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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:50:41 UTC

Update Date

2023-02-21 17:22:26 UTC

HMDB ID

HMDB0032594

Secondary Accession Numbers

HMDB32594

Metabolite Identification

Common Name

2-(Hydroxymethyl)benzoic acid

Description

2-(Hydroxymethyl)benzoic acid, also known as 2-carboxybenzyl alcohol or a-hydroxy-O-toluic acid, 8CI, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Based on a literature review a significant number of articles have been published on 2-(Hydroxymethyl)benzoic 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
2-Hydroxymethylbenzoic acid	Kegg
2-Hydroxymethylbenzoate	Generator
2-(Hydroxymethyl)benzoate	Generator
2-(Hydroxymethyl)-benzoic acid	HMDB
2-Carboxybenzyl alcohol	HMDB
2-Hydroxymethyl-benzoic acid	HMDB
2-Methylolbenzoic acid	HMDB
a-Hydroxy-O-toluic acid, 8ci	HMDB
alpha-Hydroxy-O-toluic acid	HMDB
Benzoic acid, 2-(hydroxymethyl)- (9ci)	HMDB
Benzyl alcohol 2-carboxylic acid	HMDB
O-Toluic acid, alpha-hydroxy- (8ci)	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

2-(hydroxymethyl)benzoic acid

Traditional Name

2-hydroxymethylbenzoic acid

CAS Registry Number

612-20-4

SMILES

OCC1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C8H8O3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,9H,5H2,(H,10,11)

InChI Key

MGMNPSAERQZUIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids

Alternative Parents

Substituents

Benzoic acid
Benzyl alcohol
Benzoyl
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 23516449)

Cellular substructure

Extracellular (HMDB: HMDB0032594)
Cytoplasm (HMDB: HMDB0032594)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032594)

Source

Endogenous

Endogenous (HMDB: HMDB0032594)

Plant

Plant (HMDB: HMDB0032594)

Exogenous

Food

Food (HMDB: HMDB0032594)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0032594)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 128 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.28 mg/mL at 20 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.1 g/L	ALOGPS
logP	0.73	ALOGPS
logP	0.86	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-3	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	2	ChemAxon
Refractivity	40.13 m³·mol⁻¹	ChemAxon
Polarizability	14.86 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]+	131.598	31661259
DarkChem	[M-H]-	129.953	31661259
DeepCCS	[M+H]+	130.746	30932474
DeepCCS	[M-H]-	127.03	30932474
DeepCCS	[M-2H]-	163.975	30932474
DeepCCS	[M+Na]+	139.31	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	127.9	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	130.7	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.	3.04 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3458 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	61.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1245.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	344.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	81.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	346.9 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	398.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	760.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	297.8 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	1096.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	294.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	467.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	217.7 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	182.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(Hydroxymethyl)benzoic acid	OCC1=CC=CC=C1C(O)=O	2645.8	Standard polar	33892256
2-(Hydroxymethyl)benzoic acid	OCC1=CC=CC=C1C(O)=O	1458.7	Standard non polar	33892256
2-(Hydroxymethyl)benzoic acid	OCC1=CC=CC=C1C(O)=O	1529.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(Hydroxymethyl)benzoic acid,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=CC=C1C(=O)O	1601.3	Semi standard non polar	33892256
2-(Hydroxymethyl)benzoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC=C1CO	1532.6	Semi standard non polar	33892256
2-(Hydroxymethyl)benzoic acid,2TMS,isomer #1	C[Si](C)(C)OCC1=CC=CC=C1C(=O)O[Si](C)(C)C	1607.8	Semi standard non polar	33892256
2-(Hydroxymethyl)benzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=CC=C1C(=O)O	1847.8	Semi standard non polar	33892256
2-(Hydroxymethyl)benzoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1CO	1759.3	Semi standard non polar	33892256
2-(Hydroxymethyl)benzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2063.3	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-(Hydroxymethyl)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc0-1900000000-b50a0149bf62d2c1def0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hydroxymethyl)benzoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-8390000000-55dfc04bbabec9ef4a99	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hydroxymethyl)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hydroxymethyl)benzoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 10V, Positive-QTOF	splash10-0udi-0900000000-a6f6e6f376acc5f7fa53	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 20V, Positive-QTOF	splash10-0a4r-0900000000-2cdd2340d148faea8d15	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 40V, Positive-QTOF	splash10-0a4i-9700000000-4d0dbce0e1694ce84380	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 10V, Negative-QTOF	splash10-0udi-0900000000-8eb2872e7e97946aba66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 20V, Negative-QTOF	splash10-0pk9-2900000000-4c24e96827f9f9ceaf37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 40V, Negative-QTOF	splash10-004i-9300000000-4a395bb338946eb1ca4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 10V, Negative-QTOF	splash10-00b9-5900000000-1ab5a5a6d897c8ced810	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 20V, Negative-QTOF	splash10-004i-9200000000-13c8811ab3ea7562ed3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 40V, Negative-QTOF	splash10-004i-9000000000-5cb984cc7fcaff357570	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 10V, Positive-QTOF	splash10-0673-1900000000-018c6a3866f37bdfb0b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 20V, Positive-QTOF	splash10-014l-4900000000-7c22cbb1f65d82355eea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hydroxymethyl)benzoic acid 40V, Positive-QTOF	splash10-0ftf-9100000000-942355a29c0e863ec807	2021-09-22	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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diarrhea-predominant IBS	23516449	details

Associated Disorders and Diseases

Disease References

Diarrhoea predominant irritable bowel syndrome
Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11920

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830411

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-(Hydroxymethyl)benzoic acid (HMDB0032594)

MOL for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

3D MOL for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

3D SDF for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

3D-SDF for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

PDB for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

3D PDB for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

SMILES for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

INCHI for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

Structure for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

3D Structure for HMDB0032594 (2-(Hydroxymethyl)benzoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra