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| Targets |
Glycerol monooleate functions as an agonist for G-protein coupled receptor 119 (GPR119), which is predominantly expressed in pancreatic β-cells and intestinal L-cells. Upon binding to GPR119, it stimulates a Gαs-mediated signaling cascade leading to activation of adenyl cyclase, increased intracellular cAMP levels, and subsequent secretion of glucagon-like peptide-1 (GLP-1), an incretin hormone that potentiates glucose-dependent insulin secretion.
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| ln Vitro |
In vitro, glycerol monooleate exhibits hemolytic properties and is used as an absorption enhancer in combination with bile salts. It can be utilized in drug delivery systems and siRNA delivery in cell culture models. The compound's amphiphilic nature allows it to encapsulate and control the release of various therapeutic agents in vitro. As a GPR119 agonist, it stimulates cAMP accumulation and GLP-1 secretion in intestinal L-cell models.
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| ln Vivo |
In vivo, glycerol monooleate has been studied for its potential therapeutic applications including treatment of otitis externa. Its use as an absorption enhancer has been explored in combination with bile salts to improve drug bioavailability. The compound's biocompatibility and non-toxic profile support its application in various in vivo drug delivery formulations.
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| Enzyme Assay |
GPR119 binding assays are conducted using membrane preparations from cells expressing recombinant GPR119. Radioligand binding displacement studies measure compound affinity. cAMP accumulation assays are performed in GPR119-expressing cells, where cells are stimulated with test compound and intracellular cAMP levels are quantified using ELISA or HTRF-based detection kits. For emulsification properties, phase behavior studies are conducted by mixing glycerol monooleate with aqueous buffers at varying ratios, followed by polarized light microscopy and small-angle X-ray scattering to characterize liquid crystalline phases.
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| Cell Assay |
Cells (e.g., intestinal L-cells or CHO cells expressing GPR119) are cultured in appropriate media at 37°C with 5% CO₂. For cAMP assays, cells are seeded in 96-well plates and treated with glycerol monooleate at various concentrations (typically 0.1-100 μM) for 30-60 minutes. cAMP levels are measured using a homogeneous time-resolved fluorescence (HTRF) or ELISA-based detection kit following the manufacturer's protocol. For siRNA delivery studies, cells are treated with siRNA formulated with glycerol monooleate-based delivery systems, and gene silencing efficiency is assessed by qRT-PCR or Western blot.
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| Animal Protocol |
For in vivo studies, glycerol monooleate is typically formulated as a solution or emulsion in suitable vehicles such as PBS or saline. Animal models include rodents for evaluating drug delivery efficiency and absorption enhancement. For oral administration, the compound is given by gavage at doses determined by the specific study design. For parenteral administration, it is injected intravenously or subcutaneously. Pharmacokinetic parameters are measured by collecting blood samples at various time points post-administration and analyzing compound concentrations via HPLC or LC-MS/MS.
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| ADME/Pharmacokinetics |
As a GRAS substance, glycerol monooleate is generally recognized as safe for use in food and pharmaceutical applications. It is biodegradable and biocompatible with a favorable safety profile. The compound has hemolytic properties at certain concentrations. It is a lipophilic compound with low aqueous solubility (5.3E-3 g/L at 25°C), and its absorption and distribution are primarily mediated through lipid-based transport mechanisms.
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| References | |
| Additional Infomation |
1-OleoylGlycerine is a 1-monoglyceride with an oleoyl group. It is a plant metabolite. It is an 18:1 1-acylGlycerine and also a monooleoylGlycerine. Its function is related to oleic acid. It has been reported that monooleoylGlycerine is found in lotus (Nelumbo nucifera) and saposhnikovia divaricata, and relevant data are available.
Glyceryl monooleate is classified as generally recognized as safe (GRAS) by the FDA. Beyond its role as an emulsifier and excipient, emerging research has elucidated its direct biological function as a GPR119 agonist, linking it to glucose homeostasis and metabolic regulation. Its amphiphilic nature and ability to form liquid crystalline phases make it a valuable tool for formulating cubosomes and other lipid-based nanocarriers for controlled drug delivery. It has been investigated for applications in otitis externa treatment and as an absorption enhancer in combination with bile salts. |
| Molecular Formula |
C21H40O4
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|---|---|
| Molecular Weight |
356.55
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| Exact Mass |
356.292
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| CAS # |
25496-72-4
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| PubChem CID |
5283468
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| Appearance |
PLATES FROM ETHANOL
YELLOW OIL OR SOFT SOLID |
| Density |
1.0±0.1 g/cm3
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| Boiling Point |
483.3±35.0 °C at 760 mmHg
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| Melting Point |
25 °C (UNSTABLE)
; MELTING POINT: 32 °C (UNSTABLE) /PRIMARY BETA FORM/; 35.5 °C (STABLE) /BETA FORM/
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| Flash Point |
155.4±19.4 °C
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| Vapour Pressure |
0.0±2.8 mmHg at 25°C
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| Index of Refraction |
1.479
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| LogP |
6.71
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
19
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| Heavy Atom Count |
25
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| Complexity |
315
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C(=O)CCCCCCC/C=C\CCCCCCCC)CC(CO)O
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| InChi Key |
RZRNAYUHWVFMIP-KTKRTIGZSA-N
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| InChi Code |
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-
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| Chemical Name |
2,3-dihydroxypropyl (Z)-octadec-9-enoate
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| Synonyms |
Glyceryl monooleate; Monooleoylglycerol; Aldo 40; Emasol MO 50; Emcol O; Aldo MO; Aldo MO-FG; Monoolein; (Z)-9-Octadecenoic Acid Monoester with 1,2,3-Propanetriol; Crossential GMO; Dimodan GMO 90; Dimodan LSQK; Dremulse; Dur-Em 114; Dur-Em 204; EAR 300; Edenor GMO; Emalsy MO; Emalsy OL; Alkamuls GMO 45LG; Agnique GMO; Ajax GMO; Arlacel 129; Atmer 1007; Atsurf 595; Canamex Glicepol 182; Capmul GMO 50; ; Emalsy OL 100; Emalsy OL 100H; Emasol MO; Emerest 2400; Emerest 2421; Emrite 6009; EmuldanOlein, mono- (6CI,8CI); A 300; A 300 (ester); Adchem GMO;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8047 mL | 14.0233 mL | 28.0466 mL | |
| 5 mM | 0.5609 mL | 2.8047 mL | 5.6093 mL | |
| 10 mM | 0.2805 mL | 1.4023 mL | 2.8047 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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