Record Information
Version1.0
Creation date2010-04-08 22:10:51 UTC
Update date2019-11-26 03:08:53 UTC
Primary IDFDB013702
Secondary Accession Numbers
  • FDB013721
Chemical Information
FooDB NameGeranial
DescriptionGeranial, also known as alpha-citral or (e)-citral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geranial is considered to be an isoprenoid lipid molecule. Geranial is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranial is a potentially toxic compound.
CAS Number141-27-5
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)-CitralHMDB
CitralHMDB
(2E)-3,7-Dimethyl-2,6-octadien-1-alHMDB
GeranaldehydeHMDB
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
(E)-NeralHMDB
GeranialHMDB
(2E)-3,7-Dimethylocta-2,6-dienalbiospider
(E)-3,7-Dimethyl-2,6-octadienalbiospider
(E)-3,7-Dimethylocta-2,6-dienalbiospider
(E)-Citralbiospider
(E)-Geranialbiospider
α-Citralbiospider
2,6-Octadienal, 3,7-dimethyl-, (2E)-biospider
2,6-Octadienal, 3,7-dimethyl-, (E)-biospider
α-citralGenerator
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 PointBp20 119°DFC
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 Indexn20D 1.4898DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-84bd30b4e03200f6db52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1010-8900000000-8aa62bcc7a1bcaa41a1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-79a3e6745a117da8309bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-21d238fd55ee29af690fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b84583833bad67467cf0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-a5e231c57e7f56a65d6dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-92c761fd6ee64c67e40eJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID558878
ChEMBL IDCHEMBL1080997
KEGG Compound IDC01499
Pubchem Compound ID638011
Pubchem Substance IDNot Available
ChEBI ID16980
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35092
CRC / DFC (Dictionary of Food Compounds) IDJGH37-H:JGB05-S
EAFUS IDNot Available
Dr. Duke IDCITRAL-A|CITRAL-ALPHA|GERANIAL|TRANS-CITRAL
BIGG IDNot Available
KNApSAcK IDC00003036
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID141-27-5
GoodScent IDrw1041341
SuperScent IDNot Available
Wikipedia IDGeranial
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
anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti Epstein-Barr virus22587 A substance that destroys or inhibits replication of viruses.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti yeast33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
glutathionigenicDUKE
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
spasmolyticDUKE
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. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint
  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
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.