14721-66-5,MFCD00133772
Catalog No.:AA00AQ78

14721-66-5 | PHYTANIC ACID

Pack Size
Purity
Availability
Price(USD)
Quantity
  
250mg
95%
in stock  
$58.00   $41.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00AQ78
Chemical Name:
PHYTANIC ACID
CAS Number:
14721-66-5
Molecular Formula:
C20H40O2
Molecular Weight:
312.5304
MDL Number:
MFCD00133772
SMILES:
CC(CCCC(CC(=O)O)C)CCCC(CCCC(C)C)C
NSC Number:
108698
Properties
Computed Properties
 
Complexity:
273  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
14  
Undefined Atom Stereocenter Count:
3  
Undefined Bond Stereocenter Count:
0  
XLogP3:
8.3  

Downstream Synthesis Route
1551-27-5    14721-66-5   
3,7,11,15-Tetramethyl-1-(5-propyl-thiophen-2-yl)-hexadecan-1-one 

[1]JournaloftheChemicalSociety.Chemicalcommunications,1989,p.1105-1107

1455-20-5    14721-66-5   
1-(5-Butyl-thiophen-2-yl)-3,7,11,15-tetramethyl-hexadecan-1-one 

[1]JournaloftheChemicalSociety.Chemicalcommunications,1989,p.1105-1107

[1]JustusLiebigsAnnalenderChemie,1911,vol.378,p.114

[2]Patent:US2019/275110,2019,A1

[3]Patent:US2019/275156,2019,A1

[4]Patent:US2019/275115,2019,A1

[1]Patent:WO2007/72983,2007,A1.Locationinpatent:Page/Pagecolumn25-27

40137-22-2    14721-66-5   
C24H49NO3 

[1]CrystalGrowthandDesign,2017,vol.17,p.3502-3511

Literature

Title: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.

Journal: Journal of applied toxicology : JAT 20140701

Title: Estimated phytanic acid intake and prostate cancer risk: a prospective cohort study.

Journal: International journal of cancer 20120915

Title: Phytanic acid disturbs mitochondrial homeostasis in heart of young rats: a possible pathomechanism of cardiomyopathy in Refsum disease.

Journal: Molecular and cellular biochemistry 20120701

Title: A child with night blindness: preventing serious symptoms of Refsum disease.

Journal: Journal of child neurology 20120501

Title: Tiptoeing around transgenics.

Journal: Nature biotechnology 20120307

Title: [The diagnostic of peroxisomic diseases in children].

Journal: Klinicheskaia laboratornaia diagnostika 20120301

Title: Long-term strategies for the treatment of Refsum's disease using therapeutic apheresis.

Journal: Journal of clinical apheresis 20120101

Title: Morphology of 1-methyl-1-nitrosourea induced rat mammary tumours after treatment with precursor of phytanic acid or its combination with vitamin D analogue.

Journal: Endocrine regulations 20120101

Title: Chance and serendipity in science: two examples from my own career.

Journal: The Journal of biological chemistry 20111104

Title: Phytanic acid metabolism in health and disease.

Journal: Biochimica et biophysica acta 20110901

Title: Analysis of a range of catabolic mutants provides evidence that phytanoyl-coenzyme A does not act as a substrate of the electron-transfer flavoprotein/electron-transfer flavoprotein:ubiquinone oxidoreductase complex in Arabidopsis during dark-induced senescence.

Journal: Plant physiology 20110901

Title: Phytanic acid and pristanic acid, branched-chain fatty acids associated with Refsum disease and other inherited peroxisomal disorders, mediate intracellular Ca2+ signaling through activation of free fatty acid receptor GPR40.

Journal: Neurobiology of disease 20110801

Title: AMACR polymorphisms, dietary intake of red meat and dairy and prostate cancer risk.

Journal: The Prostate 20110401

Title: Refsum's Disease-Use of the Intestinal Lipase Inhibitor, Orlistat, as a Novel Therapeutic Approach to a Complex Disorder.

Journal: Journal of obesity 20110101

Title: Effect of dairy fat on plasma phytanic acid in healthy volunteers - a randomized controlled study.

Journal: Lipids in health and disease 20110101

Title: Peroxisomal biogenesis disorder biomarkers.

Journal: Clinical laboratory 20110101

Title: Alkyl-glycerol rescues plasmalogen levels and pathology of ether-phospholipid deficient mice.

Journal: PloS one 20110101

Title: Biochemistry and genetics of inherited disorders of peroxisomal fatty acid metabolism.

Journal: Journal of lipid research 20101001

Title: In vitro evidence that phytanic acid compromises Na(+),K(+)-ATPase activity and the electron flow through the respiratory chain in brain cortex from young rats.

Journal: Brain research 20100917

Title: The effectiveness of long-term dietary therapy in the treatment of adult Refsum disease.

Journal: Journal of neurology, neurosurgery, and psychiatry 20100901

Title: Neurochemical evidence that phytanic acid induces oxidative damage and reduces the antioxidant defenses in cerebellum and cerebral cortex of rats.

Journal: Life sciences 20100828

Title: Plasma phytanic acid concentration and risk of prostate cancer: results from the European Prospective Investigation into Cancer and Nutrition.

Journal: The American journal of clinical nutrition 20100601

Title: Lanthanide phytanates: liquid-crystalline phase behavior, colloidal particle dispersions, and potential as medical imaging agents.

Journal: Langmuir : the ACS journal of surfaces and colloids 20100504

Title: A Pex7 hypomorphic mouse model for plasmalogen deficiency affecting the lens and skeleton.

Journal: Molecular genetics and metabolism 20100401

Title: Use of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline for the preparation of a hapten-protein conjugate for antibody development.

