14721-66-5

Basic information

• Product Name: PHYTANIC ACID
• Synonyms: PHYTANIC ACID;3,7,11,15-TETRAMETHYLHEXADECANOIC ACID;METHYLATED PHYTANIC ACID;C01607;Phytanate;Phytanic acid,3,7,11,15-Tetramethylhexadecanoic acid
• CAS NO: 14721-66-5
• Molecular Formula: C₂₀H₄₀O₂
• Molecular Weight: 312.53
• Mol File: 14721-66-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: -65°C
• Boiling Point: 391.36°C (estimate)
• Flash Point: 179.7 °C
• Appearance: /Liquid
• Density: 0.8888 (rough estimate)
• Vapor Pressure: 2.58E-08mmHg at 25°C
• Refractive Index: 1.4461 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.79±0.10(Predicted)
• CAS DataBase Reference: PHYTANIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PHYTANIC ACID(14721-66-5)
• EPA Substance Registry System: PHYTANIC ACID(14721-66-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 14721-66-5(Hazardous Substances Data)

Usage

Description

Phytanic acid is a saturated 20-carbon branched-chain fatty acid which can only be derived from dietary sources. In cases of peroxisomal disorders, elevated levels of phytanic acid have been observed, and this is linked to diseases such as infantile phytanic acid storage disease and Refsum’s disease.

Uses

Phytanoic Acid was useful for studying lipid metabolism in porcine oocytes.

InChI:InChI=1/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

Synthetic route

3,7,11,15-tetramethyl-hexadecanol (645-72-7) → phytanic acid (14721-66-5)

Conditions	Yield
With potassium permanganate; tetrabutylammomium bromide; acetic acid In water; 1,2-dichloro-ethane at 16℃; for 4.5h; Reflux;	94%
With potassium permanganate; tetrabutylammomium bromide; acetic acid In water; 1,2-dichloro-ethane at 16℃; for 4.5h; Reflux;	94%
With potassium permanganate; tetrabutylammomium bromide; acetic acid In water; 1,2-dichloro-ethane at 16℃; for 4.5h; Reflux;	94%

diethyl ether (60-29-7) + 3,7,11,15-tetramethyl-hexadecanol (645-72-7) → phytanic acid (14721-66-5)

Conditions	Yield
With sodium disulfite; chromic acid; acetic acid In [(2)H6]acetone; water	72.3%

3,7,11,15-tetramethyl-2-hexadecen-1-oic acid (220904-31-4) → phytanic acid (14721-66-5)

Conditions	Yield
With platinum Hydrogenation;

2,6,10,14-Tetramethyl-pentadecanon-(12)-carbonsaeure-(1) (102464-52-8) → phytanic acid (14721-66-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol at 195℃;

3,7,11,15-tetramethyl-hexadecanol (645-72-7) → phytanic acid (14721-66-5) + phytanic acid dihydrophytyl ester

3,7,11,15-tetramethyl-2-hexadecen-1-ol (7541-49-3) → phytanic acid (14721-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Katalitrische Hydrierung.Hydrogenation 2: chromic acid; glacial acetic acid; KHSO4 View Scheme
Multi-step reaction with 2 steps 1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr 2: tetrabutylammomium bromide; acetic acid; potassium permanganate / water; 1,2-dichloro-ethane / 4.5 h / 16 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: hydrogen; platinum(IV) oxide / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr 2: tetrabutylammomium bromide; acetic acid; potassium permanganate / water; 1,2-dichloro-ethane / 4.5 h / 16 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: hydrogen; platinum(IV) oxide / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr 2: tetrabutylammomium bromide; acetic acid; potassium permanganate / water; 1,2-dichloro-ethane / 4.5 h / 16 °C / Reflux View Scheme

2,6,10,14-Tetramethyl-pentadecanon-(12)-carbonsaeure-(1)-methylester (102899-50-3) → phytanic acid (14721-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / methanol 2: KOH, diethylene glycol, aq. N2H4 / 195 °C View Scheme

phytol (150-86-7) → phytanic acid (14721-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / water; ethanol / 72 h / 20 °C 2: Jones reagent / acetone / 0.5 h / 0 °C View Scheme

phytanic acid (14721-66-5) + L-proline methyl ester monohydrochloride (2133-40-6) → C26H49NO3

Conditions	Yield
Stage #1: phytanic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 0.25h; Stage #2: L-proline methyl ester monohydrochloride In chloroform at 20℃; for 18h;	95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 0 - 20℃; for 18.25h;	95%
Stage #1: phytanic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 0.25h; Stage #2: L-proline methyl ester monohydrochloride In chloroform at 20℃; for 18h;	95%

phytanic acid (14721-66-5) + L-proline methyl ester monohydrochloride (2133-40-6) → C26H49NO3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 18.25h;	95%

3-Amino-1,2-propanediol (616-30-8, 13552-31-3) + phytanic acid (14721-66-5) → N-(3',7',11',15'-tetramethyl-hexadecanoyl)-3-amino-1,2-propanediol

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	88%

formaldehyd (50-00-0) + dichloromethane hexane + phytanic acid (14721-66-5) → chloromethyl 3,7,11,15-tetramethyl-1-hexadecanoate

Conditions	Yield
With Zinc chloride In dichloromethane; chloroform	66.1%

phytanic acid (14721-66-5) + N-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)pent-4-ynamide (1638195-92-2) → 2-(pent-4-ynamido)-2-(((3,7,11,15-tetramethylhexadecanoyl)oxy)methyl)propane-1,3-diyl bis(3,7,11,15-tetramethylhexadecanoate)

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;	61%

phytanic acid (14721-66-5) + Propargylamine (2450-71-7) → 3,7,11,15-tetramethyl-N-(prop-2-yn-1-yl)hexadecanamide

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;	60%

prop-2-yn-1-yl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate (873849-85-5) + phytanic acid (14721-66-5) → 2-methyl-2-((prop-2-yn-1-yloxy)carbonyl)propane-1,3-diyl bis(3,7,11,15-tetramethylhexadecanoate)

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;	52%

phytanic acid (14721-66-5) → 3,7,11,15-tetramethyl-hexadecanol (645-72-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

phytanic acid (14721-66-5) → 2,6,10,14-Tetramethyl-pentadecylamine

Conditions	Yield
With sodium azide; sulfuric acid In chloroform

2-Methylthiophene (554-14-3) + phytanic acid (14721-66-5) → 3,7,11,15-Tetramethyl-1-(5-methyl-thiophen-2-yl)-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

2,3-dimethylthiophene (632-16-6) + phytanic acid (14721-66-5) → 1-(4,5-Dimethyl-thiophen-2-yl)-3,7,11,15-tetramethyl-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

2-ethylthiophene (872-55-9) + phytanic acid (14721-66-5) → 1-(5-Ethyl-thiophen-2-yl)-3,7,11,15-tetramethyl-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

2,4-dimethylthiophene (638-00-6) + phytanic acid (14721-66-5) → 1-(3,5-Dimethyl-thiophen-2-yl)-3,7,11,15-tetramethyl-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

2-propylthiophene (1551-27-5) + phytanic acid (14721-66-5) → 3,7,11,15-Tetramethyl-1-(5-propyl-thiophen-2-yl)-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

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

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

3-Methylthiophene (616-44-4) + phytanic acid (14721-66-5) → 3,7,11,15-Tetramethyl-1-(4-methyl-thiophen-2-yl)-hexadecan-1-one

Conditions	Yield
With oxalyl dichloride; tin(IV) chloride In dichloromethane; N,N-dimethyl-formamide

phytanic acid (14721-66-5) → 4-Methyl-2-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 2-Methyl-5-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 2,3-Dimethyl-5-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 2-Ethyl-5-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 3,5-Dimethyl-2-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 2-Propyl-5-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

phytanic acid (14721-66-5) → 2-Butyl-5-(3,7,11,15-tetramethyl-hexadecyl)-thiophene

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2, SnCl4 / CH2Cl2; dimethylformamide 2: AlCl3, LiAlH4 / diethyl ether View Scheme

Upstream product

• 102464-52-8 2,6,10,14-Tetramethyl-pentadecanon-⁽¹²⁾-carbonsaeure-⁽¹⁾ 
• 150-86-7 phytol 
• 60-29-7 diethyl ether 
• 645-72-7 3,7,11,15-tetramethyl-hexadecanol 
• 102899-50-3 2,6,10,14-Tetramethyl-pentadecanon-⁽¹²⁾-carbonsaeure-⁽¹⁾-methylester 
• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 220904-31-4 3,7,11,15-tetramethyl-2-hexadecen-1-oic acid 

Downstream Products

• 1035844-45-1 C₅₂H₉₂O₆ 
• 645-72-7 3,7,11,15-tetramethyl-hexadecanol 
• 1189-37-3 2,6,10,14-Tetramethylpentadecanoic acid 

Relevant articles and documents

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

Lanthanide salts of phytanic acid, an isoprenoid-type amphiphile, have been synthesized and characterized. Elemental analysis and FTIR spectroscopy were used to confirm the formed product and showed that three phytanate anions are complexed with one lanthanide cation. The physicochemical properties of the lanthanide phytanates were investigated using DSC, XRD, SAXS, and cross-polarized optical microscopy. Several of the hydrated salts form a liquid-crystalline hexagonal columnar mesophase at room temperature, and samarium(III) phytanate forms this phase even in the absence of water. Select lanthanide phytanates were dispersed in water, and cryo-TEM images indicate that some structure has been retained in the dispersed phase. NMR relaxivity measurements were conducted on these systems. It has been shown that a particulate dispersion of gadolinium(III) phytanate displays proton relaxivity values comparable to those of a commercial contrast agent for magnetic resonance imaging and a colloidal dispersion of europium(III) phytanate exhibits the characteristics of a fluorescence imaging agent.

COMPOSITIONS IN THE FORM OF AN INJECTALE AQUEOUS SOLUTION COMPRISING HUMAN GLUCAGON AND A CO-POLYAMINO ACID

Physically stable compositions in the form of an injectable aqueous solution, the pH of which is comprised from 6.0 to 8.0, having at least: human glucagon and a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy, in one embodiment, the compositions according to the invention further includes a gastrointestinal hormone.

COMPOSITIONS SOUS FORME D'UNE SOLUTION AQUEUSE INJECTABLE COMPRENANT DU GLUCAGON HUMAIN ET UN CO-POLYAMINOACIDE

Physically stable compositions in the form of an injectable aqueous solution, wherein the pH is from 6.0 to 8.0, includes at least: a) human glucagon andb) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy. In one embodiment, the compositions further comprise a gut hormone.