Glycerol monostearate

Glycerol monostearate, commonly known as GMS, is a

monoglyceride commonly used as an emulsifier in foods.[3]
Glycerol monostearate
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. 1-glycerol monostearate (1-isomer)

Contents
2-glycerol monostearate (2-isomer)
Structure, synthesis, and occurrence
Names
Uses
IUPAC name
See also
2,3-Dihydroxypropyl octadecanoate
Compendial status
Other names
References Glyceryl monostearate
Glycerin monostearate
Monostearin
Structure, synthesis, and occurrence Identifiers

Glycerol monostearate exists as three stereoisomers, the Compounds

enantiomeric pair of 1-glycerol monostearate and 2-glycerol (Mix): Mixture of 1- and 2- isomers
monostearate. Typically these are encountered as a mixture
(1-): 1-glycerol monostearate
as many of their properties are similar.
(2-): 2-glycerol monostearate
Commercial material used in foods is produced industrially
CAS Number (Mix): 31566-31-1 (https://
by a glycerolysis reaction between triglycerides (from either
vegetable or animal fats) and glycerol.[4] commonchemistry.cas.org/
detail?cas_rn=31566-31-
Glycerol monostearate occurs naturally in the body as a 1)
product of the breakdown of fats by pancreatic lipase. It is (1-): 123-94-4 (https://com
present at very low levels in certain seed oils.
monchemistry.cas.org/deta
il?cas_rn=123-94-4)
Uses (2-): 621-61-4 (https://com
monchemistry.cas.org/deta
GMS is a food additive used as a thickening, emulsifying, il?cas_rn=621-61-4)
anticaking, and preservative agent; an emulsifying agent for
oils, waxes, and solvents; a protective coating for 3D model (Mix): Interactive image (ht
hygroscopic powders; a solidifier and control release agent (JSmol)
tps://chemapps.stolaf.edu/j
in pharmaceuticals; and a resin lubricant. It is also used in mol/jmol.php?model=O%3
cosmetics and hair-care products.[5] DC%28OCC%28O%29C
O%29CCCCCCCCCCCCC
GMS is largely used in baking preparations to add "body"
CCCC)
to the food. It is somewhat responsible for giving ice cream
and whipped cream their smooth texture. It is sometimes Abbreviations GMS
used as an antistaling agent in bread.
ChEMBL (Mix): ChEMBL255696 (htt
It can also be used as an additive in plastic, where GMS ps://www.ebi.ac.uk/chembl
works as an antistatic and antifogging agent. This is db/index.php/compound/in
common in food packaging. spect/ChEMBL255696)
ChemSpider (Mix): 23095 (http://www.c
See also hemspider.com/Chemical-
Structure.23095.html)
Glyceryl hydroxystearate
Monolaurin ECHA InfoCard 100.004.242 (https://echa.
europa.eu/substance-infor
mation/-/substanceinfo/10
Compendial status 0.004.242)
British Pharmacopoeia [6] KEGG (Mix): D01947 (https://ww
w.kegg.jp/entry/D01947)
References PubChem CID (1-): 24699 (https://pubche
m.ncbi.nlm.nih.gov/compo
1. Averill, H. P.; Roche, J. N.; King, C. G. (March
und/24699)
1929). "Synthetic Glycerides. I. Preparation and
Melting Points of Glycerides of Known (2-): 79075 (https://pubche
Constitution1". Journal of the American Chemical m.ncbi.nlm.nih.gov/compo
Society. 51 (3): 866–872. und/79075)
doi:10.1021/ja01378a032 (https://doi.org/10.102
1%2Fja01378a032). CompTox (Mix): DTXSID7029160 (htt
Dashboard (EPA)
2. Buchnea, Dmytro (February 1967). "Acyl ps://comptox.epa.gov/dash
migration in glycerides. I. A bimolecular resonant board/DTXSID7029160)
ion complex as intermediate in acyl migration of
InChI
monoglycerides". Chemistry and Physics of
Lipids. 1 (2): 113–127. doi:10.1016/0009- (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,2-1
3084(67)90004-7 (https://doi.org/10.1016%2F000 9H2,1H3
9-3084%2867%2990004-7). Key: VBICKXHEKHSIBG-UHFFFAOYAT

3. Jens Birk Lauridsen (1976). "Food emulsifiers: (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,2-1
Surface activity, edibility, manufacture,
9H2,1H3
composition, and application". Journal of the Key: VBICKXHEKHSIBG-UHFFFAOYSA-N
American Oil Chemists' Society. 53 (6): 400–407.
doi:10.1007/BF02605731 (https://doi.org/10.100 SMILES
7%2FBF02605731). S2CID 86707965 (https://ap (Mix): O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC
i.semanticscholar.org/CorpusID:86707965). Properties
4. Sonntag, Norman O. V. (1982). "Glycerolysis of
fats and methyl esters — Status, review and Chemical formula C21H42O4
critique". Journal of the American Oil Chemists' Molar mass 358.563 g·mol−1
Society. 59 (10): 795A–802A.
Appearance White solid
doi:10.1007/BF02634442 (https://doi.org/10.100
7%2FBF02634442). ISSN 0003-021X (https://ww Density 1.03 g/cm3
w.worldcat.org/issn/0003-021X).
Melting point (Mix) 57–65 °C (135–
S2CID 84808531 (https://api.semanticscholar.org/
CorpusID:84808531). 149 °F)

5. Glycerol monostearate (http://www.intox.org/datab

(1-) 81 °C (178 °F) [1]
ank/documents/chemical/glycmono/cie536.htm)
Cheminfo (2-) 73–74 °C (163–
165 °F) [2]

Solubility in water Insoluble

 6. The British Pharmacopoeia Secretariat (2009). Hazards
"Index, BP 2009" (https://web.archive.org/web/20 Flash point 230 °C (446 °F) (open
090411071437/http://www.pharmacopoeia.co.uk/
cup)
pdf/2009_index.pdf) (PDF). Archived from the
original (http://www.pharmacopoeia.co.uk/pdf/200 Except where otherwise noted, data are given
9_index.pdf) (PDF) on 11 April 2009. Retrieved for materials in their standard state (at 25 °C
18 March 2010. [77 °F], 100 kPa).
verify (what is ?)
Infobox references

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