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Showing Compound Perillaldehyde (FDB014910)

Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2019-11-26 03:10:54 UTC
Primary IDFDB014910
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePerillaldehyde
Description(s)-perillaldehyde, also known as P-mentha-1,8-dien-7-al, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (s)-perillaldehyde is considered to be an isoprenoid lipid molecule (s)-perillaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (s)-perillaldehyde is a cherry, fat, and fatty tasting compound found in herbs and spices, which makes (s)-perillaldehyde a potential biomarker for the consumption of this food product (s)-perillaldehyde can be found primarily in saliva.
CAS Number2111-75-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-(1-Methylethenyl)-1-cyclohexene1-carboxyaldehydeChEBI
p-Mentha-1,8-dien-7-alChEBI
PerillalChEBI
PerillaldehydeChEBI
Perillic aldehydeChEBI
PerillylaldehydeChEBI
(-)-PerillaldehydeHMDB
1,8-P-Menthadien-7-alHMDB
1-PerillaldehydeHMDB
4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehydeHMDB
4-Isopropenylcyclohex-1-enecarbaldehydeHMDB
Dihydrocuminyl aldehydeHMDB
DL-Perillaldehyde(for perfumery)HMDB
FEMA no. 3557HMDB
L-PerillaldehydeHMDB
P-Mentha-1,8-dien-7-al (natural)HMDB
Para-mentha-1,8-dien-7-alHMDB
Perilla aldehydeHMDB, MeSH
4-Mentha-1,8-dien-7-alMeSH, HMDB
Perillaldehyde, (+)-isomerMeSH, HMDB
4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde, 9CIdb_source
4-Isopropenyl-1-cyclohexene-1-carboxaldehydedb_source
Perillaaldehydedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP2.97ALOGPS
logP2.25ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O
IUPAC name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
InChI IdentifierInChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3
InChI KeyRUMOYJJNUMEFDD-UHFFFAOYSA-N
Isomeric SMILES[H]C(=O)C1=CCC(CC1)C(C)=C
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
Classification
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting PointNot Available
Boiling PointNot Available
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 IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(R)-Perillaldehyde, non-derivatized, GC-MS Spectrumsplash10-005c-9700000000-a9b7244cc2e7179fa706Spectrum
GC-MS(R)-Perillaldehyde, non-derivatized, GC-MS Spectrumsplash10-014i-9400000000-a85682020d5afcb60c38Spectrum
GC-MS(R)-Perillaldehyde, non-derivatized, GC-MS Spectrumsplash10-016r-9200000000-489825eb61952c9dac22Spectrum
GC-MS(R)-Perillaldehyde, non-derivatized, GC-MS Spectrumsplash10-005c-9700000000-a9b7244cc2e7179fa706Spectrum
Predicted GC-MS(R)-Perillaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9400000000-34a520c15ee51fc09badSpectrum
Predicted GC-MS(R)-Perillaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-2d5f1aa73b10c86e86fd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0900000000-6a0c50ecfd39bc2355f12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-1900000000-18ab37b64accb9eebc8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0udi-1900000000-ff41ee428ac18fd924792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0udi-2900000000-cc26f9d1f830b389dd6e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0udi-3900000000-b569eb4964b8859e157c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0ue9-3900000000-fc9bee20ab6457dc41d62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0zgl-6900000000-e4bd19c8534ad8a4170a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0kal-9800000000-7ae871e55ee7d93e3fd42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a5c-9500000000-20075ac27a31f7c011ff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0kyl-9300000000-606866a64c1614c828b52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-00ou-9300000000-b59e349c4aa0f5f0f8b62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00or-9200000000-20bc7958608312a537f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-001i-2900000000-9efa35448eaa560e0b582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-becd5fe890a229f54bb32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-001i-9000000000-faa2f39a1de11fcce3722020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-4900000000-ff8554bb207ef1e442942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-791c4364189bf936d4c32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-93f536e9e8fea0a3f4992016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-782526b3813e79dfb68f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-0dd1165ad555b037ef422016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-200f98d44579ee015dd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-bb22a8402cb0094ac0502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-3900000000-fe4501ac4f2041d445922016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJXJ69-R:JXJ69-R
EAFUS ID2940
Dr. Duke IDPERILLA-ALDEHYDE|PERILLALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00003050
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID2111-75-3
GoodScent IDrw1399441
SuperScent IDNot Available
Wikipedia IDNot Available
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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proliferativeDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
candidicideDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
mutagenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
vibriocideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spice
  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
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grassy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cumin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fat
  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
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.