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M7765

Sigma-Aldrich

1-Oleoyl-rac-glycerol

≥99%

Synonym(s):

MG(18:1(9Z)/0:0/0:0)[rac], 1-(cis-9-Octadecenoyl)-rac-glycerol, rac-Glycerol 1-monooleate, DL-α-Monoolein, Glyceryl cis-9-octadecenoate, Monoolein

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About This Item

Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOCH2CHOHCH2OH
CAS Number:
Molecular Weight:
356.54
Beilstein:
1728976
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic (organic)

Quality Level

description

non-ionic

Assay

≥99%

form

powder

mp

35 °C

functional group

ester

lipid type

neutral glycerides

shipped in

wet ice

storage temp.

−20°C

SMILES string

O=C(CCCCCCC/C=C\CCCCCCCC)OCC(O)CO

InChI

1S/C21H40O4/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/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

InChI key

RZRNAYUHWVFMIP-KTKRTIGZSA-N

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General description

1-Oleoyl-rac-glycerol is a monoglyceride, obtained from natural oils and fats. It contains two alcohol groups that are reactive. It is soluble in chloroform and hexane. It can be crystallized from hexane.

Application

1-Oleoyl-rac-glycerol has been used:
  • to mix with the sample by two-syringe method, to achieve lipidic cubic phase in crystallization technique
  • as a substrate for monoglyceride (MG) lipase assay
  • in the preparation of MG solution for the measurement of in vitro MG hydrolase activity

Biochem/physiol Actions

1-Oleoyl-rac-glycerol shows both inhibition and anti-inhibition action on the lipoprotein lipase mediated triglyceride hydrolysis.
Monoolein (1-Oleoyl-rac-glycerol) is used in the development of monoolein-based nanoparticulate liquid dispersions as possible vehicles for drug delivery.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

309.2 °F - closed cup

Flash Point(C)

154.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tuo Zhang et al.
Science advances, 3(8), e1700344-e1700344 (2017-09-07)
Zrt/Irt-like proteins (ZIPs) play fundamental roles in metal metabolism/homeostasis and are broadly involved in numerous physiological and pathological processes. The lack of high-resolution structure of the ZIPs hinders understanding of the metal transport mechanism. We report two crystal structures of
Liron Bitan-Cherbakovsky et al.
The journal of physical chemistry. B, 115(42), 11984-11992 (2011-09-10)
The incorporation of dendrimer into three lyotropic liquid crystalline (LLCs) mesophases is demonstrated for the first time. A second generation (G2) of poly(propylene imine) dendrimer (PPI) was solubilized into lamellar, diamond reverse cubic, and reverse hexagonal LLCs composed of glycerol
Structure of the agonist-bound neurotensin receptor
White JF, et al.
Nature, 490(7421), 508-508 (2012)
Elisabetta Esposito et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 80(2), 306-314 (2011-11-09)
The physico-chemical properties and in vivo efficacies of two nanoparticulate systems delivering the antiparkinsonian drug bromocriptine (BC) were compared in the present study. Monoolein Aqueous Dispersions (MADs) and Nanostructured Lipid Carriers (NLCs) were produced and characterized. Cryogenic transmission electron microscopy
Biophysical effects of monoglycerides in membrane systems, 16-16 (1995)

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