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Record Information
Version3.6
Creation Date2006-05-22 14:17:42 UTC
Update Date2016-02-11 01:05:27 UTC
HMDB IDHMDB02214
Secondary Accession NumbersNone
Metabolite Identification
Common NameCuminaldehyde
DescriptionCuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. C. cyminum seed-derived materials have an inhibitory effect in vitro against rat lens aldose reductase and alpha-glucosidase. This inhibitory action cuminaldehyde suggest a potential utility as an antidiabetic therapeutic. (PMID: 15796577 ). Cuminaldehyde is a volatile compound representative of cumin aroma present in trace amounts in the blood and milk of ewes fed with cumin seed. (PMID: 8738023 ). The terpenoid cuminaldehyde, undergoes reduction biotransformation in mammals, but not oxidation. (PMID: 2815827 ).
Structure
Thumb
Synonyms
ValueSource
4-IsopropylbenzaldehydeChEBI
CumaldehydeChEBI
Cumic aldehydeChEBI
Cuminic aldehydeChEBI
Cuminyl aldehydeChEBI
P-Cumic aldehydeChEBI
P-IsopropylbenzaldehydeChEBI
P-IsopropylbenzenecarboxaldehydeChEBI
4-(1-Methylethyl)benzaldehydeHMDB
4-IsopropylbenzenecarboxylateHMDB
CuminalHMDB
Cuminal P-(1-methylethyl)benzaldehydeHMDB
P-Cuminic aldehydeHMDB
P-Isopropyl benzaldehydeHMDB
P-Isopropyl-benzaldehydeHMDB
Chemical FormulaC10H12O
Average Molecular Weight148.2017
Monoisotopic Molecular Weight148.088815006
IUPAC Name4-(propan-2-yl)benzaldehyde
Traditional Namecuminaldehyde
CAS Registry Number122-03-2
SMILES
CC(C)C1=CC=C(C=O)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChI KeyInChIKey=WTWBUQJHJGUZCY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Cosmetic
  • 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 PointNot AvailableNot Available
Boiling Point235.5 °CNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 mg/mLALOGPS
logP2.73ALOGPS
logP2.93ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.83 m3·mol-1ChemAxon
Polarizability17.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-0561-4900000000-eb2b3a37266bfb581bb3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
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 IDFDB008724
KNApSAcK IDC00003039
Chemspider ID21106431
KEGG Compound IDC06577
BioCyc IDCPD-1003
BiGG IDNot Available
Wikipedia LinkCuminaldehyde
NuGOwiki LinkHMDB02214
Metagene LinkHMDB02214
METLIN IDNot Available
PubChem Compound326
PDB IDNot Available
ChEBI ID366706
References
Synthesis ReferenceLebedev, I. M.; Gorker, I. A.; Mochalin, V. B. A new method for the preparation of cuminaldehyde and for the simultaneous preparation of p-isopropyl-a-methylcinnamaldehyde. Masloboino-Zhirovaya Promyshlennost (1961), 27(2), 33-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee HS: Cuminaldehyde: Aldose Reductase and alpha-Glucosidase Inhibitor Derived from Cuminum cyminum L. Seeds. J Agric Food Chem. 2005 Apr 6;53(7):2446-50. [15796577 ]
  2. Desage M, Schaal B, Soubeyrand J, Orgeur P, Brazier JL: Gas chromatographic-mass spectrometric method to characterise the transfer of dietary odorous compounds into plasma and milk. J Chromatogr B Biomed Appl. 1996 Apr 12;678(2):205-10. [8738023 ]
  3. Ishida T, Toyota M, Asakawa Y: Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Xenobiotica. 1989 Aug;19(8):843-55. [2815827 ]