Glycerol tributanoate
[CAS# 60-01-5]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aliphatic carboxylate
• Name: Glycerol tributanoate
• Synonyms: NSC 661583; Tri-n-butyrin; Tributanoin; Tributin; Tributyrin; Tributyroin; Tributyryl glyceride; Tributyrylglycerol
• Molecular Formula: C₁₅H₂₆O₆
• Molecular Weight: 302.36
• CAS Registry Number: 60-01-5
• EC Number: 200-451-5
• SMILES: CCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC

Properties

• Solubility: Very slightly soluble (0.28 g/L) (25 ºC), Calc.^*
• Density: 1.0350 g/cm³ (20 ºC)^**
• Melting point: 68 ºC^***
• Boiling point: 307-308 ºC
• Refractive index: 1.4359 (589.3 nm 20 ºC)^****
• Flash point: 174 ºC

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US)

^*** Klein, G.; Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 1936, V69B, P2066-8.

^**** Klykov, V. N.; Zhurnal Organicheskoi Khimii 1965, V1(2), P253-6.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Discovory and Applicatios

Glycerol tributanoate, also known as tributyrin, was discovered in the early 19th century during studies on the composition of fats and oils. With the molecular formula C15H26O6, tributyrin is a triglyceride consisting of glycerol esterified with three butyric acid molecules. The identification and synthesis of glycerol tributanoate provided significant insights into the structure and function of fats, contributing to the broader understanding of biochemistry and lipid chemistry.

Tributyrin is widely used in the nutraceutical industry for its potential health benefits. It serves as a source of butyric acid, a short-chain fatty acid important for gut health. Butyric acid is known to support intestinal barrier function, reduce inflammation, and promote the growth of beneficial gut bacteria.

In the pharmaceutical industry, tributyrin is used as a drug delivery agent. Its ability to release butyric acid upon hydrolysis makes it useful in formulations designed to target specific regions of the gastrointestinal tract. Tributyrin is also being researched for its potential in treating various conditions, including inflammatory bowel disease, cancer, and metabolic disorders, due to its anti-inflammatory and anti-carcinogenic properties.

Tributyrin is utilized as a flavoring agent and emulsifier in the food industry. Its pleasant buttery taste makes it an ideal additive in various food products, including baked goods, dairy products, and confections. As an emulsifier, tributyrin helps stabilize food emulsions, improving texture and shelf-life.

In the cosmetics and personal care industry, tributyrin is used for its moisturizing and emollient properties. It is incorporated into lotions, creams, and other skincare products to provide hydration and improve skin texture. Tributyrin's ability to penetrate the skin barrier and deliver butyric acid also contributes to its effectiveness in promoting skin health and reducing inflammation.

Tributyrin finds use in various industrial applications as well. It is used as a plasticizer in polymer production, enhancing the flexibility and durability of plastics. Additionally, tributyrin is employed as a lubricant and anti-corrosion agent in machinery and equipment.

References

Mi-Young Kim, Gon Seo, O Zoon Kwon and Duk Rye Chang. The exceptional activity of a phosphazenium hydroxide catalyst incorporated onto silica in the transesterification of tributyrin with methanol, Chem. Commun., 2009, 3110.