You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:22 UTC
HMDB IDHMDB00801
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhytanic acid
DescriptionPhytanic acid is a 20-carbon branched chain fatty acid, Phytanic acid is present in animal (primarily herbivores or omnivores) tissues where it may be derived from the chlorophyll in consumed plant material. Phytanic acid derives from the corresponding alcohol, phytol, and is ultimately oxidized into pristanic acid. In phytanic acid storage disease (Refsum disease) this lipid may comprise as much as 30% of the total fatty acids in plasma. These high levels in Refsum disease (a neurological disorder) are due to a phytanic acid alpha-hydroxylase deficiency.
Structure
Thumb
Synonyms
ValueSource
3,7,11,15-Tetramethyl hexadecanoic acidChEBI
3,7,11,15-Tetramethyl-hexadecanoic acidChEBI
3,7,11,15-Tetramethyl-hexadecansaeureChEBI
3,7,11,15-Tetramethyl hexadecanoateGenerator
3,7,11,15-TetramethylhexadecanoateGenerator
3,7,11,15-Tetramethyl-hexadecanoateGenerator
3,7,11,15-TetramethylhexadecoanoateHMDB
3,7,11,15-Tetramethylhexadecoanoic acidHMDB
PhytanateHMDB
PhytanoateHMDB
Phytanoic acidHMDB
Chemical FormulaC20H40O2
Average Molecular Weight312.5304
Monoisotopic Molecular Weight312.302830524
IUPAC Name3,7,11,15-tetramethylhexadecanoic acid
Traditional Namephytanic acid
CAS Registry Number14721-66-5
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O
InChI Identifier
InChI=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)
InChI KeyInChIKey=RLCKHJSFHOZMDR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.17e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.28 m3·mol-1ChemAxon
Polarizability41.09 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-1344b5ce122597753d72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00e9-9000000000-d058ed1cd7bf2496d801View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01b9-9000000000-b91cf96bf3e1ed9907c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-404c7c552fbd445291f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4790000000-c4c72f2a0388e83c4d50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9720000000-e2429e81001f3469126aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0089000000-e67aa3a53cb223588aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02tc-1094000000-c8ba97412b0185f5a5b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-8590000000-02e2e52e9c0e6f20a064View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Liver
  • Myelin
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Oxidation of Branched Chain Fatty AcidsSMP00030Not Available
Phytanic Acid Peroxisomal OxidationSMP00450Not Available
Refsum DiseaseSMP00451Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.8 (0.0-9.6) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.7 (2.0-4.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified40.3 (27.5-53.0) uMAdult (>18 years old)BothInfantile Refsum disease details
BloodDetected and Quantified6.4 (0.0-12.8) uMChildren (1-13 years old)BothNeonatal adrenoleukodystrophy details
BloodDetected and Quantified72.0 (64.0-80.0) uMChildren (1-13 years old)BothAdrenoleukodystrophy (ALD) details
BloodDetected and Quantified410.0 (46.0-1127.0) uMAdult (>18 years old)BothRefsum's Disease details
BloodDetected and Quantified296.00 (16.00-576.00) uMChildren (1-13 years old)BothInfantile Refsum disease details
BloodDetected and Quantified28.6 (26.5-30.7) uMChildren (1-13 years old)BothPeroxisomal disorders, new type, liver details
Associated Disorders and Diseases
Disease References
Adrenoleukodystrophy
  1. MetaGene [Link]
Refsum's disease
