Record Information
Version1.0
Creation date2010-04-08 22:10:52 UTC
Update date2018-05-29 01:07:16 UTC
Primary IDFDB013721
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitral
DescriptionCitral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either of, or a mixture of, a pair of terpenoids with the molecular formula C10H16O. The two compounds are double bond isomers. The E-isomer is known as geranial or citral A. The Z-isomer is known as neral or citral B. Citral is found in many foods, some of which are lime, okra, sweet bay, and wild carrot.
CAS Number5392-40-5
Structure
Thumb
Synonyms
SynonymSource
(e)-CitralChEBI
(e)-GeranialChEBI
alpha-CitralChEBI
Citral aChEBI
LemonalChEBI
trans-CitralChEBI
a-CitralGenerator
Α-citralGenerator
(2E)-3,7-Dimethyl-2,6-octadienalHMDB
(e)-3,7-Dimethyl-2,6-octadienalHMDB
(e)-3,7-Dimethylocta-2,6-dienalHMDB
3,7-Dimethyl-(2E)-2,6-octadienalHMDB
3,7-Dimethyl-(e)-2,6-octadienalHMDB
3,7-Dimethyl-trans-2,6-octadienalHMDB
alpha -CitralHMDB
beta-GeranialHMDB
Citral-aHMDB
GenanialHMDB
GeranalHMDB
trans-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-CitralMeSH
CitralMeSH
(2E)-3,7-Dimethyl-2,6-octadien-1-alHMDB
GeranaldehydeHMDB
GeranialHMDB
beta-NeralHMDB
trans-3,7-Dimethyl-2,6-octadien-1-alHMDB
trans-GeranialHMDB
β-GeranialHMDB
β-NeralHMDB
3,7-Dimethyl-2,6-octadien-1-alHMDB
3,7-Dimethyl-2,6-octadienalHMDB
FEMA 2303db_source
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP3.37ALOGPS
logP2.66ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.12 m³·mol⁻¹ChemAxon
Polarizability18.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name(2E)-3,7-dimethylocta-2,6-dienal
InChI IdentifierInChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
InChI KeyWTEVQBCEXWBHNA-JXMROGBWSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\C=O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
Classification
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-84bd30b4e03200f6db52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1010-8900000000-8aa62bcc7a1bcaa41a1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-79a3e6745a117da8309bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-21d238fd55ee29af690fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b84583833bad67467cf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-a5e231c57e7f56a65d6dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-92c761fd6ee64c67e40eView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID558878
ChEMBL IDCHEMBL1080997
KEGG Compound IDC01499
Pubchem Compound ID638011
Pubchem Substance IDNot Available
ChEBI ID23316
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35092
CRC / DFC (Dictionary of Food Compounds) IDJGH37-H:JGH37-H
EAFUS ID686
Dr. Duke IDCITRAL
BIGG IDNot Available
KNApSAcK IDC00003036
HET IDNot Available
Flavornet ID5392-40-5
GoodScent IDrw1003431
SuperScent ID638011
Wikipedia IDCitral
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti allergenic50857 A drug used to treat allergic reactions.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti helicobacter33282 A substance that kills or slows the growth of bacteria.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti shockDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
barbituate-synergistDUKE
broncho elaxant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
caspase-3 inducerDUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
estrogenicDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
glaucomagenicDUKE
glutathionigenicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
myorelaxantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostatitigenicDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
teratogenic50905 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
trichomonicideDUKE
trypanocideDUKE
tyrosinase inhibitor59997 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
lemon
  1. 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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sharp
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.