Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:47 UTC |
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Update date | 2020-09-17 15:31:20 UTC |
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Primary ID | FDB013575 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Neral |
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Description | 3,7-dimethyl-2,6-octadienal or citral, also known as lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as geranial or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID: 28974979) and pheromonal effects in nematodes and insects (PMID: 26973536). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke). |
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CAS Number | 106-26-3 |
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Structure | |
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Synonyms | Synonym | Source |
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Citral b | ChEBI | Lemonal | ChEBI | Neral | Kegg | cis-Citral | ChEBI | (Z)-Citral | MeSH, HMDB | Citral | MeSH, HMDB | (2Z)-3,7-Dimethyl-2,6-octadien-1-al | HMDB | (2Z)-3,7-Dimethyl-2,6-octadienal | HMDB | (Z)-3,7-Dimethyl-2,6-octadienal | HMDB | (Z)-Neral | HMDB | 2-cis-3,7-Dimethyl-2,6-octadienal | HMDB | 3,7-Dimethyl-2,6-octadien-1-al | HMDB | 3,7-Dimethyl-2,6-octadienal | HMDB | beta-Citral | HMDB | cis-3,7-Dimethyl-2,6-octadienal | HMDB | cis-Geranial | HMDB | β-Citral | HMDB | (2Z)-3,7-Dimethylocta-2,6-dienal | biospider | (Z)-3,7-Dimethylocta-2,6-dienal | biospider | (Z)-Geranial | manual | β-Citral | biospider | 2,6-Octadienal, 3,7-dimethyl-, (2Z)- | biospider | 2,6-Octadienal, 3,7-dimethyl-, (Z)- | biospider |
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Predicted Properties | |
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Chemical Formula | C10H16O |
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IUPAC name | (2Z)-3,7-dimethylocta-2,6-dienal |
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InChI Identifier | InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7- |
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InChI Key | WTEVQBCEXWBHNA-YFHOEESVSA-N |
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Isomeric SMILES | CC(C)=CCC\C(C)=C/C=O |
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Average Molecular Weight | 152.237 |
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Monoisotopic Molecular Weight | 152.120115135 |
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Classification |
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Description | Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Acyclic monoterpenoids |
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Alternative Parents | |
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Substituents | - Acyclic monoterpenoid
- Medium-chain aldehyde
- Enal
- Alpha,beta-unsaturated aldehyde
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 78.90%; H 10.59%; O 10.51% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp12 103° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 | n20D 1.4809 | DFC |
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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 | Neral, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0159-9300000000-625c688e32f3edaf287c | Spectrum | Predicted GC-MS | Neral, 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 | splash10-0udi-1900000000-84bd30b4e03200f6db52 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-1010-8900000000-8aa62bcc7a1bcaa41a1e | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9000000000-79a3e6745a117da8309b | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-21d238fd55ee29af690f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1900000000-b84583833bad67467cf0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9700000000-a5e231c57e7f56a65d6d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0pb9-0900000000-70e7a03f5a911f54f098 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-3128155f72d867d46318 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9100000000-9b92fab117afca4b3a0a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05o0-9100000000-9c5fcd575fed478bccf6 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05qc-9000000000-85ae79bf95f3094e7a85 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-1a9a16cf8ea66689ce6a | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09847 |
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Pubchem Compound ID | 643779 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 29020 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | JGH37-H:JFJ79-Y |
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EAFUS ID | Not Available |
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Dr. Duke ID | CITRAL-B|NERAL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003036 |
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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 | 106-26-3 |
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GoodScent ID | rw1331191 |
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SuperScent ID | Not Available |
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Wikipedia ID | Neral |
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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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anti bacterial | 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 | 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 | termiticide | | | 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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lemon |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| citral |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| lemon peel |
- 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 | Not Available |
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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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