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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 00:16:25 UTC

Update Date

2023-02-21 17:26:48 UTC

HMDB ID

HMDB0038925

Secondary Accession Numbers

HMDB38925

Metabolite Identification

Common Name

(4-Hydroxy-3-methoxyphenyl)ethanol

Description

(4-Hydroxy-3-methoxyphenyl)ethanol 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-methoxyphenyl)ethanol has been detected, but not quantified in, olives (Olea europaea) and olive oil. This could make (4-hydroxy-3-methoxyphenyl)ethanol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (4-Hydroxy-3-methoxyphenyl)ethanol.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    7    9                                                       
CONECT    7    2    4    6                                                  
CONECT    8    3    9   11                                                  
CONECT    9    6    8   12                                                  
CONECT   10    5                                                            
CONECT   11    8                                                            
CONECT   12    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(4-Guaiacyl)-ethanol	HMDB
2-(4-Hydroxy-3-methoxyphenyl)-ethanol	HMDB
3-Methoxy-4-hydroxyphenylethanol	HMDB, MeSH
4-(2-Hydroxyethyl)-2-methoxyphenol	HMDB
4-(2-Hydroxyethyl)guaiacol	HMDB
4-Hydroxy-3-methoxy-benzeneethanol	HMDB
4-Hydroxy-3-methoxybenzeneethanol	HMDB
4-Hydroxy-3-methoxyphenethanol	HMDB
4-Hydroxy-3-methoxyphenethyl alcohol	HMDB
4-Hydroxy-3-methoxyphenylethyl alcohol	HMDB
Guaiacyl ethanol	HMDB
Homovanilline alcohol	HMDB
Homovanillyl alcohol	HMDB
Alcohol, hydroxymethoxyphenethyl	MeSH
3 Methoxy 4 hydroxyphenylethanol	MeSH
Hydroxymethoxyphenethyl alcohol	MeSH
MHPE	MeSH
MOPET	MeSH
Methoxyhydroxyphenylethanol	MeSH

Chemical Formula

C₉H₁₂O₃

Average Molecular Weight

168.1898

Monoisotopic Molecular Weight

168.07864425

IUPAC Name

4-(2-hydroxyethyl)-2-methoxyphenol

Traditional Name

homovanillyl alcohol

CAS Registry Number

2380-78-1

SMILES

COC1=C(O)C=CC(CCO)=C1

InChI Identifier

InChI=1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 12888646)

Cellular substructure

Extracellular (HMDB: HMDB0038925)
Cytoplasm (HMDB: HMDB0038925)

Source

Exogenous

Exogenous (HMDB: HMDB0038925)

Food

Food (HMDB: HMDB0038925)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Fat and oil

Olive oil (HMDB: HMDB0038925)

Herb and spice

Oilseed crop

Olive oil (FooDB: FOOD00909)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038925)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	40 - 42 °C	Not Available
Boiling Point	316.00 to 317.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	80530 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.47	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.03	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-2.4	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	3	ChemAxon
Refractivity	46.07 m³·mol⁻¹	ChemAxon
Polarizability	17.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	135.423	31661259
DarkChem	[M-H]-	134.316	31661259
DeepCCS	[M+H]+	136.698	30932474
DeepCCS	[M-H]-	132.868	30932474
DeepCCS	[M-2H]-	170.352	30932474
DeepCCS	[M+Na]+	145.891	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.1	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	135.9	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4-Hydroxy-3-methoxyphenyl)ethanol	COC1=C(O)C=CC(CCO)=C1	2827.3	Standard polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol	COC1=C(O)C=CC(CCO)=C1	1503.5	Standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol	COC1=C(O)C=CC(CCO)=C1	1542.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(4-Hydroxy-3-methoxyphenyl)ethanol,1TMS,isomer #1	COC1=CC(CCO)=CC=C1O[Si](C)(C)C	1628.9	Semi standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol,1TMS,isomer #2	COC1=CC(CCO[Si](C)(C)C)=CC=C1O	1646.7	Semi standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol,2TMS,isomer #1	COC1=CC(CCO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1690.4	Semi standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol,1TBDMS,isomer #1	COC1=CC(CCO)=CC=C1O[Si](C)(C)C(C)(C)C	1880.9	Semi standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol,1TBDMS,isomer #2	COC1=CC(CCO[Si](C)(C)C(C)(C)C)=CC=C1O	1878.1	Semi standard non polar	33892256
(4-Hydroxy-3-methoxyphenyl)ethanol,2TBDMS,isomer #1	COC1=CC(CCO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2159.2	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-methoxyphenyl)ethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-ec18d0012288a1646d7b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol GC-MS (2 TMS) - 70eV, Positive	splash10-00ds-7290000000-e17e60c8a1b9b0a0a16c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 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-Hydroxy-3-methoxyphenyl)ethanol 10V, Positive-QTOF	splash10-0uxr-0900000000-e378f4d70decbf0578dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 20V, Positive-QTOF	splash10-0udi-0900000000-76e9dea293f88631d206	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 40V, Positive-QTOF	splash10-0uxr-6900000000-5598684c6eaf9935b19e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 10V, Negative-QTOF	splash10-014i-0900000000-7951a1a8dd3c9753f646	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 20V, Negative-QTOF	splash10-014r-0900000000-970cb3f15302ce8baa7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 40V, Negative-QTOF	splash10-0596-4900000000-d479161434e3f78c8e93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 10V, Positive-QTOF	splash10-0gdi-0900000000-8602c242641f709dc0e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 20V, Positive-QTOF	splash10-066r-1900000000-29fe4c8fcc201ebccd23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 40V, Positive-QTOF	splash10-0570-9500000000-cce89f878e3630a1d5ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 10V, Negative-QTOF	splash10-01bi-0900000000-12edf23b10b6c75daadd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 20V, Negative-QTOF	splash10-00di-0900000000-d4cb1b110dff3578e2e2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4-Hydroxy-3-methoxyphenyl)ethanol 40V, Negative-QTOF	splash10-01b9-7900000000-3ef50a3f2ff0be2c0ab4	2021-09-23	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

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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 643	12888646	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 643	20089783	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

643

FooDB ID

FDB018391

KNApSAcK ID

Not Available

Chemspider ID

16039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16928

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1250471

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-methoxyphenyl)ethanol (HMDB0038925)

MOL for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

3D MOL for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

3D SDF for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

3D-SDF for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

PDB for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

3D PDB for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

SMILES for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

INCHI for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

Structure for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

3D Structure for HMDB0038925 ((4-Hydroxy-3-methoxyphenyl)ethanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra