Glycerol monostearate

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Glycerol monostearate
Stearoyl-1-glycerol.png
1-glycerol monostearate (1-isomer)
Stearoyl-2-glycerol.png
2-glycerol monostearate (2-isomer)
Glycerol monostearate 3D ball.png
3D model (1-isomer)
Names
IUPAC name
2,3-Dihydroxypropyl octadecanoate
Other names
Glyceryl monostearate
Glycerin monostearate
Monostearin
GMS
Identifiers
  • Compounds
  • (Mix): Mixture of 1- and 2- isomers
  • (1-): 1-glycerol monostearate
  • (2-): 2-glycerol monostearate
3D model (JSmol)
AbbreviationsGMS
ChEMBL
ChemSpider
ECHA InfoCard 100.046.081 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • (Mix):InChI=1/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3
    Key: VBICKXHEKHSIBG-UHFFFAOYAT
  • (1-):InChI=1S/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3 Yes check.svgY
    Key: VBICKXHEKHSIBG-UHFFFAOYSA-N Yes check.svgY
  • (Mix):O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC
Properties
C21H42O4
Molar mass 358.563 g·mol−1
AppearanceWhite solid
Density 1.03 g/cm3
Melting point (Mix) 57–65 °C (135–149 °F)

(1-) 81 °C (178 °F) [1]
(2-) 73–74 °C (163–165 °F) [2]

Insoluble
Hazards
NFPA 704 (fire diamond)
0
1
0
Flash point 230 °C (446 °F) (open cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glycerol monostearate, commonly known as GMS, is a monoglyceride commonly used as an emulsifier in foods. [3] It takes the form of a white, odorless, and sweet-tasting flaky powder that is hygroscopic. Chemically it is the glycerol ester of stearic acid. It is also used as hydration powder in exercise formulas

Structure, synthesis, and occurrence

Glycerol monostearate exists as three stereoisomers, the enantiomeric pair of 1-glycerol monostearate and 2-glycerol monostearate. Typically these are encountered as a mixture as many of their properties are similar.

Commercial material used in foods is produced industrially by a glycerolysis reaction between triglycerides (from either vegetable or animal fats) and glycerol. [4]

Glycerol monostearate occurs naturally in the body as a product of the breakdown of fats by pancreatic lipase. It is present at very low levels in certain seed oils.

Uses

GMS is a food additive used as a thickening, emulsifying, anticaking, and preservative agent; an emulsifying agent for oils, waxes, and solvents; a protective coating for hygroscopic powders; a solidifier and control release agent in pharmaceuticals; and a resin lubricant. It is also used in cosmetics and hair-care products. [5]

GMS is largely used in baking preparations to add "body" to the food. It is somewhat responsible for giving ice cream and whipped cream their smooth texture. It is sometimes used as an antistaling agent in bread.

It can also be used as an additive in plastic, where GMS works as an antistatic and antifogging agent. This is common in food packaging.

See also

Compendial status

Related Research Articles

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

<span class="mw-page-title-main">Glyceride</span> Chemical esters commonly found in fats and oils

Glycerides, more correctly known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic.

<span class="mw-page-title-main">Lecithin</span> Generic term for amphiphilic substances of plant and animal origin

Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances, and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials.

<span class="mw-page-title-main">Glycerophospholipid</span> Class of lipids

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.

<span class="mw-page-title-main">Monoglyceride</span>

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

Sorbitan monostearate is an ester of sorbitan and stearic acid and is sometimes referred to as a synthetic wax.

<span class="mw-page-title-main">Polyglycerol polyricinoleate</span> Emulsion used in food production

Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids. In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another substance like lecithin to reduce viscosity. It is used at low levels, and works by decreasing the friction between the solid particles in molten chocolate, reducing the yield stress so that it flows more easily, approaching the behaviour of a Newtonian fluid. It can also be used as an emulsifier in spreads and in salad dressings, or to improve the texture of baked goods. It is made up of a short chain of glycerol molecules connected by ether bonds, with ricinoleic acid side chains connected by ester bonds.

Stillingia oil is an oil extracted from the seeds of plants of the Triadica genus such as Triadica sebifera and Triadica cochinchinensis. It is a drying oil used in paints and varnishes, and it is believed to be toxic in China. It must be distinguished from stillingia tallow, a fatty substance that surround the seeds in the fruit and must be removed before extracting the oil.

