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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:40:09 UTC

Update Date

2023-02-21 17:23:44 UTC

HMDB ID

HMDB0033895

Secondary Accession Numbers

HMDB33895

Metabolite Identification

Common Name

Anisole

Description

Anisole is a flavouring agent Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals. For example, synthetic anethole is prepared from anisole. Anisole undergoes electrophilic aromatic substitution reaction more quickly than does benzene, which in turn reacts more quickly than nitrobenzene. The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites. The enhanced nucleophilicity of anisole vs benzene reflects the influence of the methoxy group, which renders the ring more electron-rich. The methoxy group strongly affects the pi cloud of the ring, moreso than the inductive effect of the electronegative oxygen.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Anisol	ChEBI
Methoxybenzene	ChEBI
Methyl phenyl ether	ChEBI
Phenol methyl ether	ChEBI
Phenyl methyl ether	MeSH
Anisole, 8ci	HMDB
Anizol	HMDB
HSDB 44	HMDB
Methoxy-benzene	HMDB
Methoxy-benzene (anisol)	HMDB
Methyl phenyl-ether	HMDB
Phenoxymethane	HMDB

Chemical Formula

C₇H₈O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

IUPAC Name

anisole

Traditional Name

anisole

CAS Registry Number

100-66-3

SMILES

COC1=CC=CC=C1

InChI Identifier

InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

InChI Key

RDOXTESZEPMUJZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monomethoxybenzene (CHEBI:16579 )
a small molecule (CPD-395 )

Ontology

Urine (PMID: 22284503)

Cellular substructure

Extracellular (HMDB: HMDB0033895)
Cytoplasm (HMDB: HMDB0033895)

Source

Exogenous

Exogenous (HMDB: HMDB0033895)

Food

Food (HMDB: HMDB0033895)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033895)

Biological role

Nutrient (HMDB: HMDB0033895)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-37.5 °C	Not Available
Boiling Point	153.00 to 155.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.04 mg/mL at 25 °C	Not Available
LogP	2.11	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.14 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.82	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.52 m³·mol⁻¹	ChemAxon
Polarizability	11.8 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]+	121.672	31661259
DarkChem	[M-H]-	118.857	31661259
DeepCCS	[M+H]+	122.533	30932474
DeepCCS	[M-H]-	119.897	30932474
DeepCCS	[M-2H]-	156.27	30932474
DeepCCS	[M+Na]+	130.924	30932474
AllCCS	[M+H]+	120.5	32859911
AllCCS	[M+H-H2O]+	115.5	32859911
AllCCS	[M+NH4]+	125.2	32859911
AllCCS	[M+Na]+	126.5	32859911
AllCCS	[M-H]-	119.3	32859911
AllCCS	[M+Na-2H]-	121.8	32859911
AllCCS	[M+HCOO]-	124.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anisole	COC1=CC=CC=C1	1293.4	Standard polar	33892256
Anisole	COC1=CC=CC=C1	898.8	Standard non polar	33892256
Anisole	COC1=CC=CC=C1	914.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9300000000-9d7f6749c18da0bb17a5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9500000000-a1231ee8ae74f750d865	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9300000000-03da541e1b0fc350901b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9300000000-9d7f6749c18da0bb17a5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9500000000-a1231ee8ae74f750d865	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Anisole EI-B (Non-derivatized)	splash10-0ar0-9300000000-03da541e1b0fc350901b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anisole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9600000000-f06ab1867fa492dc70a4	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anisole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anisole 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 - Anisole 10V, Positive-QTOF	splash10-0a4i-0900000000-fb9a846e2f1273e85651	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 20V, Positive-QTOF	splash10-0a4i-0900000000-fd57d4e57fb46af8410b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 40V, Positive-QTOF	splash10-0ufr-9100000000-af620e455f4ce9717299	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 10V, Negative-QTOF	splash10-0a4i-0900000000-ea0356f73dec1cbb2a6f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 20V, Negative-QTOF	splash10-0a4i-0900000000-8868de2e79fc0bfe5bb9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 40V, Negative-QTOF	splash10-056r-9100000000-d3dbb7dea314eff0968f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 10V, Negative-QTOF	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 20V, Negative-QTOF	splash10-0a4i-2900000000-5c0fe116caf5f5fa594c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 40V, Negative-QTOF	splash10-01t9-9000000000-04348f17640621a98bf5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 10V, Positive-QTOF	splash10-0a4i-0900000000-a9b5691a81bc9d478706	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 20V, Positive-QTOF	splash10-0a4i-7900000000-2fb84cb3e84d8e17e508	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anisole 40V, Positive-QTOF	splash10-004i-9000000000-4441fb8ba209a5f3d576	2021-09-25	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

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

BiGG ID

Not Available

Wikipedia Link

Anisole

METLIN ID

Not Available

PubChem Compound

7519

PDB ID

Not Available

ChEBI ID

16579

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1031451

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Dong XJ, Zhu YF, Bao GH, Hu FL, Qin GW: New limonoids and a dihydrobenzofuran norlignan from the roots of Toona sinensis. Molecules. 2013 Mar 1;18(3):2840-50. doi: 10.3390/molecules18032840. [PubMed:23455673 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Anisole (HMDB0033895)

MOL for HMDB0033895 (Anisole)

3D MOL for HMDB0033895 (Anisole)

3D SDF for HMDB0033895 (Anisole)

3D-SDF for HMDB0033895 (Anisole)

PDB for HMDB0033895 (Anisole)

3D PDB for HMDB0033895 (Anisole)

SMILES for HMDB0033895 (Anisole)

INCHI for HMDB0033895 (Anisole)

Structure for HMDB0033895 (Anisole)

3D Structure for HMDB0033895 (Anisole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra