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 (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:64344
ChEMBL	ChEMBL452477
ChemSpider	61386
ECHA InfoCard	100.006.870
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	168.15 g·mol^−1
Melting point	219 to 221 °C (426 to 430 °F; 492 to 494 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,4,6-Trihydroxyacetophenone (THAP) is a phloroglucinol.

It has a plasma cholesterol-lowering activity in animals.^[1]

It 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.

References

1. Induction of human cholesterol 7α-hydroxylase in HepG2 cells by 2,4,6-trihydroxyacetophenone. Charoenteeraboon Juree, Nithipatikom Kasem, Campbell William B., Piyachaturawat Pawinee, Wilairat Prapon and Rongnoparut Pornpimol, European journal of pharmacology, 2005, vol. 515, no. 1-3, pp. 43-46