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Neral (FDB013575)

Record Information
Version1.0
Creation date2010-04-08 22:10:47 UTC
Update date2020-09-17 15:31:20 UTC
Primary IDFDB013575
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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).
CAS Number106-26-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name(2Z)-3,7-dimethylocta-2,6-dienal
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
Isomeric SMILESCC(C)=CCC\C(C)=C/C=O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
Classification
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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp12 103°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4809DFC
Spectra
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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09847
Pubchem Compound ID643779
Pubchem Substance IDNot Available
ChEBI ID29020
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJGH37-H:JFJ79-Y
EAFUS IDNot Available
Dr. Duke IDCITRAL-B|NERAL
BIGG IDNot Available
KNApSAcK IDC00003036
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID106-26-3
GoodScent IDrw1331191
SuperScent IDNot Available
Wikipedia IDNeral
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
termiticideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
lemon
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lemon peel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.