Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:45 UTC

Update Date

2023-02-21 17:18:56 UTC

HMDB ID

HMDB0029644

Secondary Accession Numbers

HMDB29644

Metabolite Identification

Common Name

2',4',6'-Trihydroxyacetophenone

Description

2',4',6'-Trihydroxyacetophenone, also known as phloracetophenone or 2-acetylphloroglucinol, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2',4',6'-Trihydroxyacetophenone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2',4',6'-Trihydroxyacetophenone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   2.694   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   3.463   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.665   1.155   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.665   1.155   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -1.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -1.154   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.463   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    9                                                  
CONECT    6    2    5    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11    7   10                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4,6-Trihydroxyacetophenone	ChEBI
2-Acetylphloroglucinol	ChEBI
Acetophloroglucine	ChEBI
Acetylphloroglucinol	ChEBI
Monoacetylphloroglucinol	ChEBI
Phloracetophenone	ChEBI
Phloroacetophenone	ChEBI
THAP	ChEBI
1-(2,4, 6-Trihydroxyphenyl)ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)-ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)ethanone, 9ci	HMDB
2',4',6'-Trihydroxy-acetophenone	HMDB
2',4',6'-Trihydroxyacetophenone monohydrate	HMDB
2-Acetyl-1,3,5-benzenetriol	HMDB
Acetophenone, 2',4',6'-trihydroxy- (8ci)	HMDB
Acetophloroglucinol	HMDB
Phloracetophene	HMDB
2,4,6-Trihydroxy-acetophenone	HMDB
4-mono-Hydroxy-acetophenone	HMDB
2,4,-Dihydroxy-acetophenone	HMDB
2,4,6-THA	HMDB

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

1-(2,4,6-trihydroxyphenyl)ethan-1-one

Traditional Name

2,4,6-trihydroxyacetophenone

CAS Registry Number

480-66-0

SMILES

CC(=O)C1=C(O)C=C(O)C=C1O

InChI Identifier

InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3

InChI Key

XLEYFDVVXLMULC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Acetophenone
Phloroglucinol derivative
Benzenetriol
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Polyol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:64344 )
aromatic ketone (CHEBI:64344 )
benzenetriol (CHEBI:64344 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029644)
Cytoplasm (HMDB: HMDB0029644)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029644)

Source

Endogenous

Endogenous (HMDB: HMDB0029644)

Plant

Plant (HMDB: HMDB0029644)

Exogenous

Food

Food (HMDB: HMDB0029644)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 °C	Not Available
Boiling Point	333.22 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	7103 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.472 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.56 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.92	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.4 m³·mol⁻¹	ChemAxon
Polarizability	15.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.739	31661259
DarkChem	[M-H]-	131.279	31661259
DeepCCS	[M+H]+	136.505	30932474
DeepCCS	[M-H]-	134.11	30932474
DeepCCS	[M-2H]-	169.614	30932474
DeepCCS	[M+Na]+	144.336	30932474
AllCCS	[M+H]+	135.5	32859911
AllCCS	[M+H-H2O]+	131.1	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	131.5	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',4',6'-Trihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1O	2413.0	Standard polar	33892256
2',4',6'-Trihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1O	1588.2	Standard non polar	33892256
2',4',6'-Trihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1O	1768.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',4',6'-Trihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=C(O)C=C(O)C=C1O[Si](C)(C)C	1682.8	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,1TMS,isomer #2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1O	1662.5	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1O[Si](C)(C)C	1732.6	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,2TMS,isomer #2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	1690.3	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,3TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	1773.2	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=C(O)C=C(O)C=C1O[Si](C)(C)C(C)(C)C	1971.4	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,1TBDMS,isomer #2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1O	1950.7	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1O[Si](C)(C)C(C)(C)C	2228.6	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,2TBDMS,isomer #2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2186.9	Semi standard non polar	33892256
2',4',6'-Trihydroxyacetophenone,3TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2452.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4',6'-Trihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-1900000000-c640fdb3756ff469be64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4',6'-Trihydroxyacetophenone GC-MS (3 TMS) - 70eV, Positive	splash10-0300-4139000000-b50f4bf400f878c9b3a6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4',6'-Trihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone Linear Ion Trap , negative-QTOF	splash10-00di-0900000000-ba8cd8b451c5fac4c8a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone Linear Ion Trap , negative-QTOF	splash10-00di-0900000000-d6ab8e4cefbdc9be671f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone Linear Ion Trap , positive-QTOF	splash10-0udi-0900000000-a0fd3047a84225da61d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone Linear Ion Trap , positive-QTOF	splash10-0udi-0900000000-e778aaab2bdbec365d68	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 10V, Positive-QTOF	splash10-014i-0900000000-8f18bfa483c344c937b5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 20V, Positive-QTOF	splash10-014i-0900000000-7b111e51f726ac74cf70	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 40V, Positive-QTOF	splash10-0udl-5900000000-3962c436b5c05a9a0ca3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 10V, Negative-QTOF	splash10-014i-0900000000-5d9a20e0063d5bba08a8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 20V, Negative-QTOF	splash10-00or-0900000000-3a050859d59d808ae070	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 40V, Negative-QTOF	splash10-0059-5900000000-3b9e89e6188f422938ac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 10V, Positive-QTOF	splash10-014i-1900000000-663bacb4b0e67d970489	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 20V, Positive-QTOF	splash10-0fr6-6900000000-f00bfc59e2420a31ed99	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 40V, Positive-QTOF	splash10-015c-9200000000-013b98101a50407d43c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 10V, Negative-QTOF	splash10-014i-0900000000-18e61dd3d41e0b51a809	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 20V, Negative-QTOF	splash10-004i-3900000000-ccfff7c1bcecb10eddf6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4',6'-Trihydroxyacetophenone 40V, Negative-QTOF	splash10-0006-9000000000-8f870a7da2d3f8dd9297	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000815

KNApSAcK ID

C00054092

Chemspider ID

61386

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,4,6-Trihydroxyacetophenone

METLIN ID

Not Available

PubChem Compound

68073

PDB ID

Not Available

ChEBI ID

64344

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1157631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2',4',6'-Trihydroxyacetophenone (HMDB0029644)

MOL for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

3D MOL for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

3D SDF for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

3D-SDF for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

PDB for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

3D PDB for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

SMILES for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

INCHI for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

Structure for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

3D Structure for HMDB0029644 (2',4',6'-Trihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra