T3DB: p-Anisidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation XML

Record Information

Version

2.0

Creation Date

2014-10-14 21:19:54 UTC

Update Date

2014-12-24 20:27:01 UTC

Accession Number

T3D4986

Identification

Common Name

p-Anisidine

Class

Small Molecule

Description

p-Anisidine is a polyphenol compound found in foods of plant origin (1). p-Anisidine belongs to the family of Anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof.

Compound Type

Food Toxin
Metabolite
Natural Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-Amino-4-methoxybenzene
1-Methoxy-4-amino-benzen (p-anisidin)
1-Methoxy-4-amino-benzene / p-anisidine
4-Aminoanisole
4-Anisidine
4-Methoxy-1-aminobenzene
4-METHOXY-ANILINE
4-Methoxy-Benzenamine
4-Methoxy-phenylamine
4-Methoxyaniline
4-Methoxybenzenamine
4-Methoxybenzeneamine
beta -anisidine
p-Amino-Anisole
P-Aminoanisole
P-Anisidine
P-Anisylamine
P-Dianisidine
p-Methoxy-Aniline
p-Methoxyaniline
p-Methoxyphenylamine
Para-anisidine

Chemical Formula

C₇H₉NO

Average Molecular Mass

123.153 g/mol

Monoisotopic Mass

123.068 g/mol

CAS Registry Number

104-94-9

IUPAC Name

4-methoxyaniline

Traditional Name

P-anisidine

SMILES

COC1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3

InChI Key

InChIKey=BHAAPTBBJKJZER-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Aniline or substituted anilines
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methoxybenzene (CHEBI:82388 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	57.2 °C
Boiling Point	Not Available
Solubility	21 mg/mL at 20 °C
LogP	0.95

Predicted Properties

Property	Value	Source
Water Solubility	23 g/L	ALOGPS
logP	1.01	ALOGPS
logP	0.99	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Basic)	5.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.22 m³·mol⁻¹	ChemAxon
Polarizability	13.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-4900000000-a2f147705f92caffa50b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-3786160ae4a86463960a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-6900000000-7b56ba31080ccebf1c7c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-4900000000-a2f147705f92caffa50b	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-3786160ae4a86463960a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-6900000000-7b56ba31080ccebf1c7c	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7900000000-ace7d2515045ec577c96	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-3900000000-9340c1e52aa934343504	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00dl-4900000000-981b7bdbdc8a245cf92b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-3900000000-63a61ad2be2d08fadf22	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-3900000000-908b34f5735c945c5af0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-006x-9600000000-6b2b1476aca3afcb35bd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-3900000000-c75e78fba9334f9906cb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-3900000000-c4dd3d97c81c38a09218	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-9200000000-b1978d72d517017bece2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0006-9100000000-0aac88621e5ecc786eb9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00dl-5900000000-7aff6600364371e72f8a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-006x-9600000000-acd97347f6da33affebb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0006-9100000000-59bdad940cf1b2fc298d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-9200000000-dff7c219aaeb1df5ce5c	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-d5da0445283dde8ccd7c	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-4341782a6b8ca513df5b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00o1-9000000000-de3205684c1de23008ac	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-2a6e63bb8854a28ac6fc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-1514385accd772fa8d7a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-16f033ef9b3412bc1f44	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-f25e1ff30b1468ce2435	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-6900000000-f0ba7c95c60a6df0881f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k96-9000000000-9840e6c411c8bfeafcc0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-c9b01cd6ed2252316c57	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9800000000-baca2db1d5267a6ee2f3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-a7e4f7fbeb7a132bb471	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Toxicity Profile

Route of Exposure

oral ingestion, inhalation or skin contact

Mechanism of Toxicity

p-Anisidine reacts with secondary oxidation products such as aldehydes and ketones in fats and oils. (Wikipedia)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (2)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

P-Anisidine is the most toxic of the three isomers of anisidine and causes blood damage upon oral ingestion, inhalation or skin contact. If heated strongly, it may release very toxic fumes of nitrogen oxides. (Wikipedia)

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB29300

PubChem Compound ID

7732

ChEMBL ID

Not Available

ChemSpider ID

13869414

KEGG ID

C19326

UniProt ID

Not Available

OMIM ID

ChEBI ID

163384

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

p-Anisidine

References

Synthesis Reference

Not Available

MSDS

T3D4986.pdf

General References

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [20428313 ]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

p-Anisidine (T3D4986)

Structure for T3D4986: p-Anisidine