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Showing Compound Perillaldehyde (FDB014910)

Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2025-11-19 00:50:41 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 ID15589
ChEMBL IDCHEMBL469537
KEGG Compound IDC02576
Pubchem Compound ID16441
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0003647
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 IDPerillaldehyde
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 An agent that kills mites and ticks, used to control infestations and prevent diseases like scabies and tick-borne illnesses. Therapeutically, acaricides are applied topically or systemically to treat parasitic infections, reducing discomfort and preventing disease transmission. Key medical uses include treating acariasis, demodectic mange, and tick paralysis.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-melanomic35610 An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.DUKE
Anti-proliferativeAn agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
VibriocideAn agent destructive to Vibrio bacteria, particularly V. cholerae, used to combat cholera and other Vibrio-mediated infections, serving as a therapeutic agent in managing diarrheal diseases and preventing waterborne illnesses.DUKE
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.