AFCDB: Cinnamic acid (FDB012052)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:58 UTC

Update date

2019-11-26 03:06:04 UTC

Primary ID

FDB012052

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cinnamic acid

Description

trans-Cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, 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 in all living species, ranging from bacteria to plants to humans. trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), olives (Olea europaea), and lingonberries (Vaccinium vitis-idaea) and in a lower concentration in corianders (Coriandrum sativum), american cranberries (Vaccinium macrocarpon), and red raspberries (Rubus idaeus). trans-Cinnamic acid has also been detected, but not quantified in, several different foods, such as black tea, broccolis (Brassica oleracea var. italica), red bell peppers (Capsicum annuum), sweet bays (Laurus nobilis), and teas (Camellia sinensis). This could make trans-cinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on trans-Cinnamic acid.

CAS Number

621-82-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H8O2

IUPAC name

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

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-SREVYHEPSA-N

Isomeric SMILES

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

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Organ and components:

Liver

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 72.96%; H 5.44%; O 21.60%	DFC
Melting Point	132-135 oC
Boiling Point	Not Available
Experimental Water Solubility	0.57 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.13	HANSCH,C ET AL. (1995)
Experimental pKa	4.44
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0f6t-6900000000-77686ecc684f3b46bea6	2014-09-20	View Spectrum
GC-MS	trans-Cinnamic acid, 1 TMS, GC-MS Spectrum	splash10-0ue9-0910000000-4a7bcdfadd383bf577dc	Spectrum
GC-MS	trans-Cinnamic acid, 1 TMS, GC-MS Spectrum	splash10-0fb9-6920000000-727a2eb761e6e52fb47d	Spectrum
GC-MS	trans-Cinnamic acid, 1 TMS, GC-MS Spectrum	splash10-117i-2920000000-f0d9ccc40786362ae4ad	Spectrum
GC-MS	trans-Cinnamic acid, non-derivatized, GC-MS Spectrum	splash10-0ue9-0910000000-4a7bcdfadd383bf577dc	Spectrum
GC-MS	trans-Cinnamic acid, non-derivatized, GC-MS Spectrum	splash10-0fb9-6920000000-727a2eb761e6e52fb47d	Spectrum
GC-MS	trans-Cinnamic acid, non-derivatized, GC-MS Spectrum	splash10-117i-2920000000-f0d9ccc40786362ae4ad	Spectrum
Predicted GC-MS	trans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ue9-2900000000-b105b3fcb63636d0d16f	Spectrum
Predicted GC-MS	trans-Cinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d	Spectrum
Predicted GC-MS	trans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	trans-Cinnamic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-3107a2a1bec368528f82	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ufr-6900000000-b0299d34fa9bb16b8258	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-0900000000-4a879de8ea4f3acb0ae2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-88ad8c9c837a057bb2a5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-18280fe18e43043d9e21	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fb9-9600000000-04d36ba7639bc85e2023	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-a8417274c4493c5b5871	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9100000000-d3712417826a69667981	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-37c486fa03918355413c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f6t-0900000000-218a5babf0ab7c31c498	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-88ad8c9c837a057bb2a5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-e3a4fcaa911f14d3790d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fb9-9600000000-04d36ba7639bc85e2023	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-a8417274c4493c5b5871	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-d3712417826a69667981	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f6t-0900000000-218a5babf0ab7c31c498	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0900000000-f095c04fe81b2890cb1a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0900000000-1bb9599f57d5b1c1688b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-37c486fa03918355413c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0900000000-f5b771d960092fa83d2c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uea-0900000000-58b4769b89ab3883fb05	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-6900000000-9f4710d90f0cafac6d7b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-d015607beb5136324414	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0900000000-ff32add65ca52cbaae83	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-3900000000-f2450299b70c3ec0faec	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

10286933

ChEMBL ID

Not Available

KEGG Compound ID

C10438

Pubchem Compound ID

5372954

Pubchem Substance ID

Not Available

ChEBI ID

27386

Phenol-Explorer ID

549

DrugBank ID

Not Available

HMDB ID

HMDB00567

CRC / DFC (Dictionary of Food Compounds) ID

HCV54-E:HCV54-E

EAFUS ID

644

Dr. Duke ID

CINNAMIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00029961

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1350711

SuperScent ID

444539

Wikipedia ID

Cinnamic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anesthetic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti mutagenic			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
choleretic			DUKE
dermatitigenic			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
laxative	50503	An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.	DUKE
lipoxygenase inhibitor	35856	A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
tyrosinase inhibitor	59997	Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.	DUKE
vermifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
cinnamon	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
honey	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
storax	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Cinnamic acid (FDB012052)

Structure for FDB012052 (Cinnamic acid)