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Cuminaldehyde (FDB008724)

Record Information
Version1.0
Creation date2010-04-08 22:08:13 UTC
Update date2020-09-17 15:35:00 UTC
Primary IDFDB008724
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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.
CAS Number122-03-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not 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
Chemical FormulaC10H12O
IUPAC name4-(propan-2-yl)benzaldehyde
InChI IdentifierInChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChI KeyWTWBUQJHJGUZCY-UHFFFAOYSA-N
Isomeric SMILES[H]C(=O)C1=CC=C(C=C1)C(C)C
Average Molecular Weight148.205
Monoisotopic Molecular Weight148.088815006
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 81.04%; H 8.16%; O 10.80%DFC
Melting PointNot Available
Boiling PointBp10 103-104°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd254 0.98DFC
Refractive Indexn20D 1.5301DFC
Spectra
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
ChemSpider ID21106431
ChEMBL IDCHEMBL161577
KEGG Compound IDC06577
Pubchem Compound ID326
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02214
CRC / DFC (Dictionary of Food Compounds) IDDTC96-Y:DTC96-Y
EAFUS ID778
Dr. Duke IDCUMINALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00003039
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID122-03-2
GoodScent IDrw1004031
SuperScent ID326
Wikipedia IDCuminaldehyde
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
irritantDUKE
larvicideDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
ulcerogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
acid
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sharp
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cumin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.