Glycerol monostearate

Glycerol monostearate
	; 1-glycerol monostearate (1-isomer)
	; 2-glycerol monostearate (2-isomer)
	; 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;
CAS Number	(Mix): 31566-31-1 ; (1-): 123-94-4; (2-): 621-61-4;
3D model (JSmol)	(Mix): Interactive image;
Abbreviations	GMS
ChEMBL	(Mix): ChEMBL255696 ;
ChemSpider	(Mix): 23095 ;
ECHA InfoCard	100.046.081
KEGG	(Mix): D01947 ;
PubChem CID	(1-): 24699; (2-): 79075;
UNII	(Mix): 258491E1RZ ;
CompTox Dashboard (EPA)	(Mix): DTXSID7027968 ;
	InChI (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 Key: VBICKXHEKHSIBG-UHFFFAOYSA-N ;
	SMILES (Mix): O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC;
Properties
Chemical formula	C21H42O4
Molar mass	358.563 g·mol−1
Appearance	White solid
Density	1.03 g/cm3
Melting point	(Mix) 57–65 °C (135–149 °F) ; (1-) 81 °C (178 °F) ; (2-) 73–74 °C (163–165 °F)
Solubility in water	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). verify (what is ?) Infobox references

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.

Compendial status

British Pharmacopoeia^[6]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ Glycerol monostearate Cheminfo
^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 18 March 2010.

[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.

[Sonntag1982-4] 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

[ib29-6] The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 18 March 2010.

[3]

[1]

[2]

[4]

[5]

[6]

Glycerol monostearate

Contents

Structure, synthesis, and occurrence

Uses

See also

Compendial status

References

Names
1-glycerol monostearate (1-isomer)
2-glycerol monostearate (2-isomer)
3D model (1-isomer)
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
CAS Number	(Mix): 31566-31-1^Y (1-): 123-94-4 (2-): 621-61-4
3D model (JSmol)	(Mix): Interactive image
Abbreviations	GMS
ChEMBL	(Mix): ChEMBL255696^Y
ChemSpider	(Mix): 23095^Y
ECHA InfoCard	100.046.081
KEGG	(Mix): D01947^Y
PubChem CID	(1-): 24699 (2-): 79075
UNII	(Mix): 258491E1RZ^Y
CompTox Dashboard (EPA)	(Mix): DTXSID7027968
InChI (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^Y Key: VBICKXHEKHSIBG-UHFFFAOYSA-N^Y
SMILES (Mix): O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC
Properties
Chemical formula	C₂₁H₄₂O₄
Molar mass	358.563 g·mol⁻¹
Appearance	White 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]
Solubility in water	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). N verify (what is ^YN ?) Infobox references