| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:08:15 UTC |
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| Update date | 2020-02-24 19:10:57 UTC |
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| Primary ID | FDB008781 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 3-Phenyl-2-propenal |
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| 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 a cinnamon and spicy tasting compound (Z)-Cinnamaldehyde has been detected, but not quantified in, ceylon cinnamons (Cinnamomum verum). This could make (Z)-cinnamaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (Z)-Cinnamaldehyde. |
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| CAS Number | 104-55-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| cis-Cinnamaldehyde | ChEBI | | cis-Cinnamic aldehyde | ChEBI | | (Z)-Cinnamaldehyde | HMDB, ChEBI | | (Z)-Cinnamylaldehyde | HMDB | | 3-Phenyl-(Z)-2-propenal | HMDB | | (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 |
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| Predicted Properties | |
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| Chemical Formula | C9H8O |
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| IUPAC name | (2Z)-3-phenylprop-2-enal |
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| InChI Identifier | InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4- |
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| InChI Key | KJPRLNWUNMBNBZ-DAXSKMNVSA-N |
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| Isomeric SMILES | O=C\C=C/C1=CC=CC=C1 |
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| Average Molecular Weight | 132.1592 |
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| Monoisotopic Molecular Weight | 132.057514878 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Cinnamaldehydes |
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| Sub Class | Not Available |
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| Direct Parent | Cinnamaldehydes |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Liquid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 81.79%; H 6.10%; O 12.11% | DFC |
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| Melting Point | -7.5 oC | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 1.42 mg/mL at 25 oC | VALVANI,SC et al. (1981) |
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| Experimental logP | 1.90 | HANSCH,C ET AL. (1995) |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f8c-4900000000-9646371bf99f8b256f77 | Spectrum | | Predicted GC-MS | 3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-4b1b083c8fdb2a27206b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-2900000000-eee6045375789bd7b511 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9400000000-ffef407879854d06bd7e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-074611feed644fd89c07 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-cbf5bec188b738c514af | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01p6-9600000000-5eb930cf87b199a5f449 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lu-2900000000-eda42d3592c23cd1e4bd | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-5900000000-5757a78bf103c73ab434 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvi-9300000000-8784eab3c86fc7a1a721 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-827b27666b5028c8cf77 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-138b8c24fd394024a31a | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-93f143b30bbb2b4ff778 | 2021-09-25 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 553117 |
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| ChEMBL ID | CHEMBL293492 |
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| KEGG Compound ID | C00903 |
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| Pubchem Compound ID | 637511 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 16731 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03441 |
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| CRC / DFC (Dictionary of Food Compounds) ID | DXH04-W:DXH04-W |
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| EAFUS ID | 641 |
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| Dr. Duke ID | CINNAMIC-ALDEHYDE|CINNAMALDEHYDE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00002725 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | rw1002631 |
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| SuperScent ID | 637511 |
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| Wikipedia ID | Cinnamaldehyde |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| 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 |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| 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.
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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