2,4,6-Trihydroxyacetophenone

2,4,6-Trihydroxyacetophenone
Names
	Preferred IUPAC name 1-(2,4,6-Trihydroxyphenyl)ethan-1-one
	Other names 1-(2,4,6-Trihydroxyphenyl)ethanone; 2-Acetylphloroglucinol; THAP; Phloroacetophenone
Identifiers
CAS Number	480-66-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:64344 ;
ChEMBL	ChEMBL452477 ;
ChemSpider	61386 ;
ECHA InfoCard	100.006.870
EC Number	207-556-5;
KEGG	C21895;
PubChem CID	68073;
UNII	8L7XD8830T ;
CompTox Dashboard (EPA)	DTXSID5060061 ;
	InChI InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3 Key: XLEYFDVVXLMULC-UHFFFAOYSA-N ; InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3 Key: XLEYFDVVXLMULC-UHFFFAOYAA;
	SMILES CC(=O)c1c(cc(cc1O)O)O; O=C(c1c(O)cc(O)cc1O)C;
Properties
Chemical formula	C8H8O4
Molar mass	168.148 g·mol−1
Melting point	219 to 221 °C (426 to 430 °F; 492 to 494 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302 P352, P304 P340, P305 P351 P338, P312, P321, P332 P313, P337 P313, P362, P403 P233, P405, P501
	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

2,4,6-Trihydroxyacetophenone (THAP) is a chemical compound that is a derivative of phloroglucinol.

In an animal model, THAP was reported to enhance cholesterol 7 alpha-hydroxylase (CYP7A1) activity.^[1]

THAP is also used as a matrix in matrix-assisted laser desorption/ionization (MALDI) for the analysis of acidic glycans and glycopeptides in negative ion mode.

Derivatives

THAP is a chemical precursor that can be used to form part of the backbone of 5,7-dihydroxyflavones like noreugenin,^[2] apigenin, luteolin, diosmetin, naringenin, and hesperetin.

^ Charoenteeraboon, Juree; Nithipatikom, Kasem; Campbell, William B.; Piyachaturawat, Pawinee; Wilairat, Prapon; Rongnoparut, Pornpimol (2005). "Induction of human cholesterol 7α-hydroxylase in HepG2 cells by 2,4,6-trihydroxyacetophenone". European Journal of Pharmacology. 515 (1–3): 43–46. doi:10.1016/j.ejphar.2005.03.039. PMID 15896733.
^ Bruder, Marjorie; Haseler, Paul L.; Muscarella, Marina; Lewis, William; Moody, Christopher J. (2010). "Synthesis of the Oxepinochromone Natural Products Ptaeroxylin (Desoxykarenin), Ptaeroxylinol, and Eranthin". The Journal of Organic Chemistry. 75 (2): 353–358. doi:10.1021/jo902117e. ISSN 0022-3263. PMID 20000660.