Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:35 UTC

Update Date

2023-02-21 17:22:24 UTC

HMDB ID

HMDB0032578

Secondary Accession Numbers

HMDB32578

Metabolite Identification

Common Name

4-Hydroxybenzylamine

Description

4-Hydroxybenzylamine, also known as 4-(aminomethyl)phenol or a-amino-p-cresol, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. Based on a literature review a significant number of articles have been published on 4-Hydroxybenzylamine.

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-(Aminomethyl)phenol	HMDB
4-(Aminomethyl)-phenol	HMDB
4-(Aminomethyl)phenol, 9ci	HMDB
a-Amino-p-cresol	HMDB
Para-hydroxybenzylamine	HMDB
4-Hydroxybenzylamine hydrochloride	HMDB
4-Hydroxybenzylamine, sulfate(2:1) salt	HMDB
4-Hydroxybenzylamine	MeSH

Chemical Formula

C₇H₉NO

Average Molecular Weight

123.1525

Monoisotopic Molecular Weight

123.068413915

IUPAC Name

4-(aminomethyl)phenol

Traditional Name

4-(aminomethyl)phenol

CAS Registry Number

696-60-6

SMILES

NCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C7H9NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H,5,8H2

InChI Key

RQJDUEKERVZLLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Phenylmethylamine
Benzylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032578)
Cytoplasm (HMDB: HMDB0032578)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032578)

Source

Endogenous

Endogenous (HMDB: HMDB0032578)

Plant

Plant (HMDB: HMDB0032578)

Exogenous

Food

Food (HMDB: HMDB0032578)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0032578)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	114 - 115 °C	Not Available
Boiling Point	262.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.350 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	35.3 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	0.08	ChemAxon
logS	-0.54	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.51 m³·mol⁻¹	ChemAxon
Polarizability	13.29 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]+	125.316	31661259
DarkChem	[M-H]-	121.583	31661259
DeepCCS	[M+H]+	125.798	30932474
DeepCCS	[M-H]-	122.089	30932474
DeepCCS	[M-2H]-	159.422	30932474
DeepCCS	[M+Na]+	134.668	30932474
AllCCS	[M+H]+	126.5	32859911
AllCCS	[M+H-H2O]+	121.7	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	125.1	32859911
AllCCS	[M+Na-2H]-	127.2	32859911
AllCCS	[M+HCOO]-	129.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzylamine	NCC1=CC=C(O)C=C1	2349.5	Standard polar	33892256
4-Hydroxybenzylamine	NCC1=CC=C(O)C=C1	1393.7	Standard non polar	33892256
4-Hydroxybenzylamine	NCC1=CC=C(O)C=C1	1341.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzylamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CN)C=C1	1386.5	Semi standard non polar	33892256
4-Hydroxybenzylamine,1TMS,isomer #2	C[Si](C)(C)NCC1=CC=C(O)C=C1	1595.4	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TMS,isomer #1	C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C=C1	1564.4	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TMS,isomer #1	C[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C)C=C1	1542.9	Standard non polar	33892256
4-Hydroxybenzylamine,2TMS,isomer #2	C[Si](C)(C)N(CC1=CC=C(O)C=C1)[Si](C)(C)C	1733.4	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TMS,isomer #2	C[Si](C)(C)N(CC1=CC=C(O)C=C1)[Si](C)(C)C	1749.2	Standard non polar	33892256
4-Hydroxybenzylamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1	1757.8	Semi standard non polar	33892256
4-Hydroxybenzylamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C)[Si](C)(C)C)C=C1	1708.6	Standard non polar	33892256
4-Hydroxybenzylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CN)C=C1	1642.7	Semi standard non polar	33892256
4-Hydroxybenzylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=CC=C(O)C=C1	1803.2	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2065.2	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2013.3	Standard non polar	33892256
4-Hydroxybenzylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	2180.9	Semi standard non polar	33892256
4-Hydroxybenzylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	2188.3	Standard non polar	33892256
4-Hydroxybenzylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2441.9	Semi standard non polar	33892256
4-Hydroxybenzylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2321.1	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-Hydroxybenzylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-5bd339841edaff8969ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzylamine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9800000000-d2f02a0037edc9ef770b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzylamine 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 - 4-Hydroxybenzylamine 10V, Positive-QTOF	splash10-05fr-0900000000-b04e0cc0b04704b96636	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 20V, Positive-QTOF	splash10-0a4i-1900000000-cb910a00dfe4de3d3dcf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 40V, Positive-QTOF	splash10-0a6r-9600000000-6a0c5d1ae2fb3d77a340	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 10V, Negative-QTOF	splash10-00di-1900000000-93ad671f1652fc6d74ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 20V, Negative-QTOF	splash10-00di-3900000000-1c5f06f90987762c629b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 40V, Negative-QTOF	splash10-0006-9200000000-ccf709fa26d211b1af44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 10V, Positive-QTOF	splash10-0ab9-1900000000-d85777e7c4c743fe7df4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 20V, Positive-QTOF	splash10-0a4i-5900000000-1acbbc3a6a28117f38f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 40V, Positive-QTOF	splash10-0fvi-9000000000-84bfbb4b1bf0a9dba97e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 10V, Negative-QTOF	splash10-00dl-6900000000-e2af19bd886822872f68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 20V, Negative-QTOF	splash10-006x-9400000000-2170963284d3573f0eac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzylamine 40V, Negative-QTOF	splash10-0006-9100000000-0b0ff530be79466d95cf	2021-09-22	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

FDB010515

KNApSAcK ID

C00053988

Chemspider ID

87979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97472

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1628011

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 4-Hydroxybenzylamine (HMDB0032578)

MOL for HMDB0032578 (4-Hydroxybenzylamine)

3D MOL for HMDB0032578 (4-Hydroxybenzylamine)

3D SDF for HMDB0032578 (4-Hydroxybenzylamine)

3D-SDF for HMDB0032578 (4-Hydroxybenzylamine)

PDB for HMDB0032578 (4-Hydroxybenzylamine)

3D PDB for HMDB0032578 (4-Hydroxybenzylamine)

SMILES for HMDB0032578 (4-Hydroxybenzylamine)

INCHI for HMDB0032578 (4-Hydroxybenzylamine)

Structure for HMDB0032578 (4-Hydroxybenzylamine)

3D Structure for HMDB0032578 (4-Hydroxybenzylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra