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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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.54 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7301 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1710.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	418.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	262.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	467.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	592.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1031.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	407.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1214.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	228.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	84.4 seconds	40023050

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra