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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-24 12:35:05 UTC

Update Date

2023-02-21 17:17:04 UTC

HMDB ID

HMDB0004815

Secondary Accession Numbers

HMDB04815

Metabolite Identification

Common Name

4-Hydroxy-3-methylbenzoic acid

Description

4-Hydroxy-3-methylbenzoic acid, also known as 4,3-cresotic acid or 4-hydroxy-m-toluic acid, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxy-3-methylbenzoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-hydroxy-3-methylbenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxy-3-methylbenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 4-Hydroxy-3-methylbenzoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,3-Cresotic acid	ChEBI
4-Hydroxy-m-toluic acid	ChEBI
4,3-Cresotate	Generator
4-Hydroxy-m-toluate	Generator
4-Hydroxy-3-methylbenzoate	Generator
3-Methyl-4-hydroxybenzoate	HMDB
3-Methyl-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3-methyl-benzoate	HMDB
4-Hydroxy-3-methyl-benzoic acid	HMDB
4-Hydroxy-3-methoxybenzoic acid	HMDB
Vanillic acid	HMDB
4-Hydroxy-3-methylbenzoic acid	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

4-hydroxy-3-methylbenzoic acid

Traditional Name

4-hydroxy-3-methylbenzoic acid

CAS Registry Number

499-76-3

SMILES

CC1=CC(=CC=C1O)C(O)=O

InChI Identifier

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

InChI Key

LTFHNKUKQYVHDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Hydroxybenzoic acid
Benzoic acid
O-cresol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

toluenes (CHEBI:85239 )
monohydroxybenzoic acid (CHEBI:85239 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004815)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004815)

Source

Endogenous

Endogenous (HMDB: HMDB0004815)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.6 mg/mL at 100 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.52 g/L	ALOGPS
logP	1.86	ALOGPS
logP	1.84	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.34 m³·mol⁻¹	ChemAxon
Polarizability	15.01 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]+	134.1	31661259
DarkChem	[M-H]-	128.82	31661259
DeepCCS	[M+H]+	127.531	30932474
DeepCCS	[M-H]-	123.806	30932474
DeepCCS	[M-2H]-	161.059	30932474
DeepCCS	[M+Na]+	136.268	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	128.4	32859911
AllCCS	[M+Na-2H]-	129.7	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methylbenzoic acid	CC1=CC(=CC=C1O)C(O)=O	2775.7	Standard polar	33892256
4-Hydroxy-3-methylbenzoic acid	CC1=CC(=CC=C1O)C(O)=O	1413.5	Standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid	CC1=CC(=CC=C1O)C(O)=O	1565.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methylbenzoic acid,1TMS,isomer #1	CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C	1685.4	Semi standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid,1TMS,isomer #2	CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O	1675.4	Semi standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid,2TMS,isomer #1	CC1=CC(C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1717.5	Semi standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid,1TBDMS,isomer #1	CC1=CC(C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	1941.4	Semi standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid,1TBDMS,isomer #2	CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	1916.6	Semi standard non polar	33892256
4-Hydroxy-3-methylbenzoic acid,2TBDMS,isomer #1	CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2229.7	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 - 4-Hydroxy-3-methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-2900000000-8c797b085363527030ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methylbenzoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05gi-8290000000-f504bba638b849bb3e3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0pb9-0900000000-7116c4f6bc6a16489f93	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-002f-9100000000-5cb5ac07c526f364ec47	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00or-9000000000-48da170e5bf8545c76ad	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOF	splash10-00r2-9400000000-74e1e2ded12f501df2e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOF	splash10-005c-9700000000-ec74ea932b54181ecf7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOF	splash10-0a4r-2900000000-3a1e1188e20892c5b6ea	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Positive-QTOF	splash10-0udr-0900000000-b71e7e5af0f2a18fde93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Positive-QTOF	splash10-052r-0900000000-a09894245cfcd228962f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Positive-QTOF	splash10-056r-9400000000-a4f7437005df1701ba6f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOF	splash10-0udi-0900000000-09bb3008e287bfe7e21d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOF	splash10-0pb9-0900000000-ab8a808b767d57f51fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOF	splash10-0a4i-9800000000-685fd00ed340ca85a59e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Positive-QTOF	splash10-0a4r-2900000000-b91d4b89123d2144bea5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Positive-QTOF	splash10-0a4l-4900000000-f7ca6adae4dd477716c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Positive-QTOF	splash10-004i-9000000000-805028da81d33adb9331	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-4d5dcc5d2bfbb145667f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-1a6a31d05eb4cafd05c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylbenzoic acid 40V, Negative-QTOF	splash10-0a4i-9500000000-7b09fe32d2bcc847325d	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	13.1 (3.6-54.0) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	7.5 (6.7-17.1) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	6.0 (0.9-28.6) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.3 (2.7-8.9) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.0 (1.3-9.7) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	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

FDB023425

KNApSAcK ID

Not Available

Chemspider ID

61446

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68138

PDB ID

Not Available

ChEBI ID

85239

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

King, L. Carroll; McWhirter, Margaret; Barton, Daniel M. Reactions of acetophenols with iodine and pyridine and the preparation of hydroxybenzoic acids. Journal of the American Chemical Society (1945), 67 2089-92.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]

Showing metabocard for 4-Hydroxy-3-methylbenzoic acid (HMDB0004815)

MOL for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

3D MOL for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

3D SDF for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

3D-SDF for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

PDB for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

3D PDB for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

SMILES for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

INCHI for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

Structure for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

3D Structure for HMDB0004815 (4-Hydroxy-3-methylbenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra