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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:44 UTC

Update Date

2023-02-21 17:22:27 UTC

HMDB ID

HMDB0032603

Secondary Accession Numbers

HMDB32603

Metabolite Identification

Common Name

2-Hydroxy-4-methylbenzaldehyde

Description

2-Hydroxy-4-methylbenzaldehyde belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 2-Hydroxy-4-methylbenzaldehyde is an almond, bitter, and phenolic tasting compound. Based on a literature review very few articles have been published on 2-Hydroxy-4-methylbenzaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4-Cresotaldehyde	HMDB
2-Formyl-5-methylphenol	HMDB
2-Hydroxy-4-methyl-benzaldehyde	HMDB
2-Hydroxy-P-tolualdehyde	HMDB
4-Methyl salicylaldehyde	HMDB
4-Methyl-2-hydroxybenzaldehyde	HMDB
4-Methylsalicyclic aldehyde	HMDB
4-Methylsalicylaldehyde	HMDB
FEMA 3697	HMDB
m-Cresol-6-aldehyde	HMDB
m-Homosalicylaldehyde	HMDB

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

2-hydroxy-4-methylbenzaldehyde

Traditional Name

2-hydroxy-4-methylbenzaldehyde

CAS Registry Number

698-27-1

SMILES

CC1=CC(O)=C(C=O)C=C1

InChI Identifier

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

InChI Key

JODRRPJMQDFCBJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
M-cresol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
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

Bitter

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032603)
Cytoplasm (HMDB: HMDB0032603)

Source

Endogenous

Endogenous (HMDB: HMDB0032603)

Exogenous

Food

Food (HMDB: HMDB0032603)

Exogenous (HMDB: HMDB0032603)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032603)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 61 °C	Not Available
Boiling Point	760.00 to 223.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.987 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.04 g/L	ALOGPS
logP	1.62	ALOGPS
logP	2.55	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-6	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	39.66 m³·mol⁻¹	ChemAxon
Polarizability	14.05 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]+	127.645	31661259
DarkChem	[M-H]-	124.097	31661259
DeepCCS	[M+H]+	130.679	30932474
DeepCCS	[M-H]-	126.935	30932474
DeepCCS	[M-2H]-	164.551	30932474
DeepCCS	[M+Na]+	140.089	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	125.0	32859911
AllCCS	[M+Na-2H]-	126.6	32859911
AllCCS	[M+HCOO]-	128.4	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.	4.12 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1633 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.73 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1734.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	501.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	336.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	577.3 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	729.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	159.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1161.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	425.4 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	1273.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	499.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	584.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	350.6 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	133.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-methylbenzaldehyde	CC1=CC(O)=C(C=O)C=C1	1749.8	Standard polar	33892256
2-Hydroxy-4-methylbenzaldehyde	CC1=CC(O)=C(C=O)C=C1	1202.2	Standard non polar	33892256
2-Hydroxy-4-methylbenzaldehyde	CC1=CC(O)=C(C=O)C=C1	1246.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-methylbenzaldehyde,1TMS,isomer #1	CC1=CC=C(C=O)C(O[Si](C)(C)C)=C1	1419.1	Semi standard non polar	33892256
2-Hydroxy-4-methylbenzaldehyde,1TBDMS,isomer #1	CC1=CC=C(C=O)C(O[Si](C)(C)C(C)(C)C)=C1	1678.7	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-4-methylbenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-4052b4a288f06f475324	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde GC-MS (1 TMS) - 70eV, Positive	splash10-059f-5910000000-cea8942474688b7860d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 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-4-methylbenzaldehyde 10V, Positive-QTOF	splash10-000i-0900000000-fc28f6cad5b71dfa1b93	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 20V, Positive-QTOF	splash10-000i-1900000000-9b624a6fdedb3b39cf75	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 40V, Positive-QTOF	splash10-0gbc-9300000000-59642e232473c7fbc15a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 10V, Negative-QTOF	splash10-000i-0900000000-6b594181399136d2a753	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 20V, Negative-QTOF	splash10-000i-0900000000-ce15f1695ea495210bba	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 40V, Negative-QTOF	splash10-014r-9500000000-5167cc652f69e61e920d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 10V, Negative-QTOF	splash10-000i-0900000000-85183aae6dd12de03af0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 20V, Negative-QTOF	splash10-0a4r-0900000000-d46ee5c300e7bbe8b31d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 40V, Negative-QTOF	splash10-0gbc-9100000000-cb519b02d4a2ddcd5a1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 10V, Positive-QTOF	splash10-05mx-4900000000-7a975bd37bb97f9bea4f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 20V, Positive-QTOF	splash10-05p6-9400000000-a2e83245f29b7907b48f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-methylbenzaldehyde 40V, Positive-QTOF	splash10-004l-9000000000-6f38f5ec418e76db3a4e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB010543

KNApSAcK ID

C00050721

Chemspider ID

55144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxy-4-methylbenzaldehyde

METLIN ID

Not Available

PubChem Compound

61200

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037471

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-4-methylbenzaldehyde (HMDB0032603)

MOL for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

3D MOL for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

3D SDF for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

3D-SDF for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

PDB for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

3D PDB for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

SMILES for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

INCHI for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

Structure for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

3D Structure for HMDB0032603 (2-Hydroxy-4-methylbenzaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra