Record Information
Version1.0
Creation date2010-04-08 22:08:06 UTC
Update date2020-09-17 15:36:12 UTC
Primary IDFDB008492
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCuminyl alcohol
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).
CAS Number536-60-7
Structure
Thumb
Synonyms
SynonymSource
(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
4-(1-methylethyl)-benzenemethanolbiospider
4-(1-methylethyl)benzene methanolbiospider
4-(1-methylethyl)benzenemethanolbiospider
4-(1-Methylethyl)benzenemethanol, 9CIdb_source
Benzenemethanol, 4-(1-methylethyl)-biospider
Benzyl alcohol, p-isopropyl-biospider
cuminol ( p-cymen-7-ol)biospider
P-cumic alcoholbiospider
p-Cymen-7-ol, 8CIdb_source
p-cymene-7-olbiospider
P-isopropyl benzyl alcoholbiospider
P-Isopropyl-benzyl alcoholHMDB
para-Cymen-7-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14O
IUPAC name[4-(propan-2-yl)phenyl]methanol
InChI IdentifierInChI=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
Isomeric SMILESCC(C)C1=CC=C(CO)C=C1
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
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
  • 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:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting Point28 oC
Boiling PointBp20 140°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd20 0.98DFC
Refractive Indexn24D 1.5220DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pvr-3900000000-c32a1e404d8621266f63JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kbr-6900000000-b8aff71f0bcacbaf724dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-2900000000-6f5a43e9b74338868204JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pvr-3900000000-c32a1e404d8621266f63JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kbr-6900000000-b8aff71f0bcacbaf724dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-2900000000-6f5a43e9b74338868204JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap0-2900000000-9ad147d8683aed279c39JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9640000000-185db6c067a7714570b7JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-001i-0900000000-965c655548a8c5943e62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-001i-0900000000-d470f06f07de65e5fce2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-51c04eee2d1ab848b219JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-66853009b21b51fb3918JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-c7fb4e6f07ac2569c2f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-1e3d9dd752086e6d38dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a59-1900000000-13c15749c4bc029cd711JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-1900000000-4c8786e398c1c4e67a0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-2900000000-3b399b4f5dec9e21d1bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-066u-4900000000-84309740d600e582f78fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014l-5900000000-1958c690160b7b74935aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014l-8900000000-b1d89479c198cc9b0ca6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-014l-9500000000-db7f4bb92ad19f1a9c58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-1900000000-2d288b863a32ab45d687JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-0ae8d2338f48c17984cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-1900000000-be041ab7f72bfcfcad35JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a6r-4900000000-24a5e7ac32f1e350402eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a6r-7900000000-92fad9231825a0574657JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-056r-9600000000-82ac2a7ea87a2815ed6bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-36f30ea1b9be9f546dd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-7222268cccd775494a3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-3900000000-58cdb5f06cfb7f743bffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e8e0e1000bf092241a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0900000000-59bdaabd30beafe9a597JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-d489f29c4bfd8ceb31c4JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0550-5900000000-13fde8b7ff0067424578JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID21105932
ChEMBL IDCHEMBL3183500
KEGG Compound IDC06576
Pubchem Compound ID325
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31817
CRC / DFC (Dictionary of Food Compounds) IDDLW56-E:DLW56-E
EAFUS ID1912
Dr. Duke IDCUMINYL-ALCOHOL|CUMIN-ALCOHOL|CUMINIC-ALCOHOL
BIGG IDNot Available
KNApSAcK IDC00032864
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID536-60-7
GoodScent IDrw1016451
SuperScent IDNot Available
Wikipedia IDNot Available
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
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  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
herb
  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
strong
  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.
caraway
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  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.
leather
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).