Milk Composition Database: Showing metabocard for trans-Cinnamic acid (BMDB0000930)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:44 UTC

Update Date

2020-04-22 15:06:00 UTC

MCDB ID

BMDB0000930

Secondary Accession Numbers

BMDB00930

Metabolite Identification

Common Name

trans-Cinnamic acid

Description

trans-Cinnamic acid, also known as (2E)-3-phenylacrylate or (e)-cinnamate, 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. trans-Cinnamic acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. trans-Cinnamic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-Phenyl-2-propenoic acid	ChEBI
(2E)-3-Phenylacrylic acid	ChEBI
(e)-3-Phenyl-2-propenoic acid	ChEBI
(e)-Cinnamate	ChEBI
(e)-Cinnamic acid	ChEBI
Benzeneacrylic acid	ChEBI
PHENYLETHYLENECARBOXYLIC ACID	ChEBI
trans-3-Phenylacrylic acid	ChEBI
trans-beta-Carboxystyrene	ChEBI
trans-Cinnamate	ChEBI
trans-Zimtsaeure	ChEBI
(2E)-3-Phenyl-2-propenoate	Generator
(2E)-3-Phenylacrylate	Generator
(e)-3-Phenyl-2-propenoate	Generator
Benzeneacrylate	Generator
PHENYLETHYLENECARBOXYLate	Generator
trans-3-Phenylacrylate	Generator
trans-b-Carboxystyrene	Generator
trans-Β-carboxystyrene	Generator
(2E)-2-Phenyl-2-propenoate	HMDB
(2E)-2-Phenyl-2-propenoic acid	HMDB
(e)-3-Phenylacrylate	HMDB
(e)-3-Phenylacrylic acid	HMDB
(e)-3-Phenylprop-2-enoate	HMDB
(e)-3-Phenylprop-2-enoic acid	HMDB
trans-3-Phenyl-2-propenoate	HMDB
trans-3-Phenyl-2-propenoic acid	HMDB
Cinnamic acid, 14C-labeled CPD	HMDB
Cinnamic acid, 2-(14)C-labeled CPD	HMDB
Cinnamic acid, 3-(14)C-labeled CPD	HMDB
Cinnamic acid, (Z)-isomer	HMDB
Cinnamic acid, 2-(13)C-labeled CPD	HMDB
Cinnamic acid, 3H-labeled CPD (e)-isomer	HMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomer	HMDB
Cinnamic acid, ion(1-)-(e)-isomer	HMDB
Cinnamic acid, sodium salt	HMDB
Cinnamic acid, sodium salt(e)-isomer	HMDB
Cinnamic acid, sodium salt(Z)-isomer	HMDB
Cinnamic acid, (trans)-(e)-isomer	HMDB
Cinnamic acid, 14C-labeled CPD (e)-isomer	HMDB
Cinnamic acid, ion(1-)	HMDB
Cinnamic acid, nickel (+2) salt	HMDB
Cinnamic acid, potassium salt	HMDB
Cinnamic acid, zinc salt(e)-isomer	HMDB
Cinnamic acid, 13C-labeled CPD	HMDB
Cinnamic acid	HMDB
(2E)-3-Phenylprop-2-enoic acid	HMDB
(2E)-Cinnamic acid	HMDB
3-Phenyl-(e)-2-propenoic acid	HMDB
3-Phenyl-2-propenoic acid	HMDB
3-Phenylacrylic acid	HMDB
Phenylacrylic acid	HMDB
beta-Phenylacrylic acid	HMDB
Β-phenylacrylic acid	HMDB
trans-Cinnamic acid	HMDB

Chemical Formula

C₉H₈O₂

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

IUPAC Name

(2E)-3-phenylprop-2-enoic acid

Traditional Name

cinnamic acid

CAS Registry Number

140-10-3

SMILES

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

InChI Identifier

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

InChI Key

WBYWAXJHAXSJNI-VOTSOKGWSA-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
Styrene
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamic acid (CHEBI:35697 )
Monolignols (C00423 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	133 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.55 mg/mL	Not Available
LogP	2.13	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.38	ALOGPS
logP	2.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.06 m³·mol⁻¹	ChemAxon
Polarizability	15.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0ue9-0910000000-4a7bcdfadd383bf577dc	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0fb9-6920000000-727a2eb761e6e52fb47d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-117i-2920000000-f0d9ccc40786362ae4ad	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ue9-0910000000-4a7bcdfadd383bf577dc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fb9-6920000000-727a2eb761e6e52fb47d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-117i-2920000000-f0d9ccc40786362ae4ad	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-2900000000-b105b3fcb63636d0d16f	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-3107a2a1bec368528f82	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ufr-6900000000-b0299d34fa9bb16b8258	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-0900000000-4a879de8ea4f3acb0ae2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-88ad8c9c837a057bb2a5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-18280fe18e43043d9e21	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fb9-9600000000-04d36ba7639bc85e2023	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-a8417274c4493c5b5871	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9100000000-d3712417826a69667981	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-37c486fa03918355413c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f6t-0900000000-218a5babf0ab7c31c498	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-88ad8c9c837a057bb2a5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-e3a4fcaa911f14d3790d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fb9-9600000000-04d36ba7639bc85e2023	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-a8417274c4493c5b5871	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-d3712417826a69667981	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f6t-0900000000-218a5babf0ab7c31c498	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0900000000-f095c04fe81b2890cb1a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0900000000-1bb9599f57d5b1c1688b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-37c486fa03918355413c	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0900000000-f5b771d960092fa83d2c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uea-0900000000-58b4769b89ab3883fb05	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-6900000000-9f4710d90f0cafac6d7b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-d015607beb5136324414	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0900000000-ff32add65ca52cbaae83	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-3900000000-f2450299b70c3ec0faec	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6t-6900000000-77686ecc684f3b46bea6	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 26686724	details

External Links

HMDB ID

HMDB0000930

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Cinnamic_acid

METLIN ID

5880

PubChem Compound

444539

PDB ID

Not Available

ChEBI ID

35697

References

Synthesis Reference

Zhu, Min; Shentu, Chao; Zhou, Zhong Shi. Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts. Chinese Chemical Letters (2007), 18(3), 272-274.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Showing metabocard for trans-Cinnamic acid (BMDB0000930)

Structure for BMDB0000930 (trans-Cinnamic acid)