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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:39 UTC
Update Date2023-02-21 17:21:19 UTC
HMDB IDHMDB0031817
Secondary Accession Numbers
  • HMDB31817
Metabolite Identification
Common 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-erythritol-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 ).
Structure
Data?1677000079
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 Weight150.221
Monoisotopic Molecular Weight150.104465071
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling Point135.00 to 136.00 °C. @ 26.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.370The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.5531661259
DarkChem[M-H]-132.12231661259
DeepCCS[M+H]+141.80930932474
DeepCCS[M-H]-137.98230932474
DeepCCS[M-2H]-175.62630932474
DeepCCS[M+Na]+151.16430932474
AllCCS[M+H]+130.832859911
AllCCS[M+H-H2O]+126.232859911
AllCCS[M+NH4]+135.032859911
AllCCS[M+Na]+136.332859911
AllCCS[M-H]-135.232859911
AllCCS[M+Na-2H]-136.732859911
AllCCS[M+HCOO]-138.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cuminyl alcoholCC(C)C1=CC=C(CO)C=C12076.0Standard polar33892256
Cuminyl alcoholCC(C)C1=CC=C(CO)C=C11233.1Standard non polar33892256
Cuminyl alcoholCC(C)C1=CC=C(CO)C=C11289.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cuminyl alcohol,1TMS,isomer #1CC(C)C1=CC=C(CO[Si](C)(C)C)C=C11399.9Semi standard non polar33892256
Cuminyl alcohol,1TBDMS,isomer #1CC(C)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C11610.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol EI-B (Non-derivatized)splash10-0pvr-3900000000-c32a1e404d8621266f632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol EI-B (Non-derivatized)splash10-0kbr-6900000000-b8aff71f0bcacbaf724d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol GC-EI-TOF (Non-derivatized)splash10-001i-2900000000-6f5a43e9b743388682042017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol EI-B (Non-derivatized)splash10-0pvr-3900000000-c32a1e404d8621266f632018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol EI-B (Non-derivatized)splash10-0kbr-6900000000-b8aff71f0bcacbaf724d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cuminyl alcohol GC-EI-TOF (Non-derivatized)splash10-001i-2900000000-6f5a43e9b743388682042018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminyl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap0-2900000000-9ad147d8683aed279c392017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminyl alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9640000000-185db6c067a7714570b72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cuminyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0550-5900000000-13fde8b7ff00674245782015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol NA , positive-QTOFsplash10-001i-0900000000-965c655548a8c5943e622020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 1V, positive-QTOFsplash10-001i-0900000000-d470f06f07de65e5fce22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 2V, positive-QTOFsplash10-001i-0900000000-51c04eee2d1ab848b2192020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 2V, positive-QTOFsplash10-001i-0900000000-66853009b21b51fb39182020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 3V, positive-QTOFsplash10-053r-0900000000-c7fb4e6f07ac2569c2f72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 3V, positive-QTOFsplash10-053r-0900000000-1e3d9dd752086e6d38dc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 3V, positive-QTOFsplash10-0a59-1900000000-13c15749c4bc029cd7112020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 4V, positive-QTOFsplash10-0a4i-1900000000-4c8786e398c1c4e67a0f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 5V, positive-QTOFsplash10-0a4i-2900000000-3b399b4f5dec9e21d1bc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 6V, positive-QTOFsplash10-066u-4900000000-84309740d600e582f78f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 8V, positive-QTOFsplash10-014l-5900000000-1958c690160b7b74935a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 10V, positive-QTOFsplash10-014l-8900000000-b1d89479c198cc9b0ca62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 12V, positive-QTOFsplash10-014l-9500000000-db7f4bb92ad19f1a9c582020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol n/a 10V, positive-QTOFsplash10-0a4i-1900000000-2d288b863a32ab45d6872020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol n/a 10V, positive-QTOFsplash10-004i-9000000000-0ae8d2338f48c17984cd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 3V, positive-QTOFsplash10-0a4i-1900000000-be041ab7f72bfcfcad352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 4V, positive-QTOFsplash10-0a6r-4900000000-24a5e7ac32f1e350402e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 5V, positive-QTOFsplash10-0a6r-7900000000-92fad9231825a05746572020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cuminyl alcohol Orbitrap 6V, positive-QTOFsplash10-056r-9600000000-82ac2a7ea87a2815ed6b2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 10V, Positive-QTOFsplash10-0ue9-0900000000-36f30ea1b9be9f546dd12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 20V, Positive-QTOFsplash10-001i-1900000000-7222268cccd775494a3e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 40V, Positive-QTOFsplash10-00lr-3900000000-58cdb5f06cfb7f743bff2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 10V, Negative-QTOFsplash10-0002-0900000000-e8e0e1000bf092241a572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 20V, Negative-QTOFsplash10-00kb-0900000000-59bdaabd30beafe9a5972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cuminyl alcohol 40V, Negative-QTOFsplash10-014i-2900000000-d489f29c4bfd8ceb31c42016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016451
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.