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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 02:30:13 UTC
Update Date2021-10-13 04:42:11 UTC
HMDB IDHMDB0003647
Secondary Accession Numbers
  • HMDB0006315
  • HMDB03647
  • HMDB06315
Metabolite Identification
Common NamePerillyl aldehyde
DescriptionPerillyl aldehyde 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. Thus, perillyl aldehyde is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on Perillyl aldehyde.
Structure
Data?1582752285
Synonyms
ValueSource
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
Chemical FormulaC10H14O
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
Traditional Name(+)-perillaldehyde
CAS Registry Number2111-75-3
SMILES
[H]C(=O)C1=CCC(CC1)C(C)=C
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point238.00 to 240.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility160.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.546Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP10(2.97) g/LALOGPS
logP10(2.25) g/LChemAxon
logS10(-2.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.3931661259
DarkChem[M-H]-129.35131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1862.0Standard polar33892256
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1241.5Standard non polar33892256
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1261.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized)splash10-005c-9700000000-a9b7244cc2e7179fa7062014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde EI-B (Non-derivatized)splash10-014i-9400000000-a85682020d5afcb60c382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde EI-B (Non-derivatized)splash10-016r-9200000000-489825eb61952c9dac222017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized)splash10-005c-9700000000-a9b7244cc2e7179fa7062017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-34a520c15ee51fc09bad2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-2d5f1aa73b10c86e86fd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-0900000000-6a0c50ecfd39bc2355f12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-1900000000-18ab37b64accb9eebc8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-1900000000-ff41ee428ac18fd924792020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-2900000000-cc26f9d1f830b389dd6e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-3900000000-b569eb4964b8859e157c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 4V, positive-QTOFsplash10-0ue9-3900000000-fc9bee20ab6457dc41d62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 5V, positive-QTOFsplash10-0zgl-6900000000-e4bd19c8534ad8a4170a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 6V, positive-QTOFsplash10-0kal-9800000000-7ae871e55ee7d93e3fd42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 8V, positive-QTOFsplash10-0a5c-9500000000-20075ac27a31f7c011ff2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 9V, positive-QTOFsplash10-0kyl-9300000000-606866a64c1614c828b52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 11V, positive-QTOFsplash10-00ou-9300000000-b59e349c4aa0f5f0f8b62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 14V, positive-QTOFsplash10-00or-9200000000-20bc7958608312a537f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-001i-2900000000-9efa35448eaa560e0b582020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-becd5fe890a229f54bb32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-001i-9000000000-faa2f39a1de11fcce3722020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-0a4i-4900000000-ff8554bb207ef1e442942020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-791c4364189bf936d4c32020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 10V, Positive-QTOFsplash10-0udi-1900000000-93f536e9e8fea0a3f4992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 20V, Positive-QTOFsplash10-0udi-5900000000-782526b3813e79dfb68f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 40V, Positive-QTOFsplash10-0uxu-9100000000-0dd1165ad555b037ef422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 10V, Negative-QTOFsplash10-0002-0900000000-200f98d44579ee015dd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 20V, Negative-QTOFsplash10-0002-0900000000-bb22a8402cb0094ac0502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 40V, Negative-QTOFsplash10-0159-3900000000-fe4501ac4f2041d445922016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014910
KNApSAcK IDC00003050
Chemspider ID15589
KEGG Compound IDC02576
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPerillaldehyde
METLIN IDNot Available
PubChem Compound16441
PDB IDNot Available
ChEBI ID15421
Food Biomarker OntologyNot Available
VMH IDPYLALD
MarkerDB IDNot Available
Good Scents IDrw1399441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails