Glycerol monostearate: Difference between revisions

{{distinguish|glycol monostearate}}

{{Use dmy dates|date=June 2021}}

| 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<br/>Glycerin monostearate<br/>Monostearin<br>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

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

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

| InChI1_Ref = {{stdinchicite|correct|chemspider}}<!-- todo: check if this is InChI for index 1 or 2 DePiep Jan2018 -->

| 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 = 31566-31-1

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

| UNII = 258491E1RZ

| CASNo1 = 123-94-4

| CASNo2 = 621-61-4

| PubChem1 = 24699

| PubChem2 = 79075

| 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}} <BR />

(1-) {{convert|81|C|F}} <ref>{{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}}</ref> <BR />

(2-) {{convert|73|-|74|C|F}} <ref>{{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}}</ref>

| BoilingPtC =

| Solubility = Insoluble

}}

| Section3 = {{Chembox Hazards

| NFPA-H = 0

| NFPA-F = 1

| NFPA-I = 0

| NFPA-S =

| AutoignitionPt = }}

'''Glycerol monostearate''', commonly known as '''GMS''', is a [[monoglyceride]] commonly used as an [[emulsifier]] in foods.<ref>{{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 }}</ref> 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 [[enantiomer|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 [[triglyceride]]s (from either [[vegetable]] or [[animal]] fats) and glycerol.<ref name="Sonntag1982">{{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}}</ref>

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 agent|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.<ref>[http://www.intox.org/databank/documents/chemical/glycmono/cie536.htm Glycerol monostearate] Cheminfo</ref>

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==

* [[Glyceryl hydroxystearate]]

* [[Monolaurin]]

* [[British Pharmacopoeia]]<ref name=ib29>{{cite web

|last=The British Pharmacopoeia Secretariat

|title=Index, BP 2009

|date=2009

|url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf

|access-date=18 March 2010

|url-status=dead

|archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf

|archive-date=11 April 2009

}}</ref>

[[Category:Vicinal diols]]

[[Category:Fatty acid esters]]

[[Category:Non-ionic surfactants]]

[[Category:Glycerol esters]]

[[Category:Stearate esters]]