glycerol monostearate

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 415508712

| Name = Glycerol monostearate

| ImageAlt1 = Structural formula of 1-glycerol monostearate

| ImageFile1 = Stearoyl-1-glycerol.png

| ImageFile2 = Stearoyl-2-glycerol.png

| ImageSize1 = 250px

| ImageSize2 = 250px

| ImageFile3 = Glycerol monostearate 3D ball.png

| ImageCaption1 = 1-glycerol monostearate (1-isomer)

| ImageCaption2 = 2-glycerol monostearate (2-isomer)

| IUPACName = 2,3-Dihydroxypropyl octadecanoate

| ImageCaption3 = 3D model (1-isomer)

| OtherNames = Glyceryl monostearate
Glycerin monostearate
Monostearin
GMS

| Section1 = {{Chembox Identifiers

| index_label = (Mix)

| index1_label = (1-)

| index2_label = (2-)

| index_comment = Mixture of 1- and 2- isomers

| index1_comment = 1-glycerol monostearate

| index2_comment = 2-glycerol monostearate

| Abbreviations = GMS

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 23095

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01947

| 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

| InChIKey = VBICKXHEKHSIBG-UHFFFAOYAT

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 255696

| InChI1_Ref = {{stdinchicite|correct|chemspider}}

| InChI1 = 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

| InChIKey1_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey1 = VBICKXHEKHSIBG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 31566-31-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 258491E1RZ

| CASNo1 = 123-94-4

| CASNo2 = 621-61-4

| PubChem1 = 24699

| PubChem2 = 79075

| SMILES = O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC

}}

| Section2 = {{Chembox Properties

| C=21|H=42|O=4

| Appearance = White solid

| Density = 1.03 g/cm³

| MeltingPt_notes = (Mix) {{convert|57|-|65|C|F}}

(1-) {{convert|81|C|F}} {{cite journal|last1=Averill|first1=H. P.|last2=Roche|first2=J. N.|last3=King|first3=C. G.|title=Synthetic Glycerides. I. Preparation and Melting Points of Glycerides of Known Constitution1|journal=Journal of the American Chemical Society|date=March 1929|volume=51|issue=3|pages=866–872|doi=10.1021/ja01378a032|bibcode=1929JAChS..51..866A }}

(2-) {{convert|73|-|74|C|F}} {{cite journal|last1=Buchnea|first1=Dmytro|title=Acyl migration in glycerides. I. A bimolecular resonant ion complex as intermediate in acyl migration of monoglycerides|journal=Chemistry and Physics of Lipids|date=February 1967|volume=1|issue=2|pages=113–127|doi=10.1016/0009-3084(67)90004-7}}

| BoilingPtC =

| Solubility = Insoluble

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| NFPA-H = 0

| NFPA-F = 1

| NFPA-I = 0

| NFPA-S =

| FlashPt = {{convert|230|°C|°F|abbr=on}} (open cup)

| AutoignitionPt = }}

}}

Glycerol monostearate, commonly known as GMS, is a monoglyceride commonly used as an emulsifier in foods.{{cite journal | title = Food emulsifiers: Surface activity, edibility, manufacture, composition, and application | journal = Journal of the American Oil Chemists' Society | volume = 53 | issue = 6 | year = 1976 | pages = 400–407 | author = Jens Birk Lauridsen | doi = 10.1007/BF02605731| s2cid = 86707965 }} 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, 2-glycerol monostearate and the enantiomeric pair of 1-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.{{cite journal|last1=Sonntag|first1=Norman O. V.|title=Glycerolysis of fats and methyl esters – Status, review and critique|journal=Journal of the American Oil Chemists' Society|volume=59|issue=10|year=1982|pages=795A–802A|issn=0003-021X|doi=10.1007/BF02634442|s2cid=84808531}}

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.[http://www.intox.org/databank/documents/chemical/glycmono/cie536.htm Glycerol monostearate] Cheminfo

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.