621-71-6

Basic information

• Product Name: TRICAPRIN
• Synonyms: GLYCEROL TRIDECANOATE;GLYCERINTRICAPRATE;1,2,3-TRIDECANOYLGLYCEROL;1,2,3-TRIDECANOYL-RAC-GLYCEROL;TRICAPRIN;TRICAPRIN (C10:0);TRIDECANOIN;TRI-N-CAPRIN
• CAS NO: 621-71-6
• Molecular Formula: C₃₃H₆₂O₆
• Molecular Weight: 554.84
• EINECS: 210-702-0
• Mol File: 621-71-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 31-32 °C
• Boiling Point: 254 °C / 5mmHg
• Flash Point: 20 °C
• Appearance: white or white crystaline powder
• Density: 0.949 g/cm³
• Refractive Index: approximate 1.44
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly, Sonicated)
• BRN: 1717683
• CAS DataBase Reference: TRICAPRIN(CAS DataBase Reference)
• NIST Chemistry Reference: TRICAPRIN(621-71-6)
• EPA Substance Registry System: TRICAPRIN(621-71-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22
• Safety Statements: 26-28
• RIDADR: UN 1282 3/PG 2
• RTECS: HE0100000
• Hazardous Substances Data: 621-71-6(Hazardous Substances Data)

Usage

Description

1,2,3-Tridecanoyl glycerol is a triacylglycerol that contains decanoic acid at the sn-1, sn-2, and sn-3 positions. It has been found in human breast milk. 1,2,3-Tridecanoyl glycerol has been used as a standard for the quantification of triacylglycerols in fish oils by RP-HPLC. Formulations containing 1,2,3-tridecanoyl glycerol have been used in cosmetic products as thickening and skin-conditioning agents.

Uses

Tricaprin is used to construct solid lipid nanoparticles (SLNs) as delivery system for bromocriptine (B682600, Mesylate salt). It is also used in cationic SLNs to enhance p53 tumor suppressor gene transfer to lung cancer cells.

Definition

ChEBI: A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by capric (decanoic) acid.

InChI:InChI=1/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3

Synthetic route

1-decanoic acid (334-48-5) + glycerol (56-81-5) → capric acid triglyceride (621-71-6)

Conditions	Yield
With tungsten(VI) oxide at 175℃; under 1 Torr; for 22h; Reagent/catalyst;	93%
With Twitchell's reagent at 100℃; analog dem Tricaprylin;
im Vakuum unter Durchleiten eines trocknen Luftstroms;
With dmap; dicyclohexyl-carbodiimide 1.) CH2Cl2, 2.) CH2Cl2; Multistep reaction;
at 240℃; under 150.015 - 760.014 Torr; for 3h; Temperature; Inert atmosphere;	412 g

n-decanoyl chloride (112-13-0) + glycerol (56-81-5) → capric acid triglyceride (621-71-6) + pyridine hydrochloride (628-13-7)

Conditions	Yield
Stage #1: n-decanoyl chloride; glycerol With pyridine In dichloromethane at 20 - 35℃; for 0.0833333 - 0.25h; Stage #2: With dmap at 20℃;	A 86% B n/a

n-decanoyl chloride (112-13-0) + glycerol (56-81-5) → capric acid triglyceride (621-71-6)

Conditions	Yield
With pyridine; chloroform

1-decanoic acid (334-48-5) + glycerol (56-81-5) → capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1, 3-dicaprin (17598-93-5)

Conditions	Yield
In 2,2,4-trimethylpentane at 25℃; for 10h; Product distribution; liophilized lipase F-AP15 from Rhizopus javanicus, phosphate buffer pH=10; other lipases from various microbial origins, other temperature, solvents and var. pH;
With Lipozyme RM IM In n-heptane at 60℃; for 6h; Solvent; Time; Enzymatic reaction;

decanoic acid ethyl ester (110-38-3) + glycerol (56-81-5) → capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 2-decanoyloxy-propane-1,3-diol (3376-48-5) + 1,2-didecanoyl glycerol (17863-69-3) + 1, 3-dicaprin (17598-93-5)

Conditions	Yield
With triacylglycerol acyl hydrolase on EP100 (porous polypropylene) at 40℃; Product distribution; other donors; effect of water content; var. temp.; different molar ratios;

1-decanoic acid (334-48-5) + glycerol (56-81-5) → capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1,2-didecanoyl glycerol (17863-69-3) + 1, 3-dicaprin (17598-93-5)

Conditions	Yield
With lipozyme at 35℃; under 3 Torr; for 12h; Esterification;	A 6.62 % Chromat. B 6.15 % Chromat. C 0.83 % Chromat. D 84.37 % Chromat.

