621-70-5

Basic information

• Product Name: TRIHEXANOIN
• Synonyms: TRICAPROIN;TRICAPROIN (C6:0);TRI-N-CAPROIN;TRIHEXANION;TRIHEXANOIN;1,2,3-TRICAPROYLGLYCEROL;1,2,3-TRIHEXANOYLGLYCEROL;GLYCERINTRICAPROATE
• CAS NO: 621-70-5
• Molecular Formula: C₂₁H₃₈O₆
• Molecular Weight: 386.52
• EINECS: 210-701-5
• Product Categories: Biochemicals and Reagents;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Glycerolipids;Lipids;Organic Building Blocks;Triacylglycerols
• Mol File: 621-70-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: -60℃
• Boiling Point: 244 °C / 28mmHg
• Flash Point: 180.2 °C
• Appearance: CLEAR COLORLESS LIQUID
• Density: 0.98 g/mL(lit.)
• Vapor Pressure: 1.36E-07mmHg at 25°C
• Refractive Index: n20/D 1.442
• Storage Temp.: −20°C
• BRN: 1806732
• CAS DataBase Reference: TRIHEXANOIN(CAS DataBase Reference)
• NIST Chemistry Reference: TRIHEXANOIN(621-70-5)
• EPA Substance Registry System: TRIHEXANOIN(621-70-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 1
• RTECS: MB2700000
• Hazardous Substances Data: 621-70-5(Hazardous Substances Data)

Usage

Chemical Properties

It is very soluble in alcohol and ether and insoluble in water.

Uses

Tricaproin is used as a delivery system for Paclitaxel (P132500) which is an anticancer agent.

Definition

ChEBI: A triglyceride obtained by condensation of each of the three hydroxy groups of glycerol with hexanoic (caproic) acid.

InChI:InChI=1/C21H38O6/c1-4-7-10-13-19(22)25-16-18(27-21(24)15-12-9-6-3)17-26-20(23)14-11-8-5-2/h18H,4-17H2,1-3H3

Synthetic route

glycerol (56-81-5) + hexanoic acid (142-62-1) → hexanoic acid, 1,2,3-propanetriyl ester (621-70-5)

Conditions	Yield
With sulfonated charcoal In benzene for 7h; Heating;	94%
With glucose-diphenylaminium tosylate-derived carbon solid acid (GDTCSA) In n-heptane at 80℃; for 18h;	93%
With tungsten(VI) oxide at 175℃; under 10 Torr; for 22h; Reagent/catalyst; Dean-Stark;	85%
im Vakuum bvei geichzeitigen Durchleiten eines schwachen Stromes trockner Luft;
With dmap; dicyclohexyl-carbodiimide 1.) CH2Cl2, 2.) CH2Cl2; Multistep reaction;

glycerol (56-81-5) + hexanoic acid (142-62-1) → 2,3-dihydroxypropyl hexanoate (502-53-4) + 2-hexanoyloxy-propane-1,3-diol (70916-55-1) + O,O-1,2-dihexanoylglycerol (17598-91-3) + hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) + hexanoic acid 3-hexanoyloxy-2-hydroxypropyl ester (17598-92-4)

Conditions	Yield
With Nafion silica-13 nanocomposite

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → hexanenitrile (628-73-9)

Conditions	Yield
With ammonia at 220℃; for 40h; Autoclave;	93%

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → hexan-1-ol (111-27-3)

Conditions	Yield
With 5 wt% Re/TiO2; hydrogen In neat (no solvent) at 220℃; under 37503.8 Torr; for 36h; Autoclave;	82%

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) + 2,2'-iminobis[ethanol] (111-42-2) → hexanoyl diethanolamide (29752-80-5)

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; for 24h;	18.2%

Geraniol (106-24-1) + hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → geraniol hexanoate (10032-02-7)

Conditions	Yield
With Pseudomonas sp. lipase PS In hexane at 30℃; for 24h; also DL-citronellol and tributyrin; effect of enzyme load, concentration of reagents, addtion of water and pH; var. temp. and solvents;

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → 1,2-dihexanoyl-sn-glycerol (30403-47-5) + Hexanoic acid (R)-2-hexanoyloxy-1-hydroxymethyl-ethyl ester

Conditions	Yield
With oat seed lipase; water at 37℃; for 0.0833333h; pH 8.5 (Tris-HCl buffer);

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) + penicillium glaucum → 2-Pentanone (107-87-9)

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → hexanoic acid (142-62-1)

Conditions	Yield
With Psychrobacter sp. TA144 lipase, recombinant, containing MPILPV sequence at N-terminal, apparent molecular mass: ca. 48000 Da In acetonitrile at 35℃; pH=8; Kinetics; aq. buffer; Enzymatic reaction;
With recombinant esterase from Rhizomucor miehei In aq. phosphate buffer at 50℃; for 0.166667h; pH=6.5; Catalytic behavior; Enzymatic reaction;

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → Caproamide (628-02-4)

Conditions	Yield
With ammonia at 180℃; for 5h; Autoclave;	82 %Chromat.

hexanoic acid, 1,2,3-propanetriyl ester (621-70-5) → hexan-1-amine (111-26-2) + dihexylamine (143-16-8)

Conditions	Yield
With ammonium hydroxide; hydrogen at 220℃; under 41254.1 Torr; for 36h; Autoclave;	A 48 %Chromat. B 33 %Chromat.

Upstream product

• 56-81-5 glycerol 
• 142-62-1 hexanoic acid 

Downstream Products

• 30403-47-5 1,2-dihexanoyl-sn-glycerol 
• 75685-80-2 Hexanoic acid (R)-2-hexanoyloxy-1-hydroxymethyl-ethyl ester 
• 107-87-9 2-Pentanone 
• 29752-80-5 hexanoyl diethanolamide 
• 111-27-3 hexan-1-ol 
• 111-26-2 hexan-1-amine 
• 143-16-8 dihexylamine 
• 628-73-9 hexanenitrile 
• 628-02-4 Caproamide 
• 142-62-1 hexanoic acid 
• 10032-02-7 geraniol hexanoate 

Relevant articles and documents

The carbon material functionalized with NH2+ and SO3H groups catalyzed esterification with high activity and selectivity

A novel carbon-based solid acid was conveniently prepared by heating a mixture of d-glucose, p-toluenesulfonic acid and diphenylammonium tosylate. Its structure was measured by XRD, FT-IR, XPS, 13C MAS NMR and EA to illustrate that the carbon material has been functionalized with NH2+ and SO3H groups and has a strong "hydrophobic effect". It can be used to catalyze the esterification reaction of carboxylic acids with equimolar amounts of sterically demanding and acid-sensitive alcohols with high reactivity (yield up to 90%) and selectivity (up to 95%) in heptane at 80 °C. It could be easily recovered and reused more than ten times without loss of activity.

METHOD FOR THE PREPARATION OF TRIGLYCERIDES OF MEDIUM-CHAIN LENGTH FATTY ACIDS

A method is disclosed for the preparation of glycerol esters (triglycerides) of medium-chain length monocarboxylic fatty acids which consists of the reaction of the precursor free fatty acid and glycerol in the presence of a catalyst under partial vacuum. The process preferably uses a metal catalyst such as an oxide or a chloride of tungsten, molybdenum, calcium, zinc, chromium or magnesium. The method of the invention allows the preparation in high yield and high purity (>99.5%) of the final triglyceride. The present method allows the formation of triglycerides without solvent. Are also contemplated, the triglyceride obtained by the method, and the pharmaceutical composition containing the triglyceride as an excipient or as an active ingredient.

Preparation of Carboxylate Esters of Polyhydric Alcohols by Using a Sulfonated Charcoal Catalyst

Ethane-1,2-diol, propane-1,2-diol, butane-1,4-diol and propane-1,2,3-triol are readily esterified by carboxylic acids in near quantitative yields in the presence of a sulfonated charcoal catalyst.