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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 17:31:52 UTC

Update Date

2023-02-21 17:18:58 UTC

HMDB ID

HMDB0029658

Secondary Accession Numbers

HMDB29658

Metabolite Identification

Common Name

2',3'-Dihydroxyacetophenone

Description

2',3'-Dihydroxyacetophenone 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. Based on a literature review very few articles have been published on 2',3'-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
1-(2,3-Dihydroxyphenyl)ethanone, 9ci	HMDB
3-Acetylcatechol	HMDB
2,6-Dihydroxyacetophenone	MeSH
Dihydroxyacetophenone	MeSH

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(2,3-dihydroxyphenyl)ethan-1-one

Traditional Name

1-(2,3-dihydroxyphenyl)ethanone

CAS Registry Number

13494-10-5

SMILES

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

InChI Identifier

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

InChI Key

HEJLFBLJYFSKCE-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
Catechol
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029658)
Cytoplasm (HMDB: HMDB0029658)

Source

Endogenous

Endogenous (HMDB: HMDB0029658)

Exogenous

Food

Food (HMDB: HMDB0029658)

Exogenous (HMDB: HMDB0029658)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029658)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	97 - 98 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.07 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-4.5	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	14.81 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]+	132.544	31661259
DarkChem	[M-H]-	128.156	31661259
DeepCCS	[M+H]+	131.027	30932474
DeepCCS	[M-H]-	128.259	30932474
DeepCCS	[M-2H]-	164.674	30932474
DeepCCS	[M+Na]+	140.071	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	126.8	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	130.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',3'-Dihydroxyacetophenone	CC(=O)C1=C(O)C(O)=CC=C1	2136.3	Standard polar	33892256
2',3'-Dihydroxyacetophenone	CC(=O)C1=C(O)C(O)=CC=C1	1263.1	Standard non polar	33892256
2',3'-Dihydroxyacetophenone	CC(=O)C1=C(O)C(O)=CC=C1	1362.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',3'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC=CC(O)=C1O[Si](C)(C)C	1542.2	Semi standard non polar	33892256
2',3'-Dihydroxyacetophenone,1TMS,isomer #2	CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1O	1507.3	Semi standard non polar	33892256
2',3'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	1597.8	Semi standard non polar	33892256
2',3'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C	1787.1	Semi standard non polar	33892256
2',3'-Dihydroxyacetophenone,1TBDMS,isomer #2	CC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O	1782.9	Semi standard non polar	33892256
2',3'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2079.3	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',3'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-ec669a6777f72c9e7bf4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',3'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-ec669a6777f72c9e7bf4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',3'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-4900000000-0cbe64d7a148362183af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',3'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-6590000000-870036bae21c9c593acd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',3'-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-769759d6fab1602de408	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-1900000000-e7370e11205809339d3e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-004i-9200000000-3d20d9f1756ca1792c1b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-ea9584bd84b424466005	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0udi-1900000000-1f2255b151c95b35e30d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0a4i-8900000000-c99238c15b0a93accd48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-1900000000-e533f514440a15d699db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-052f-9700000000-0e45d12287ae0b5cd92a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-0006-9000000000-a909fa87c1d1e46dd8d8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-865bcd5db1cde43e8846	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0a4i-2900000000-8c4f1807c7c873f4a489	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',3'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-05ru-9500000000-0d1a1b6363057e1a596e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB000832

KNApSAcK ID

Not Available

Chemspider ID

4934487

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6429110

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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',3'-Dihydroxyacetophenone (HMDB0029658)

MOL for HMDB0029658 (2',3'-Dihydroxyacetophenone)

3D MOL for HMDB0029658 (2',3'-Dihydroxyacetophenone)

3D SDF for HMDB0029658 (2',3'-Dihydroxyacetophenone)

3D-SDF for HMDB0029658 (2',3'-Dihydroxyacetophenone)

PDB for HMDB0029658 (2',3'-Dihydroxyacetophenone)

3D PDB for HMDB0029658 (2',3'-Dihydroxyacetophenone)

SMILES for HMDB0029658 (2',3'-Dihydroxyacetophenone)

INCHI for HMDB0029658 (2',3'-Dihydroxyacetophenone)

Structure for HMDB0029658 (2',3'-Dihydroxyacetophenone)

3D Structure for HMDB0029658 (2',3'-Dihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra