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cis-Citral (CHEM003822)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-11 05:19:58 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003822
Identification
Common Namecis-Citral
ClassSmall Molecule
DescriptionCitral is found in carrot. Citral, 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 has been shown to exhibit apoptotic, anti-nociceptive and anti-inflammatory functions (1, 2, 3). Citral belongs to the family of Monoterpenes. These are compounds contaning a chain of two isoprene units.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC10H16O
Average Molecular Mass152.237 g/mol
Monoisotopic Mass152.120 g/mol
CAS Registry Number5392-40-5
IUPAC Name(2E)-3,7-dimethylocta-2,6-dienal
Traditional Nameα-citral
SMILESCC(C)=CCC\C(C)=C\C=O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point229°C (444.2°F)
SolubilityNot 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0159-9300000000-625c688e32f3edaf287cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kf-9000000000-90723459c49195367705View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014l-9000000000-ccb0a3f327b5d2362bb9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-131249cb1d7fb343fe10View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-dcdfd8342f2d4ce5a439View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-9100000000-3c1a8e898f563c833b2cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kf-9000000000-90723459c49195367705View 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 Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035078
FooDB IDFDB013702
Phenol Explorer IDNot Available
KNApSAcK IDC00003035
BiGG IDNot Available
BioCyc IDGERANIAL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCitral
Chemspider ID553578
ChEBI ID16980
PubChem Compound ID638011
Kegg Compound IDC01499
YMDB IDYMDB01656
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23938144
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24682420
3. 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.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. 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.
6. 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.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
9. The lipid handbook with CD-ROM