Showing Compound Card for Phytol (CDB000048)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 12 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:51 UTC
Updated at2020-12-07 19:07:00 UTC
CannabisDB IDCDB000048
Secondary Accession NumbersNot Available
Cannabis Compound 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, 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. In one study (PMID: 6991645 ) phytol was the only diterpene reported to exist in the essential oil of cannabis. Phytol is also used in some Cannabis distillate vapes as a diluent
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight296.54
Monoisotopic Molecular Weight296.3079
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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point203 - 204 °C at 10 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Retinoic acid receptor RXR-betaRXRB6p21.3P28702 details
Retinoic acid receptor RXR-alphaRXRA9q34.3P19793 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Retinoic acid receptor RXR-betaRXRB6p21.3P28702 details
Retinoic acid receptor RXR-alphaRXRA9q34.3P19793 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Retinoic acid receptor RXR-betaRXRB6p21.3P28702 details
Retinoic acid receptor RXR-alphaRXRA9q34.3P19793 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Retinoic acid receptor RXR-betaRXRB6p21.3P28702 details
Retinoic acid receptor RXR-alphaRXRA9q34.3P19793 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Concentrations Data
Not Available
HMDB IDHMDB0002019
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031117
KNApSAcK IDC00003467
Chemspider ID4444094
KEGG Compound IDC01389
BioCyc IDPHYTOL
BiGG IDNot Available
Wikipedia LinkPhytol
METLIN ID391
PubChem Compound5280435
PDB IDNot Available
ChEBI ID17327
References
General References
  1. Wierzbicki AS: Peroxisomal disorders affecting phytanic acid alpha-oxidation: a review. Biochem Soc Trans. 2007 Nov;35(Pt 5):881-6. doi: 10.1042/BST0350881. [PubMed:17956237 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Enzymes

Enzyme Details
1. Retinoic acid receptor RXR-beta
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)
Gene Name:
RXRB
Uniprot ID:
P28702
Molecular weight:
56921.4
Enzyme Details
2. Retinoic acid receptor RXR-alpha
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA). ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular weight:
50810.8
Enzyme Details
3. Peroxisome proliferator-activated receptor alpha
General function:
Involved in DNA binding
Specific function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl- 2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular weight:
52224.6

Only showing the first 10 proteins. There are 12 proteins in total.

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