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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0550-5900000000-13fde8b7ff0067424578Spectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0pvr-3900000000-c32a1e404d8621266f63Spectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0kbr-6900000000-b8aff71f0bcacbaf724dSpectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-6f5a43e9b74338868204Spectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0pvr-3900000000-c32a1e404d8621266f63Spectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0kbr-6900000000-b8aff71f0bcacbaf724dSpectrum
GC-MSCuminyl alcohol, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-6f5a43e9b74338868204Spectrum
Predicted GC-MSCuminyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ap0-2900000000-9ad147d8683aed279c39Spectrum
Predicted GC-MSCuminyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9640000000-185db6c067a7714570b7Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-001i-0900000000-965c655548a8c5943e62Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-001i-0900000000-d470f06f07de65e5fce2Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-51c04eee2d1ab848b219Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-001i-0900000000-66853009b21b51fb3918Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-c7fb4e6f07ac2569c2f7Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-053r-0900000000-1e3d9dd752086e6d38dcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a59-1900000000-13c15749c4bc029cd711Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-1900000000-4c8786e398c1c4e67a0fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-2900000000-3b399b4f5dec9e21d1bcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-066u-4900000000-84309740d600e582f78fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014l-5900000000-1958c690160b7b74935aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014l-8900000000-b1d89479c198cc9b0ca6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-014l-9500000000-db7f4bb92ad19f1a9c58Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-1900000000-2d288b863a32ab45d687Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-0ae8d2338f48c17984cdSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-1900000000-be041ab7f72bfcfcad35Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a6r-4900000000-24a5e7ac32f1e350402eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a6r-7900000000-92fad9231825a0574657Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-056r-9600000000-82ac2a7ea87a2815ed6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-36f30ea1b9be9f546dd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-7222268cccd775494a3eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-3900000000-58cdb5f06cfb7f743bffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e8e0e1000bf092241a57Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0900000000-59bdaabd30beafe9a597Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-d489f29c4bfd8ceb31c4Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
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).