Tricaprylin

Base Information

• Chemical Name: Tricaprylin
• CAS No.: 538-23-8
• Deprecated CAS: 114355-15-6
• Molecular Formula: C27H50 O6
• Molecular Weight: 470.69
• Hs Code.: 2915900090
• European Community (EC) Number: 208-686-5
• NSC Number: 4059
• UNII: 6P92858988
• DSSTox Substance ID: DTXSID6021375
• Nikkaji Number: J54.226A
• Wikipedia: Axona
• Wikidata: Q2747851
• NCI Thesaurus Code: C29861
• RXCUI: 1314420
• Metabolomics Workbench ID: 153211
• ChEMBL ID: CHEMBL1406148
• Mol file: 538-23-8.mol

Synonyms:2-ethylhexanoic acid, 1,2,3-propanetriyl ester;glycerol tricaprylate;glycerol trioctanoate;glyceryl tricaprylate;glyceryl trioctanoate;octanoic acid, 1,2,3- propanetriyl ester;Panasate 800;tricaprylin;triethylhexanoin;trioctanoin;trioctanoylglyceride

Chemical Property of Tricaprylin

Chemical Property:

• Appearance/Colour: clear colorless to yellow viscous liquid
• Vapor Pressure: 1.92E-10mmHg at 25°C
• Melting Point: 9-10 °C
• Refractive Index: n20/D 1.448
• Boiling Point: 233 °C1 mm Hg(lit.)
• Flash Point: 209.3 °C
• PSA: 78.90000
• Density: 0.956 g/mL at 20 °C(lit.)
• LogP: 7.06610
• Storage Temp.: 2-8°C
• Solubility.: Miscible with most organic solvents including ethanol (95%). Captex 8000 is insoluble in water.
• Water Solubility.: 65mg/L at 20℃
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 26
• Exact Mass: 470.36073931
• Heavy Atom Count: 33
• Complexity: 461

Purity/Quality:

98%, ^*data from raw suppliers

Tricaprylin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Fatty Acids and Fats
• Canonical SMILES: CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)OC(=O)CCCCCCC
• Recent ClinicalTrials: A Phase III Multi Regional Clinical Trial (MRCT) of Tricaprilin in Mild to Moderately Severe Probable Alzheimer's Disease With Optional Open Label Extension
• Description: 1,2,3-Trioctanoyl glycerol is a triacylglycerol that contains octanoic acid at the sn-1, sn-2, and sn-3 positions. Dietary administration of 1,2,3-trioctanoyl glycerol (260 g/kg diet) increases hepatic and adipose tissue glucose-6-phosphate dehydrogenase (G6PDH), citrate cleavage enzyme (CCE), and malic enzyme activities in rats. It induces nuclear edema and cytolysis in tumor cells, but not normal hepatic cells, in a murine hepatic carcinoma model.
• Uses: glyceryl trioctanoate is an emollient with skin-softening abilities. tricaprylin is a skin-conditioning agent. Glytex(R) 273 is a low viscosity polyol ester suggested for use as a synthetic fiber lubricant. It offers a balance of moderate volatility and low varnishing behavior. For low to moderate denier polyester and nylon filament and staple yarn applications. Product Data Sheet

Technology Process of Tricaprylin

There total 9 articles about Tricaprylin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

Octanoic acid (124-07-2) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → tricaprilin (538-23-8)

Guidance literature:

With acetic acid; at 275 ℃; for 0.5h;

Reference yield:

Octanoic acid (124-07-2) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → tricaprilin (538-23-8) + monocaprylin (19670-49-6,502-54-5) + 1,3-dicaprylin (1429-66-9)

Guidance literature:

With sulfuric acid; In water; at 100 ℃; for 5h; under 400 Torr;

Reference yield:

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) + n-octanoic acid chloride (111-64-8) → tricaprilin (538-23-8)

Guidance literature:

With potassium hydroxide; water; at -10 - 0 ℃;

DOI:10.1021/ja01267a506

upstream raw materials:

Octanoic acid

glycerol

n-octanoic acid chloride

methyl octanate

Downstream raw materials:

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Octanoic acid

glycerol

propane

Refernces

• 1、 -. "METHOD FOR PREPARING MONOGLYCERIDES". Paragraph 0079-0081; 0084; 0085. . Retrieved 2020/08/18.
• 2、 -. "For producing fatty acid triglyceride method and of esterification reaction of esterification reaction device". Paragraph 0032-0033. . Retrieved 2017/03/21.