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Monoolein

Cat No.:V72369 Purity: ≥98%
Monoolein is an endogenously produced metabolite.
Monoolein
Monoolein Chemical Structure CAS No.: 111-03-5
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
Other Sizes

Other Forms of Monoolein:

  • Monoolein-d5
  • Monoolein-d7
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Monoolein is an endogenously produced metabolite.
Monoolein (CAS#: 111-03-5) is a biocompatible lipid molecule with the molecular formula C₂₁H₄₀O₄ and a molecular weight of 356.54 g/mol. It is a surfactant that releases free glycerol and oleic acid upon hydrolysis. Monoolein exhibits anti-inflammatory activity by inhibiting the immune response induced by LPS. It exerts its anti-inflammatory effects by reducing the production of immune response factors such as IL-12 p40, IL-6, and TNF-α, and inhibiting the generation of NO. Monoolein has been used in liquid crystal studies and research shows that in the presence of monoolein, the penetration of the drug cisplatin is doubled. The compound can be used as a carrier for bone repair. Monoolein inhibits the enzyme cyclooxygenase-2 (COX2) with an inhibition rate of 24.7% at a concentration of 50 µM, and inhibits the enzyme secretory phospholipase A2-2A (sPLA2-2A) with an inhibition rate of 60.6% at a concentration of 10 µM. Monoolein can be used in drug delivery and research in the field of inflammatory diseases.
Biological Activity I Assay Protocols (From Reference)
Targets
Monoolein targets multiple inflammatory enzymes and pathways. It inhibits the enzyme cyclooxygenase-2 (COX2) with an inhibition rate of 24.7% at a concentration of 50 µM. COX2 is a key enzyme in the inflammatory cascade that produces prostaglandins. Monoolein also inhibits the enzyme secretory phospholipase A2-2A (sPLA2-2A) with an inhibition rate of 60.6% at a concentration of 10 µM. sPLA2-2A is involved in the release of arachidonic acid from membrane phospholipids, which is a precursor for prostaglandin synthesis. Monoolein inhibits DGKalpha in human erythrocytes by interacting with OAG as a substrate, with a Ki value of 91000 nM. The compound exerts its anti-inflammatory effects by reducing the production of immune response factors such as IL-12 p40, IL-6, and TNF-α, and inhibiting the generation of NO. As a biocompatible lipid molecule, monoolein can interact with cell membranes and modulate membrane fluidity and permeability. Its ability to enhance drug penetration suggests that it may interact with membrane transporters or modify membrane structure.
ln Vitro
In vitro, Monoolein exhibits anti-inflammatory activity by inhibiting the immune response induced by LPS. It reduces the production of immune response factors such as IL-12 p40, IL-6, and TNF-α, and inhibits the generation of NO. Monoolein inhibits the enzyme COX2 with an inhibition rate of 24.7% at 50 µM, and sPLA2-2A with an inhibition rate of 60.6% at 10 µM. In cell-based assays, monoolein is used to study its effects on inflammation and immune responses. Cells are cultured in appropriate medium and treated with monoolein at various concentrations (typically 1-100 μM) for 24-72 hours. Following treatment, the production of cytokines (IL-12 p40, IL-6, TNF-α) and NO is measured by ELISA or Griess assay. Monoolein has been used in liquid crystal studies and research shows that in the presence of monoolein, the penetration of the drug cisplatin is doubled. This suggests that monoolein can enhance drug delivery in vitro. The compound's biocompatibility makes it suitable for use in drug delivery systems and as a carrier for bone repair.
ln Vivo
In vivo, Monoolein can be used as a carrier for bone repair. It exhibits anti-inflammatory activity by inhibiting the immune response induced by LPS. Monoolein can be used in drug delivery and research in the field of inflammatory diseases. In animal models, monoolein has been studied for its ability to enhance drug delivery and reduce inflammation. The compound's biocompatibility and biodegradability make it suitable for various biomedical applications. However, comprehensive in vivo pharmacokinetic and toxicology studies have not been extensively reported. Further in vivo studies are needed to fully characterize the compound's therapeutic potential and safety profile. The compound is classified as a research chemical and is not approved for human use.
Enzyme Assay
In vitro enzyme assays for Monoolein typically involve the use of COX2, sPLA2-2A, and DGKalpha. For COX2 inhibition assays, the enzyme is incubated with monoolein and a substrate (e.g., arachidonic acid), and the production of prostaglandins is measured by ELISA or mass spectrometry. For sPLA2-2A inhibition assays, the enzyme is incubated with monoolein and a phospholipid substrate, and the release of free fatty acids is measured. For DGKalpha assays, the enzyme is incubated with monoolein, OAG, and [gamma-32P]ATP, and the formation of phosphatidic acid is measured. The inhibition of enzyme activity is calculated from the decrease in product formation. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems, with reaction products measured by spectrophotometry, fluorometry, or radiometric detection.
Cell Assay
In vitro cell-based assays for Monoolein are performed using various cell lines to study its anti-inflammatory effects. Cells are cultured in appropriate medium and treated with monoolein at various concentrations (typically 1-100 μM) for 24-72 hours. Following treatment, cells are stimulated with LPS to induce an inflammatory response. The production of pro-inflammatory cytokines (IL-12 p40, IL-6, TNF-α) is measured by ELISA or multiplex bead-based assays. The production of NO is measured by Griess assay. Cell viability is assessed using MTT or LDH assays to ensure that observed effects are not due to cytotoxicity. For studies of drug delivery, cells are treated with monoolein and a drug (e.g., cisplatin), and drug uptake and penetration are measured. Each experiment includes appropriate controls (untreated cells, vehicle controls, and positive controls such as known anti-inflammatory agents) and is performed in triplicate to ensure statistical reliability. The compound is typically dissolved in DMSO as a stock solution and diluted in culture medium to the desired final concentration, with the final DMSO concentration kept below 0.1% to avoid solvent effects.
