Showing Compound Card for Cuminol (CDB000719)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:52:56 UTC
Updated at2020-12-07 19:07:43 UTC
CannabisDB IDCDB000719
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCuminol
DescriptionCuminol or Cuminyl alcohol, also known as p-cumin-7-ol or 4-Isopropylbenzyl alcohol, 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 (PMID: 7640522 ). 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. Cuminol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cuminol is an alcohol derivative of p-Cymene. It exists as a clear, colorless liquid that is poorly soluble in water. Cuminol can be used as a food additive or as a cosmetic fragrance. It has a cumin, caraway or spicy, herbal aroma and a similar spicy, herbal or peppery taste. Cuminol is found naturally in a number of plants, spices and foods including cumin seed and cumin oils, caraway eucalyptus oils, thyme, sunflowers, tuermeric, guava fruit and other spices and essential oils. Cumin, a widely used spice, is known to have anti-diabetic properties and two of its phytochemicals: cuminol and cuminaldehyde appear to be among the most active components. Cuminol is a potent insulinotrophic molecule that can enhance insulin secretion by up to 4-fold (in rat islet cells) (PMID: 23507295 ). It also exhibits strong beta-cell protective action (PMID: 23507295 ). Cuminol is one of the terpenoids that present only in traces in cannabis plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4-Isopropylphenyl)methanolChEBI
(4-Propan-2-ylphenyl)methanolChEBI
4-(1-Methylethyl)benzenemethanolChEBI
Cumic alcoholChEBI
Cumin alcoholChEBI
Cuminic alcoholChEBI
CuminolChEBI
Cumyl alcoholChEBI
p-Cumic alcoholChEBI
p-Cumin-7-olChEBI
p-Cymen-7-olChEBI
p-Isopropylbenzyl alcoholChEBI
p-Mentha-1,3,5-trien-7-olChEBI
Para-cymen-7-olChEBI
4-Isopropylbenzyl alcoholKegg
4-(1-Methylethyl)-benzenemethanolHMDB
4-(1-Methylethyl)benzene methanolHMDB
4-(1-Methylethyl)benzenemethanol, 9ciHMDB
4-Isopropyl benzyl alcoholHMDB
4-ISOPROPYLBENZENEMETHANOLHMDB
Cuminol ( P-cymen-7-ol)HMDB
CuminylalcoholHMDB
FEMA 2933HMDB
P-Cymen-7-ol, 8ciHMDB
P-Cymene-7-olHMDB
P-Isopropyl benzyl alcoholHMDB
P-Isopropyl-benzyl alcoholHMDB
Cuminyl alcoholChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name[4-(propan-2-yl)phenyl]methanol
Traditional Namecuminol
CAS Registry Number536-60-7
SMILES
CC(C)C1=CC=C(CO)C=C1
InChI Identifier
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3
InChI KeyOIGWAXDAPKFNCQ-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
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Benzyl alcohol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.63ALOGPS
logP2.45ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)15.05ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.06 m³·mol⁻¹ChemAxon
Polarizability17.98 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)splash10-0550-5900000000-13fde8b7ff00674245782015-03-01View Spectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-0pvr-3900000000-c32a1e404d8621266f63Spectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-0kbr-6900000000-b8aff71f0bcacbaf724dSpectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-6f5a43e9b74338868204Spectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-0pvr-3900000000-c32a1e404d8621266f63Spectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-0kbr-6900000000-b8aff71f0bcacbaf724dSpectrum
GC-MSCuminol, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-6f5a43e9b74338868204Spectrum
Predicted GC-MSCuminol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ap0-2900000000-9ad147d8683aed279c39Spectrum
Predicted GC-MSCuminol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9640000000-185db6c067a7714570b7Spectrum
Predicted GC-MSCuminol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCuminol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-001i-0900000000-965c655548a8c5943e622020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-001i-0900000000-d470f06f07de65e5fce22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-51c04eee2d1ab848b2192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-66853009b21b51fb39182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-c7fb4e6f07ac2569c2f72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-1e3d9dd752086e6d38dc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a59-1900000000-13c15749c4bc029cd7112020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-1900000000-4c8786e398c1c4e67a0f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-2900000000-3b399b4f5dec9e21d1bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-066u-4900000000-84309740d600e582f78f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014l-5900000000-1958c690160b7b74935a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014l-8900000000-b1d89479c198cc9b0ca62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-014l-9500000000-db7f4bb92ad19f1a9c582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-1900000000-2d288b863a32ab45d6872020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-0ae8d2338f48c17984cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-1900000000-be041ab7f72bfcfcad352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a6r-4900000000-24a5e7ac32f1e350402e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a6r-7900000000-92fad9231825a05746572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-056r-9600000000-82ac2a7ea87a2815ed6b2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-36f30ea1b9be9f546dd12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-7222268cccd775494a3e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-3900000000-58cdb5f06cfb7f743bff2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e8e0e1000bf092241a572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0900000000-59bdaabd30beafe9a5972016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-d489f29c4bfd8ceb31c42016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 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 IDHMDB0031817
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008492
KNApSAcK IDC00032864
Chemspider ID21105932
KEGG Compound IDC06576
BioCyc IDCPD-1002
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound325
PDB IDNot Available
ChEBI ID27628
References
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. Patil SB, Takalikar SS, Joglekar MM, Haldavnekar VS, Arvindekar AU: Insulinotropic and beta-cell protective action of cuminaldehyde, cuminol and an inhibitor isolated from Cuminum cyminum in streptozotocin-induced diabetic rats. Br J Nutr. 2013 Oct;110(8):1434-43. doi: 10.1017/S0007114513000627. Epub 2013 Mar 14. [PubMed:23507295 ]
  3. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]