Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2021-10-13 04:37:02 UTC
HMDB IDHMDB0002019
Secondary Accession Numbers
  • HMDB02019
Metabolite Identification
Common NamePhytol
DescriptionPhytol, also known as trans-phytol or (e)-phytol, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Phytol.
Structure
Data?1582752224
Synonyms
ValueSource
(2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecen-1-olChEBI
trans-PhytolChEBI
3,7,11,15-Tetramethylhexadec-2-en-1-olHMDB
(e)-PhytolHMDB
(7R,11R,2E)-PhytolPhytoBank
(E,R,R)-PhytolPhytoBank
Chemical FormulaC20H40O
Average Molecular Weight296.539
Monoisotopic Molecular Weight296.307915908
IUPAC Name(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
Traditional Namephytol
CAS Registry Number150-86-7
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO
InChI Identifier
InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1
InChI KeyBOTWFXYSPFMFNR-PYDDKJGSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Long chain fatty alcohol
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point202.00 to 204.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP8.230 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP10(7.89) g/LALOGPS
logP10(7.04) g/LChemAxon
logS10(-6.4) g/LALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity96.24 m³·mol⁻¹ChemAxon
Polarizability40.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.24231661259
DarkChem[M-H]-174.67531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhytolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO2623.5Standard polar33892256
PhytolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO2092.9Standard non polar33892256
PhytolCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO2127.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phytol,1TMS,isomer #1C/C(=C\CO[Si](C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C2171.0Semi standard non polar33892256
Phytol,1TBDMS,isomer #1C/C(=C\CO[Si](C)(C)C(C)(C)C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C2397.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phytol GC-MS (1 TMS)splash10-0006-4900000000-7447218963eba1d74f202014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phytol GC-EI-TOF (Non-derivatized)splash10-006x-9700000000-13462fc1cbd6fd4b40fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phytol GC-MS (Non-derivatized)splash10-0006-4900000000-7447218963eba1d74f202017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phytol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-6970000000-fdad871a8c1dec20de252017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phytol GC-MS (1 TMS) - 70eV, Positivesplash10-0w9u-9754000000-d3d00e401c3881a14e522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phytol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phytol LC-ESI-QTOF , positive-QTOFsplash10-001i-1190000000-012d6cbb70838da781752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phytol , positive-QTOFsplash10-0002-0190000000-7e0502dddd7079c46c0c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phytol n/a 20V, negative-QTOFsplash10-014i-0090000000-001e551ca75449e4a3e92020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 10V, Positive-QTOFsplash10-002b-0190000000-9e856f1b9601cc4574cc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 20V, Positive-QTOFsplash10-004i-6690000000-9b70d911525f7693f51f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 40V, Positive-QTOFsplash10-0aor-9620000000-156ac00c175028d944552016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 10V, Negative-QTOFsplash10-0002-0090000000-6eed94e81ee36c04f1592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 20V, Negative-QTOFsplash10-014j-0090000000-9c27bc3d6b3fdea545842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 40V, Negative-QTOFsplash10-01r7-4490000000-4aaf489201cc9b04c2aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 10V, Negative-QTOFsplash10-0002-0090000000-2f702178cb616025d7f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 20V, Negative-QTOFsplash10-0002-0090000000-5d33ba625719de98593b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 40V, Negative-QTOFsplash10-004j-1290000000-73d0d7e134d9c2e14d772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 10V, Positive-QTOFsplash10-0092-3390000000-2c3b2aa940fa734936072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 20V, Positive-QTOFsplash10-06y9-9610000000-0f7ff3ff5cbf2c1745d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytol 40V, Positive-QTOFsplash10-0a4i-9000000000-4bff76bff84b349363e12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031117
KNApSAcK IDC00003467
Chemspider ID4444094
KEGG Compound IDC01389
BioCyc IDPHYTOL
BiGG IDNot Available
Wikipedia LinkPhytol
METLIN ID391
PubChem Compound5280435
PDB IDNot Available
ChEBI ID17327
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002361
References
Synthesis ReferenceGramatica, Paola; Manitto, Paolo; Monti, Diego; Speranza, Giovanna. Microbial-mediated syntheses of EPC. Part 4. Stereoselective total synthesis of natural phytol via double bond reductions by baker's yeast. Tetrahedron (1987), 43(19), 4481-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hase J, Kobashi K, Nakai N, Onosaka S: Binding of retinol-binding protein obtained from human urine with vitamin A derivatives and terpenoids. J Biochem. 1976 Feb;79(2):373-80. [PubMed:1270409 ]
  2. Baxter JH: Absorption of chlorophyll phytol in normal man and in patients with Refsum's disease. J Lipid Res. 1968 Sep;9(5):636-41. [PubMed:4177872 ]
  3. van den Brink DM, van Miert JM, Wanders RJ: A novel assay for the prenatal diagnosis of Sjogren-Larsson syndrome. J Inherit Metab Dis. 2005;28(6):965-9. [PubMed:16435189 ]
  4. van den Brink DM, van Miert JN, Dacremont G, Rontani JF, Jansen GA, Wanders RJ: Identification of fatty aldehyde dehydrogenase in the breakdown of phytol to phytanic acid. Mol Genet Metab. 2004 May;82(1):33-7. [PubMed:15110319 ]