Journal: Bioorganic & medicinal chemistry letters 20100301

Title: Phytanic acid--an overlooked bioactive fatty acid in dairy fat?

Journal: Annals of the New York Academy of Sciences 20100301

Title: Compartmentalization of the Edinburgh Human Metabolic Network.

Journal: BMC bioinformatics 20100101

Title: Adult Refsum disease: a form of tapetoretinal dystrophy accessible to therapy.

Journal: Survey of ophthalmology 20100101

Title: Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions.

Journal: BMC physiology 20100101

Title: Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20091208

Title: The influence of the branched-chain fatty acids pristanic acid and Refsum disease-associated phytanic acid on mitochondrial functions and calcium regulation of hippocampal neurons, astrocytes, and oligodendrocytes.

Journal: Neurobiology of disease 20091101

Title: A PEX10 defect in a patient with no detectable defect in peroxisome assembly or metabolism in cultured fibroblasts.

Journal: Journal of inherited metabolic disease 20090201

Title: Phytol-induced hepatotoxicity in mice.

Journal: Toxicologic pathology 20090101

Title: Identification of marker genes for lipid-lowering effect of a short-chain fructooligosaccharide by DNA microarray analysis.

Journal: Journal of dietary supplements 20090101

Title: Rapid UPLC-MS/MS method for routine analysis of plasma pristanic, phytanic, and very long chain fatty acid markers of peroxisomal disorders.

Journal: Journal of lipid research 20080801

Title: Comment concerning the article: 'Phytanic acid impairs mitochondrial respiration through protonophoric action' by Komen et al.: branched chain phytanic acid inhibits the activity of the mitochondrial respiratory chain.

Journal: Cellular and molecular life sciences : CMLS 20080701

Title: Non-manifesting Refsum heterozygotes carrying the c.135-2A>G PAHX gene transition.

Journal: Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20080601

Title: Refsum disease due to the splice-site mutation c.135-2A>G before exon 3 of the PHYH gene, diagnosed eight years after detection of retinitis pigmentosa.

Journal: Journal of the neurological sciences 20080315

Title: Phytanic acid: measurement of plasma concentrations by gas-liquid chromatography-mass spectrometry analysis and associations with diet and other plasma fatty acids.

Journal: The British journal of nutrition 20080301

Title: Plasmalogen levels in Gaucher disease.

Journal: Blood cells, molecules & diseases 20080101

Title: Dietary fat-gene interactions in cancer.

Journal: Cancer metastasis reviews 20071201

Title: Phytanic acid impairs mitochondrial respiration through protonophoric action.

Journal: Cellular and molecular life sciences : CMLS 20071201

Title: Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid.

Journal: Biochemical Society transactions 20071101

Title: Peroxisomal disorders affecting phytanic acid alpha-oxidation: a review.

Journal: Biochemical Society transactions 20071101

Title: Peroxisomes contain a specific phytanoyl-CoA/pristanoyl-CoA thioesterase acting as a novel auxiliary enzyme in alpha- and beta-oxidation of methyl-branched fatty acids in mouse.

Journal: The Journal of biological chemistry 20070914

Title: Dual subcellular localization in the endoplasmic reticulum and peroxisomes and a vital role in protecting against oxidative stress of fatty aldehyde dehydrogenase are achieved by alternative splicing.

Journal: The Journal of biological chemistry 20070713

Title: Effect of SCP-x gene ablation on branched-chain fatty acid metabolism.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20070301

Title: Cell proliferation inhibition and alterations in retinol esterification induced by phytanic acid and docosahexaenoic acid.

Journal: Journal of lipid research 20070101

Title: PPARs in the Control of Uncoupling Proteins Gene Expression.

Journal: PPAR research 20070101

Title: Alpha-oxidation.

Journal: Biochimica et biophysica acta 20061201

Title: Refsum's disease may mimic familial Guillain Barre syndrome.

Journal: Neuromuscular disorders : NMD 20061101

Title: CYP4 isoform specificity in the omega-hydroxylation of phytanic acid, a potential route to elimination of the causative agent of Refsum's disease.

Journal: The Journal of pharmacology and experimental therapeutics 20060801

Title: Phytanic acid: production from phytol, its breakdown and role in human disease.

Journal: Cellular and molecular life sciences : CMLS 20060801

Title: Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid.

Journal: FEBS letters 20060710

Title: A study of the cytotoxicity of branched-chain phytanic acid with mitochondria and rat brain astrocytes.

Journal: Experimental gerontology 20060701

Title: Thiamine pyrophosphate: an essential cofactor for the alpha-oxidation in mammals--implications for thiamine deficiencies?

Journal: Cellular and molecular life sciences : CMLS 20060701

Title: Brain pyruvate and 2-oxoglutarate dehydrogenase complexes are mitochondrial targets of the CoA ester of the Refsum disease marker phytanic acid.

Journal: FEBS letters 20060612

Title: Peroxisomal trans-2-enoyl-CoA reductase is involved in phytol degradation.

Journal: FEBS letters 20060403

Title: Phytanic acid, AMACR and prostate cancer risk.

Journal: Future oncology (London, England) 20060401

Title: Rotenone-like action of the branched-chain phytanic acid induces oxidative stress in mitochondria.

Journal: The Journal of biological chemistry 20060317

Title: Mechanism of toxicity of the branched-chain fatty acid phytanic acid, a marker of Refsum disease, in astrocytes involves mitochondrial impairment.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20060101

Title: [alpha-Oxidation of 3-methyl-branched fatty acids: unraveling of a pathway].

Journal: Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie 20060101

Title: Structure of human phytanoyl-CoA 2-hydroxylase identifies molecular mechanisms of Refsum disease.

Journal: The Journal of biological chemistry 20051209

Title: Phytol directly activates peroxisome proliferator-activated receptor alpha (PPARalpha) and regulates gene expression involved in lipid metabolism in PPARalpha-expressing HepG2 hepatocytes.

Journal: Biochemical and biophysical research communications 20051118

Title: Serum levels of phytanic acid are associated with prostate cancer risk.

Journal: The Journal of urology 20051101

Title: [Adult Refsum disease. A retinal dystrophy with therapeutic options].

Journal: Der Ophthalmologe : Zeitschrift der Deutschen Ophthalmologischen Gesellschaft 20050801

Title: Characterization of the final step in the conversion of phytol into phytanic acid.

Journal: The Journal of biological chemistry 20050722

Title: Characterization of phytanic acid omega-hydroxylation in human liver microsomes.

Journal: Molecular genetics and metabolism 20050701

Title: [Refsum's disease with severe neuropathy: efficiency of the diet and plasmapheresis].

Journal: La Revue de medecine interne 20050601

Title: Serum levels of phytanic acid are associated with prostate cancer risk.

Journal: The Prostate 20050515

Title: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids.

Journal: The Journal of biological chemistry 20050318

Title: The Refsum disease marker phytanic acid, a branched chain fatty acid, affects Ca2+ homeostasis and mitochondria, and reduces cell viability in rat hippocampal astrocytes.

Journal: Neurobiology of disease 20050201

Title: A study on the causes for the elevated n-3 fatty acids in cows' milk of alpine origin.

Journal: Lipids 20050201

Title: Up-regulation of PPARgamma coactivator-1alpha as a strategy for preventing and reversing insulin resistance and obesity.

Journal: Medical hypotheses 20050101

Title: Assay for Sjögren-Larsson syndrome based on a deficiency of phytol degradation.

Journal: Clinical chemistry 20050101

Title: Orthotopic liver transplantation from a living-related donor in an infant with a peroxisome biogenesis defect of the infantile Refsum disease type.

Journal: Journal of inherited metabolic disease 20050101

Title: A novel assay for the prenatal diagnosis of Sjögren-Larsson syndrome.

Journal: Journal of inherited metabolic disease 20050101

Title: Clinical significance of oxidation from phytol to phytanic acid in man.

Journal: Molecular genetics and metabolism 20041201

Title: Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands.

Journal: Archives of toxicology 20041101

Title: Phytanic acid accumulation is associated with conduction delay and sudden cardiac death in sterol carrier protein-2/sterol carrier protein-x deficient mice.

Journal: Journal of cardiovascular electrophysiology 20041101

Title: In brain mitochondria the branched-chain fatty acid phytanic acid impairs energy transduction and sensitizes for permeability transition.

Journal: The Biochemical journal 20041001

Title: Tremor and deep white matter changes in alpha-methylacyl-CoA racemase deficiency.

Journal: Neurology 20040713

Title: Omega-hydroxylation of phytanic acid in rat liver microsomes: implications for Refsum disease.

Journal: Journal of lipid research 20040701

Title: Hyperpipecolic acidaemia: a diagnostic tool for peroxisomal disorders.

Journal: Molecular genetics and metabolism 20040701

Title: Reinvestigation of trihydroxycholestanoic acidemia reveals a peroxisome biogenesis disorder.

Journal: Neurology 20040608

Title: Identification of fatty aldehyde dehydrogenase in the breakdown of phytol to phytanic acid.

Journal: Molecular genetics and metabolism 20040501

Title: Liver fatty acid binding protein expression enhances branched-chain fatty acid metabolism.

Journal: Molecular and cellular biochemistry 20040401

Title: Molecular basis of Refsum disease: sequence variations in phytanoyl-CoA hydroxylase (PHYH) and the PTS2 receptor (PEX7).

Journal: Human mutation 20040301

Title: Measurement of plasma pristanic, phytanic and very long chain fatty acids by liquid chromatography-electrospray tandem mass spectrometry for the diagnosis of peroxisomal disorders.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031205

Title: Further studies on the substrate spectrum of phytanoyl-CoA hydroxylase: implications for Refsum disease?

Journal: Journal of lipid research 20031201

Title: Gas chromatography/mass spectrometry analysis of very long chain fatty acids, docosahexaenoic acid, phytanic acid and plasmalogen for the screening of peroxisomal disorders.

Journal: Brain & development 20031001

Title: Impaired neuronal migration and endochondral ossification in Pex7 knockout mice: a model for rhizomelic chondrodysplasia punctata.

Journal: Human molecular genetics 20030915

Title: Sterol carrier protein-2/sterol carrier protein-x expression differentially alters fatty acid metabolism in L cell fibroblasts.

Journal: Journal of lipid research 20030901

Title: The chemical biology of branched-chain lipid metabolism.

Journal: Progress in lipid research 20030901

Title: Metabolism of phytanic acid and 3-methyl-adipic acid excretion in patients with adult Refsum disease.

Journal: Journal of lipid research 20030801

Title: Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition.

Journal: Transfusion and apheresis science : official journal of the World Apheresis Association : official journal of the European Society for Haemapheresis 20030801

Title: Branched fatty acids in dairy and beef products markedly enhance alpha-methylacyl-CoA racemase expression in prostate cancer cells in vitro.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20030801

Title: Hearing loss in adult Refsum's disease.

Journal: Clinical otolaryngology and allied sciences 20030601

Title: Alpha-oxidation of 3-methyl-substituted fatty acids and its thiamine dependence.

Journal: European journal of biochemistry 20030401

Title: Phytanic acid alpha-oxidation, new insights into an old problem: a review.

