2,4,6-Trihydroxyacetophenone

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2,4,6-Trihydroxyacetophenone
2,4,6-Trihydroxyacetophenone.svg
2,4,6-Trihydroxyacetophenone-3D-balls.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.870
UNII
Properties
C8H8O4
Molar mass 168.148 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 chemical compound that is a derivative of phloroglucinol.

Contents

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.

See also

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References

  1. 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.
  2. 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.