60-01-5 Usage
Description
Tributyrin (C15H26O6), also known as butyrin or glyceryl tributyrate, is the triester of glycerin and butyric acid. It is prepared by esterifcation of glycerin with excess butyric acid. Glycerol tributyrate has a characteristic odor and a bitter taste.Tributyrin is essentially a triacylglyceride (TAG), which is an ester derived from glycerol and 3 fatty acids. Tributyrin requires lipase to release the butyrate attached to the glycerol. Although 1 tributyrin contains 3 butyrate, not all 3 butyrate is guaranteed to be released. This is because lipase is regioselective. It can hydrolyse triacylglycerides at R1 and R3, only R2, or non-specifically. Lipase also has substrate specificity in that the enzyme can differentiate between acyl chains attached to the glycerol and preferentially cleaving certain types. Since tributyrin requires lipase to release its butyrate, there may be competition between tributyrin and other TAGs for lipase.
Chemical Properties
Different sources of media describe the Chemical Properties of 60-01-5 differently. You can refer to the following data:
1. Glycerol tributyrate has a characteristic odor and bitter taste.
2. Tributyrin is a colorless, oily liquid
with a bitter taste. It is soluble in alcohol and ether and fairly insoluble in water.
Uses
Different sources of media describe the Uses of 60-01-5 differently. You can refer to the following data:
1. Tributyrin is a stable and rapidly absorbed prodrug of butyric acid which enhances antiproliferative effects of dihydroxycholecalciferol in human colon cancer cells.
2. Tributyrin is a flavoring agent that is the triester of glycerin and
butyric acid. it is prepared by esterification of glycerin with excess
butyric acid. it is used in the following foods: baked goods; alcoholic
beverages; nonalcoholic beverages; fats and oils; frozen dairy des-
serts and mixes; gelatins, puddings and fillings; and soft candy. it is
also termed butyrin and glyceryl tributyrate.
Preparation
Prepared by esterifcation of glycerol with excess butyric acid.
Production Methods
Tributyrin is manufactured via esterification of glycerol
with butyric acid.
Definition
ChEBI: A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.
Taste threshold values
Taste characteristics at 30 ppm: bitter, waxy, fatty, cheese and butter nuances.
General Description
Tributyrin is a short-chain triacylglycerol that mainly occurs in butter. It shows potent anti-cancer property.
Safety Profile
Poison by intravenous
route. Low toxicity by ingestion.
Questionable carcinogen with experimental
tumorigenic data. Combustible liquid. When
heated to decomposition it emits acrid
smoke and irritating fumes. See also
ESTERS
Carcinogenicity
Administration of sodium
butyrate in drinking water potentiates 1,2-dimethylhydrazine-
induced colon cancer in rats . In mice, dietary
administration of 5% tributyrin for 48 weeks did not lead to
an increase in colonic tumor incidence or focal areas of
dysplasia as compared to controls . Therefore, it has
been suggested that the agent responsible for enhanced
tumorigenesis in the rat study was sodium, rather than
butyrate.
Check Digit Verification of cas no
The CAS Registry Mumber 60-01-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 60-01:
(4*6)+(3*0)+(2*0)+(1*1)=25
25 % 10 = 5
So 60-01-5 is a valid CAS Registry Number.
60-01-5Relevant articles and documents
Efficient and regioselective ring-opening of epoxides with carboxylic acid catalyzed by graphite oxide
Mirza-Aghayan, Maryam,Tavana, Mahdieh Molaee,Niazi, Elaheh Golam Alipour,Boukherroub, Rabah
, p. 532 - 538 (2020/07/17)
An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleo-phile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.
Method for synthesizing butyrin
-
Paragraph 0017-0019, (2017/09/08)
The invention provides a method for synthesizing butyrin. According to the method, butyric acid, glycerinum, a catalyst and a solid dehydrating agent are subjected to an esterification reaction under the heating condition, after the reaction is finished, filtration is conducted, a sodium hydroxide solution is dropwise added to the filtrate until the filtrate is neutral, then still standing and layering are conducted, the supernatant oil phase is taken to pass through an anhydrous sodium sulfate dry column, and the butyrin product is obtained. According to the method, it is avoided that an organic solvent serves as a water-carrying agent, the evaporation cost is decreased, the potential production safety hazard is reduced, pollution to the environment is avoided, and the synthesis technology is environmentally friendlier and safer; meanwhile, it is avoided that the organic solvent possibly remains in the product to cause potential safety hazard when the product is applied to feed-products; in addition, the esterification reaction is more efficient by the addition of the solid dehydrating agent, the reaction time is shortened and the reaction conversion ratio is increased.
A method for preparing butyrin
-
Paragraph 0025-0026, (2017/03/17)
The invention provides a method for preparing tributyrin. The method comprises the following steps: reacting glycerinum with butyryl chloride by taking organic alkali as a acid-binding agent, thereby obtaining a mixture containing tributyrin, wherein the mole ratio of the three materials, namely, glycerinum, butyryl chloride and organic alkali, is 1:(3-3.3):3.3. The method further comprises the following steps: extracting a mixture containing tributyrin by using water, collecting an organic phase, and performing reduction vaporization to remove a solvent in the organic phase, thereby obtaining tributyrin. In the method, the mole ratio of butyryl chloride to glycerinum is kept at (3-3.3):1 during reaction, and massive over amount is not needed. In addition, after the reaction is completed, residual trace butyryl chloride can be hydrated into butyric acid and hydrochloric acid in the following water washing process and can be carried away by a water phase together with residual glycerinum, thus a purpose that butyryl chloride is separated from a target object is achieved.
