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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:42 UTC
Update Date2022-03-07 02:49:13 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
p-Isopropyl benzaldehydeMeSH
4-(1-Methylethyl)benzaldehydeHMDB
4-IsopropylbenzenecarboxylateHMDB
CuminalHMDB
Cuminal P-(1-methylethyl)benzaldehydeHMDB
P-Cuminic aldehydeHMDB
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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point235.5 °CNot Available
Water Solubility282 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP3.170The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.91631661259
DarkChem[M-H]-130.25531661259
DeepCCS[M+H]+140.80130932474
DeepCCS[M-H]-138.40630932474
DeepCCS[M-2H]-172.97530932474
DeepCCS[M+Na]+147.18630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cuminaldehyde[H]C(=O)C1=CC=C(C=C1)C(C)C1850.0Standard polar33892256
Cuminaldehyde[H]C(=O)C1=CC=C(C=C1)C(C)C1244.7Standard non polar33892256
Cuminaldehyde[H]C(=O)C1=CC=C(C=C1)C(C)C1245.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cuminaldehyde EI-B (Non-derivatized)splash10-0561-6900000000-5b0379bb7c7e6a17d1172017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminaldehyde EI-B (Non-derivatized)splash10-0561-6900000000-5b0379bb7c7e6a17d1172018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-3900000000-c02dbd8bf81f7768fc262017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0561-4900000000-eb2b3a37266bfb581bb32015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 1V, positive-QTOFsplash10-0002-0900000000-dd3cd824f2abace2f4742020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 1V, positive-QTOFsplash10-0002-0900000000-3863618aab6990def3992020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 2V, positive-QTOFsplash10-0002-0900000000-3ebdf69e4e2457ce0b462020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 3V, positive-QTOFsplash10-0002-1900000000-22d80605ba571f6e3b962020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 4V, positive-QTOFsplash10-056s-4900000000-a041347a1b69614389192020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 5V, positive-QTOFsplash10-004i-9500000000-b789239b57425020f5782020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 6V, positive-QTOFsplash10-004i-9300000000-e621b7ac20c46d9259272020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 8V, positive-QTOFsplash10-004i-9400000000-360e53edba5bc955bbf32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 9V, positive-QTOFsplash10-056r-9600000000-335c1d31bf11a5ce9c2c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 11V, positive-QTOFsplash10-056r-9600000000-7bb47d6aadc7432161d12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 13V, positive-QTOFsplash10-004i-9400000000-2f10fbe6182d457e96c72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde Orbitrap 15V, positive-QTOFsplash10-0fb9-9100000000-2c7cf248afc0d63a82812020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde n/a 10V, positive-QTOFsplash10-0a4i-3900000000-e7825163b5aabc2346102020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminaldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 10V, Positive-QTOFsplash10-0002-0900000000-7f1cf4b9bc08e57766722016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 20V, Positive-QTOFsplash10-0002-1900000000-46a2d5a1f371a61f108e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 40V, Positive-QTOFsplash10-0ldl-8900000000-60bce59455892fc6d3d92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 10V, Negative-QTOFsplash10-0002-0900000000-36f6419f699e5430f11e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 20V, Negative-QTOFsplash10-0002-0900000000-9449fabcebe90dca9d032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 40V, Negative-QTOFsplash10-0002-4900000000-bbbb090a22b8e62ed75f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 10V, Positive-QTOFsplash10-0002-2900000000-a82bc8469ac9379cd5822021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 20V, Positive-QTOFsplash10-0a4l-4900000000-9c19251b8683aebd8d312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 40V, Positive-QTOFsplash10-00mn-9300000000-df0d9626eb18c3efd1622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 10V, Negative-QTOFsplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminaldehyde 20V, Negative-QTOFsplash10-0002-0900000000-532ba12d245835d697bd2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
Good Scents IDrw1004031
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 ]