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Showing Compound phytol (FDB031117)

Record Information
Version1.0
Creation date2015-05-07 21:03:15 UTC
Update date2020-09-17 15:29:57 UTC
Primary IDFDB031117
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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, but soluble in most organic solvents. It is a colorless clear liquid with a floral, balsamic or waxy odor and a green, berry, tropical or waxy taste. Phytol is a constituent of chlorophyll and is produced in all photosynthesizing plants. Phytol is found in animals that consume plants wherein gut fermentation of ingested plant materials liberates phytol. Phytol has been detected, but not quantified in, several different foods, such as parsnips, rosemaries, red raspberries, common chokecherries, and white cabbages. . Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid which is then stored in fats. Refsum disease is an autosomal recessive disorder that results in the accumulation of large stores of phytanic acid in tissues. This disease manifests with peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss (PMID:17956237). Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha and retinoid X receptor (RXR). Phytol is used in the fragrance industry and in cosmetics, shampoos, toilet soaps, household cleaners, and detergents.
CAS Number7541-49-3 150-86-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Chemical FormulaC20H40O
IUPAC name(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
InChI IdentifierInChI=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
Isomeric SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO
Average Molecular Weight296.539
Monoisotopic Molecular Weight296.307915908
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSphytol, 1 TMS, GC-MS Spectrumsplash10-0006-4900000000-7447218963eba1d74f20Spectrum
GC-MSphytol, non-derivatized, GC-MS Spectrumsplash10-006x-9700000000-13462fc1cbd6fd4b40fdSpectrum
GC-MSphytol, non-derivatized, GC-MS Spectrumsplash10-0006-4900000000-7447218963eba1d74f20Spectrum
Predicted GC-MSphytol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-6970000000-fdad871a8c1dec20de25Spectrum
Predicted GC-MSphytol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w9u-9754000000-d3d00e401c3881a14e52Spectrum
Predicted GC-MSphytol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-1190000000-012d6cbb70838da781752017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0190000000-7e0502dddd7079c46c0c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, negativesplash10-014i-0090000000-001e551ca75449e4a3e92020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0190000000-9e856f1b9601cc4574cc2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-6690000000-9b70d911525f7693f51f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9620000000-156ac00c175028d944552016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-6eed94e81ee36c04f1592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-9c27bc3d6b3fdea545842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r7-4490000000-4aaf489201cc9b04c2aa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-2f702178cb616025d7f32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-5d33ba625719de98593b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-1290000000-73d0d7e134d9c2e14d772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0092-3390000000-2c3b2aa940fa734936072021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06y9-9610000000-0f7ff3ff5cbf2c1745d02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4bff76bff84b349363e12021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference