(3R,7R,11R)-1-Phytanoic acid (CHEM028883)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:46:23 UTC
Update Date2016-11-09 01:18:46 UTC
Accession NumberCHEM028883
Identification
Common Name(3R,7R,11R)-1-Phytanoic acid
ClassSmall Molecule
DescriptionConstituent of butter 3D,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumulates in blood and tissues of patients with Refsum disease (RD, an inborn error of lipid metabolism inherited as an autosomal recessive trait (OMIM 266500)), and is a reliable identifier of RD from a large number of other neurological disorders. Phytanic acid also accumulates in a number of other disorders with a very different clinical course: disorders of peroxisome biogenesis (Zellweger syndrome (OMIM 214100), neonatal adrenoleukodystrophy (OMIM 202370), infantile Refsum disease (OMIM 266510)) and rhizomelic chondrodysplasia punctata, type 1 (OMIM 215100). Phytanic acid is a 3-methyl fatty acid that cannot be beta-oxidized directly, and first undergoes an alpha-oxidation a reaction catalyzed by the enzyme phytanoyl-CoA hydroxylase, which is deficient in RD, the only true disorder of phytanic acid alpha-oxidation. (The Metabolic and Molecular Bases of Inherited Disease). (3R,7R,11R)-1-Phytanoic acid is found in milk and milk products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3D,7D,11D-PhytanateGenerator
((3R,7R,11R)-)3,7,11,15-TetramethylhexadecanoateHMDB
((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acidHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoateHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acidHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoateHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acidHMDB
D,D,D-PhytanateHMDB
D,D,D-Phytanic acidHMDB
(3R,7R,11R)-1-PhytanoateHMDB
Chemical FormulaC20H40O2
Average Molecular Mass312.530 g/mol
Monoisotopic Mass312.303 g/mol
CAS Registry Number18654-64-3
IUPAC Name(3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid
Traditional Namephytanoic acid
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O
InChI IdentifierInChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19-/m1/s1
InChI KeyRLCKHJSFHOZMDR-GUDVDZBRSA-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 acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.2e-05 g/LALOGPS
logP7.28ALOGPS
logP7.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)5.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.28 m³·mol⁻¹ChemAxon
Polarizability40.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9780000000-d08f456f5acb304b7ea2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9443000000-5bbc79ddca11ee15c346Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0194000000-076273f1edebfb1f7163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-4890000000-ced9d745a9185ff0418fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9820000000-a5081751e548b4df90abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0059000000-ad0c503c6bf877381cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1096000000-41b47d7194262d8befceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9470000000-4f142588383dd12f544fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4569000000-0ae84af33d4a6cee1563Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06y9-9720000000-8d0e05ef1818d392c4fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-19bc307031b7da7b3414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-849ba1e3311607445182Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0029000000-1d86a3df25ae3d6f62b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-8393000000-8564c0781362b5ca2da4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000417
FooDB IDFDB013514
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5406
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8556273
ChEBI IDNot Available
PubChem Compound ID10380830
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sita, Lawrence R. Convenient highly stereoselective syntheses of (3R,7R,11R)- and (3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid (phytanic acid) and the corresponding 3,7,11,15-tetramethylhexadecan-1-ols. Journal of Organic Chemistry (1993), 58(19), 5285-7.