Journal: Biochimica et biophysica acta 20030317

Title: Identification of PEX7 as the second gene involved in Refsum disease.

Journal: American journal of human genetics 20030201

Title: Biochemical markers predicting survival in peroxisome biogenesis disorders.

Journal: Advances in experimental medicine and biology 20030101

Title: Phytanic and pristanic acid are naturally occuring ligands.

Journal: Advances in experimental medicine and biology 20030101

Title: Role of phytanoyl-CoA 2-hydroxylase in phytanic acid metabolism.

Journal: Advances in experimental medicine and biology 20030101

Title: Branched chain fatty acids induce nitric oxide-dependent apoptosis in vascular smooth muscle cells.

Journal: The Journal of biological chemistry 20021220

Title: Biochemical markers predicting survival in peroxisome biogenesis disorders.

Journal: Neurology 20021210

Title: Expression of fatty acid binding proteins inhibits lipid accumulation and alters toxicity in L cell fibroblasts.

Journal: American journal of physiology. Cell physiology 20020901

Title: The chlorophyll-derived metabolite phytanic acid induces white adipocyte differentiation.

Journal: International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity 20020901

Title: [Refsum disease].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20020901

Title: Phytanic acid, a natural peroxisome proliferator-activated receptor (PPAR) agonist, regulates glucose metabolism in rat primary hepatocytes.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020501

Title: Glucuronidation of the dietary fatty acids, phytanic acid and docosahexaenoic acid, by human UDP-glucuronosyltransferases.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020501

Title: Utilization of sterol carrier protein-2 by phytanoyl-CoA 2-hydroxylase in the peroxisomal alpha oxidation of phytanic acid.

Journal: Chemistry & biology 20020501

Title: Phytanic acid, but not pristanic acid, mediates the positive effects of phytol derivatives on brown adipocyte differentiation.

Journal: FEBS letters 20020424

Title: Photoaffinity labeling of human retinoid X receptor beta (RXRbeta) with 9-cis-retinoic acid: identification of phytanic acid, docosahexaenoic acid, and lithocholic acid as ligands for RXRbeta.

Journal: Biochemistry 20020416

Title: Prevention of vitamin A teratogenesis by phytol or phytanic acid results from reduced metabolism of retinol to the teratogenic metabolite, all-trans-retinoic acid.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20020401

Title: Stereochemistry of the peroxisomal branched-chain fatty acid alpha- and beta-oxidation systems in patients suffering from different peroxisomal disorders.

Journal: Journal of lipid research 20020301

Title: Refsum's disease: a peroxisomal disorder affecting phytanic acid alpha-oxidation.

Journal: Journal of neurochemistry 20020301

Title: Phytanic acid, a novel activator of uncoupling protein-1 gene transcription and brown adipocyte differentiation.

Journal: The Biochemical journal 20020215

Title: [Refsum's disease: evolution 35 years after diagnosis].

Journal: Revue neurologique 20020201

Title: Peroxisomal fatty acid oxidation and cellular redox.

Journal: Methods in enzymology 20020101

Title: Effects of phytanic acid on the vitamin E status, lipid composition and physical properties of retinal cell membranes: implications for adult Refsum disease.

Journal: Clinical science (London, England : 1979) 20011201

Title: Human metabolism of phytanic acid and pristanic acid.

Journal: Progress in lipid research 20011101

Title: Refsum disease, peroxisomes and phytanic acid oxidation: a review.

Journal: Journal of neuropathology and experimental neurology 20011101

Title: Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.

Journal: Biochimica et biophysica acta 20011031

Title: Studies on phytanoyl-CoA 2-hydroxylase and synthesis of phytanoyl-coenzyme A.

Journal: Bioorganic & medicinal chemistry letters 20010917

Title: Refsum's disease.

Journal: QJM : monthly journal of the Association of Physicians 20010801

Title: Identification of pristanal dehydrogenase activity in peroxisomes: conclusive evidence that the complete phytanic acid alpha-oxidation pathway is localized in peroxisomes.

Journal: Biochemical and biophysical research communications 20010511

Title: [Refsum disease].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20010301

Title: The chlorophyll metabolite phytanic acid is a natural rexinoid--potential for treatment and prevention of diabetes.

Journal: Medical hypotheses 20010201

Title: Normal and defective neuronal membranes: structure and function: neuronal lesions in peroxisomal disorders.

Journal: Journal of molecular neuroscience : MN 20010101

Title: Pristanic acid and phytanic acid: naturally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor alpha.

Journal: Journal of lipid research 20001101

Title: Phytanic acid is ligand and transcriptional activator of murine liver fatty acid binding protein.

Journal: Journal of lipid research 19990401

Title: Phytanic acid is a retinoid X receptor ligand.

Journal: European journal of biochemistry 19960215

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:14721-66-5 Molecular Formula|14721-66-5 MDL|14721-66-5 SMILES|14721-66-5 PHYTANIC ACID
Catalog No.: AA00AQ78
14721-66-5,MFCD00133772
14721-66-5 | PHYTANIC ACID
Pack Size: 250mg
Purity: 95%
in stock
$58.00 $41.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00AQ78
Chemical Name: PHYTANIC ACID
CAS Number: 14721-66-5
Molecular Formula: C20H40O2
Molecular Weight: 312.5304
MDL Number: MFCD00133772
SMILES: CC(CCCC(CC(=O)O)C)CCCC(CCCC(C)C)C
NSC Number: 108698
Properties
Complexity: 273  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 22  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 14  
Undefined Atom Stereocenter Count: 3  
Undefined Bond Stereocenter Count: 0  
XLogP3: 8.3  
Downstream Synthesis Route
1551-27-5    14721-66-5   
3,7,11,15-Tetramethyl-1-(5-propyl-thiophen-2-yl)-hexadecan-1-one 

[1]JournaloftheChemicalSociety.Chemicalcommunications,1989,p.1105-1107

1455-20-5    14721-66-5   
1-(5-Butyl-thiophen-2-yl)-3,7,11,15-tetramethyl-hexadecan-1-one 

[1]JournaloftheChemicalSociety.Chemicalcommunications,1989,p.1105-1107

7541-49-3    14721-66-5 

[1]JustusLiebigsAnnalenderChemie,1911,vol.378,p.114

[2]Patent:US2019/275110,2019,A1

[3]Patent:US2019/275156,2019,A1

[4]Patent:US2019/275115,2019,A1

2425-41-4    14721-66-5    1035844-45-1 

[1]Patent:WO2007/72983,2007,A1.Locationinpatent:Page/Pagecolumn25-27

40137-22-2    14721-66-5   
C24H49NO3 

[1]CrystalGrowthandDesign,2017,vol.17,p.3502-3511

Literature fold

Title: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.

Journal: Journal of applied toxicology : JAT20140701

Title: Estimated phytanic acid intake and prostate cancer risk: a prospective cohort study.

Journal: International journal of cancer20120915

Title: Phytanic acid disturbs mitochondrial homeostasis in heart of young rats: a possible pathomechanism of cardiomyopathy in Refsum disease.

Journal: Molecular and cellular biochemistry20120701

Title: A child with night blindness: preventing serious symptoms of Refsum disease.

Journal: Journal of child neurology20120501

Title: Tiptoeing around transgenics.

Journal: Nature biotechnology20120307

Title: [The diagnostic of peroxisomic diseases in children].

Journal: Klinicheskaia laboratornaia diagnostika20120301

Title: Long-term strategies for the treatment of Refsum's disease using therapeutic apheresis.

Journal: Journal of clinical apheresis20120101

Title: Morphology of 1-methyl-1-nitrosourea induced rat mammary tumours after treatment with precursor of phytanic acid or its combination with vitamin D analogue.

Journal: Endocrine regulations20120101

Title: Chance and serendipity in science: two examples from my own career.

Journal: The Journal of biological chemistry20111104

Title: Phytanic acid metabolism in health and disease.

Journal: Biochimica et biophysica acta20110901

Title: Analysis of a range of catabolic mutants provides evidence that phytanoyl-coenzyme A does not act as a substrate of the electron-transfer flavoprotein/electron-transfer flavoprotein:ubiquinone oxidoreductase complex in Arabidopsis during dark-induced senescence.

Journal: Plant physiology20110901

Title: Phytanic acid and pristanic acid, branched-chain fatty acids associated with Refsum disease and other inherited peroxisomal disorders, mediate intracellular Ca2+ signaling through activation of free fatty acid receptor GPR40.

Journal: Neurobiology of disease20110801

Title: AMACR polymorphisms, dietary intake of red meat and dairy and prostate cancer risk.

Journal: The Prostate20110401

Title: Refsum's Disease-Use of the Intestinal Lipase Inhibitor, Orlistat, as a Novel Therapeutic Approach to a Complex Disorder.

Journal: Journal of obesity20110101

Title: Effect of dairy fat on plasma phytanic acid in healthy volunteers - a randomized controlled study.

Journal: Lipids in health and disease20110101

Title: Peroxisomal biogenesis disorder biomarkers.

Journal: Clinical laboratory20110101

Title: Alkyl-glycerol rescues plasmalogen levels and pathology of ether-phospholipid deficient mice.

Journal: PloS one20110101

Title: Biochemistry and genetics of inherited disorders of peroxisomal fatty acid metabolism.

Journal: Journal of lipid research20101001

Title: In vitro evidence that phytanic acid compromises Na(+),K(+)-ATPase activity and the electron flow through the respiratory chain in brain cortex from young rats.

Journal: Brain research20100917

Title: The effectiveness of long-term dietary therapy in the treatment of adult Refsum disease.

Journal: Journal of neurology, neurosurgery, and psychiatry20100901

Title: Neurochemical evidence that phytanic acid induces oxidative damage and reduces the antioxidant defenses in cerebellum and cerebral cortex of rats.

Journal: Life sciences20100828

Title: Plasma phytanic acid concentration and risk of prostate cancer: results from the European Prospective Investigation into Cancer and Nutrition.

Journal: The American journal of clinical nutrition20100601

Title: Lanthanide phytanates: liquid-crystalline phase behavior, colloidal particle dispersions, and potential as medical imaging agents.

Journal: Langmuir : the ACS journal of surfaces and colloids20100504

Title: A Pex7 hypomorphic mouse model for plasmalogen deficiency affecting the lens and skeleton.

Journal: Molecular genetics and metabolism20100401

Title: Use of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline for the preparation of a hapten-protein conjugate for antibody development.

Journal: Bioorganic & medicinal chemistry letters20100301

Title: Phytanic acid--an overlooked bioactive fatty acid in dairy fat?

Journal: Annals of the New York Academy of Sciences20100301

Title: Compartmentalization of the Edinburgh Human Metabolic Network.

Journal: BMC bioinformatics20100101

Title: Adult Refsum disease: a form of tapetoretinal dystrophy accessible to therapy.

Journal: Survey of ophthalmology20100101

Title: Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions.

Journal: BMC physiology20100101

Title: Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis.

Journal: Proceedings of the National Academy of Sciences of the United States of America20091208

Title: The influence of the branched-chain fatty acids pristanic acid and Refsum disease-associated phytanic acid on mitochondrial functions and calcium regulation of hippocampal neurons, astrocytes, and oligodendrocytes.

Journal: Neurobiology of disease20091101

Title: A PEX10 defect in a patient with no detectable defect in peroxisome assembly or metabolism in cultured fibroblasts.

Journal: Journal of inherited metabolic disease20090201

Title: Phytol-induced hepatotoxicity in mice.

Journal: Toxicologic pathology20090101

Title: Identification of marker genes for lipid-lowering effect of a short-chain fructooligosaccharide by DNA microarray analysis.

Journal: Journal of dietary supplements20090101

Title: Rapid UPLC-MS/MS method for routine analysis of plasma pristanic, phytanic, and very long chain fatty acid markers of peroxisomal disorders.

Journal: Journal of lipid research20080801

Title: Comment concerning the article: 'Phytanic acid impairs mitochondrial respiration through protonophoric action' by Komen et al.: branched chain phytanic acid inhibits the activity of the mitochondrial respiratory chain.

Journal: Cellular and molecular life sciences : CMLS20080701

Title: Non-manifesting Refsum heterozygotes carrying the c.135-2A>G PAHX gene transition.

Journal: Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology20080601

Title: Refsum disease due to the splice-site mutation c.135-2A>G before exon 3 of the PHYH gene, diagnosed eight years after detection of retinitis pigmentosa.

Journal: Journal of the neurological sciences20080315

Title: Phytanic acid: measurement of plasma concentrations by gas-liquid chromatography-mass spectrometry analysis and associations with diet and other plasma fatty acids.

Journal: The British journal of nutrition20080301

Title: Plasmalogen levels in Gaucher disease.

Journal: Blood cells, molecules & diseases20080101

Title: Dietary fat-gene interactions in cancer.

Journal: Cancer metastasis reviews20071201

Title: Phytanic acid impairs mitochondrial respiration through protonophoric action.

Journal: Cellular and molecular life sciences : CMLS20071201

Title: Peroxisomes, Refsum's disease and the alpha- and omega-oxidation of phytanic acid.

Journal: Biochemical Society transactions20071101

Title: Peroxisomal disorders affecting phytanic acid alpha-oxidation: a review.

Journal: Biochemical Society transactions20071101

Title: Peroxisomes contain a specific phytanoyl-CoA/pristanoyl-CoA thioesterase acting as a novel auxiliary enzyme in alpha- and beta-oxidation of methyl-branched fatty acids in mouse.

Journal: The Journal of biological chemistry20070914

Title: Dual subcellular localization in the endoplasmic reticulum and peroxisomes and a vital role in protecting against oxidative stress of fatty aldehyde dehydrogenase are achieved by alternative splicing.

Journal: The Journal of biological chemistry20070713

Title: Effect of SCP-x gene ablation on branched-chain fatty acid metabolism.

Journal: American journal of physiology. Gastrointestinal and liver physiology20070301

Title: Cell proliferation inhibition and alterations in retinol esterification induced by phytanic acid and docosahexaenoic acid.

Journal: Journal of lipid research20070101

Title: PPARs in the Control of Uncoupling Proteins Gene Expression.

Journal: PPAR research20070101

Title: Alpha-oxidation.

Journal: Biochimica et biophysica acta20061201

Title: Refsum's disease may mimic familial Guillain Barre syndrome.

Journal: Neuromuscular disorders : NMD20061101

Title: CYP4 isoform specificity in the omega-hydroxylation of phytanic acid, a potential route to elimination of the causative agent of Refsum's disease.

Journal: The Journal of pharmacology and experimental therapeutics20060801

Title: Phytanic acid: production from phytol, its breakdown and role in human disease.

Journal: Cellular and molecular life sciences : CMLS20060801

Title: Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid.

Journal: FEBS letters20060710

Title: A study of the cytotoxicity of branched-chain phytanic acid with mitochondria and rat brain astrocytes.

Journal: Experimental gerontology20060701

Title: Thiamine pyrophosphate: an essential cofactor for the alpha-oxidation in mammals--implications for thiamine deficiencies?

Journal: Cellular and molecular life sciences : CMLS20060701

Title: Brain pyruvate and 2-oxoglutarate dehydrogenase complexes are mitochondrial targets of the CoA ester of the Refsum disease marker phytanic acid.

Journal: FEBS letters20060612

Title: Peroxisomal trans-2-enoyl-CoA reductase is involved in phytol degradation.

Journal: FEBS letters20060403

Title: Phytanic acid, AMACR and prostate cancer risk.

Journal: Future oncology (London, England)20060401

Title: Rotenone-like action of the branched-chain phytanic acid induces oxidative stress in mitochondria.

Journal: The Journal of biological chemistry20060317

Title: Mechanism of toxicity of the branched-chain fatty acid phytanic acid, a marker of Refsum disease, in astrocytes involves mitochondrial impairment.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience20060101

Title: [alpha-Oxidation of 3-methyl-branched fatty acids: unraveling of a pathway].

Journal: Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie20060101

Title: Structure of human phytanoyl-CoA 2-hydroxylase identifies molecular mechanisms of Refsum disease.

Journal: The Journal of biological chemistry20051209

Title: Phytol directly activates peroxisome proliferator-activated receptor alpha (PPARalpha) and regulates gene expression involved in lipid metabolism in PPARalpha-expressing HepG2 hepatocytes.

Journal: Biochemical and biophysical research communications20051118

Title: Serum levels of phytanic acid are associated with prostate cancer risk.

Journal: The Journal of urology20051101

Title: [Adult Refsum disease. A retinal dystrophy with therapeutic options].

Journal: Der Ophthalmologe : Zeitschrift der Deutschen Ophthalmologischen Gesellschaft20050801

Title: Characterization of the final step in the conversion of phytol into phytanic acid.

Journal: The Journal of biological chemistry20050722

Title: Characterization of phytanic acid omega-hydroxylation in human liver microsomes.

Journal: Molecular genetics and metabolism20050701

Title: [Refsum's disease with severe neuropathy: efficiency of the diet and plasmapheresis].

Journal: La Revue de medecine interne20050601

Title: Serum levels of phytanic acid are associated with prostate cancer risk.

Journal: The Prostate20050515

Title: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids.

Journal: The Journal of biological chemistry20050318

Title: The Refsum disease marker phytanic acid, a branched chain fatty acid, affects Ca2+ homeostasis and mitochondria, and reduces cell viability in rat hippocampal astrocytes.

Journal: Neurobiology of disease20050201

Title: A study on the causes for the elevated n-3 fatty acids in cows' milk of alpine origin.

Journal: Lipids20050201

Title: Up-regulation of PPARgamma coactivator-1alpha as a strategy for preventing and reversing insulin resistance and obesity.

Journal: Medical hypotheses20050101

Title: Assay for Sjögren-Larsson syndrome based on a deficiency of phytol degradation.

Journal: Clinical chemistry20050101

Title: Orthotopic liver transplantation from a living-related donor in an infant with a peroxisome biogenesis defect of the infantile Refsum disease type.

Journal: Journal of inherited metabolic disease20050101

Title: A novel assay for the prenatal diagnosis of Sjögren-Larsson syndrome.

Journal: Journal of inherited metabolic disease20050101

Title: Clinical significance of oxidation from phytol to phytanic acid in man.

Journal: Molecular genetics and metabolism20041201

Title: Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands.

Journal: Archives of toxicology20041101

Title: Phytanic acid accumulation is associated with conduction delay and sudden cardiac death in sterol carrier protein-2/sterol carrier protein-x deficient mice.

Journal: Journal of cardiovascular electrophysiology20041101

Title: In brain mitochondria the branched-chain fatty acid phytanic acid impairs energy transduction and sensitizes for permeability transition.

Journal: The Biochemical journal20041001

Title: Tremor and deep white matter changes in alpha-methylacyl-CoA racemase deficiency.

Journal: Neurology20040713

Title: Omega-hydroxylation of phytanic acid in rat liver microsomes: implications for Refsum disease.

Journal: Journal of lipid research20040701

Title: Hyperpipecolic acidaemia: a diagnostic tool for peroxisomal disorders.

Journal: Molecular genetics and metabolism20040701

Title: Reinvestigation of trihydroxycholestanoic acidemia reveals a peroxisome biogenesis disorder.

Journal: Neurology20040608

Title: Identification of fatty aldehyde dehydrogenase in the breakdown of phytol to phytanic acid.

Journal: Molecular genetics and metabolism20040501

Title: Liver fatty acid binding protein expression enhances branched-chain fatty acid metabolism.

Journal: Molecular and cellular biochemistry20040401

Title: Molecular basis of Refsum disease: sequence variations in phytanoyl-CoA hydroxylase (PHYH) and the PTS2 receptor (PEX7).

Journal: Human mutation20040301

Title: Measurement of plasma pristanic, phytanic and very long chain fatty acids by liquid chromatography-electrospray tandem mass spectrometry for the diagnosis of peroxisomal disorders.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20031205

Title: Further studies on the substrate spectrum of phytanoyl-CoA hydroxylase: implications for Refsum disease?

Journal: Journal of lipid research20031201

Title: Gas chromatography/mass spectrometry analysis of very long chain fatty acids, docosahexaenoic acid, phytanic acid and plasmalogen for the screening of peroxisomal disorders.

Journal: Brain & development20031001

Title: Impaired neuronal migration and endochondral ossification in Pex7 knockout mice: a model for rhizomelic chondrodysplasia punctata.

Journal: Human molecular genetics20030915

Title: Sterol carrier protein-2/sterol carrier protein-x expression differentially alters fatty acid metabolism in L cell fibroblasts.

Journal: Journal of lipid research20030901

Title: The chemical biology of branched-chain lipid metabolism.

Journal: Progress in lipid research20030901

Title: Metabolism of phytanic acid and 3-methyl-adipic acid excretion in patients with adult Refsum disease.

Journal: Journal of lipid research20030801

Title: Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition.

Journal: Transfusion and apheresis science : official journal of the World Apheresis Association : official journal of the European Society for Haemapheresis20030801

Title: Branched fatty acids in dairy and beef products markedly enhance alpha-methylacyl-CoA racemase expression in prostate cancer cells in vitro.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology20030801

Title: Hearing loss in adult Refsum's disease.

Journal: Clinical otolaryngology and allied sciences20030601

Title: Alpha-oxidation of 3-methyl-substituted fatty acids and its thiamine dependence.

Journal: European journal of biochemistry20030401

Title: Phytanic acid alpha-oxidation, new insights into an old problem: a review.

Journal: Biochimica et biophysica acta20030317

Title: Identification of PEX7 as the second gene involved in Refsum disease.

Journal: American journal of human genetics20030201

Title: Biochemical markers predicting survival in peroxisome biogenesis disorders.

Journal: Advances in experimental medicine and biology20030101

Title: Phytanic and pristanic acid are naturally occuring ligands.

Journal: Advances in experimental medicine and biology20030101

Title: Role of phytanoyl-CoA 2-hydroxylase in phytanic acid metabolism.

Journal: Advances in experimental medicine and biology20030101

Title: Branched chain fatty acids induce nitric oxide-dependent apoptosis in vascular smooth muscle cells.