methyl octanate (111-11-5) + Methyl decanoate (110-42-9) + glycerol (56-81-5) → decanoic acid 2-decanoyloxy-3-octanoyloxypropyl ester + decanoic acid 2-octanoyloxy-1-octanoyloxymethylethyl ester + decanoic acid 2,3-bis-octanoyloxypropyl ester + decanoic acid 3-decanoyloxy-2-octanoyloxypropyl ester + tricaprilin (538-23-8) + capric acid triglyceride (621-71-6)

Conditions	Yield
potassium methanolate at 60 - 200℃; for 0.916667h; Industry scale; Under nitrogen;

...Expand

1-decanoic acid (334-48-5) + glycerol (56-81-5) → (S)-1,2-O-didecanoyl-sn-glycerol (60514-49-0) + capric acid triglyceride (621-71-6) + 3-decanoyloxy-propane-1,2-diol (2277-23-8) + 1, 3-dicaprin (17598-93-5) + (R)-2,3-O-didecanoyl-sn-glycerol (172588-12-4)

Conditions	Yield
With Rhizomucor miehei 1,3-specific lipase immobilized by adsorption on anion exchange phenolic resin Duolite A-568; silica gel In n-heptane at 50℃; for 6h; Concentration; Temperature; Enzymatic reaction;

capric acid triglyceride (621-71-6) → 1-Decanol (112-30-1) + glycerol (56-81-5)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; water at 70℃; for 4h;	A 93% B n/a

methanol (67-56-1) + capric acid triglyceride (621-71-6) → Methyl decanoate (110-42-9) + glycerol (56-81-5)

Conditions	Yield
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane for 8.5h; Heating;	A 89% B 82%

capric acid triglyceride (621-71-6) → n-decanenitrile (1975-78-6)

Conditions	Yield
With ammonia at 220℃; for 40h; Autoclave;	89%

capric acid triglyceride (621-71-6) + ethanol (64-17-5) → decanoic acid ethyl ester (110-38-3)

Conditions	Yield
With C30H42N2; potassium tert-butylate In tetrahydrofuran at 20℃; for 8h; Molecular sieve;	84%

capric acid triglyceride (621-71-6) → 1-Decanol (112-30-1)

Conditions	Yield
With 5 wt% Re/TiO2; hydrogen In neat (no solvent) at 230℃; under 37503.8 Torr; for 24h; Autoclave;	80%

tricaprilin (538-23-8) + capric acid triglyceride (621-71-6) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin octanoic acid monoester + di-O-octanoyl-all-trans-astaxanthin + astaxanthin decanoic acid monoester + astaxanthin decanoic acid diester

Conditions	Yield
immobilized lipase In hexane; water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	A 9.5% B 1% C 9.1% D 1%
immobilized lipase In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	A 7.2% B 1% C 6.1% D 1%
lipase OF (from Candida) In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	A 3.9% B 1% C 3% D 1%

capric acid triglyceride (621-71-6) → 1,2-didecanoyl glycerol (17863-69-3)

Conditions	Yield
for 2h; Ambient temperature; phosphate buffer pH 7.00; Rhizopus oryzae lipase;

capric acid triglyceride (621-71-6) + 1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane (537-40-6) → 2-decanoyl-1,3-dilinoleoylglycerol

Conditions	Yield
With 1,3-specific lipase at 60℃; for 5h;

capric acid triglyceride (621-71-6) → 2-decanoyloxy-propane-1,3-diol (3376-48-5) + (R)-2,3-O-didecanoyl-sn-glycerol (172588-12-4)

Conditions	Yield
With ethanol; immobilized Rhizomucor miehei lipase at 25℃; for 0.833333h;

capric acid triglyceride (621-71-6) → Decanoic acid 1-decanoyloxymethyl-2-(2-fluoro-2-naphthalen-2-yl-acetoxy)-ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / Ambient temperature; phosphate buffer pH 7.00; Rhizopus oryzae lipase 2: dicyclohexylcarbodiimide, 4-dimethylpyridine / CH2Cl2 / Ambient temperature View Scheme

capric acid triglyceride (621-71-6) → Decanoic acid 1-decanoyloxymethyl-2-(2-fluoro-2-naphthalen-1-yl-acetoxy)-ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / Ambient temperature; phosphate buffer pH 7.00; Rhizopus oryzae lipase 2: dicyclohexylcarbodiimide, 4-dimethylpyridine / CH2Cl2 / Ambient temperature View Scheme

capric acid triglyceride (621-71-6) → Decanoic acid 1-decanoyloxymethyl-2-(2-fluoro-2-naphthalen-1-yl-propionyloxy)-ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / Ambient temperature; phosphate buffer pH 7.00; Rhizopus oryzae lipase 2: dicyclohexylcarbodiimide, 4-dimethylpyridine / CH2Cl2 / Ambient temperature View Scheme

capric acid triglyceride (621-71-6) → methyl nonyl ketone (112-12-9)

Conditions	Yield
With acetic acid at 400℃;

capric acid triglyceride (621-71-6) → 2-decanoyloxy-propane-1,3-diol (3376-48-5)

Conditions	Yield
With pancreatin lipase In aq. buffer at 37℃; for 3h; pH=6.5; Enzymatic reaction;

capric acid triglyceride (621-71-6) + ethyl ferulate (28028-62-8, 74257-26-4, 4046-02-0) → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + C33H42O10 + C33H52O8 + C23H34O7 + C23H34O7 + 1-O-feruloyl glycerol

Conditions	Yield
With Novozym 435 at 60℃; for 504h; Inert atmosphere; Enzymatic reaction;	A n/a B 14.35 %Chromat. C 44.4 %Chromat. D 1.36 %Chromat. E 5.98 %Chromat. F n/a

capric acid triglyceride (621-71-6) → decanamide (2319-29-1)

Conditions	Yield
With ammonia at 180℃; for 5h; Autoclave;	86 %Chromat.

capric acid triglyceride (621-71-6) → 1-aminodecane (2016-57-1) + didecylamine (1120-49-6)

Conditions	Yield
With ammonium hydroxide; hydrogen at 220℃; under 41254.1 Torr; for 36h; Autoclave;	A 51 %Chromat. B 30 %Chromat.

Upstream product

• 112-13-0 n-decanoyl chloride 
• 56-81-5 glycerol 
• 334-48-5 1-decanoic acid 
• 110-38-3 decanoic acid ethyl ester 
• 111-11-5 methyl octanate 
• 110-42-9 Methyl decanoate 

Downstream Products

• 112-30-1 1-Decanol 
• 56-81-5 glycerol 
• 2016-57-1 1-aminodecane 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 110-38-3 decanoic acid ethyl ester 
• 112-12-9 methyl nonyl ketone 
• 3376-48-5 2-decanoyloxy-propane-1,3-diol 
• 172588-12-4 (R)-2,3-O-didecanoyl-sn-glycerol 
• 110-42-9 Methyl decanoate 
• 1120-49-6 didecylamine 
• 1975-78-6 n-decanenitrile 
• 2319-29-1 decanamide 
• 17863-69-3 1,2-didecanoyl glycerol 

Relevant articles and documents

MANUFACTURING METHOD OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE, AND MANUFACTURING DEVICE OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE

PROBLEM TO BE SOLVED: To provide a method capable of manufacturing a middle chain aliphatic acid triglyceride having good color tone and excellent stability, and a manufacturing device using the method. SOLUTION: There is disclosed a manufacturing method of middle chain aliphatic acid triglyceride and a manufacturing device of middle chain aliphatic acid triglyceride. The manufacturing method includes (a) a process for supplying a reaction system containing middle chain aliphatic acid and glycerin to an esterification reaction to obtain a reaction product containing the middle chain aliphatic acid triglyceride, (b) a process for removing unreacted middle chain aliphatic acid from the reaction product to obtain a reacted de-aliphatic acid product, and (c) a process for distilling the reacted de-aliphatic acid product using a thin film distillation machine to obtain a distilled product. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2019,JPOandINPIT

Separation of acylglycerides obtained by enzymatic esterification using solvent extraction

New avenues to add value to glycerol are currently being explored. One of them is the synthesis of structured lipids through glycerol esterification. In this work we have analyzed the recovery and purification of dicaprin obtained by esterification of glycerol with capric acid (C) in heptane, mediated by Lipozyme RM IM. This is an intermediate step to obtain lipids MLM. In the first stage, the diglyceride synthesis MGM (being G a central HC-OH) was carried out. When M = C, the diglyceride is CGC. Recovery of the diglyceride CGC is required to carry out the esterification of the sn-2 position with palmitic acid (P), thus obtaining the triglyceride CPC. Different solvents were evaluated using Ecofac 1.0 (a molecular design software solvent) through a theoretical approach to explore the best solvents for the acylglycerides separation. Then, the performance of the selected solvents to separate dicaprin from mono and tricaprin was experimentally studied in a liquid-liquid extraction process. Previously, the remaining fatty acid had been neutralized. With liquid-liquid extraction in three simple steps, using ethanol/water, 94 % of the dicaprin obtained by enzymatic esterification was recovered with a purity of 89 % (wt%). It was also possible to obtain dicaprin with a purity of 97 % but with a yield of 56 %.

TREATMENT OF NEURODEGENERATIVE CONDITIONS

A method is provided for treating a patient in need of therapy for a neurodegenerative disease comprising administering to that patient a therapeutically effective dose of a lipid glyceride comprising a glycerol moiety and a fatty acid moiety, the fatty acid moiety being selected from the group consisting of γ-linolenic acid, dihomo-γ-linolenic acid and arachidonic acid characterised in that the selected fatty acid moiety is attached to the glycerol moiety at its sn-2 position. Preferably the method is that wherein the lipid is administered for a duration and at a dose sufficient to maintain or elevate TGF-β1 levels in the patient to therapeutic levels.