2,4,6-Trihydroxyacetophenone

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2,4,6-Trihydroxyacetophenone
Skeletal formula
Skeletal formula
Ball-and-stick model
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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EC Number
  • 207-556-5
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KEGG
UNII
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  • InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3 checkY
    Key: XLEYFDVVXLMULC-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
    Key: XLEYFDVVXLMULC-UHFFFAOYAA
  • CC(=O)c1c(cc(cc1O)O)O
  • O=C(c1c(O)cc(O)cc1O)C
Properties
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:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).
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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

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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

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