<span class="mw-page-title-main">Fatty acid ester</span>

Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary fats are chemically triglycerides.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

<span class="mw-page-title-main">Dough conditioner</span>

A dough conditioner, flour treatment agent, improving agent or bread improver is any ingredient or chemical added to bread dough to strengthen its texture or otherwise improve it in some way. Dough conditioners may include enzymes, yeast nutrients, mineral salts, oxidants and reductants, bleaching agents and emulsifiers. They are food additives combined with flour to improve baking functionality. Flour treatment agents are used to increase the speed of dough rising and to improve the strength and workability of the dough. While they are an important component of modern factory baking, some small-scale bakers reject them in favour of longer fermentation periods that produce greater depth of flavour.

Monolaurin (abbreviated GML; also called glycerol monolaurate, glyceryl laurate, and 1-lauroyl-glycerol) is a monoglyceride. It is the mono-ester formed from glycerol and lauric acid. Its chemical formula is C15H30O4.

<span class="mw-page-title-main">Glycerolysis</span>

In organic chemistry glycerolysis refers to any process in which chemical bonds are broken via a reaction with glycerol. The term refers almost exclusively to the transesterification reaction of glycerol with triglycerides (fats/oils) to form mixtures of monoglycerides and diglycerides. These find a variety of uses; as food emulsifiers, 'low fat' cooking oils and surfactants.

<span class="mw-page-title-main">Mono- and diglycerides of fatty acids</span> Emulsifier

Mono- and diglycerides of fatty acids (E471) refers to a naturally occurring class of food additive composed of diglycerides and monoglycerides which is used as an emulsifier. It is also used as a fruit coating agent. This mixture is also sometimes referred to as partial glycerides.

<span class="mw-page-title-main">Glyceryl behenate</span> Chemical compound

Glyceryl behenate is a fat used in cosmetics, foods, and oral pharmaceutical formulations. In cosmetics, it is mainly used as a viscosity-increasing agent in emulsions.

Lactylates are organic compounds that are FDA approved for use as food additives and cosmetic ingredients, e.g. as food-grade emulsifiers. These additives are non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks. Owing to their safety and versatile functionality, lactylates are used in a wide variety of food and non-food applications. In the United States, the Food Chemicals Codex specifies the labeling requirements for food ingredients including lactylates. In the European Union, lactylates must be labelled in accordance with the requirements of the applicable EU regulation. Lactylates may be labelled as calcium stearoyl lactylate (CSL), sodium stearoyl lactylate (SSL), or lactylic esters of fatty acids (LEFA).

<span class="mw-page-title-main">Diglyceride</span> Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

<span class="mw-page-title-main">Sucrose esters</span> Class of chemical compounds

Sucrose esters or sucrose fatty acid esters are a group of non-naturally occurring surfactants chemically synthesized from the esterification of sucrose and fatty acids. This group of substances is remarkable for the wide range of hydrophilic-lipophilic balance (HLB) that it covers. The polar sucrose moiety serves as a hydrophilic end of the molecule, while the long fatty acid chain serves as a lipophilic end of the molecule. Due to this amphipathic property, sucrose esters act as emulsifiers; i.e., they have the ability to bind both water and oil simultaneously. Depending on the HLB value, some can be used as water-in-oil emulsifiers, and some as oil-in-water emulsifiers. Sucrose esters are used in cosmetics, food preservatives, food additives, and other products. A class of sucrose esters with highly substituted hydroxyl groups, olestra, is also used as a fat replacer in food.

References

  1. Averill, H. P.; Roche, J. N.; King, C. G. (March 1929). "Synthetic Glycerides. I. Preparation and Melting Points of Glycerides of Known Constitution1". Journal of the American Chemical Society. 51 (3): 866–872. doi:10.1021/ja01378a032.
  2. Buchnea, Dmytro (February 1967). "Acyl migration in glycerides. I. A bimolecular resonant ion complex as intermediate in acyl migration of monoglycerides". Chemistry and Physics of Lipids. 1 (2): 113–127. doi:10.1016/0009-3084(67)90004-7.
  3. Jens Birk Lauridsen (1976). "Food emulsifiers: Surface activity, edibility, manufacture, composition, and application". Journal of the American Oil Chemists' Society. 53 (6): 400–407. doi:10.1007/BF02605731. S2CID   86707965.
  4. Sonntag, Norman O. V. (1982). "Glycerolysis of fats and methyl esters – Status, review and critique". Journal of the American Oil Chemists' Society. 59 (10): 795A–802A. doi:10.1007/BF02634442. ISSN   0003-021X. S2CID   84808531.
  5. Glycerol monostearate Cheminfo
  6. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 18 March 2010.