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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:01:20 UTC
Update Date2018-05-19 23:37:47 UTC
HMDB IDHMDB0035078
Secondary Accession Numbers
  • HMDB35078
Metabolite Identification
Common NameGeranial
DescriptionGeranial, also known as alpha-citral or neral, 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 exists as a liquid and is considered to be practically insoluble (in water) and relatively neutral. Geranial has been primarily detected in saliva. Within the cell, geranial is primarily located in the membrane (predicted from logP) and cytoplasm. Geranial exists in all eukaryotes, ranging from yeast to humans. Geranial can be converted into 2,3-epoxygerianial. Geranial is a sweet, bitter, and lemon tasting compound that can be found in a number of food items such as sweet bay, sweet marjoram, pepper (spice), and sunflower. This makes geranial a potential biomarker for the consumption of these food products. Geranial is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(e)-CitralChEBI
(e)-GeranialChEBI
alpha-CitralChEBI
Citral aChEBI
LemonalChEBI
NeralChEBI
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
(e)-NeralHMDB
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
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name(2E)-3,7-dimethylocta-2,6-dienal
Traditional Nameα-citral
CAS Registry Number141-27-5
SMILES
CC(C)=CCC\C(C)=C\C=O
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+
InChI KeyWTEVQBCEXWBHNA-JXMROGBWSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 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:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013702
KNApSAcK IDC00003035
Chemspider ID553578
KEGG Compound IDC01499
BioCyc IDGERANIAL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound638011
PDB IDNot Available
ChEBI ID16980
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duarte MC, Figueira GM, Sartoratto A, Rehder VL, Delarmelina C: Anti-Candida activity of Brazilian medicinal plants. J Ethnopharmacol. 2005 Feb 28;97(2):305-11. Epub 2005 Jan 5. [PubMed:15707770 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.