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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:2,4,6-Trihydroxyacetophenone|oldid=465591173}} 465591173] of page [[2,4,6-Trihydroxyacetophenone]] with values updated to verified values.}}
{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 412502710
| verifiedrevid = 477210870
| ImageFile = 2,4,6-Trihydroxyacetophenone.svg
| ImageFile = 2,4,6-Trihydroxyacetophenone.svg
| ImageSize = 180px
| ImageSize = 180px
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| ImageSize1 = 180px
| ImageSize1 = 180px
| ImageName1 = Ball-and-stick model
| ImageName1 = Ball-and-stick model
|IUPACName= 1-(2,4,6-trihydroxyphenyl)ethanone
| PIN = 1-(2,4,6-Trihydroxyphenyl)ethan-1-one
|OtherNames= 2-Acetylphloroglucinol<br>THAP<br>Phloroacetophenone
| OtherNames = 1-(2,4,6-Trihydroxyphenyl)ethanone<br />2-Acetylphloroglucinol<br />THAP<br />Phloroacetophenone
|Reference=
| Reference =
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =480-66-0
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61386
| ChemSpiderID = 61386
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| InChI = 1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
| ChEBI = 64344
⚫
| InChIKey = XLEYFDVVXLMULC-UHFFFAOYAA
⚫
| SMILES1 = O=C(c1c(O)cc(O)cc1O)C
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 452477
| ChEMBL = 452477
| EC_number = 207-556-5
| KEGG = C21895
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8L7XD8830T
⚫
| PubChem = 68073
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
| StdInChI = 1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XLEYFDVVXLMULC-UHFFFAOYSA-N
| StdInChIKey = XLEYFDVVXLMULC-UHFFFAOYSA-N
⚫
| InChI = 1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
⚫
| CASNo_Ref = {{cascite|correct|??}}=
⚫
| InChIKey = XLEYFDVVXLMULC-UHFFFAOYAA
| CASNo = <!-- blanked - oldvalue: 480-66-0 -->
⚫
| SMILES1 = O=C(c1c(O)cc(O)cc1O)C
⚫
| PubChem=
| SMILES= CC(=O)c1c(cc(cc1O)O)O
| SMILES = CC(=O)c1c(cc(cc1O)O)O
⚫
}}
|Section2= {{Chembox Properties
⚫
| C=8|H=8|O=4
| Appearance=
| Density=
| MeltingPt=219–221&nbsp;°C
| BoilingPt=
| Solubility=
}}
}}
|Section3= {{Chembox Hazards
|Section2={{Chembox Properties
⚫
| C=8 | H=8 | O=4
| MainHazards=
| Appearance =
| FlashPt=
| Density =
| Autoignition=
| MeltingPtC = 219 to 221
| MeltingPt_notes =
| BoilingPt =
| Solubility =
}}
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
⚫
}}
}}
}}

'''2,4,6-Trihydroxyacetophenone''' (THAP) is a chemical compound that is a [[derivative (chemistry)|derivative]] of [[phloroglucinol]].

In an animal model, THAP was reported to enhance [[cholesterol 7 alpha-hydroxylase]] (CYP7A1) activity.<ref>{{cite journal | doi = 10.1016/j.ejphar.2005.03.039| pmid = 15896733| title = Induction of human cholesterol 7α-hydroxylase in HepG2 cells by 2,4,6-trihydroxyacetophenone| journal = European Journal of Pharmacology| volume = 515| issue = 1–3| pages = 43–46| year = 2005| last1 = Charoenteeraboon| first1 = Juree| last2 = Nithipatikom| first2 = Kasem| last3 = Campbell| first3 = William B.| last4 = Piyachaturawat| first4 = Pawinee| last5 = Wilairat| first5 = Prapon| last6 = Rongnoparut| first6 = Pornpimol}}</ref>

THAP is also used as a matrix in [[matrix-assisted laser desorption/ionization]] (MALDI) for the analysis of acidic [[glycan]]s and [[glycopeptide]]s 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]],<ref name="BruderHaseler2010">{{cite journal|last1=Bruder|first1=Marjorie|last2=Haseler|first2=Paul L.|last3=Muscarella|first3=Marina|last4=Lewis|first4=William|last5=Moody|first5=Christopher J.|title=Synthesis of the Oxepinochromone Natural Products Ptaeroxylin (Desoxykarenin), Ptaeroxylinol, and Eranthin|journal=The Journal of Organic Chemistry|volume=75|issue=2|year=2010|pages=353–358|issn=0022-3263|doi=10.1021/jo902117e|pmid=20000660 }}</ref> [[apigenin]], [[luteolin]], [[diosmetin]], [[naringenin]], and [[hesperetin]].

==See also==
*[[Flopropione]]

==References==
{{reflist}}

{{DEFAULTSORT:Trihydroxyacetophenone, 2,4,6-}}
[[Category:Phloroglucinols]]
[[Category:Aromatic ketones]]
[[Category:3-Hydroxypropenals]]
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