You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-13 02:30:13 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03647
Secondary Accession Numbers
  • HMDB06315
Metabolite Identification
Common NamePerillyl aldehyde
DescriptionPerillaldehyde, or perilla aldehyde, is a natural organic compound found most abundantly in the perennial herb perilla, but also in a wide variety of other plants and essential oils. It is a monoterpenoid containing an aldehyde functional group.
Structure
Thumb
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
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
Traditional Name(+)-perillaldehyde
CAS Registry Number2111-75-3
SMILES
CC(=C)C1CCC(C=O)=CC1
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 KeyInChIKey=RUMOYJJNUMEFDD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.546Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.58 mg/mLALOGPS
logP2.97ALOGPS
logP2.25ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.27 m3·mol-1ChemAxon
Polarizability17.3 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-005c-9700000000-a9b7244cc2e7179fa706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014789
KNApSAcK IDC00010871
Chemspider ID15589
KEGG Compound IDC02576
BioCyc IDNot Available
BiGG ID40121
Wikipedia LinkPerillyl aldehyde
NuGOwiki LinkHMDB03647
Metagene LinkHMDB03647
METLIN IDNot Available
PubChem Compound16441
PDB IDNot Available
ChEBI ID15421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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