D'Ans-Lax: Pocket book for chemists and physicists , 3rd edition, Volume 1, Springer-Verlag, Berlin-Göttingen-Heidelberg 1967 ( ChemieOnline - pK _b and pK _s values ).
↑ M. Arunachalam, N. Mohan, R. Sugadev, P. Chellappan, A. Mahadevan (2003): Degradation of (+) - catechin by Acinetobacter calcoaceticus MTC 127 , in: Biochimica et Biophysica Acta , 1621 (3), p 261-265, PMID 12787923 ; doi: 10.1016 / S0304-4165 (03) 00077-1
↑ C. García Barroso, R. Cela Torrijos, JA Pérez-Bustamante (1983): HPLC separation of benzoic and hydroxycinnamic acids in wines , in: Chromatographia , 17 (5), pp. 249-252; doi: 10.1007 / BF02263033 .

[CRC_HANDBOOK-1] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-502.

[ALDRICH-2] ta sheet 2,4,6-Trihydroxybenzoic acid monohydrate from Sigma-Aldrich , accessed on May 18, 2012 ( PDF ).

[3] D'Ans-Lax: Pocket book for chemists and physicists , 3rd edition, Volume 1, Springer-Verlag, Berlin-Göttingen-Heidelberg 1967 ( ChemieOnline - pK _b and pK _s values ).

[4] M. Arunachalam, N. Mohan, R. Sugadev, P. Chellappan, A. Mahadevan (2003): Degradation of (+) - catechin by Acinetobacter calcoaceticus MTC 127 , in: Biochimica et Biophysica Acta , 1621 (3), p 261-265, PMID 12787923 ; doi: 10.1016 / S0304-4165 (03) 00077-1

[5] C. García Barroso, R. Cela Torrijos, JA Pérez-Bustamante (1983): HPLC separation of benzoic and hydroxycinnamic acids in wines , in: Chromatographia , 17 (5), pp. 249-252; doi: 10.1007 / BF02263033 .