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Oleacein

Cat No.:V84879 Purity: ≥98%
Oleacein
Oleacein Chemical Structure CAS No.: 149183-75-5
Product category: ACE
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
Official Supplier of:
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Product Description
Oleacein (Compound 9) is an ACE inhibitor isolated from J. grandiflorum. Oleacein is orally active and can be used in the study of metabolic and cardiovascular diseases.
Oleacein (CAS#: 149183-75-5) is a chiral secoiridoid polyphenol. Its systematic name is 2-(3,4-dihydroxyphenyl)ethyl (E,3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate. It has the molecular formula C17H20O6 and a molecular weight of 320.34. Oleacein is a compound found in olive oil and has been reported to have antioxidant, anti-metastatic, anticancer, and anti-inflammatory activities. It is an ACE inhibitor and has oral activity.
Biological Activity I Assay Protocols (From Reference)
Targets
Oleacein targets angiotensin-converting enzyme (ACE), acting as an inhibitor. It also inhibits STAT3 and activates the apoptotic machinery. These activities contribute to its potential roles in cardiovascular and metabolic diseases, as well as its anticancer and anti-inflammatory effects.
ln Vitro
In vitro, Oleacein has been shown to have antioxidant, anti-metastatic, anticancer, and anti-inflammatory activities. It inhibits STAT3 and activates apoptotic pathways. Its activity as an ACE inhibitor has also been demonstrated. These diverse activities make it a compound of interest for studying various disease processes.
ln Vivo
In vivo, Oleacein has oral activity and is used in research on metabolic and cardiovascular diseases. It can be used as an adjuvant to improve insulin sensitivity in humans and may play a potential role in the prevention of inflammatory disease related to atherosclerosis.
Enzyme Assay
In vitro enzyme assay protocols for Oleacein typically involve measuring its inhibition of ACE activity. This can be done using a fluorometric or spectrophotometric assay with a synthetic substrate. Its STAT3 inhibitory activity can be assessed in cell-based assays by measuring STAT3 phosphorylation.
Cell Assay
In vitro cell-based assay protocols for Oleacein involve treating various cell lines, such as cancer cells or immune cells, with the compound to assess its effects on cell viability, inflammation, and signaling pathways. For example, its anti-inflammatory activity can be assessed by measuring cytokine production in stimulated macrophages.
Animal Protocol
In vivo animal experimental protocols for Oleacein would typically involve administering the compound orally to animal models of metabolic syndrome, cardiovascular disease, or cancer. Endpoints would include blood pressure, lipid profiles, inflammatory markers, and tumor growth.
ADME/Pharmacokinetics
Pharmacokinetic properties of Oleacein indicate it has oral activity. It is soluble in DMSO, dichloromethane, or acetonitrile and slightly soluble in methanol. Specific parameters such as half-life and bioavailability have not been detailed in the provided literature.
Toxicity/Toxicokinetics
Toxicological data for Oleacein are not extensively detailed in the current literature. As a natural polyphenol, it is generally considered safe, but it is intended for research use only.
References

[1].Angiotensin converting enzyme (ACE) inhibitors from Jasminum azoricum and Jasminum grandiflorum. Planta Med. 1998 Apr;64(3):246-50.

[2].Effects of Oleacein on High-Fat Diet-Dependent Steatosis, Weight Gain, and Insulin Resistance in Mice.

Additional Infomation
2-(3,4-Dihydroxyphenyl)ethyl(E,3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate has been reported in jasmine (Jasminum grandiflorum) and olive (Olea europaea), and relevant data are available.
See also: oleuropein (note moved to).
Oleacein is a research-grade natural product with multiple biological activities, including antioxidant, anti-inflammatory, anticancer, and ACE inhibitory effects. It has been studied for its potential role in metabolic and cardiovascular diseases. It has not entered clinical trials as a drug but is a compound of interest for research. Its mechanism of action involves ACE inhibition and STAT3 inhibition. The compound is available exclusively for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H20O6
Molecular Weight
320.34
Exact Mass
320.125
CAS #
149183-75-5
PubChem CID
23624475
Appearance
Typically exists as solid at room temperature
Density
1.234±0.06 g/cm3(Predicted)
Boiling Point
551.4±50.0 °C(Predicted)
LogP
1.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
10
Heavy Atom Count
23
Complexity
431
Defined Atom Stereocenter Count
1
SMILES
C/C=C(/C=O)\[C@@H](CC=O)CC(=O)OCCC1=CC(=C(C=C1)O)O
InChi Key
XLPXUPOZUYGVPD-VMPILDALSA-N
InChi Code
InChI=1S/C17H20O6/c1-2-13(11-19)14(5-7-18)10-17(22)23-8-6-12-3-4-15(20)16(21)9-12/h2-4,7,9,11,14,20-21H,5-6,8,10H2,1H3/b13-2-/t14-/m0/s1
Chemical Name
2-(3,4-dihydroxyphenyl)ethyl (E,3S)-4-formyl-3-(2-oxoethyl)hex-4-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)
Typically soluble in DMSO (e.g. 10 mM)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1217 mL 15.6084 mL 31.2168 mL
5 mM 0.6243 mL 3.1217 mL 6.2434 mL
10 mM 0.3122 mL 1.5608 mL 3.1217 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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