glyceryl monostearate

Glycerol monostearate
Names
	IUPAC name 2,3-Dihydroxypropyl octadecanoate
	Other names Glyceryl monostearate; Glycerin monostearate; Monostearin
Identifiers
Abbreviations	GMS
CAS Registry Number	123-94-4
ChEMBL	ChEMBL255696
ChemSpider	23095
	InChI 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 ; 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 ;
Jmol-3D images	Image
KEGG	D01947
PubChem	24699
	SMILES O=C(OCC(O)CO)CCCCCCCCCCCCCCCCC ;
Properties
Molecular formula	C21H42O4
Molar mass	358.56 g·mol−1
Appearance	White to yellowish solid
Density	0.97 g/cm3
Melting point	58 °C (136 °F; 331 K)
Boiling point	238 °C (460 °F; 511 K)
Solubility in water	Insoluble
Hazards
Flash point	230 °C (446 °F) (open cup)
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

モノステアリン酸グリセリン

WordNet

a trivalent radical derived from glycerol by removing the three hydroxyl radicals

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/03/09 13:09:11」(JST)

wiki en

[Wiki en表示]

Glycerol monostearate, commonly known as GMS, is an organic molecule used as an emulsifier.^[1] GMS is a colorless, odorless, and sweet-tasting flaky powder that is hygroscopic. It is a glycerol ester of stearic acid. It occurs naturally in the body as a by-product of the breakdown of fats, and is also found in fatty foods.

GMS is a food additive used as a thickening, emulsifying, anti-caking, 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.^[2]

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

§Compendial status

British Pharmacopoeia ^[3]

§References

^ 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.
^ Glycerol monostearate Cheminfo
^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". Retrieved 18 March 2010.

UpToDate Contents

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English Journal

Investigating the correlation between in vivo absorption and in vitro release of fenofibrate from lipid matrix particles in biorelevant medium.

Borkar N, Xia D, Holm R, Gan Y, Müllertz A, Yang M, Mu H.Author information Department of Pharmacy, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark.AbstractLipid matrix particles (LMP) may be used as better carriers for poorly water-soluble drugs than liquid lipid carriers because of reduced drug mobilization in the formulations. However, the digestion process of solid lipid particles and their effect on the absorption of poorly water-soluble drugs are not fully understood. This study aimed at investigating the effect of particle size of LMP on drug release in vitro as well as absorption in vivo in order to get a better understanding on the effect of degradation of lipid particles on drug solubilisation and absorption. Fenofibrate, a model poorly water-soluble drug, was incorporated into LMP in this study using probe ultrasound sonication. The resultant LMP were characterised in terms of particle size, size distribution, zeta potential, entrapment efficiency, in vitro lipolysis and in vivo absorption in rat model. LMP of three different particle sizes i.e. approximately 100nm, 400nm, and 10μm (microparticles) were produced with high entrapment efficiencies. The in vitro lipolysis study showed that the recovery of fenofibrate in the aqueous phase for 100nm and 400nm LMP was significantly higher (p<0.05) than that of microparticles after 30min of lipolysis, suggesting that nano-sized LMP were digested to a larger extent due to greater specific surface area. The 100nm LMP showed faster initial digestion followed by 400nm LMP and microparticles. The area under the plasma concentration-time curve (AUC) following oral administration of 100nm LMP was significantly higher (p<0.01) than that of microparticles and fenofibrate crystalline suspension (control). However, no significant difference was observed between the AUCs of 100nm and 400nm LMP. The same rank order on the in vivo absorption and the in vitro response was observed. The recovery (%) of fenofibrate partitioning into the aqueous phase during in vitro lipolysis and the AUC of plasma concentration-time curve of fenofibric acid was in the order of 100nm LMP>microparticles>control. In summary, the present study demonstrated the particle size dependence of bioavailability of fenofibrate loaded LMP in rat model which correlates well with the in vitro drug release performed in the biorelevant medium.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2014 Jan 23;51:204-10. doi: 10.1016/j.ejps.2013.09.022. Epub 2013 Oct 14.
Lipid matrix particles (LMP) may be used as better carriers for poorly water-soluble drugs than liquid lipid carriers because of reduced drug mobilization in the formulations. However, the digestion process of solid lipid particles and their effect on the absorption of poorly water-soluble drugs are
PMID 24134899

Binary blend of glyceryl monooleate and glyceryl monostearate for magnetically induced thermo-responsive local drug delivery system.

Mengesha AE, Wydra RJ, Hilt JZ, Bummer PM.Author information College of Pharmacy & Health Sciences, Drake University, Des Moines, Iowa, 50311, USA.AbstractPURPOSE: To develop a novel monoglycerides-based thermal-sensitive drug delivery system, specifically for local intracavitary chemotherapy.
Pharmaceutical research.Pharm Res.2013 Dec;30(12):3214-24. doi: 10.1007/s11095-013-1230-1. Epub 2013 Oct 25.
PURPOSE: To develop a novel monoglycerides-based thermal-sensitive drug delivery system, specifically for local intracavitary chemotherapy.METHODS: Lipid matrices containing mixtures of glyceryl monooleate (GMO) and glyceryl monostearate (GMS) were evaluated for their potential application as magnet
PMID 24158728

Exploration of hydrophobic modification degree of chitosan-based nanocomplexes on the oral delivery of enoxaparin.

Wang L, Li L, Sun Y, Tian Y, Li Y, Li C, Junyaprasert VB, Mao S.Author information School of Pharmacy, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016, China.AbstractThe objective of this paper is to elucidate the influence of lipophilic modification degree of chitosan on the peroral absorption of enoxaparin. A series of novel chitosan grafted glyceryl monostearate (GM) copolymers with different GM substitution degree were synthesized and the successful synthesis was confirmed by (1)H NMR, FTIR and X-ray diffraction. Enoxaparin loaded nanocomplexes with different carriers were prepared by self-assembly process. Influence of GM substitution degree and chitosan molecular weight in the copolymer on the properties of the nanocomplexes was investigated. Morphology of the nanocomplexes was observed by atomic force microscopy. Mucoadhesive properties of the nanocomplexes were characterized using mucin particle method. Initially, mucoadhesion of the nanocomplexes increased with the increase of GM substitution degree and it started to decrease when the substitution degree was up to 18.6%. A good linear relationship between GM substitution degree and in vivo absorption of enoxaparin in fasted rats was established in the substitution degree range of 0-11.1%. In agreement with mucoadhesion data, further increasing GM substitution degree to 18.6% caused a decrease in oral absorption. In conclusion, oral bioavailability of enoxaparin can be enhanced by structure modification of the carriers and the bioavailability is hydrophobic modification degree dependent.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2013 Nov 20;50(3-4):263-71. doi: 10.1016/j.ejps.2013.07.009. Epub 2013 Jul 26.
The objective of this paper is to elucidate the influence of lipophilic modification degree of chitosan on the peroral absorption of enoxaparin. A series of novel chitosan grafted glyceryl monostearate (GM) copolymers with different GM substitution degree were synthesized and the successful synthesi
PMID 23896170

Japanese Journal

Properties of Gastroretentive Sustained Release Tablets Prepared by Combination of Melt/Sublimation Actions of L-Menthol and Penetration of Molten Polymers into Tablets

Fukuda Mamoru,Goto Akinori
Chemical and Pharmaceutical Bulletin 59(10), 1221-1226, 2011
… On the other hand, faster sustained release properties were obtained by using glyceryl monostearate (GMS) due to its low hydrophobic nature. …
NAID 130001087087

既存添加物ウルシロウの成分分析

金哲龍,多田敦子,杉本直樹 [他],佐藤恭子,増田愛乃,山形一雄,山崎壮,棚元憲一
食品衛生学雑誌 = Journal of the Food Hygienics Society of Japan 47(4), 167-172, 2006-08-25
… リグリセリドであり，glyceryl tripalmitate (30.7%)，glyceryl dipalmitate monooleate (21.2%)，glyceryl dioleate monopalmitate (2.1%)，glyceryl monooleate monopalmitate monostearate(2.6%)，glyceryl dipalmitate monostearate (5.6%), glyceryl distearate monopalmitate(1.4%)を含んでいた．また，glyceryl dipalmitate monooleateの脂 …
NAID 10020349898

Optimum Heat Treatment Conditions for Masking the Bitterness of the Clarithromycin Wax Matrix

Yajima Toshio,Itai Shigeru,Takeuchi Hirofumi [他],KAWASHIMA Yoshiaki
Chemical & pharmaceutical bulletin 51(11), 1223-1226, 2003-11-01
… The effects of the contents of aminoalkyl methacrylate copolymer E (AMCE) in a wax matrix on the mechanism of polymorphic transformation of glyceryl monostearate (GM) were clarified by evaluating the enthalpy change defined as 1.51 (ΔH_1-ΔH_2)/ΔH_2, where ΔH_1 and ΔH_2 denote the enthalpies in the first and second thermal analyses, respectively. …
NAID 110003615192

Related Pictures

[1] 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.

[2] Glycerol monostearate Cheminfo

[ib29-3] The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". Retrieved 18 March 2010.

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