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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:50:32 UTC

Update Date

2023-02-21 17:22:21 UTC

HMDB ID

HMDB0032568

Secondary Accession Numbers

HMDB32568

Metabolite Identification

Common Name

2'-Hydroxyacetophenone

Description

2'-Hydroxyacetophenone, also known as 2-acetylphenol or 2-hydroxyacetylbenzene, 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'-Hydroxyacetophenone is a sweet, hawthorne, and herbal tasting compound. 2'-hydroxyacetophenone has been detected, but not quantified, in several different foods, such as chinese cinnamons, tea, coffee and coffee products, alcoholic beverages, and garden tomato.

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-Hydroxyphenyl)ethanone	ChEBI
2-Hydroxyphenyl methyl ketone	ChEBI
Methyl 2-hydroxyphenyl ketone	ChEBI
O-Acetylphenol	ChEBI
O-Hydroxyacetophenone	ChEBI
O-Hydroxyphenyl methyl ketone	ChEBI
1-(2-Hydroxyphenyl)ethanone, 9ci	HMDB
2-Acetylphenol	HMDB
2-Hydroxyacetophenone	HMDB
2-Hydroxyacetylbenzene	HMDB
Acetophenone, 2'-hydroxy- (8ci)	HMDB
FEMA 3548	HMDB
1-(2-Hydroxyphenyl)ethanone, sodium salt	MeSH
2'-Hydroxyacetophenone	MeSH

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

1-(2-hydroxyphenyl)ethan-1-one

Traditional Name

o-acetylphenol

CAS Registry Number

118-93-4

SMILES

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

InChI Identifier

InChI=1S/C8H8O2/c1-6(9)7-4-2-3-5-8(7)10/h2-5,10H,1H3

InChI Key

JECYUBVRTQDVAT-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
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

Sweet

Urine (PMID: 19754154)

Cellular substructure

Extracellular (HMDB: HMDB0032568)
Cytoplasm (HMDB: HMDB0032568)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032568)

Source

Endogenous

Endogenous (HMDB: HMDB0032568)

Plant

Exogenous

Food

Food (HMDB: HMDB0032568)

Tea

Vegetable

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

Herbs and Spices (FooDB: FOOD00866)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0032568)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032568)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	4 - 6 °C	Not Available
Boiling Point	213.00 °C. @ 717.00 mm Hg	The Good Scents Company Information System
Water Solubility	7571 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.92	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.53 g/L	ALOGPS
logP	1.57	ALOGPS
logP	1.88	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.44 m³·mol⁻¹	ChemAxon
Polarizability	13.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.849	31661259
DarkChem	[M-H]-	123.983	31661259
DeepCCS	[M+H]+	129.212	30932474
DeepCCS	[M-H]-	126.841	30932474
DeepCCS	[M-2H]-	162.761	30932474
DeepCCS	[M+Na]+	137.626	30932474
AllCCS	[M+H]+	127.2	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.9	32859911
AllCCS	[M-H]-	125.1	32859911
AllCCS	[M+Na-2H]-	126.8	32859911
AllCCS	[M+HCOO]-	128.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxyacetophenone	CC(=O)C1=CC=CC=C1O	1710.0	Standard polar	33892256
2'-Hydroxyacetophenone	CC(=O)C1=CC=CC=C1O	1155.9	Standard non polar	33892256
2'-Hydroxyacetophenone	CC(=O)C1=CC=CC=C1O	1172.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC=CC=C1O[Si](C)(C)C	1362.9	Semi standard non polar	33892256
2'-Hydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1605.9	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'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-5900000000-ea1d13b06231dbf578d1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00di-9700000000-721a4c1cfd24489043f3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-7900000000-46e56b157939e4c29b8b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-2900000000-227d105f2ffa3af8da6c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-0fyc-9100000000-6aa38be570fc2e4c3c7e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone GC-EI-TOF (Non-derivatized)	splash10-0k9i-6930000000-dbe69fc655dc199f5f15	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone GC-EI-TOF (Non-derivatized)	splash10-000i-9730000000-e2422666dabed3fe1c7b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-5900000000-ea1d13b06231dbf578d1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00di-9700000000-721a4c1cfd24489043f3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-7900000000-46e56b157939e4c29b8b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-00dr-2900000000-227d105f2ffa3af8da6c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone EI-B (Non-derivatized)	splash10-0fyc-9100000000-6aa38be570fc2e4c3c7e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone GC-EI-TOF (Non-derivatized)	splash10-0k9i-6930000000-dbe69fc655dc199f5f15	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Hydroxyacetophenone GC-EI-TOF (Non-derivatized)	splash10-000i-9730000000-e2422666dabed3fe1c7b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-7900000000-d4cc6f063afec6b5730d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxyacetophenone GC-MS (1 TMS) - 70eV, Positive	splash10-0fdo-9800000000-21426c50efa3a817edef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-6900000000-254acf7b1631315eeb6a	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 10V, Positive-QTOF	splash10-000i-0900000000-aff77b5e75f726399250	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 20V, Positive-QTOF	splash10-000i-2900000000-da4cbd45db4878901a39	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 40V, Positive-QTOF	splash10-0v04-9200000000-0553a3dde84aa619c916	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 10V, Negative-QTOF	splash10-000i-0900000000-e0f43dc550abdf84e9ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 20V, Negative-QTOF	splash10-000i-1900000000-0cb226ca106d7a723ef4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 40V, Negative-QTOF	splash10-00kf-9400000000-dcfaefaf22e699717842	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 10V, Positive-QTOF	splash10-00kr-3900000000-e42da4f6e13dded313d0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 20V, Positive-QTOF	splash10-0006-9300000000-0a8e1834cbac8bd92ecd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 40V, Positive-QTOF	splash10-0f6x-9000000000-09dd2c8a2c7f8f87cbb3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 10V, Negative-QTOF	splash10-000i-1900000000-c22473505fd741d60379	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 20V, Negative-QTOF	splash10-000f-9500000000-b112dcef1a6ca5d4c2ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxyacetophenone 40V, Negative-QTOF	splash10-014l-9200000000-4ae3fa84bbff3c78d2b5	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)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19754154	details

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

FDB010500

KNApSAcK ID

C00054088

Chemspider ID

21105920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8375

PDB ID

Not Available

ChEBI ID

145716

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013131

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'-Hydroxyacetophenone (HMDB0032568)

MOL for HMDB0032568 (2'-Hydroxyacetophenone)

3D MOL for HMDB0032568 (2'-Hydroxyacetophenone)

3D SDF for HMDB0032568 (2'-Hydroxyacetophenone)

3D-SDF for HMDB0032568 (2'-Hydroxyacetophenone)

PDB for HMDB0032568 (2'-Hydroxyacetophenone)

3D PDB for HMDB0032568 (2'-Hydroxyacetophenone)

SMILES for HMDB0032568 (2'-Hydroxyacetophenone)

INCHI for HMDB0032568 (2'-Hydroxyacetophenone)

Structure for HMDB0032568 (2'-Hydroxyacetophenone)

3D Structure for HMDB0032568 (2'-Hydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra