Showing Compound Card for Cuminaldehyde (CDB000587)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:45:14 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000587
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCuminaldehyde
DescriptionCuminaldehyde belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminaldehyde, or 4-isopropylbenzaldehyde, is a natural organic compound with the molecular formula C10 H12O. It is a benzaldehyde with an isopropyl group in the 4-position. Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. Cuminaldehyde is a volatile compound representative of the cumin aroma. It has been detected to be present in trace amounts in the blood and milk of ewes fed with cumin seed (PMID: 8738023 ). In mammals, cuminaldehyde is metabolized by reduction but not by oxidation (PMID: 2815827 ). Cuminaldehyde is a constituent of the essential oils of eucalyptus, myrrh, cassia, and cumin, among others. It has a pleasant smell and contributes to the aroma of these oils. Cuminaldehyde has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). Cuminaldehyde can also be synthesized by the reduction of 4-isopropylbenzoyl chloride or by the formylation of cumene. It is used commercially in perfumes and other cosmetics.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight148.21
Monoisotopic Molecular Weight148.0888
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 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:

Role

Biological role:

Industrial application:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0561-4900000000-eb2b3a37266bfb581bb32015-03-01View Spectrum
GC-MSCuminaldehyde, non-derivatized, GC-MS Spectrumsplash10-0561-6900000000-5b0379bb7c7e6a17d117Spectrum
GC-MSCuminaldehyde, non-derivatized, GC-MS Spectrumsplash10-0561-6900000000-5b0379bb7c7e6a17d117Spectrum
Predicted GC-MSCuminaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-3900000000-c02dbd8bf81f7768fc26Spectrum
Predicted GC-MSCuminaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0900000000-dd3cd824f2abace2f4742020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0900000000-3863618aab6990def3992020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-3ebdf69e4e2457ce0b462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-1900000000-22d80605ba571f6e3b962020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-056s-4900000000-a041347a1b69614389192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-004i-9500000000-b789239b57425020f5782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-004i-9300000000-e621b7ac20c46d9259272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-004i-9400000000-360e53edba5bc955bbf32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-056r-9600000000-335c1d31bf11a5ce9c2c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-056r-9600000000-7bb47d6aadc7432161d12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-004i-9400000000-2f10fbe6182d457e96c72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0fb9-9100000000-2c7cf248afc0d63a82812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-3900000000-e7825163b5aabc2346102020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7f1cf4b9bc08e57766722016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-46a2d5a1f371a61f108e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-8900000000-60bce59455892fc6d3d92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-36f6419f699e5430f11e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-9449fabcebe90dca9d032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4900000000-bbbb090a22b8e62ed75f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2900000000-a82bc8469ac9379cd5822021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4900000000-9c19251b8683aebd8d312021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mn-9300000000-df0d9626eb18c3efd1622021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-532ba12d245835d697bd2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002214
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. 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. doi: 10.1016/0378-4347(95)00527-7. [PubMed:8738023 ]
  2. 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. doi: 10.3109/00498258909043145. [PubMed:2815827 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]