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2,4,6-Trihydroxyacetophenone

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2,4,6-Trihydroxyacetophenone
Skeletal formula
Ball-and-stick model
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.870 Edit this at Wikidata
EC Number
  • 207-556-5
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3Key: XLEYFDVVXLMULC-UHFFFAOYSA-N
  • InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3Key: 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
Melting point 219 to 221 °C (426 to 430 °F; 492 to 494 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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, apigenin, luteolin, diosmetin, naringenin, and hesperetin.

See also

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. PMID 20000660.
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