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 17:31:53 UTC

Update Date

2023-02-21 17:18:59 UTC

HMDB ID

HMDB0029662

Secondary Accession Numbers

HMDB29662

Metabolite Identification

Common Name

3',5'-Dihydroxyacetophenone

Description

3',5'-Dihydroxyacetophenone, also known as 5-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. Based on a literature review very few articles have been published on 3',5'-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 5-Dihydroxyacetophenone	HMDB
1-(3,5-Dihydroxyphenyl)ethan-1-one	HMDB
1-(3,5-Dihydroxyphenyl)ethanone, 9ci	HMDB
3,5-Dihydroxyacetophenone	HMDB
5-Acetylresorcinol	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(3,5-dihydroxyphenyl)ethan-1-one

Traditional Name

1-(3,5-dihydroxyphenyl)ethanone

CAS Registry Number

51863-60-6

SMILES

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

InChI Identifier

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

InChI Key

WQXWIKCZNIGMAP-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
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: HMDB0029662)
Cytoplasm (HMDB: HMDB0029662)

Source

Endogenous

Endogenous (HMDB: HMDB0029662)

Exogenous

Food

Food (HMDB: HMDB0029662)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 - 148 °C	Not Available
Boiling Point	316.75 °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	1.019 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.97 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.92	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-5.7	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	14.95 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]+	135.038	31661259
DarkChem	[M-H]-	130.867	31661259
DeepCCS	[M+H]+	131.535	30932474
DeepCCS	[M-H]-	127.913	30932474
DeepCCS	[M-2H]-	165.586	30932474
DeepCCS	[M+Na]+	141.125	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.6	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
3',5'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=CC(O)=C1	2440.4	Standard polar	33892256
3',5'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=CC(O)=C1	1525.6	Standard non polar	33892256
3',5'-Dihydroxyacetophenone	CC(=O)C1=CC(O)=CC(O)=C1	1750.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3',5'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC(O)=CC(O[Si](C)(C)C)=C1	1665.1	Semi standard non polar	33892256
3',5'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	1697.4	Semi standard non polar	33892256
3',5'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1	1919.3	Semi standard non polar	33892256
3',5'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2163.3	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',5'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-1900000000-a4cd58790ad212f8ca30	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',5'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-0089-2290000000-7a06d6b21768c0b0c674	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',5'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3',5'-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',5'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-b0cb58145b7ef4c9fb63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-3063e508f1ec7572b914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-00ku-5900000000-68426fa37395a4e5423c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-11e2bfd7cad0d26d98d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0udi-0900000000-fba62bfc58d002ef0058	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0a4l-6900000000-1cb202d16dea09054ea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0006-9300000000-a41a386c4daaad3447d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0f6x-8900000000-216f627410b422ce1d59	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-0006-9000000000-74168aee18529cd6c350	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-ab4c726a1d68fe71093c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0zfr-0900000000-5afc010d4a935a946b02	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3',5'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-00kf-9100000000-74d503dd8691ec92f955	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)	2021-09-30	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB000837

KNApSAcK ID

Not Available

Chemspider ID

93889

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

103993

PDB ID

Not Available

ChEBI ID

574890

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1181421

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',5'-Dihydroxyacetophenone (HMDB0029662)

MOL for HMDB0029662 (3',5'-Dihydroxyacetophenone)

3D MOL for HMDB0029662 (3',5'-Dihydroxyacetophenone)

3D SDF for HMDB0029662 (3',5'-Dihydroxyacetophenone)

3D-SDF for HMDB0029662 (3',5'-Dihydroxyacetophenone)

PDB for HMDB0029662 (3',5'-Dihydroxyacetophenone)

3D PDB for HMDB0029662 (3',5'-Dihydroxyacetophenone)

SMILES for HMDB0029662 (3',5'-Dihydroxyacetophenone)

INCHI for HMDB0029662 (3',5'-Dihydroxyacetophenone)

Structure for HMDB0029662 (3',5'-Dihydroxyacetophenone)

3D Structure for HMDB0029662 (3',5'-Dihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra