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 17:32:07 UTC

Update Date

2023-02-21 17:19:03 UTC

HMDB ID

HMDB0029696

Secondary Accession Numbers

HMDB29696

Metabolite Identification

Common Name

Mequinol

Description

Mequinol, also known as 4-hydroxyanisole or leucodinine b, 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. Mequinol is a phenolic tasting compound. Mequinol has been detected, but not quantified in, anises (Pimpinella anisum) and sweet marjorams (Origanum majorana). This could make mequinol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Mequinol.

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-Hydroxyanisole	MeSH
4-Hydroxyanisole, potassium salt	MeSH
4-Hydroxyanisole, sodium salt	MeSH
Leucodinine b	MeSH
Hydroquinone methyl ether	MeSH
Hydroquinone monomethyl ether	MeSH
p-Hydroxyanisole	MeSH
Para-methoxyphenol	MeSH
Menthyl anthranilate	ChEMBL, HMDB
novo-Dermoquinona	ChEMBL, HMDB
Leucodine b	ChEMBL, HMDB
BMS-181158P-Guaiacol	ChEMBL, HMDB
4-Methoxyphenol	ChEMBL, HMDB
4HA	ChEMBL, HMDB
Leucobasal	ChEMBL, HMDB
Mechinolum	ChEMBL, HMDB
Menthyl anthranilic acid	Generator, HMDB
1-Hydroxy-4-methoxybenzene	HMDB
4-Methoxy-phenol	HMDB
Hydroxyanisole	HMDB
Hydroxyquinone methyl ether	HMDB
Mequinol, inn, usan	HMDB
mono Methyl ether hydroquinone	HMDB
Monomethyl ether hydroquinone	HMDB
P-Hydroxymethoxybenzene	HMDB
P-Methoxyphenol	HMDB
HQMME
hydroxyquinone methyl ether
HQMME; hydroxyquinone methyl ether	HMDB

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.1372

Monoisotopic Molecular Weight

124.0524295

IUPAC Name

4-methoxyphenol

Traditional Name

methoxyphenol

CAS Registry Number

150-76-5

SMILES

COC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

InChI Key

NWVVVBRKAWDGAB-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
4-alkoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:69441 )
methoxybenzene (CHEBI:69441 )

Ontology

Physiological effect

Organoleptic effect

Odor

Phenolic

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029696)
Cytoplasm (HMDB: HMDB0029696)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029696)

Source

Exogenous

Exogenous (HMDB: HMDB0029696)

Food

Food (HMDB: HMDB0029696)

Herb and spice

Herb

Anise (FooDB: FOOD00137)
Sweet marjoram (FooDB: FOOD00122)

Endogenous

Endogenous (HMDB: HMDB0029696)

Plant

Plant (HMDB: HMDB0029696)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029696)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	53 °C	Not Available
Boiling Point	243.00 to 245.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	40 mg/mL at 25 °C	Not Available
LogP	1.58	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	36.1 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.51	ChemAxon
logS	-0.54	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.5 m³·mol⁻¹	ChemAxon
Polarizability	12.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.162	31661259
DarkChem	[M-H]-	122.798	31661259
DeepCCS	[M+H]+	126.521	30932474
DeepCCS	[M-H]-	122.788	30932474
DeepCCS	[M-2H]-	160.147	30932474
DeepCCS	[M+Na]+	135.388	30932474
AllCCS	[M+H]+	125.4	32859911
AllCCS	[M+H-H2O]+	120.6	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.2	32859911
AllCCS	[M-H]-	123.1	32859911
AllCCS	[M+Na-2H]-	125.2	32859911
AllCCS	[M+HCOO]-	127.6	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.	3.34 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3255 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1473.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	391.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	247.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	473.4 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	456.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	959.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	346.8 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	975.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	531.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.3 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	115.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mequinol	COC1=CC=C(O)C=C1	2120.3	Standard polar	33892256
Mequinol	COC1=CC=C(O)C=C1	1182.9	Standard non polar	33892256
Mequinol	COC1=CC=C(O)C=C1	1200.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mequinol,1TMS,isomer #1	COC1=CC=C(O[Si](C)(C)C)C=C1	1287.0	Semi standard non polar	33892256
Mequinol,1TBDMS,isomer #1	COC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1515.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-00du-9300000000-7365fadaa1b55aee92c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-0ab9-3900000000-b24cf2309ebe14f7ea37	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-05gi-8900000000-22bed3d3611c3a5cd0d6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-0ab9-3900000000-b406ffca43dc64f80356	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-05fr-3900000000-5f100d415313d60a9ba0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-00du-9300000000-7365fadaa1b55aee92c0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-0ab9-3900000000-b24cf2309ebe14f7ea37	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-05gi-8900000000-22bed3d3611c3a5cd0d6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-0ab9-3900000000-b406ffca43dc64f80356	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mequinol EI-B (Non-derivatized)	splash10-05fr-3900000000-5f100d415313d60a9ba0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mequinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7900000000-55f898f30c9805b4268e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mequinol GC-MS (1 TMS) - 70eV, Positive	splash10-00ea-6900000000-adc42694c52a9cf1ab97	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mequinol 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 - Mequinol 10V, Positive-QTOF	splash10-004i-0900000000-3d4bc54dec9d0d2bf71d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 20V, Positive-QTOF	splash10-004i-1900000000-cd190cc17b12c804fb8d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 40V, Positive-QTOF	splash10-0691-9200000000-f98954ef6d73d4d0fc19	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 10V, Negative-QTOF	splash10-00di-0900000000-3cb1894d95675088e7b2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 20V, Negative-QTOF	splash10-00di-0900000000-125ba3d5d60e387415e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 40V, Negative-QTOF	splash10-0a4i-9600000000-c374964c5ebd2e35933e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 10V, Negative-QTOF	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 20V, Negative-QTOF	splash10-00dl-5900000000-b042371b5dd653689b36	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 40V, Negative-QTOF	splash10-0ufu-9000000000-f159f82bc0ae0498fa49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 10V, Positive-QTOF	splash10-004i-0900000000-c91956e06e080706e4b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 20V, Positive-QTOF	splash10-00kb-9100000000-4d814c03b4eb6b3e4ad7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mequinol 40V, Positive-QTOF	splash10-0j7m-9000000000-91642d9378817b499b9b	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

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

DB09516

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000886

KNApSAcK ID

C00035022

Chemspider ID

8665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mequinol

METLIN ID

Not Available

PubChem Compound

9015

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027421

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 Mequinol (HMDB0029696)

MOL for HMDB0029696 (Mequinol)

3D MOL for HMDB0029696 (Mequinol)

3D SDF for HMDB0029696 (Mequinol)

3D-SDF for HMDB0029696 (Mequinol)

PDB for HMDB0029696 (Mequinol)

3D PDB for HMDB0029696 (Mequinol)

SMILES for HMDB0029696 (Mequinol)

INCHI for HMDB0029696 (Mequinol)

Structure for HMDB0029696 (Mequinol)

3D Structure for HMDB0029696 (Mequinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra