Showing Compound 3-Phenyl-2-propenal (FDB008781)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:15 UTC

Update date

2020-02-24 19:10:57 UTC

Primary ID

FDB008781

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Phenyl-2-propenal

Description

(Z)-Cinnamaldehyde, also known as cis-cinnamic aldehyde, belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal (Z)-Cinnamaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa) (Z)-Cinnamaldehyde is a cinnamon and spicy tasting compound (Z)-Cinnamaldehyde has been detected, but not quantified in, ceylon cinnamons. This could make (Z)-cinnamaldehyde a potential biomarker for the consumption of these foods.

CAS Number

104-55-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
cis-Cinnamaldehyde	ChEBI
cis-Cinnamic aldehyde	ChEBI
(Z)-Cinnamylaldehyde	HMDB
3-Phenyl-(Z)-2-propenal	HMDB
(Z)-Cinnamaldehyde	HMDB, ChEBI
(e)-3-Phenyl-propenal	ChEBI
(e)-Phenylvinyl aldehyde	ChEBI
2-Propenal, 3-phenyl-	biospider
2-Propenaldehyde, 3-phenyl-	biospider
3-Fenylpropenal	HMDB
3-Phenyl-2-propen-1-al	biospider
3-Phenyl-2-propenaldehyde	biospider
3-Phenylacrolein	db_source
3-Phenylacrylaldehyde	biospider
3-Phenylprop-2-enal	biospider
3-Phenylprop-2-enaldehyde	biospider
3-Phenylpropenal	biospider
Benzylideneacetaldehyde	biospider
beta-Phenylacrolein	biospider
beta-Phenylcrolein	biospider
Cinnamal	db_source
Cinnamaldehyde	ChEBI
Cinnamaldehyde, 8CI	db_source
Cinnamic aldehyde	db_source
Cinnamyl aldehyde	biospider
Cinnamylaldehyde	HMDB
Cinnemaldehyde	HMDB
FEMA 2286	db_source
Propenaldehyde, 3-phenyl-	biospider
Zimtaldehyde	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	2	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.13 m³·mol⁻¹	ChemAxon
Polarizability	14.36 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

C9H8O

IUPAC name

(2Z)-3-phenylprop-2-enal

InChI Identifier

InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4-

InChI Key

KJPRLNWUNMBNBZ-DAXSKMNVSA-N

Isomeric SMILES

O=C\C=C/C1=CC=CC=C1

Average Molecular Weight

132.1592

Monoisotopic Molecular Weight

132.057514878

Classification

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Styrene
Benzenoid
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 81.79%; H 6.10%; O 12.11%	DFC
Melting Point	-7.5 oC
Boiling Point	Not Available
Experimental Water Solubility	1.42 mg/mL at 25 oC	VALVANI,SC et al. (1981)
Experimental logP	1.90	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
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)	splash10-0f8c-4900000000-9646371bf99f8b256f77	Spectrum
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-8900000000-5b42adf83e422cffefb6	Spectrum
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-24fa3ff739ff064312ab	Spectrum
Predicted GC-MS	3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f8c-4900000000-9646371bf99f8b256f77	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-4b1b083c8fdb2a27206b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-2900000000-eee6045375789bd7b511	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-ffef407879854d06bd7e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-074611feed644fd89c07	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-cbf5bec188b738c514af	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p6-9600000000-5eb930cf87b199a5f449	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lu-2900000000-eda42d3592c23cd1e4bd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-5757a78bf103c73ab434	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9300000000-8784eab3c86fc7a1a721	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-827b27666b5028c8cf77	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-138b8c24fd394024a31a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-93f143b30bbb2b4ff778	Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16731

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03441

CRC / DFC (Dictionary of Food Compounds) ID

DXH04-W:DXH04-W

EAFUS ID

641

Dr. Duke ID

CINNAMIC-ALDEHYDE|CINNAMALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

C00002725

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1002631

SuperScent ID

637511

Wikipedia ID

Cinnamaldehyde

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
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
adrenergic	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
allelochemic			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 aggregant			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti enterococcic			DUKE
anti escherichic			DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti klebsiellic			DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti mutagenic			DUKE
anti pneumonic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti pseudomonic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti urease	50635	EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the activity of urease (EC 3.5.1.5), reducing hydrolysis.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
choleretic			DUKE
chronotropic			DUKE
circulatory stimulant			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	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
histaminic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
hypothermic			DUKE
inotropic			DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			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
monoaminergic			DUKE
mutagenic			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	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
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
sprout inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
teratogenic	50905	A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.	DUKE
termiticide			DUKE
tranquilizer			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
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE
vibriocide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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