Oleuropein is a naturally occuring antioxidant polyphenol isolated from olive leaf. In both J774A.1 cells and primary mouse macrophages, Oleuropein increases LPS-induced NO production. Oleuropein prevents oxidative myocardial injury induced by ischemia and reperfusion. In TF-1a; 786-O, T-47D, RPMI-7951, LoVo, and NL-Fib cells, Oleuropein inhibits cell proliferation and migration. In swiss albino mice that spontaneously develop soft tissue sarcomas, Oleuropein (i.p. or p.o.) completely regresses tumors. In rats, Oleuropein (40 mg/kg, p.o.) protects from cardiac remodeling process after isoproterenol-induced myocardial infarction through inhibiting angiotensin-converting enzyme activity.

Physicochemical Properties

Molecular Formula	C25H32O13
Molecular Weight	540.51
Exact Mass	540.184
CAS #	32619-42-4
Related CAS #	32619-42-4
PubChem CID	5281544
Appearance	White to light yellow solid powder
Density	1.5±0.1 g/cm3
Boiling Point	772.9±60.0 °C at 760 mmHg
Melting Point	89-90ºC
Flash Point	257.0±26.4 °C
Vapour Pressure	0.0±2.8 mmHg at 25°C
Index of Refraction	1.630
LogP	-0.91
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	11
Heavy Atom Count	38
Complexity	873
Defined Atom Stereocenter Count	7
SMILES	C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
InChi Key	RFWGABANNQMHMZ-ZCHJGGQASA-N
InChi Code	InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
Chemical Name	methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms	Methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
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)

Biological Activity

ln Vitro	In the context of treating breast cancer, the cytochrome P450 enzyme aromatase represents a significant pharmacological target[2].
ln Vivo	In swiss albino mice that spontaneously develop soft tissue sarcomas, Oleuropein (i.p. or p.o.) completely regresses tumors. In rats, Oleuropein (40 mg/kg, p.o.) protects from cardiac remodeling process after isoproterenol-induced myocardial infarction through inhibiting angiotensin-converting enzyme activity.
Animal Protocol	Dissolved in PBS; 50 μg/mouse; i.p. or p.o. administration Swiss albino mice that spontaneously develops soft tissue sarcomas
References	[1]. Oleuropein as an inhibitor of peroxisome proliferator-activated receptor gamma. Genes Nutr. 2014 Jan;9(1):376. [2]. Potential Health Benefits of Olive Oil and Plant Polyphenols. Int J Mol Sci. 2018 Feb 28;19(3). pii: E686.
Additional Infomation	Oleuropein is a secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars. It has a role as a plant metabolite, a radical scavenger, an anti-inflammatory agent, an antineoplastic agent, an antihypertensive agent, a NF-kappaB inhibitor, an apoptosis inducer, an antioxidant and a nutraceutical. It is a secoiridoid glycoside, a beta-D-glucoside, a methyl ester, a member of catechols, a diester and a member of pyrans. Oleuropein has been reported in Ligustrum obtusifolium, Fraxinus insularis, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO:100 mg/mL (185.0 mM) Water:100 mg/mL (185.0 mM) Ethanol:100 mg/mL (185.0 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (3.85 mM) (saturation unknown) in 10% DMSO + 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 20.8 mg/mL clear DMSO 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: ≥ 2.08 mg/mL (3.85 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 20.8 mg/mL clear DMSO 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.85 mM) (saturation unknown) in 10% DMSO + 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: PBS: 30mg/mL  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8501 mL	9.2505 mL	18.5010 mL
	5 mM	0.3700 mL	1.8501 mL	3.7002 mL
	10 mM	0.1850 mL	0.9251 mL	1.8501 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.