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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:12 UTC

Update Date

2023-02-21 17:21:27 UTC

HMDB ID

HMDB0032012

Secondary Accession Numbers

HMDB32012

Metabolite Identification

Common Name

4-Hydroxy-3-methoxybenzenemethanol

Description

4-Hydroxy-3-methoxybenzenemethanol, also known as 4-hydroxy-3-methoxybenzyl alcohol or 3-methoxy-4-hydroxybenzyl alcohol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-Hydroxy-3-methoxybenzenemethanol is a drug. 4-Hydroxy-3-methoxybenzenemethanol is a sweet, anise, and balsam tasting compound. 4-hydroxy-3-methoxybenzenemethanol has been detected, but not quantified, in fruits and herbs and spices. This could make 4-hydroxy-3-methoxybenzenemethanol a potential biomarker for the consumption of these foods.

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-Hydroxy-3-methoxy-benzenemethanol	ChEBI
4-Hydroxy-3-methoxybenzyl alcohol	ChEBI
3-Methoxy-4-hydroxybenzyl alcohol	HMDB
4-(Hydroxymethyl)-2-methoxyphenol	HMDB
4-HYDROXY-3-methoxy-benzyl alcohol	HMDB
4-Hydroxy-3-methoxybenzenemethanol, 9ci	HMDB
4-Hydroxy-3-methoxyphenyl methanol	HMDB
4-Hydroxy-3-methoxyphenylmethanol	HMDB
a,4-Dihydroxy-3-methoxytoluene	HMDB
FEMA 3737	HMDB
V 0018 (Alcohol)	HMDB
Vanillic alcohol	HMDB
Vanillin alcohol	HMDB
Vanillol	HMDB
Vanillyl alcohol	HMDB
Vanillyl-alcohol	HMDB
4-Hydroxy-3-methoxybenzenemethanol	ChEBI

Chemical Formula

C₈H₁₀O₃

Average Molecular Weight

154.1632

Monoisotopic Molecular Weight

154.062994186

IUPAC Name

4-(hydroxymethyl)-2-methoxyphenol

Traditional Name

vanillyl alcohol

CAS Registry Number

498-00-0

SMILES

COC1=CC(CO)=CC=C1O

InChI Identifier

InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3

InChI Key

ZENOXNGFMSCLLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Benzyl alcohol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Primary alcohol
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:18353 )
benzyl alcohols (CHEBI:18353 )
monomethoxybenzene (CHEBI:18353 )
a small molecule (VANILLYL-ALCOHOL )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032012)
Cytoplasm (HMDB: HMDB0032012)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032012)

Source

Endogenous

Endogenous (HMDB: HMDB0032012)

Plant

Plant (HMDB: HMDB0032012)

Exogenous

Food

Food (HMDB: HMDB0032012)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032012)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032012)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	114 - 115 °C	Not Available
Boiling Point	312.00 to 313.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2 mg/mL at 20 °C	Not Available
LogP	0.420	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29.4 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.74	ChemAxon
logS	-0.72	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.32 m³·mol⁻¹	ChemAxon
Polarizability	15.74 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]+	133.781	31661259
DarkChem	[M-H]-	130.27	31661259
DeepCCS	[M+H]+	140.04	30932474
DeepCCS	[M-H]-	136.212	30932474
DeepCCS	[M-2H]-	173.734	30932474
DeepCCS	[M+Na]+	149.273	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.4	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	132.2	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxybenzenemethanol	COC1=C(O)C=CC(CO)=C1	2741.8	Standard polar	33892256
4-Hydroxy-3-methoxybenzenemethanol	COC1=C(O)C=CC(CO)=C1	1419.0	Standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol	COC1=C(O)C=CC(CO)=C1	1481.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxybenzenemethanol,1TMS,isomer #1	COC1=CC(CO)=CC=C1O[Si](C)(C)C	1551.4	Semi standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol,1TMS,isomer #2	COC1=CC(CO[Si](C)(C)C)=CC=C1O	1564.4	Semi standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol,2TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1623.9	Semi standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol,1TBDMS,isomer #1	COC1=CC(CO)=CC=C1O[Si](C)(C)C(C)(C)C	1795.2	Semi standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol,1TBDMS,isomer #2	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O	1788.3	Semi standard non polar	33892256
4-Hydroxy-3-methoxybenzenemethanol,2TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2078.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-EI-TOF (Non-derivatized)	splash10-05ot-1980000000-90c0d7b9d5ab2ad49ebd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-EI-TOF (Non-derivatized)	splash10-05ot-1980000000-90c0d7b9d5ab2ad49ebd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1900000000-4bfb638326b97e8c9eeb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-7390000000-dfd8ee944e68b10e2514	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 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-methoxybenzenemethanol DI-ESI-qTof , Negative-QTOF	splash10-0udr-0900000000-cae1bb4557de8c5c425e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol DI-ESI-qTof , Negative-QTOF	splash10-0udi-0900000000-a953d3d5aa4c7a4bbb1d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Positive-QTOF	splash10-0a4r-0900000000-8cec776a8684a3c300ba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Positive-QTOF	splash10-000i-0900000000-c5e19bc7f2c583cdd9d1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Positive-QTOF	splash10-052r-5900000000-5795c57b2d2294956f78	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Negative-QTOF	splash10-0udi-0900000000-da35d09bba9c4f0150c1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Negative-QTOF	splash10-0uki-1900000000-bddb6a9312eb8cd5304d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Negative-QTOF	splash10-0a4i-9800000000-8b1a492cf5623f10508d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Negative-QTOF	splash10-0udi-0900000000-55caab0c9e31716e1c83	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Negative-QTOF	splash10-0zmr-0900000000-622397e9193433d15622	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Negative-QTOF	splash10-0zfr-9500000000-e4dfb45f82af81f401b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Positive-QTOF	splash10-00di-2900000000-01d9f9426f095b48367d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Positive-QTOF	splash10-0a4r-1900000000-97c5e5bea153c9d79651	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Positive-QTOF	splash10-0pc0-9300000000-7d51ed335759aaf044c4	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

DB12087

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

Vanillyl_alcohol

METLIN ID

Not Available

PubChem Compound

62348

PDB ID

Not Available

ChEBI ID

18353

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037781

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-Hydroxy-3-methoxybenzenemethanol (HMDB0032012)

MOL for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

3D MOL for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

3D SDF for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

3D-SDF for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

PDB for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

3D PDB for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

SMILES for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

INCHI for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

Structure for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

3D Structure for HMDB0032012 (4-Hydroxy-3-methoxybenzenemethanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra