74563-64-7

Basic information

• Product Name: PHYTANTRIOL
• Synonyms: 1,2,3-TRIHYDROXY-3,7,11,15-TETRAMETHYLHEXADECANE;3,7,11,15-TETRAMETHYLHEXADECANE-1,2,3-TRIOL;PHYTANTRIOL;3,7,11,15-tetramethyl-1,2,3-hexadecane-triol;phytantriol,3,7,11,15-tetramethyl-1,2,3trihydroxy-hexadecane;3,7,11,15-TETRAMETHYL-1,2,3-HEXA- DECANETRIOL, 95%, MIXTURE OF ISOMERS;Phytanetriol;Phytantriol(mixtureofisomers)
• CAS NO: 74563-64-7
• Molecular Formula: C₂₀H₄₂O₃
• Molecular Weight: 330.55
• EINECS: 277-923-2
• Product Categories: Biochemistry;Terpenes;Terpenes (Others)
• Mol File: 74563-64-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 56-57°
• Boiling Point: 130 °C0.01 mm Hg(lit.)
• Flash Point: 199 °C
• Appearance: /liquid (viscous)
• Density: 0.932 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.51E-08mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly)
• PKA: 14.40±0.29(Predicted)
• Water Solubility: 352μg/L at 20℃
• Merck: 14,7386
• CAS DataBase Reference: PHYTANTRIOL(CAS DataBase Reference)
• NIST Chemistry Reference: PHYTANTRIOL(74563-64-7)
• EPA Substance Registry System: PHYTANTRIOL(74563-64-7)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 74563-64-7(Hazardous Substances Data)

Usage

Uses

Penetration enhancer in hair and skin care products.

Definition

ChEBI: A triol that consists of 3,7,11,15-tetramethylhexadecane bearing three hydroxy substituents at positions 1, 2 and 3.

General Description

The temperature?composition phase diagram of phytantriol/water mixtures is qualitatively similar to that of aqueous glycerol monooleate so its stability makes it an interesting alternative to exploit various applications of the cubic liquid crystalline phases.

Biochem/physiol Actions

Phytantriol is a majorly used ingredient in skin and hair based cosmetics. It is viscous and enhances penetration of amino acids and vitamin components of cosmetics. It is structurally stable than glyceryl monooleate (GMO). Phytantriol in combination with the polymer (F127) and a hydrotrope (propyleneglycol) is used in the preparation of cubosomes for protein or vaccine delivery.

InChI:InChI=1/C20H42O3/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-20(5,23)19(22)15-21/h16-19,21-23H,6-15H2,1-5H3

Synthetic route

6,10,14-Trimethyl-2-(2-phenyl-[1,3]dioxolan-4-yl)-pentadecan-2-ol (105873-65-2) → 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7)

Conditions	Yield
With hydrogen; toluene-4-sulfonic acid; palladium In ethanol	78%

2-methyl-3,4-epoxy-1-butene (7437-61-8) → 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / tetrakis(triphenylphosphine)palladium 2: 88 percent / m-CPBA, Na2CO3 3: 95 percent / H2O / Li2CuCl4 (4 molpercent) 4: 78 percent / H2, p-toluene sulfonic acid / palladium black / ethanol View Scheme

4-Isopropenyl-2-phenyl-[1,3]dioxolane (105873-61-8) → 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / m-CPBA, Na2CO3 2: 95 percent / H2O / Li2CuCl4 (4 molpercent) 3: 78 percent / H2, p-toluene sulfonic acid / palladium black / ethanol View Scheme

4-(1,2-epoxy-1-methylethyl)-2-phenyl-1,3-dioxolane (105873-62-9) → 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / H2O / Li2CuCl4 (4 molpercent) 2: 78 percent / H2, p-toluene sulfonic acid / palladium black / ethanol View Scheme

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) + acetyl chloride (75-36-5) → C22H44O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -70 - 20℃; for 4h;	34%

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) + p-toluenesulfonyl chloride (98-59-9) → C27H48O5S (519753-34-5)

Conditions	Yield
Stage #1: 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane; p-toluenesulfonyl chloride In hexane at 20℃; for 0.166667h; Stage #2: With triethylamine; pyridine In hexane at 0 - 20℃; for 12h;

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) + acetone (67-64-1) → C23H46O3 (518991-65-6)

Conditions	Yield
toluene-4-sulfonic acid for 15h; Heating / reflux;

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) → C40H81NO4

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / chloroform / 12 h / 0 - 20 °C 2: triethylamine / chloroform / 10 h / Reflux 3: triethylamine / chloroform / 5 h / 0 - 20 °C View Scheme

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) → C22H47NO3

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / chloroform / 12 h / 0 - 20 °C 2: triethylamine / chloroform / 10 h / Reflux View Scheme

3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane (74563-64-7) + p-toluenesulfonyl chloride (98-59-9) → C27H48O4S

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 12h;

Upstream product

• 105873-65-2 6,10,14-Trimethyl-2-(2-phenyl-[1,3]dioxolan-4-yl)-pentadecan-2-ol 
• 7437-61-8 2-methyl-3,4-epoxy-1-butene 
• 105873-61-8 4-Isopropenyl-2-phenyl-[1,3]dioxolane 
• 105873-62-9 4-(1,2-epoxy-1-methylethyl)-2-phenyl-1,3-dioxolane 

Relevant articles and documents

NEW APPROACH TO POLYISOPRENEPOLYOLS POSSESSING GLYCEROL TERMINI BY USING A HIGHLY OXYGENATED C5-UNIT

Polyisoprenepolyols possessing glycerol termini have been synthesized by using 4-(1,2-epoxy-1-methylethyl)-2-phenyl-1,3-dioxolane as a novel highly oxygenated C5-unit.