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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:53 UTC

Update Date

2023-02-21 17:18:59 UTC

HMDB ID

HMDB0029661

Secondary Accession Numbers

HMDB29661

Metabolite Identification

Common Name

3',4'-Dihydroxyacetophenone

Description

3',4'-Dihydroxyacetophenone, also known as 4-acetylpyrocatechol or 1-(3,4-dihydroxyphenyl)-ethanone, 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 3',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
3,4-Dihydroxyacetophenone	ChEBI
4-Acetylpyrocatechol	ChEBI
1-(3,4-Dihydroxyphenyl)-ethanone	HMDB
1-(3,4-Dihydroxyphenyl)ethanone	HMDB
1-(3,4-Dihydroxyphenyl)ethanone, 9ci	HMDB
4-Acetocatechol	HMDB
4-Acetopyrocatechol	HMDB
Acetophenone-3',4'-dihydroxy	HMDB
Acetopyrocatechol	HMDB
Acetylpyrocatechol	HMDB
Qingxintong	HMDB
1-(3,4-Dihydroxyphenyl)ethan-1-one	PhytoBank
3',4'-Dihydroxyacetophenone	PhytoBank
3’,4’-Dihydroxyacetophenone	PhytoBank
4-Acetyl-1,2-benzenediol	PhytoBank
4-Acetylcatechol	PhytoBank

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(3,4-dihydroxyphenyl)ethan-1-one

Traditional Name

3',4'-dihydroxyacetophenone

CAS Registry Number

1197-09-7

SMILES

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

InChI Identifier

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

InChI Key

UCQUAMAQHHEXGD-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
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:19868 )
dihydroxyacetophenone (CHEBI:19868 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029661)
Cytoplasm (HMDB: HMDB0029661)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029661)

Source

Endogenous

Endogenous (HMDB: HMDB0029661)

Plant

Coffea (HMDB: HMDB0029661)

Exogenous

Food

Food (HMDB: HMDB0029661)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	116 °C	Not Available
Boiling Point	372.41 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	69430 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.056 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.52 g/L	ALOGPS
logP	1.22	ALOGPS
logP	0.92	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-6.3	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	14.91 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]+	134.86	31661259
DarkChem	[M-H]-	129.981	31661259
DeepCCS	[M+H]+	133.645	30932474
DeepCCS	[M-H]-	130.526	30932474
DeepCCS	[M-2H]-	167.547	30932474
DeepCCS	[M+Na]+	143.059	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.1	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
3',4'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=C(O)C=C1	2338.3	Standard polar	33892256
3',4'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=C(O)C=C1	1358.4	Standard non polar	33892256
3',4'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=C(O)C=C1	1686.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3',4'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1592.4	Semi standard non polar	33892256
3',4'-Dihydroxyacetophenone,1TMS,isomer #2	CC(=O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1628.5	Semi standard non polar	33892256
3',4'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1675.9	Semi standard non polar	33892256
3',4'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	1847.6	Semi standard non polar	33892256
3',4'-Dihydroxyacetophenone,1TBDMS,isomer #2	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	1889.7	Semi standard non polar	33892256
3',4'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2141.9	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 - 3',4'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9i-2900000000-69baaddbb3d690d8f6d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',4'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-4390000000-9341301a39bcb820f912	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',4'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-39a8d86185e9fa2fa7f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-713d405158a1e7db939b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-0fbi-9500000000-f7364a806add71c7f049	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-d3834609c64722d23608	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0udi-0900000000-d0b9b325202c12a29b63	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0a4u-8900000000-c4b864eedaadb3d3e891	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-1750905022a298264c01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0zmj-3900000000-855cde19e6da37b58297	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0006-9000000000-771f8558a3b6a27b2bcb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0006-9500000000-1a8f882c4cfc3504cf1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0006-9200000000-2734e7ddf9afda9c8b99	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',4'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-0006-9000000000-9fe84d535c3fe40e4b94	2021-09-22	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

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

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

14530

PDB ID

Not Available

ChEBI ID

19868

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1469471

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 3',4'-Dihydroxyacetophenone (HMDB0029661)

MOL for HMDB0029661 (3',4'-Dihydroxyacetophenone)

3D MOL for HMDB0029661 (3',4'-Dihydroxyacetophenone)

3D SDF for HMDB0029661 (3',4'-Dihydroxyacetophenone)

3D-SDF for HMDB0029661 (3',4'-Dihydroxyacetophenone)

PDB for HMDB0029661 (3',4'-Dihydroxyacetophenone)

3D PDB for HMDB0029661 (3',4'-Dihydroxyacetophenone)

SMILES for HMDB0029661 (3',4'-Dihydroxyacetophenone)

INCHI for HMDB0029661 (3',4'-Dihydroxyacetophenone)

Structure for HMDB0029661 (3',4'-Dihydroxyacetophenone)

3D Structure for HMDB0029661 (3',4'-Dihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra