Showing Compound Card for Neral (CDB000190)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:28:07 UTC
Updated at2020-12-07 19:07:14 UTC
CannabisDB IDCDB000190
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNeral
Description3,7-dimethyl-2,6-octadienal or citral, also known as lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as geranial or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID: 6991645 , 26657499 ). Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID: 28974979 ) and pheromonal effects in nematodes and insects (PMID: 26973536 ). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke).
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 Weight152.24
Monoisotopic Molecular Weight152.1201
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

Route of exposure:

Biological location:

Source:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point229 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeral, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287cSpectrum
Predicted GC-MSNeral, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-84bd30b4e03200f6db522016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1010-8900000000-8aa62bcc7a1bcaa41a1e2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-79a3e6745a117da8309b2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-21d238fd55ee29af690f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b84583833bad67467cf02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-a5e231c57e7f56a65d6d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-70e7a03f5a911f54f0982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3128155f72d867d463182021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9100000000-9b92fab117afca4b3a0a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o0-9100000000-9c5fcd575fed478bccf62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05qc-9000000000-85ae79bf95f3094e7a852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1a9a16cf8ea66689ce6a2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035092
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  3. Mokarizadeh M, Kafil HS, Ghanbarzadeh S, Alizadeh A, Hamishehkar H: Improvement of citral antimicrobial activity by incorporation into nanostructured lipid carriers: a potential application in food stuffs as a natural preservative. Res Pharm Sci. 2017 Oct;12(5):409-415. doi: 10.4103/1735-5362.213986. [PubMed:28974979 ]
  4. Larsdotter-Mellstrom H, Eriksson K, Liblikas I I, Wiklund C, Borg-Karlson AK, Nylin S, Janz N, Carlsson MA: It's All in the Mix: Blend-Specific Behavioral Response to a Sexual Pheromone in a Butterfly. Front Physiol. 2016 Feb 29;7:68. doi: 10.3389/fphys.2016.00068. eCollection 2016. [PubMed:26973536 ]
  5. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]