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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2020-02-26 21:23:44 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 lipid molecule. Phytol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP7.89ALOGPS
logP7.04ChemAxon
logS-6.4ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-4900000000-7447218963eba1d74f20Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-9700000000-13462fc1cbd6fd4b40fdSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-4900000000-7447218963eba1d74f20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-6970000000-fdad871a8c1dec20de25Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0w9u-9754000000-d3d00e401c3881a14e52Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-1190000000-012d6cbb70838da78175Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0190000000-7e0502dddd7079c46c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0190000000-9e856f1b9601cc4574ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-6690000000-9b70d911525f7693f51fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9620000000-156ac00c175028d94455Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-6eed94e81ee36c04f159Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-9c27bc3d6b3fdea54584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r7-4490000000-4aaf489201cc9b04c2aaSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>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
FoodDB IDFDB014472
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
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 ]