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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:31:52 UTC

Update Date

2023-02-21 17:18:58 UTC

HMDB ID

HMDB0029659

Secondary Accession Numbers

HMDB29659

Metabolite Identification

Common Name

2',4'-Dihydroxyacetophenone

Description

2',4'-Dihydroxyacetophenone, also known as resacetophenone or 4-acetylresorcinol, 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'-Dihydroxyacetophenone 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 significant number of articles have been published on 2',4'-Dihydroxyacetophenone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4-Dihydroxyacetophenone	ChEBI
4-Acetylresorcinol	ChEBI
Resacetophenone	ChEBI
1-(2,4-Dihydroxyphenyl)-ethanone	HMDB
1-(2,4-Dihydroxyphenyl)ethanone, 9ci	HMDB
2',4'-Dihydroxy-acetophenone	HMDB
4-Acetyl-1,3-benzenediol	HMDB
4-Acetyl-resorcinol	HMDB
Resoacetophenone	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(2,4-dihydroxyphenyl)ethan-1-one

Traditional Name

2',4'-dihydroxyacetophenone

CAS Registry Number

89-84-9

SMILES

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

InChI Identifier

InChI=1S/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H3

InChI Key

SULYEHHGGXARJS-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
Acetophenone
Aryl alkyl ketone
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:18414 )
dihydroxyacetophenone (CHEBI:18414 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029659)
Cytoplasm (HMDB: HMDB0029659)

Source

Endogenous

Endogenous (HMDB: HMDB0029659)

Exogenous

Food

Food (HMDB: HMDB0029659)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029659)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 °C	Not Available
Boiling Point	319.27 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15070 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.480 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	127.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002106
[M+H]+	Not Available	127.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002106

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.82 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.57	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.42 m³·mol⁻¹	ChemAxon
Polarizability	14.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	133.586	31661259
DarkChem	[M-H]-	129.408	31661259
DeepCCS	[M+H]+	133.457	30932474
DeepCCS	[M-H]-	130.372	30932474
DeepCCS	[M-2H]-	167.329	30932474
DeepCCS	[M+Na]+	142.845	30932474
AllCCS	[M+H]+	131.7	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	130.4	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',4'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1	2168.2	Standard polar	33892256
2',4'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1	1427.8	Standard non polar	33892256
2',4'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=C(O)C=C1	1603.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',4'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC=C(O)C=C1O[Si](C)(C)C	1620.1	Semi standard non polar	33892256
2',4'-Dihydroxyacetophenone,1TMS,isomer #2	CC(=O)C1=CC=C(O[Si](C)(C)C)C=C1O	1609.4	Semi standard non polar	33892256
2',4'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	1680.1	Semi standard non polar	33892256
2',4'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C	1883.7	Semi standard non polar	33892256
2',4'-Dihydroxyacetophenone,1TBDMS,isomer #2	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O	1859.7	Semi standard non polar	33892256
2',4'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2151.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-2900000000-eb08d342b85b33b724f7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-000i-3900000000-2c2de3cf148f6a68d182	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-0900000000-13c30ac7365b0868e35e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-2900000000-647d0e62b5caf8adccc9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-2900000000-eb08d342b85b33b724f7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-000i-3900000000-2c2de3cf148f6a68d182	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-0900000000-13c30ac7365b0868e35e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',4'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-2900000000-647d0e62b5caf8adccc9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-3900000000-af75ab719e134e1e17c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-5490000000-ae7155fd9dd68c56f89e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',4'-Dihydroxyacetophenone 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'-Dihydroxyacetophenone ESI-TOF , Negative-QTOF	splash10-000i-0091300000-17f56b4a47fb7d35624e	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone ESI-TOF 10V, Negative-QTOF	splash10-000i-0091300000-17f56b4a47fb7d35624e	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone ESI-TOF 20V, Negative-QTOF	splash10-0a4i-0900000000-637e6febb080916d6386	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone ESI-TOF , Negative-QTOF	splash10-0udi-0900000000-60efa271dda3d29e827b	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone ESI-TOF 10V, Negative-QTOF	splash10-0udi-0900000000-4bd37b3dfc68805fa01f	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone ESI-TOF 20V, Negative-QTOF	splash10-0a4i-0900000000-637e6febb080916d6386	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone , negative-QTOF	splash10-0udi-0900000000-dadfd2be7812ccb127e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone LC-ESI-TOF , negative-QTOF	splash10-0udi-0900000000-4bd37b3dfc68805fa01f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone LC-ESI-TOF , negative-QTOF	splash10-0a4i-0900000000-637e6febb080916d6386	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-3377fa4d61778c554180	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-05mo-9500000000-a489329b08b05f4cfb90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0a4i-0900000000-637e6febb080916d6386	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-00kf-9000000000-1647bfc4d6110b519c2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-4bd37b3dfc68805fa01f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-004r-9700000000-4e764a64679ce0ac7833	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-004l-9000000000-8240da17b0e59774a5ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-1900000000-1084b7bfa0b1d95023fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-052f-9800000000-305be6af97d4ae1ae203	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-004i-9000000000-b376db5f4d842ff7a72a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-9e7fecd78677e7e31e36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-d4103fb4f851e96dd665	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-000l-9800000000-12112c36505ef861e8cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-13b2b28a4ce8d4794ac0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0udi-0900000000-a850dd43572d42504409	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',4'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0aou-9700000000-e988bf4ad2a5b11b6a10	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6990

PDB ID

Not Available

ChEBI ID

18414

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1157701

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'-Dihydroxyacetophenone (HMDB0029659)

MOL for HMDB0029659 (2',4'-Dihydroxyacetophenone)

3D MOL for HMDB0029659 (2',4'-Dihydroxyacetophenone)

3D SDF for HMDB0029659 (2',4'-Dihydroxyacetophenone)

3D-SDF for HMDB0029659 (2',4'-Dihydroxyacetophenone)

PDB for HMDB0029659 (2',4'-Dihydroxyacetophenone)

3D PDB for HMDB0029659 (2',4'-Dihydroxyacetophenone)

SMILES for HMDB0029659 (2',4'-Dihydroxyacetophenone)

INCHI for HMDB0029659 (2',4'-Dihydroxyacetophenone)

Structure for HMDB0029659 (2',4'-Dihydroxyacetophenone)

3D Structure for HMDB0029659 (2',4'-Dihydroxyacetophenone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra