You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-11 20:01:20 UTC
Update Date2016-02-11 02:37:04 UTC
HMDB IDHMDB35078
Secondary Accession NumbersNone
Metabolite Identification
Common NameGeranial
DescriptionGeranial is found in apricot. Geranial occurs in lemon grass oil (Cymbopogon citratus), lemon, orange and many other essential oils; flavouring ingredient Geranial has been shown to exhibit anti-microbial function (PMID 15707770 ). Geranial belongs to the family of Monoterpenes. These are compounds contaning a chain of two isoprene units. (Inferred from compound structure)Geranial is the E-isomer of citral.
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 Weight152.2334
Monoisotopic Molecular Weight152.120115134
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 KeyInChIKey=WTEVQBCEXWBHNA-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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
  • anti-microbial
Application
  • Flavoring Agent
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
logP3.37ALOGPS
logP2.66ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.12 m3·mol-1ChemAxon
Polarizability18.6 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-92c761fd6ee64c67e40eView in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013702
KNApSAcK IDC00003035
Chemspider ID553578
KEGG Compound IDC01499
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGeranial
NuGOwiki LinkHMDB35078
Metagene LinkHMDB35078
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. [15707770 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.