PHYTOL (CED0002674)

Record Information
Version1.0
Creation Date2016-05-19 02:22:33 UTC
Update Date2026-04-16 22:58:38 UTC
Accession NumberCHEM007200
Identification
Common NamePHYTOL
ClassSmall Molecule
Description
PHYTOL (C20H40O) is an organic compound with an average molecular weight of 296.54 g/mol. PHYTOL belongs to the diterpenoids, a subclass of prenol lipids within the organic compounds. Biologically, it acts as an antioxidant (PMC12235017, PMC9598661) and an analgesic (PMC9598661). In industrial applications, it is utilized as a fragrance, a nutrient, and a flavouring (PMC12235017, PMC9598661). The compound is found in or released from 13 recorded sources. These include household cleaning and consumer products such as tobacco pipes, pipe accessories, tobacco product cases, other smoking requisites, non electric simulated smoking devices, and one additional source. It is also associated with food, food processing and cookware, specifically in the treatment of hops, the preparation of wort, the preparation of wine or sparkling wine, and food contact materials. Additionally, it is found in antennas within electrical and electronic equipment, indoor air, and drinking water. Recorded exposure routes include touch, oral, and inhalation. Regarding plastics, PHYTOL is present in polyethylene terephthalate and is released in polystyrene and polypropylene.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass296.539 g/mol
Monoisotopic Mass296.308 g/mol
CAS Registry Number150-86-7
IUPAC Name(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
Traditional Namephytol
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0006-4900000000-7447218963eba1d74f20Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-006x-9700000000-13462fc1cbd6fd4b40fdNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-4900000000-7447218963eba1d74f20Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000x-6970000000-fdad871a8c1dec20de25Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0w9u-9754000000-d3d00e401c3881a14e52Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1190000000-012d6cbb70838da78175Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0190000000-7e0502dddd7079c46c0cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-001e551ca75449e4a3e9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0190000000-9e856f1b9601cc4574ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-6690000000-9b70d911525f7693f51fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-9620000000-156ac00c175028d94455Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6eed94e81ee36c04f159Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014j-0090000000-9c27bc3d6b3fdea54584Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01r7-4490000000-4aaf489201cc9b04c2aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-2f702178cb616025d7f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-5d33ba625719de98593bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004j-1290000000-73d0d7e134d9c2e14d77Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0092-3390000000-2c3b2aa940fa73493607Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06y9-9610000000-0f7ff3ff5cbf2c1745d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-4bff76bff84b349363e1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6239.0Log mg/kg[3500:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
506AntennasElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureHTH-type quorum-sensing regulator RhlRP54292Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)1.24559
Click to view 3D structureSqualene epoxidaseA7L861Sus scrofaPredicted (SEA)1.08989
Click to view 3D structureLanosterol synthaseQ04782YeastPredicted (SEA)2.17978
Click to view 3D structureLanosterol synthaseQ96WJ0Pneumocystis cariniiPredicted (SEA)8.17417
Lanosterol synthase structureClick to view 3D structureLanosterol synthaseP48449HumansPredicted (SEA)55.1951
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)2564.9
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseP32584Saccharomyces cerevisiae S288cPredicted (SEA)5.3716
Click to view 3D structureInhibin alpha chainP05111HumansPredicted (SEA)33.2416
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseQ9WVM4Rattus norvegicusPredicted (SEA)5.76084
Click to view 3D structureLanosterol synthaseP48450Rattus norvegicusPredicted (SEA)3.03612
Thrombospondin-1 structureClick to view 3D structureThrombospondin-1P07996HumansPredicted (SEA)174.071
Click to view 3D structure3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomeraseP9WQP7Mycobacterium tuberculosisPredicted (SEA)36.9005
Click to view 3D structureS-methylmethionine--homocysteine S-methyltransferase BHMT2Q9H2M3HumansPredicted (SEA)19.4623
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)4292.37
DNA-directed RNA polymerase subunit beta structureClick to view 3D structureDNA-directed RNA polymerase subunit betaP0A8V2Escherichia coli (strain K12)Predicted (SEA)35.9663
Macrophage scavenger receptor types I and II structureClick to view 3D structureMacrophage scavenger receptor types I and IIP21757HumansPredicted (SEA)9.809
Nuclear receptor ROR-gamma structureClick to view 3D structureNuclear receptor ROR-gammaP51449HumansPredicted (SEA)4917.66
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)3065.39
Click to view 3D structureTransient receptor potential cation channel subfamily M member 8Q8R455Rattus norvegicusPredicted (SEA)1622.3
Click to view 3D structurePutative inactive group IIC secretory phospholipase A2Q5R387HumansPredicted (SEA)132.499
Click to view 3D structureSqualene synthase ERG9P29704Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)Predicted (SEA)7.00643
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)6605.74
M-phase inducer phosphatase 1 structureClick to view 3D structureM-phase inducer phosphatase 1P30304HumansPredicted (SEA)941.275
Receptor-type tyrosine-protein phosphatase C structureClick to view 3D structureReceptor-type tyrosine-protein phosphatase CP08575HumansPredicted (SEA)2763.8
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)4187.74
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0002019
FooDB IDFDB031117
Phenol Explorer IDNot Available
KNApSAcK IDC00003467
BiGG IDNot Available
BioCyc IDPHYTOL
METLIN ID391
PDB IDNot Available
Wikipedia LinkPhytol
Chemspider ID4444094
ChEBI ID17327
PubChem Compound ID5280435
Kegg Compound IDC01389
YMDB IDNot Available
ECMDB IDM2MDB005757
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17015885
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333358
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24392173
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24422895
5. Gramatica, 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.
6. 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.
7. 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.
8. 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.
9. 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.