  1. Wierzbicki AS, Mayne PD, Lloyd MD, Burston D, Mei G, Sidey MC, Feher MD, Gibberd FB: Metabolism of phytanic acid and 3-methyl-adipic acid excretion in patients with adult Refsum disease. J Lipid Res. 2003 Aug;44(8):1481-8. Epub 2003 Apr 16. [12700346 ]
  2. Poll-The BT, Saudubray JM, Ogier H, Schutgens RB, Wanders RJ, Schrakamp G, van den Bosch H, Trijbels JM, Poulos A, Moser HW, et al.: Infantile Refsum's disease: biochemical findings suggesting multiple peroxisomal dysfunction. J Inherit Metab Dis. 1986;9(2):169-74. [2427795 ]
  3. MetaGene [Link]
Peroxisomal disorders, new type, liver
  1. MetaGene [Link]
Adrenoleukodystrophy, neonatal
  1. MetaGene [Link]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022252
KNApSAcK IDNot Available
Chemspider ID25001
KEGG Compound IDC01607
BioCyc IDNot Available
BiGG ID37991
Wikipedia LinkPhytanic acid
NuGOwiki LinkHMDB00801
Metagene LinkHMDB00801
METLIN ID5765
PubChem Compound26840
PDB IDNot Available
ChEBI ID16285
References
Synthesis ReferenceKarrer, P.; Epprecht, A.; Konig, Hans. General method of preparation for 2-methyl-3-alkylnaphthoquinones. Constitution and vitamin K activity. Helvetica Chimica Acta (1940), 23 272-83.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zomer AW, van Der Burg B, Jansen GA, Wanders RJ, Poll-The BT, van Der Saag PT: Pristanic acid and phytanic acid: naturally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor alpha. J Lipid Res. 2000 Nov;41(11):1801-7. [11060349 ]
  2. Komen JC, Duran M, Wanders RJ: Characterization of phytanic acid omega-hydroxylation in human liver microsomes. Mol Genet Metab. 2005 Jul;85(3):190-5. Epub 2005 Mar 17. [15979030 ]
  3. Schonfeld P, Struy H: Refsum disease diagnostic marker phytanic acid alters the physical state of membrane proteins of liver mitochondria. FEBS Lett. 1999 Aug 27;457(2):179-83. [10471774 ]
  4. Xu J, Thornburg T, Turner AR, Vitolins M, Case D, Shadle J, Hinson L, Sun J, Liu W, Chang B, Adams TS, Zheng SL, Torti FM: Serum levels of phytanic acid are associated with prostate cancer risk. Prostate. 2005 May 15;63(3):209-14. [15712232 ]
  5. Molzer B, Kainz-Korschinsky M, Sundt-Heller R, Bernheimer H: Phytanic acid and very long chain fatty acids in genetic peroxisomal disorders. J Clin Chem Clin Biochem. 1989 May;27(5):309-14. [2474624 ]
  6. Cakirer S, Savas MR: Infantile Refsum disease: serial evaluation with MRI. Pediatr Radiol. 2005 Feb;35(2):212-5. Epub 2004 Oct 6. [15480616 ]
  7. Bernscherer G, Berenyi E, Karabelyos C, Laszlo A, David Z, Hollody K, Toth EZ: [Refsum disease] Orv Hetil. 2000 Jan 2;141(1):31-4. [10673856 ]
  8. Heim M, Johnson J, Boess F, Bendik I, Weber P, Hunziker W, Fluhmann B: Phytanic acid, a natural peroxisome proliferator-activated receptor (PPAR) agonist, regulates glucose metabolism in rat primary hepatocytes. FASEB J. 2002 May;16(7):718-20. Epub 2002 Mar 26. [11923221 ]
  9. Pahan K, Singh I: Intraorganellar localization of CoASH-independent phytanic acid oxidation in human liver peroxisomes. FEBS Lett. 1993 Oct 25;333(1-2):154-8. [8224157 ]
  10. Poggi-Travert F, Fournier B, Poll-The BT, Saudubray JM: Clinical approach to inherited peroxisomal disorders. J Inherit Metab Dis. 1995;18 Suppl 1:1-18. [9053544 ]
  11. Yao JK, Dyck PJ: Tissue distribution of phytanic acid and its analogues in a kinship with Refsum's disease. Lipids. 1987 Feb;22(2):69-75. [2436023 ]
  12. Young SP, Johnson AW, Muller DP: Effects of phytanic acid on the vitamin E status, lipid composition and physical properties of retinal cell membranes: implications for adult Refsum disease. Clin Sci (Lond). 2001 Dec;101(6):697-705. [11724659 ]