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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:15 UTC
Update Date2021-10-13 06:57:23 UTC
HMDB IDHMDB0036579
Secondary Accession Numbers
  • HMDB36579
Metabolite Identification
Common NameCarotol
DescriptionCarotol is found in carrot. Carotol is a constituent of Daucus carota (carrot) Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as a antifungal, herbicidal and insecticidal agent. It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This later reaction, regardless of how plausible it may appear to be on paper, is energetically undesired and through the diligent work of M. Soucek and coworkers it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route.
Structure
Data?1563862892
Synonyms
ValueSource
(+)-CarotolHMDB
cis-Dauc-8-en-5beta -ol (carotol)HMDB
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-3a-ol
Traditional Namecarotol
CAS Registry Number465-28-1
SMILES
CC(C)C1CCC2(C)CC=C(C)CCC12O
InChI Identifier
InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3
InChI KeyXZYQCFABZDVOPN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Daucane sesquiterpenoid
  • Sesquiterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point109.00 °C. @ 1.50 mm HgThe Good Scents Company Information System
Water Solubility8.51 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.465 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP10(4.65) g/LALOGPS
logP10(3.79) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Basic)0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.13 m³·mol⁻¹ChemAxon
Polarizability27.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.5831661259
DarkChem[M-H]-150.6531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarotolCC(C)C1CCC2(C)CC=C(C)CCC12O2057.7Standard polar33892256
CarotolCC(C)C1CCC2(C)CC=C(C)CCC12O1614.5Standard non polar33892256
CarotolCC(C)C1CCC2(C)CC=C(C)CCC12O1588.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carotol,1TMS,isomer #1CC1=CCC2(C)CCC(C(C)C)C2(O[Si](C)(C)C)CC11700.3Semi standard non polar33892256
Carotol,1TBDMS,isomer #1CC1=CCC2(C)CCC(C(C)C)C2(O[Si](C)(C)C(C)(C)C)CC11950.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carotol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-3910000000-78f3009388119ba724c32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carotol GC-MS (1 TMS) - 70eV, Positivesplash10-0200-3090000000-3adcde312055f37d24612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carotol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carotol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 10V, Positive-QTOFsplash10-0ab9-0190000000-010a0378a3d865b1ef1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 20V, Positive-QTOFsplash10-05ai-8790000000-043981cd1e8aad9f50d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 40V, Positive-QTOFsplash10-05o9-9500000000-11dacc05a509cf2d394d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 10V, Negative-QTOFsplash10-00di-0090000000-c229abad4ae29b356be02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 20V, Negative-QTOFsplash10-00di-0190000000-df9ec002da314b33f3c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 40V, Negative-QTOFsplash10-0k9i-2920000000-0ece9f40f0637b7b5de42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 10V, Positive-QTOFsplash10-00di-0190000000-d9db26ad9ef6f66807a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 20V, Positive-QTOFsplash10-007c-7910000000-914b81f58b5c346b04892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 40V, Positive-QTOFsplash10-0a4u-9400000000-700ae1733923d3b829e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 10V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 20V, Negative-QTOFsplash10-00di-0090000000-caa5a644e1dcbfa0bac52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carotol 40V, Negative-QTOFsplash10-0079-0920000000-754708042fa30dc4ff142021-09-24Wishart 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 IDFDB015487
KNApSAcK IDC00003109
Chemspider ID253697
KEGG Compound IDC09628
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarotol
METLIN IDNot Available
PubChem Compound287687
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014541
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.