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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:02:08 UTC
Update Date2022-03-07 02:54:21 UTC
HMDB IDHMDB0035092
Secondary Accession Numbers
  • HMDB35092
Metabolite Identification
Common Namecis-Citral
Descriptioncis-Citral, also known as citral b or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, cis-citral is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on cis-Citral.
Structure
Data?1563862664
Synonyms
ValueSource
Citral bChEBI
LemonalChEBI
NeralKegg
cis-CitralChEBI
(Z)-CitralMeSH, HMDB
CitralMeSH, HMDB
(2Z)-3,7-Dimethyl-2,6-octadien-1-alHMDB
(2Z)-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-3,7-Dimethyl-2,6-octadienalHMDB
(Z)-NeralHMDB
2-cis-3,7-Dimethyl-2,6-octadienalHMDB
3,7-Dimethyl-2,6-octadien-1-alHMDB
3,7-Dimethyl-2,6-octadienalHMDB
beta-CitralHMDB
cis-3,7-Dimethyl-2,6-octadienalHMDB
cis-GeranialHMDB
β-CitralHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dienal
Traditional Nameneral
CAS Registry Number106-26-3
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-YFHOEESVSA-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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point228.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility84.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.170The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability18.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+140.65230932474
DeepCCS[M-H]-138.09830932474
DeepCCS[M-2H]-174.42530932474
DeepCCS[M+Na]+149.71330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-CitralCC(C)=CCC\C(C)=C/C=O1681.3Standard polar33892256
cis-CitralCC(C)=CCC\C(C)=C/C=O1212.4Standard non polar33892256
cis-CitralCC(C)=CCC\C(C)=C/C=O1257.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-Citral GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Citral GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Positive-QTOFsplash10-0udi-1900000000-84bd30b4e03200f6db522016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Positive-QTOFsplash10-1010-8900000000-8aa62bcc7a1bcaa41a1e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Positive-QTOFsplash10-0gb9-9000000000-79a3e6745a117da8309b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Negative-QTOFsplash10-0udi-0900000000-21d238fd55ee29af690f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Negative-QTOFsplash10-0udi-1900000000-b84583833bad67467cf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Negative-QTOFsplash10-052f-9700000000-a5e231c57e7f56a65d6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Negative-QTOFsplash10-0pb9-0900000000-70e7a03f5a911f54f0982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Negative-QTOFsplash10-00di-0900000000-3128155f72d867d463182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Negative-QTOFsplash10-014i-9100000000-9b92fab117afca4b3a0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 10V, Positive-QTOFsplash10-05o0-9100000000-9c5fcd575fed478bccf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 20V, Positive-QTOFsplash10-05qc-9000000000-85ae79bf95f3094e7a852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Citral 40V, Positive-QTOFsplash10-00kf-9000000000-1a9a16cf8ea66689ce6a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013575
KNApSAcK IDC00003036
Chemspider ID558878
KEGG Compound IDC09847
BioCyc IDCPD-9762
BiGG IDNot Available
Wikipedia LinkNeral
METLIN IDNot Available
PubChem Compound643779
PDB IDNot Available
ChEBI ID29020
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1331191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dudai N, Weinstein Y, Krup M, Rabinski T, Ofir R: Citral is a new inducer of caspase-3 in tumor cell lines. Planta Med. 2005 May;71(5):484-8. [PubMed:15931590 ]
  2. Ortiz MI, Ramirez-Montiel ML, Gonzalez-Garcia MP, Ponce-Monter HA, Castaneda-Hernandez G, Carino-Cortes R: The combination of naproxen and citral reduces nociception and gastric damage in rats. Arch Pharm Res. 2010 Oct;33(10):1691-7. doi: 10.1007/s12272-010-1020-9. Epub 2010 Oct 30. [PubMed:21052946 ]
  3. Lee HJ, Jeong HS, Kim DJ, Noh YH, Yuk DY, Hong JT: Inhibitory effect of citral on NO production by suppression of iNOS expression and NF-kappa B activation in RAW264.7 cells. Arch Pharm Res. 2008 Mar;31(3):342-9. doi: 10.1007/s12272-001-1162-0. Epub 2008 Apr 13. [PubMed:18409048 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.