Monoglyceride

Molecular structure of 1-monoacylglycerol
Molecular structure of 2-monoacylglycerol

A Monoglyceride is a glyceride in which each glycerol molecule has formed an ester bond with exactly one fatty acid molecule. The more formally correct terms in modern convention are acylglycerol and monoacylglycerol.

Any monoacylglycerol is either a 1-monoacylglycerol or a 2-monoacylglycerol, depending on the position of the ester bond on the glycerol moiety. 1-monoacylglycerides possess a chiral centre at carbon 2.

Monoacylglycerols are variously produced by biological or industrial chemical processes. Biochemically they commonly are formed by enzymatic hydrolysis of triglycerides by the action of lipoprotein lipase, by enzymatic hydrolysis of a fatty acid from diacylglycerol by the action of diacylglycerol lipase, or as an intermediate in the alkanoylation of glycerol to form fats.

In normal metabolic processes, monoacylglycerols are hydrolysed by monoacylglycerol lipase to produce glycerol and a free fatty acid as required.

Together with diglycerides, monoglycerides are commonly added to commercial food products in small quantities (e.g. Monolaurin). In these applications they are useful as emulsifiers, helping to mix ingredients such as oily materials and water that otherwise would blend poorly.[1] The values given in the nutritional labels for total fat, saturated fat, and trans fat do not include those present in mono- and diglycerides as fats are defined as being triglycerides.

The commercial raw materials for the production of monoacylglycerols may be either vegetable or animal fats and oils. Bulk animal sources typically are cattle or hogs, but any economically available triacylglycerols with acceptable fatty-acid composition may be used as preferred. Monoacylglycerols also may be made synthetically. They are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections.[2] In bakery products, monoglycerides are useful in improving loaf volume and texture, and as antistaling agents.[3][4]

One particular monoacylglycerol, 2-arachidonoylglycerol, is a full agonist of CB1 cannabinoid receptors.

Another monoacylglycerol agonist is 2-oleoylglycerol, which is a GPR119 agonist.[5]

See also

References

  1. ↑ "Questions About Food Ingredients". Vegetarian Resource Group. Retrieved 13 November 2011.
  2. ↑ Zdzislaw Z. E. Sikorski; Anna Kolakowska (30 July 2002). Chemical and Functional Properties of Food Lipids. CRC Press. pp. 218–. ISBN 978-1-4200-3199-7.
  3. ↑ Y. H. Hui (15 February 2008). Bakery Products: Science and Technology. John Wiley & Sons. pp. 350–. ISBN 978-0-470-27632-7.
  4. ↑ Gerard L. Hasenhuettl; Richard W. Hartel (1 January 1997). Food Emulsifiers and Their Applications. Springer. ISBN 978-0-412-07621-3.
  5. ↑ Hansen, K. B.; Rosenkilde, M. M.; Knop, F. K.; Wellner, N.; Diep, T. A.; Rehfeld, J. F.; Andersen, U. B.; Holst, J. J.; Hansen, H. S. (2011). "2-Oleoyl Glycerol is a GPR119 Agonist and Signals GLP-1 Release in Humans". Journal of Clinical Endocrinology & Metabolism 96 (9): E1409–E1417. doi:10.1210/jc.2011-0647. PMID 21778222.


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