ChemFOnt: Showing chemical card for 4-Methoxycinnamic acid (CFc000001368)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:59 UTC

Chemfont ID

CFc000001368

Molecule Identification

Common Name

4-Methoxycinnamic acid

Definition

4-Methoxycinnamic acid, also known as para-methoxycinnamate or O-methyl-p-coumarate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Outside of the human body, 4-Methoxycinnamic acid is found, on average, in the highest concentration within turmerics. 4-Methoxycinnamic acid has also been detected, but not quantified in cow milk and wild celeries. This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Methoxycinnamate	Generator
3-(4-Methoxyphenyl)acrylic acid	ChEMBL, HMDB
Para-methoxycinnamic acid	ChEMBL, HMDB
3-(4-Methoxyphenyl)acrylate	Generator, HMDB
Para-methoxycinnamate	Generator, HMDB
(e)-3-(4-Methoxyphenyl)acrylate	HMDB
(e)-3-(4-Methoxyphenyl)acrylic acid	HMDB
3-(4-Methoxy-phenyl)-acrylate	HMDB
3-(4-Methoxy-phenyl)-acrylic acid	HMDB
3-(4-Methoxyphenyl)-2-propenoate	HMDB
3-(4-Methoxyphenyl)-2-propenoic acid	HMDB
4-Methoxy cinnamate	HMDB
4-Methoxy cinnamic acid	HMDB
O-Methyl-P-coumarate	HMDB
O-Methyl-P-coumaric acid	HMDB
P-Hydroxy methyl cinnamate	HMDB
P-Methoxy ciannamate	HMDB
P-Methoxy ciannamic acid	HMDB
P-Methoxycinnamate	HMDB
P-Methoxycinnamic acid	HMDB
trans-4-Methoxycinnamate	HMDB
trans-4-Methoxycinnamic acid	HMDB
4-Methoxycinnamate, aluminum salt	MeSH, HMDB
4-Methoxycinnamate, (e)-isomer	MeSH, HMDB
4-Methoxycinnamate, (Z)-isomer	MeSH, HMDB
4-Methoxycinnamate, zinc salt	MeSH, HMDB
4-Methoxycinnamate, zirconium salt	MeSH, HMDB
e-P-Methoxycinnamic acid	MeSH, HMDB
4-Methoxycinnamate, calcium salt	MeSH, HMDB
4-Methoxycinnamate, magnesium salt	MeSH, HMDB
4-Methoxycinnamate, potassium salt	MeSH, HMDB
4-Methoxycinnamate, sodium salt	MeSH, HMDB
(2E)-3-(4-Methoxyphenyl)prop-2-enoate	Generator, HMDB
4-Methoxycinnamic acid	MeSH
(2E)-3-(4-Methoxyphenyl)-2-propenoic acid	HMDB
(E)-3-(4-Methoxyphenyl)-2-propenoic acid	HMDB
(E)-3-(4-Methoxyphenyl)acrylic acid	HMDB
(E)-4-Methoxycinnamic acid	HMDB
(E)-p-Methoxycinnamic acid	HMDB
3-(4-Methoxyphenyl)propenoic acid	HMDB
4'-Methoxycinnamic acid	HMDB
4-Methyoxycinnamic acid	HMDB
4’-Methoxycinnamic acid	HMDB
O-Methyl-p-coumaric acid	HMDB
p-Methoxycinnamic acid	HMDB
trans-3-(4-Methoxyphenyl)-2-propenoic acid	HMDB
trans-p-Methoxycinnamic acid	HMDB
trans-p-Methoxycinnamate	Generator, HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

(2E)-3-(4-methoxyphenyl)prop-2-enoic acid

Traditional Name

p-methoxy-cinnamic acid

CAS Registry Number

943-89-5

SMILES

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

InChI Identifier

InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+

InChI Key

AFDXODALSZRGIH-QPJJXVBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19812218)

Cellular substructure

Membrane (HMDB: HMDB0002040)
Cell membrane (HMDB: HMDB0002040)

Excreta

Biofluid or Excreta

Urine (PMID: 19812218)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002040)

Source

Endogenous

Endogenous (HMDB: HMDB0002040)

Plant

Plant (HMDB: HMDB0002040)

Exogenous

Food

Food (HMDB: HMDB0002040)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)
Turmeric (FooDB: FOOD00068)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0002040)

Pesticide (HMDB: HMDB0002040)

Antipyretic (HMDB: HMDB0002040)
Hypoglycemic agent (HMDB: HMDB0002040)

Biological role

Hemolytic (HMDB: HMDB0002040)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.52 m³·mol⁻¹	ChemAxon
Polarizability	18.34 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

External Links

HMDB ID

HMDB0002040

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002667

KNApSAcK ID

Not Available

Chemspider ID

609479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6453

PubChem Compound

699414

PDB ID

Not Available

ChEBI ID

260249

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Puscaru, E.; Zotta, V.; Serper, Ana; Popescu, Margareta; Hociung, Jana; Gasmet, Ana; Spataru, Rodica. The N-methyl series of piperazine. II. Cinnamic acid derivatives. Farmacia (Bucharest, Romania) (1961), 9 345-50.

Showing chemical card for 4-Methoxycinnamic acid (CFc000001368)

MOL for CFc000001368 (4-Methoxycinnamic acid)

3D MOL for CFc000001368 (4-Methoxycinnamic acid)

3D SDF for CFc000001368 (4-Methoxycinnamic acid)

3D-SDF for CFc000001368 (4-Methoxycinnamic acid)

PDB for CFc000001368 (4-Methoxycinnamic acid)

3D PDB for CFc000001368 (4-Methoxycinnamic acid)

SMILES for CFc000001368 (4-Methoxycinnamic acid)

INCHI for CFc000001368 (4-Methoxycinnamic acid)

Structure for CFc000001368 (4-Methoxycinnamic acid)

3D Structure for CFc000001368 (4-Methoxycinnamic acid)