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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:42 UTC
Update Date2020-02-26 21:23:56 UTC
HMDB IDHMDB0002214
Secondary Accession Numbers
  • HMDB02214
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
Data?1582752236
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 Weight148.205
Monoisotopic Molecular Weight148.088815006
IUPAC Name4-(propan-2-yl)benzaldehyde
Traditional Namecuminaldehyde
CAS Registry Number122-03-2
SMILES
[H]C(=O)C1=CC=C(C=C1)C(C)C
InChI Identifier
InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChI KeyWTWBUQJHJGUZCY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Cumene
  • Phenylpropane
  • Benzaldehyde
  • Benzoyl
  • Aryl-aldehyde
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Aldehyde
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateLiquid
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 g/LALOGPS
logP2.73ALOGPS
logP2.93ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.83 m³·mol⁻¹ChemAxon
Polarizability17.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0561-6900000000-5b0379bb7c7e6a17d117Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0561-6900000000-5b0379bb7c7e6a17d117Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-3900000000-c02dbd8bf81f7768fc26Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0900000000-dd3cd824f2abace2f474Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0900000000-3863618aab6990def399Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-3ebdf69e4e2457ce0b46Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-1900000000-22d80605ba571f6e3b96Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-056s-4900000000-a041347a1b6961438919Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-004i-9500000000-b789239b57425020f578Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-004i-9300000000-e621b7ac20c46d925927Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-004i-9400000000-360e53edba5bc955bbf3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-056r-9600000000-335c1d31bf11a5ce9c2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-056r-9600000000-7bb47d6aadc7432161d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-004i-9400000000-2f10fbe6182d457e96c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0fb9-9100000000-2c7cf248afc0d63a8281Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-3900000000-e7825163b5aabc234610Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-46d4cee1b5ac630ba9b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7f1cf4b9bc08e5776672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-46a2d5a1f371a61f108eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-8900000000-60bce59455892fc6d3d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-36f6419f699e5430f11eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-9449fabcebe90dca9d03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4900000000-bbbb090a22b8e62ed75fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0561-4900000000-eb2b3a37266bfb581bb3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008724
KNApSAcK IDC00003039
Chemspider ID21106431
KEGG Compound IDC06577
BioCyc IDCPD-1003
BiGG IDNot Available
Wikipedia LinkCuminaldehyde
METLIN IDNot Available
PubChem Compound326
PDB IDNot Available
ChEBI ID28671
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed: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. [PubMed: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. [PubMed:2815827 ]