2,6-Octadienal, 3,7-dimethyl-, (2Z)- (CHEM009165)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:59:21 UTC
Update Date2016-11-09 01:13:56 UTC
Accession NumberCHEM009165
Identification
Common Name2,6-Octadienal, 3,7-dimethyl-, (2Z)-
ClassSmall Molecule
DescriptionAn enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass152.237 g/mol
Monoisotopic Mass152.120 g/mol
CAS Registry Number106-26-3
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dienal
Traditional Nameneral
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-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
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
Polarizability18.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-84bd30b4e03200f6db52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1010-8900000000-8aa62bcc7a1bcaa41a1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-79a3e6745a117da8309bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-21d238fd55ee29af690fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b84583833bad67467cf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-a5e231c57e7f56a65d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-70e7a03f5a911f54f098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3128155f72d867d46318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9100000000-9b92fab117afca4b3a0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o0-9100000000-9c5fcd575fed478bccf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05qc-9000000000-85ae79bf95f3094e7a85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1a9a16cf8ea66689ce6aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035092
FooDB IDFDB013575
Phenol Explorer IDNot Available
KNApSAcK IDC00003036
BiGG IDNot Available
BioCyc IDCPD-9762
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNeral
Chemspider ID558878
ChEBI ID29020
PubChem Compound ID643779
Kegg Compound IDC09847
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15931590
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21809949
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23938144
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24066512
5. 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.
6. 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.
7. 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.
8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
9. 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.
10. 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.
11. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
13. The lipid handbook with CD-ROM