Journal: The Journal of biological chemistry20021220

Title: Biochemical markers predicting survival in peroxisome biogenesis disorders.

Journal: Neurology20021210

Title: Expression of fatty acid binding proteins inhibits lipid accumulation and alters toxicity in L cell fibroblasts.

Journal: American journal of physiology. Cell physiology20020901

Title: The chlorophyll-derived metabolite phytanic acid induces white adipocyte differentiation.

Journal: International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity20020901

Title: [Refsum disease].

Journal: Nihon rinsho. Japanese journal of clinical medicine20020901

Title: Phytanic acid, a natural peroxisome proliferator-activated receptor (PPAR) agonist, regulates glucose metabolism in rat primary hepatocytes.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20020501

Title: Glucuronidation of the dietary fatty acids, phytanic acid and docosahexaenoic acid, by human UDP-glucuronosyltransferases.

Journal: Drug metabolism and disposition: the biological fate of chemicals20020501

Title: Utilization of sterol carrier protein-2 by phytanoyl-CoA 2-hydroxylase in the peroxisomal alpha oxidation of phytanic acid.

Journal: Chemistry & biology20020501

Title: Phytanic acid, but not pristanic acid, mediates the positive effects of phytol derivatives on brown adipocyte differentiation.

Journal: FEBS letters20020424

Title: Photoaffinity labeling of human retinoid X receptor beta (RXRbeta) with 9-cis-retinoic acid: identification of phytanic acid, docosahexaenoic acid, and lithocholic acid as ligands for RXRbeta.

Journal: Biochemistry20020416

Title: Prevention of vitamin A teratogenesis by phytol or phytanic acid results from reduced metabolism of retinol to the teratogenic metabolite, all-trans-retinoic acid.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20020401

Title: Stereochemistry of the peroxisomal branched-chain fatty acid alpha- and beta-oxidation systems in patients suffering from different peroxisomal disorders.

Journal: Journal of lipid research20020301

Title: Refsum's disease: a peroxisomal disorder affecting phytanic acid alpha-oxidation.

Journal: Journal of neurochemistry20020301

Title: Phytanic acid, a novel activator of uncoupling protein-1 gene transcription and brown adipocyte differentiation.

Journal: The Biochemical journal20020215

Title: [Refsum's disease: evolution 35 years after diagnosis].

Journal: Revue neurologique20020201

Title: Peroxisomal fatty acid oxidation and cellular redox.

Journal: Methods in enzymology20020101

Title: Effects of phytanic acid on the vitamin E status, lipid composition and physical properties of retinal cell membranes: implications for adult Refsum disease.

Journal: Clinical science (London, England : 1979)20011201

Title: Human metabolism of phytanic acid and pristanic acid.

Journal: Progress in lipid research20011101

Title: Refsum disease, peroxisomes and phytanic acid oxidation: a review.

Journal: Journal of neuropathology and experimental neurology20011101

Title: Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.

Journal: Biochimica et biophysica acta20011031

Title: Studies on phytanoyl-CoA 2-hydroxylase and synthesis of phytanoyl-coenzyme A.

Journal: Bioorganic & medicinal chemistry letters20010917

Title: Refsum's disease.

Journal: QJM : monthly journal of the Association of Physicians20010801

Title: Identification of pristanal dehydrogenase activity in peroxisomes: conclusive evidence that the complete phytanic acid alpha-oxidation pathway is localized in peroxisomes.

Journal: Biochemical and biophysical research communications20010511

Title: [Refsum disease].

Journal: Nihon rinsho. Japanese journal of clinical medicine20010301

Title: The chlorophyll metabolite phytanic acid is a natural rexinoid--potential for treatment and prevention of diabetes.

Journal: Medical hypotheses20010201

Title: Normal and defective neuronal membranes: structure and function: neuronal lesions in peroxisomal disorders.

Journal: Journal of molecular neuroscience : MN20010101

Title: Pristanic acid and phytanic acid: naturally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor alpha.

Journal: Journal of lipid research20001101

Title: Phytanic acid is ligand and transcriptional activator of murine liver fatty acid binding protein.

Journal: Journal of lipid research19990401

Title: Phytanic acid is a retinoid X receptor ligand.

Journal: European journal of biochemistry19960215

Building Blocks More >
1829-60-3
1829-60-3
Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
AA00AQDA | MFCD03060497
167303-60-8
167303-60-8
Benzyl N-[(dimethylcarbamoyl)methyl]carbamate
AA00AQG2 | MFCD22421521
18614-67-0
18614-67-0
2-Methyl-5-nitropyridin-4-ol
AA00AQND | MFCD21604168
1704069-21-5
1704069-21-5
(3-((2-methoxyphenyl)carbamoyl)phenyl)boronic acid
AA00AR4Y | MFCD28384303
186392-94-9
186392-94-9
5,6-Dichloro-1H-indole-2-carboxylic acid
AA00ARUH | MFCD09802223
1860947-01-8
1860947-01-8
(2S)-2-(4-Bromophenyl)pyrrolidine hcl
AA00AS85 | MFCD12910618
1664-59-1
1664-59-1
3-(3-Nitro-phenyl)-acrylic acid methyl ester
AA00ASTG | MFCD00024570
163630-79-3
163630-79-3
Lu 28-179
AA00AT7J | MFCD28016590
19447-06-4
19447-06-4
1-(2,6-Dimethylphenyl)ethanol
AA00ATZ5 | MFCD00016856
157563-54-7
157563-54-7
Carbamic acid, (3-amino-2-methylphenyl)-, methyl ester (9CI)
AA00AWD7 | MFCD11128936
Submit
© 2017 AA BLOCKS, INC. All rights reserved.