Animal Protocol
In vivo animal experiments with Monoolein are conducted in mouse or rat models of inflammatory diseases or bone repair. Typically, 6-8 week old rodents are used, and the compound is administered via oral gavage, intraperitoneal injection, or local injection at doses ranging from 1-100 mg/kg. In models of inflammation, monoolein is administered before or after the induction of inflammation (e.g., by LPS injection), and markers of inflammation (e.g., cytokine levels, tissue damage) are assessed. In models of bone repair, monoolein is used as a carrier for bone repair materials, and bone healing is assessed by imaging and histology. In drug delivery studies, monoolein is used as a carrier for drugs, and drug distribution and efficacy are assessed. Blood samples are collected to measure compound concentrations and biomarkers of efficacy and toxicity. At the end of the experiment, animals are euthanized, and tissues are collected for histopathological examination. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=6-10 per group) to ensure statistical power. The compound is formulated for administration using appropriate vehicles such as saline, DMSO/PEG mixtures, or oil-based formulations, depending on its solubility. Endpoints include inflammatory markers, bone healing scores, and histopathological scores.
ADME/Pharmacokinetics
The pharmacokinetic properties of Monoolein are characteristic of a lipid molecule. With a molecular weight of 356.54 g/mol and moderate lipophilicity, the compound is expected to be well-absorbed following oral administration. Monoolein is a surfactant that releases free glycerol and oleic acid upon hydrolysis. The compound is metabolized through lipid metabolic pathways, including hydrolysis by lipases and esterases. The elimination half-life is expected to be relatively short (hours) due to rapid metabolism and clearance. The compound is primarily excreted as metabolites. The pharmacokinetics of monoolein may be influenced by its formulation, with various vehicles affecting absorption rates and bioavailability. As with all research chemicals, appropriate pharmacokinetic studies should be conducted to fully characterize the compound's absorption, distribution, metabolism, and excretion.
Toxicity/Toxicokinetics
The toxicological profile of Monoolein is generally favorable, as the compound is a biocompatible lipid molecule. Monoolein is used as a food additive and in pharmaceutical formulations, indicating a reasonable safety profile. In cell-based assays, monoolein has been shown to have anti-inflammatory activity without significant cytotoxicity at low concentrations. However, comprehensive toxicology studies including acute, subchronic, and chronic toxicity assessments, as well as genotoxicity and reproductive toxicity evaluations, have not been extensively reported. The compound is classified as a research chemical and is not approved for human use as a therapeutic agent. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment. As with all chemicals, ingestion, inhalation, and skin contact should be avoided. The compound should be stored in a cool, dry place, away from light and moisture.
Additional Infomation
1-Oleoylglycerol is a 1-monoglyceride with an oleoyl group. It is a plant metabolite. It is an 18:1 1-acylglycerol and also a monooleoylglycerol. Its function is related to oleic acid. It has been reported that monooleoylglycerol is found in lotus (Nelumbo nucifera) and saposhnikovia divaricata, and relevant data are available.
Monoolein is a valuable research tool for studying inflammation, drug delivery, and lipid biology. It is a biocompatible lipid molecule with the molecular formula C₂₁H₄₀O₄ and a molecular weight of 356.54 g/mol. Monoolein is a surfactant that releases free glycerol and oleic acid upon hydrolysis. It exhibits anti-inflammatory activity by inhibiting the immune response induced by LPS. Monoolein inhibits COX2 and sPLA2-2A, and inhibits DGKalpha. It can be used as a carrier for bone repair and in drug delivery systems. The compound is not approved for any clinical indication and is strictly for research use only. Its biocompatibility and anti-inflammatory properties make it a valuable tool for research in inflammation, drug delivery, and tissue engineering.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H40O4
Molecular Weight
356.54
Exact Mass
356.292
CAS #
111-03-5
Related CAS #
Monoolein-d5;565183-24-6;Monoolein-d7;2260669-49-4
PubChem CID
5283468
Appearance
White to off-white solid powder
Density
0.9407 g/cm3 (35 ºC)
Boiling Point
483.3±35.0 °C at 760 mmHg
Melting Point
38.5 ºC (acetone )
Flash Point
155.4±19.4 °C
Vapour Pressure
0.0±2.8 mmHg at 25°C
Index of Refraction
1.46384 (589.3 nm 35 ºC)
LogP
6.71
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
19
Heavy Atom Count
25
Complexity
315
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)OCC(CO)O
InChi Key
RZRNAYUHWVFMIP-KTKRTIGZSA-N
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-
Chemical Name
2,3-dihydroxypropyl (Z)-octadec-9-enoate
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
Ethanol: 100 mg/mL (280.47 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.01 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (7.01 mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.01 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8047 mL 14.0237 mL 28.0473 mL
5 mM 0.5609 mL 2.8047 mL 5.6095 mL
10 mM 0.2805 mL 1.4024 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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