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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:40 UTC

Update Date

2023-02-21 17:22:26 UTC

HMDB ID

HMDB0032592

Secondary Accession Numbers

HMDB32592

Metabolite Identification

Common Name

2'-Hydroxy-5'-methylacetophenone

Description

2'-Hydroxy-5'-methylacetophenone 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'-Hydroxy-5'-methylacetophenone is a sweet, floral, and heavy tasting compound. 2'-Hydroxy-5'-methylacetophenone has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2'-hydroxy-5'-methylacetophenone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2'-Hydroxy-5'-methylacetophenone.

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-Hydroxy-5-methylphenyl)-ethanone	HMDB
1-(2-Hydroxy-5-methylphenyl)ethanone	HMDB
1-(2-Hydroxy-5-methylphenyl)ethanone, 9ci	HMDB
1-Hydroxy-2-acetyl-4-methylbenzene	HMDB
2'-Hydroxy-5'-methyl-acetophenone	HMDB
2-Acetyl-4-methylphenol	HMDB
2-Acetyl-P-cresol	HMDB
2-Hydroxy-5-methylacetophenone	HMDB
Methyl 6-hydroxy-m-tolyl ketone	HMDB
O-Acetyl-P-cresol	HMDB

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

1-(2-hydroxy-5-methylphenyl)ethan-1-one

Traditional Name

2-acetyl-4-methylphenol

CAS Registry Number

1450-72-2

SMILES

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

InChI Identifier

InChI=1S/C9H10O2/c1-6-3-4-9(11)8(5-6)7(2)10/h3-5,11H,1-2H3

InChI Key

YNPDFBFVMJNGKZ-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
P-cresol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Toluene
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

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032592)
Cytoplasm (HMDB: HMDB0032592)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032592)

Source

Endogenous

Endogenous (HMDB: HMDB0032592)

Plant

Coffea (HMDB: HMDB0032592)

Exogenous

Food

Food (HMDB: HMDB0032592)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0032592)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032592)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	50 °C	Not Available
Boiling Point	210.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2038 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.941 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.48 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.39	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.5	ChemAxon
pKa (Strongest Basic)	-4.2	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	43.48 m³·mol⁻¹	ChemAxon
Polarizability	16.03 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]+	133.273	31661259
DarkChem	[M-H]-	131.069	31661259
DeepCCS	[M+H]+	134.872	30932474
DeepCCS	[M-H]-	131.412	30932474
DeepCCS	[M-2H]-	168.869	30932474
DeepCCS	[M+Na]+	144.407	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	133.9	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	129.0	32859911
AllCCS	[M+Na-2H]-	130.3	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxy-5'-methylacetophenone	CC(=O)C1=C(O)C=CC(C)=C1	1834.9	Standard polar	33892256
2'-Hydroxy-5'-methylacetophenone	CC(=O)C1=C(O)C=CC(C)=C1	1276.4	Standard non polar	33892256
2'-Hydroxy-5'-methylacetophenone	CC(=O)C1=C(O)C=CC(C)=C1	1266.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxy-5'-methylacetophenone,1TMS,isomer #1	CC(=O)C1=CC(C)=CC=C1O[Si](C)(C)C	1446.0	Semi standard non polar	33892256
2'-Hydroxy-5'-methylacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC(C)=CC=C1O[Si](C)(C)C(C)(C)C	1705.8	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 - 2'-Hydroxy-5'-methylacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc9-2900000000-e951f0957eb44bc9f313	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-5'-methylacetophenone GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9760000000-43f0f53ae58ddd85aa91	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 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'-Hydroxy-5'-methylacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-2bedbd136aa1bc56b658	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Positive-QTOF	splash10-0udi-1900000000-20831b6c52d65cce7292	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Positive-QTOF	splash10-0kau-7900000000-07b8d20195dcd7ade99e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Negative-QTOF	splash10-0002-0900000000-75c3d53ce83ee89c3d91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Negative-QTOF	splash10-0002-0900000000-5102a3f8aa849eb48034	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Negative-QTOF	splash10-0a4i-5900000000-bc0c006306db2d57909d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Positive-QTOF	splash10-0ue9-0900000000-1b7e40a5a029f99a026b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Positive-QTOF	splash10-0a7l-6900000000-837d6f16e4f4e3de02dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Positive-QTOF	splash10-004i-9300000000-fb8d5f4815934be81adf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Negative-QTOF	splash10-0002-0900000000-e0b12c10ffeec106d759	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Negative-QTOF	splash10-0a4i-0900000000-b8a70d97cc6153760dcc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Negative-QTOF	splash10-053s-9700000000-a106c9acc126ee48d420	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

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

FDB010529

KNApSAcK ID

Not Available

Chemspider ID

14340

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15068

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1158081

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'-Hydroxy-5'-methylacetophenone (HMDB0032592)

MOL for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

3D MOL for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

3D SDF for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

3D-SDF for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

PDB for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

3D PDB for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

SMILES for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

INCHI for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

Structure for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

3D Structure for HMDB0032592 (2'-Hydroxy-5'-methylacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra