Milk Composition Database: Showing metabocard for 4-Methoxycinnamic acid (BMDB0002040)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:50:19 UTC

Update Date

2020-04-22 15:09:30 UTC

MCDB ID

BMDB0002040

Secondary Accession Numbers

BMDB02040

Metabolite Identification

Common Name

4-Methoxycinnamic acid

Description

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. 4-Methoxycinnamic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.

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

830-09-1

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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	173 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 mg/mL at 25 °C	Not Available
LogP	2.68	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-03du-2920000000-dece72c3ca5c90bfc547	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-a59af9ca91b1d5bd7182	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-7900000000-6075ede461ba4ee4c7cd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-1900000000-e899894a8c3562db43a5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03du-2920000000-dece72c3ca5c90bfc547	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gi-1900000000-cc8f6e9174dff780d643	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0080-9650000000-bb37ec4824ae491674e5	2017-10-06	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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-12552bc1ab86525703a0	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00pi-5900000000-9632d41fa295f06b5381	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004u-9100000000-a6dac09530cfcfc28868	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-004i-0900000000-a59af9ca91b1d5bd7182	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-004i-7900000000-8e025153eeb590c13daa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0fb9-0900000000-c6baccb046bfcd7d6282	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-014i-1900000000-3927439c287110a6a2f1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03e9-1900000000-03cba42101a868fcbdbb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03e9-1900000000-53a3d7a661e7d42fabbf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00mo-9600000000-b0e876994fe40230d56f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lr-1900000000-32372664024a7a1cba27	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fb9-0900000000-c6baccb046bfcd7d6282	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-1900000000-3927439c287110a6a2f1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-1900000000-03cba42101a868fcbdbb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-1900000000-53a3d7a661e7d42fabbf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00mo-9600000000-1dd0b8897a3d399d48fc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-1900000000-32372664024a7a1cba27	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-2c4cab05840440c8ef92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0900000000-3954121d114e7a125401	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-f0f239b49fe3cc116d97	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0900000000-d7031d18cf315b765cbf	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9800000000-881ce76bbf7add1a8162	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-0d57f82612687cf62c68	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-0900000000-c2111775e672e2666fbd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02u3-1900000000-295574bc9205dd1a7c79	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 27999311	details

External Links

HMDB ID

HMDB0002040

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]

Showing metabocard for 4-Methoxycinnamic acid (BMDB0002040)

Structure for BMDB0002040 (4-Methoxycinnamic acid)