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49960

Sigma-Aldrich

1-Oleoyl-rac-glycerol

technical, ~40% (TLC)

Synonym(s):

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:
111-03-5
Molecular Weight:
356.54
Beilstein/REAXYS Number:
1728976
EC Number:
203-827-7
MDL number:
MFCD00042735
UNSPSC Code:
12352100
PubChem Substance ID:
57651231
NACRES:
NA.22

description

non-ionic

grade

technical

concentration

~40% (TLC)

impurities

15-40% diglyceride
15-40% triglyceride

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 commonly known as monoolein (MO). It is an amphiphilic molecule that is made up of a glycerol backbone and a hydrocarbon chain.

application

  • Bovine Serum Albumin (BSA) Encapsulated in DODAB: MO (1: 2) Liposomes for Targeted Drug Delivery: Development and Characterization: This study focuses on developing liposomes consisting of Dioctadecyldimethylammonium Bromide (DODAB) and 1-oleoyl-rac-glycerol for targeted drug delivery (A VAN DIJCK, 2014).
  • An Innovative Nanocarrier for Neuroprotection: Investigates the therapeutic benefits of encapsulating curcumin in stealth nanocarriers of DODAB and 1-oleoyl-rac-glycerol (MO) (1: 2) (T Soares, No Date Provided).
  • Supporting Information Light-responsive Molecular Release from Cubosomes using Swell-Squeeze Lattice Control: Discusses molecular release mechanisms in structures containing 1-oleoyl-rac-glycerol (BE Jones et al., No Date Provided).
  • The Potential of Macroporous Silica—Nanocrystalline Cellulose Combination for Formulating Dry Emulsion Systems with Improved Flow Properties: A DoE Study: Details the formulation of dry emulsion systems incorporating 1-oleoyl-rac-glycerol for improved pharmaceutical applications (M Pohlen, L Pirker, R Dreu, 2021).
  • The Metabolomic Bioenergetic Signature of Opa1-Disrupted Mouse Embryonic Fibroblasts Highlights Aspartate Deficiency: Includes an analysis of metabolic changes, noting the role of 1-oleoyl-rac-glycerol among other compounds (C Bocca et al., 2018).

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

309.2 °F - closed cup

flash_point_c

154.0 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Monoolein: a magic lipid?
Kulkarni CV, et al.
Physical Chemistry Chemical Physics, 13(8), 3004-3021 (2011)
Mona Basha et al.
International journal of pharmaceutics, 532(1), 478-490 (2017-09-20)
The current article highlights the application of spray drying technique to produce an ultra-fine powder encapsulating the antihyperlipidemic drug, atorvastatin calcium (ATV). First, ATV was dissolved in an emulsion formulation, and different carriers (pectin, alginate, chitosan HCl and hydroxypropylmethyl cellulose)
Nicholas J Wright et al.
Nature structural & molecular biology, 26(7), 599-606 (2019-06-27)
The human equilibrative nucleoside transporter 1 (hENT1), a member of the SLC29 family, plays crucial roles in adenosine signaling, cellular uptake of nucleoside for DNA and RNA synthesis, and nucleoside-derived anticancer and antiviral drug transport in humans. Because of its
Hyeun Wook Chang et al.
Bioorganic & medicinal chemistry letters, 18(12), 3589-3592 (2008-05-20)
Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the
Xiuhua You et al.
International journal of pharmaceutics, 471(1-2), 276-284 (2014-05-27)
Microemulsions show excellent potential as drug delivery systems, but the surfactants used to prepare them can cause side effects. Researchers have explored various strategies to expand microemulsion area and thereby reduce the surfactant content necessary, but how these strategies affect
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