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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-01-27 04:21:50 UTC
HMDB IDHMDB0000801
Secondary Accession Numbers
  • HMDB00801
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
PhytanateGenerator
3,7,11,15-Tetramethyl-hexadecanoateGenerator
3,7,11,15-TetramethylhexadecanoateHMDB
3,7,11,15-Tetramethylhexadecanoic acidHMDB
3,7,11,15-TetramethylhexadecoanoateHMDB
3,7,11,15-Tetramethylhexadecoanoic acidHMDB
PhytanoateHMDB
Phytanoic acidHMDB
Acid, phytanicMeSH
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 KeyRLCKHJSFHOZMDR-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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Physiological effect

Health effect:

  Health condition:

Disposition

Biological location:

  Subcellular:

  Cell and elements:

    Cell:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Industrial application:

Biological role:

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 Solubility8.2e-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
Polarizability41.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9780000000-d08f456f5acb304b7ea2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9443000000-5bbc79ddca11ee15c346View in MoNA
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
  • Feces
Tissue Location
  • Fibroblasts
  • Liver
  • Myelin
  • Prostate
Pathways
NameSMPDB/PathwhizKEGG
Oxidation of Branched Chain Fatty AcidsPw000155Pw000155 greyscalePw000155 simpleNot Available
Phytanic Acid Peroxisomal OxidationPw000041Pw000041 greyscalePw000041 simpleNot Available
Refsum DiseasePw000122Pw000122 greyscalePw000122 simpleNot 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
BloodDetected and Quantified<12.800 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0-12.799 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified1.600-11.199 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified3.93 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified5.77 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.86 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified6.719 uMNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified40.3 (27.5-53.0) uMAdult (>18 years old)BothInfantile Refsum disease details
BloodDetected and Quantified72.0 (64.0-80.0) uMChildren (1-13 years old)BothAdrenoleukodystrophy (ALD)
    • MetaGene: Metabol...
details
BloodDetected and Quantified410.0 (46.0-1127.0) uMAdult (>18 years old)BothRefsum's Disease details
BloodDetected and Quantified20 uMAdult (>18 years old)Male
Alpha-Methylacyl-CoA racemase deficiency
details
BloodDetected and Quantified5.46 uMNewborn (0-30 days old)Not Specified
Zellweger syndrome
details
BloodDetected and Quantified9.75 uMInfant (0-1 year old)Male
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified197 uMNewborn (0-30 days old)Female
Rhizomelic chondrodysplasia punctata
details
BloodDetected and Quantified1439.86 uMInfant (0-1 year old)Not Specified
Refsum disease, classic, adult-onset
details
BloodDetected and Quantified6335.384 uMInfant (0-1 year old)Not Specified
Refsum disease, classic, early-onset
details
BloodDetected and Quantified0-2335.773 uMAdult (>18 years old)Not SpecifiedClassicle Refsum's disease details
BloodDetected and Quantified0-50.300 uMNewborn (0-30 days old)Not Specified
Neonatal adrenoleukodystrophy
details
BloodDetected and Quantified26.557-30.717 uMChildren (1-13 years old)Male
Peroxisomal disorders, new type, liver
details
BloodDetected and Quantified3.200-1391.865 uMChildren (1-13 years old)BothZellweger syndrome details
BloodDetected and Quantified3.200-15.998 uMChildren (1-13 years old)Not SpecifiedAdrenoleukodystrophy, X-linked details
BloodDetected and Quantified34.800-274 uMChildren (1-13 years old)Female
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified399.961-479.953 uMChildren (1-13 years old)Not Specified
Refsum disease, infantile
details
BloodDetected and Quantified6.400-34.800 uMNewborn (0-30 days old)Female
Peroxisomal biogenesis disorder
details
BloodDetected and Quantified9.599-28.797 uMNewborn (0-30 days old)BothNeonatal adrenoleukodystrophy details
BloodDetected and Quantified9.599-67.193 uMChildren (1-13 years old)Not Specified
Refsum disease, juvenile
details
BloodDetected and Quantified9.599-86.392 uMInfant (0-1 year old)Both
Zellweger syndrome
details
BloodDetected and Quantified8.639 uMAdult (>18 years old)Male
27-hydroxylase deficiency
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
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. [PubMed:12700346 ]
Cerebrotendinous xanthomatosis
  1. Siman-Tov T, Meiner V, Gadoth N: Could steroids mask the diagnosis of cerebrotendinous xanthomatosis? J Neurol Sci. 2006 Apr 15;243(1-2):83-6. Epub 2006 Jan 30. [PubMed:16445943 ]
Alpha-Methylacyl-CoA racemase deficiency
  1. McLean BN, Allen J, Ferdinandusse S, Wanders RJ: A new defect of peroxisomal function involving pristanic acid: a case report. J Neurol Neurosurg Psychiatry. 2002 Mar;72(3):396-9. [PubMed:11861706 ]
Associated OMIM IDs
  • 266500 (Refsum's disease)
  • 614307 (Alpha-Methylacyl-CoA racemase deficiency)
  • 213700 (Cerebrotendinous xanthomatosis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022252
KNApSAcK IDNot Available
Chemspider ID25001
KEGG Compound IDC01607
BioCyc IDNot Available
BiGG ID37991
Wikipedia LinkPhytanic acid
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11724659 ]