2,4,6-trihydroxyacetophenone

Structural formula
General
Surname	2,4,6-trihydroxyacetophenone
other names	2-acetylphloroglucinol; 2 ', 4', 6'-trihydroxyacetophenone; THAP;
Molecular formula	C 8 H 8 O 4
Brief description	light yellow solid
External identifiers / databases
EC number	207-556-5
ECHA InfoCard	100.006.870
PubChem	68073
ChemSpider	61386
Wikidata	Q4596772
properties
Molar mass	168.15 g mol −1
Physical state	firmly
density	1.25 g cm −3 (monohydrate)
Melting point	219-221 ° C
solubility	slightly soluble in water, chloroform and benzene ; easily soluble in ethanol, ether and acetone;
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 .

2,4,6-Trihydroxyacetophenone is an aromatic compound which is derived from both acetophenone and phloroglucinol (1,3,5-trihydroxybenzene). The structure consists of a benzene ring with an attached acetyl group (-COCH ₃ ) and three hydroxyl groups (-OH) as substituents .

Occurrence

2,4,6-Trihydroxyacetophenone occurs naturally in plants (such as plums and myrtle plants ).

Extraction and presentation

2,4,6-Trihydroxyacetophenone can be obtained by reacting acetic anhydride , acetyl chloride or acetonitrile with phloroglucinol. It is also possible to produce it by reacting acetic acid with phloroglucinol and zinc chloride ( Nencki reaction ).

properties

2,4,6-Trihydroxyacetophenone is a light yellow solid that is sparingly soluble in water. It is an efficient inhibitor of glucose transport in human erythrocytes .

use

2,4,6-Trihydroxyacetophenone is used as a matrix for matrix-assisted laser desorptions / ionizations .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet 2 ′, 4 ′, 6′-Trihydroxyacetophenone monohydrate, 98% from Sigma-Aldrich , accessed on September 22, 2017 ( PDF ).
^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2008, ISBN 978-0-8155-1990-4 , pp. 238 ( books.google.de ).
^ ^A ^b ^c William M. Haynes: CRC Handbook of Chemistry and Physics, 95th Edition . tape 3 . CRC Press, 2014, ISBN 978-1-4822-0868-9 , pp. 530 ( books.google.de ).
↑ Eduardo Antonio Ferreira, Eliana Fortes Gris, Jussara Matos Rebello, João Francisco Gomes Correia, Luis Flávio Souza de Oliveira, Danilo Wilhelm Filho, Rozangela Curi Pedrosa: The 2 ′, 4 ′, 6′-Trihydroxyacetophenone Isolated from Myrcia multiflora Has Antiobesity and Mixed Hypolipidemic Effects with the Reduction of Lipid Intestinal Absorption , Planta Med , 2011; 77 (14): 1569-1574, doi : 10.1055 / s-0030-1270956 , PMID 21472649 .
↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8352-1 , pp. 1917 ( books.google.de ).
^ Robert Martin: Handbook of Hydroxyacetophenones . Springer Science & Business Media, 2013, ISBN 978-94-017-1745-8 , pp. 57 ( books.google.de ).
↑ 2,4,6-Trihydroxyacetophenon - Lexicon of Biology . ( Spektrum.de ).
↑ Data sheet 2 ′, 4 ′, 6′-Trihydroxyacetophenone from AlfaAesar, accessed on September 22, 2017 ( PDF )(JavaScript required) .

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet 2 ′, 4 ′, 6′-Trihydroxyacetophenone monohydrate, 98% from Sigma-Aldrich , accessed on September 22, 2017 ( PDF ).

[2] Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2008, ISBN 978-0-8155-1990-4 , pp. 238 ( books.google.de ).

[William_M._Haynes-3] A ^b ^c William M. Haynes: CRC Handbook of Chemistry and Physics, 95th Edition . tape 3 . CRC Press, 2014, ISBN 978-1-4822-0868-9 , pp. 530 ( books.google.de ).

[4] Eduardo Antonio Ferreira, Eliana Fortes Gris, Jussara Matos Rebello, João Francisco Gomes Correia, Luis Flávio Souza de Oliveira, Danilo Wilhelm Filho, Rozangela Curi Pedrosa: The 2 ′, 4 ′, 6′-Trihydroxyacetophenone Isolated from Myrcia multiflora Has Antiobesity and Mixed Hypolipidemic Effects with the Reduction of Lipid Intestinal Absorption , Planta Med , 2011; 77 (14): 1569-1574, doi : 10.1055 / s-0030-1270956 , PMID 21472649 .

[5] Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8352-1 , pp. 1917 ( books.google.de ).

[6] Robert Martin: Handbook of Hydroxyacetophenones . Springer Science & Business Media, 2013, ISBN 978-94-017-1745-8 , pp. 57 ( books.google.de ).

[7] 2,4,6-Trihydroxyacetophenon - Lexicon of Biology . ( Spektrum.de ).

[Alfa-8] Data sheet 2 ′, 4 ′, 6′-Trihydroxyacetophenone from AlfaAesar, accessed on September 22, 2017 ( PDF )(JavaScript required) .