OLEUROPEIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H32O13
Molecular Weight	540.5138
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OCCC3=CC=C(O)C(O)=C3

InChI

InChIKey=RFWGABANNQMHMZ-ZCHJGGQASA-N

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

HIDE SMILES / InChI

Molecular Formula	C25H32O13
Molecular Weight	540.5138
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3002804/
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27928616 | https://www.ncbi.nlm.nih.gov/pubmed/21333710 | https://www.ncbi.nlm.nih.gov/pubmed/27916806 | https://www.ncbi.nlm.nih.gov/pubmed/26474288

Oleuropein is a phenylethanoid, a type of phenolic compound found in olive leaf together with other closely related compounds such as 10-hydroxyoleuropein, ligstroside, and 10-hydroxyligstroside. Oleuropein is traditionally removed from olives due to its bitterness. In preliminary laboratory research, oleuropein had activity as an agonist of the G-protein estrogen receptor. Oleuropein inhibited the enzymatic activity of mammalian target of rapamycin (mTOR), suggesting that mTOR inhibition is at least one of the reasons for the reported anti-cancer properties of oleuropein.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Mediterranean diet polyphenols reduce inflammatory angiogenesis through MMP-9 and COX-2 inhibition in human vascular endothelial cells: a potentially protective mechanism in atherosclerotic vascular disease and cancer.	2012-11-15	22595400
Hypolipidimic and antioxidant activities of oleuropein and its hydrolysis derivative-rich extracts from Chemlali olive leaves.	2008-11-25	18823963
Combining computational and biochemical studies for a rationale on the anti-aromatase activity of natural polyphenols.	2007-12	17910019
Discovery of small-molecule HIV-1 fusion and integrase inhibitors oleuropein and hydroxytyrosol: Part I. fusion [corrected] inhibition.	2007-03-23	17275783
Acute doxorubicin cardiotoxicity is successfully treated with the phytochemical oleuropein through suppression of oxidative and nitrosative stress.	2007-03	17223128
Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals.	2003-04-01	12615669
In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents.	2001-11	11724241

Patents

Sample Use Guides

In Vivo Use Guide

he effects of oleuropein was examined in rats with heart failure induced by permanent ligation of left coronary arteries. Twenty-four hours after the operation, the rats were assigned to five groups including a sham assigned to receive vehicle (1 ml/day) and four coronary ligated groups assigned to receive vehicle or oleuropein at 5, 10, or 20 mg/kg/day. Five weeks later, echocardiographic and hemodynamic parameters, serum concentrations of oxidative stress, and inflammatory markers were determined.

Route of Administration: Oral

In Vitro Use Guide

The minimum inhibitory concentration (expressed as MIC 90%) of oleuropein against C. Albicans ATCC 10231 was assessed using serial broth microdilution of oleuropein in RPMI 1640% + 2% glucose (w/v) from 25 mg/mL to 12.21 mkg/mL. Minimal inhibitory concentration (MIC) of oleuropein against C. albicans was 12.5 mg/ml

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:30 GMT 2025`
Record UNII	2O4553545L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER, (2S-(2.ALPHA.,3E,4.BETA.))-

Preferred Name

English

OLEUROPEIN

Official Name

English

OLEUROPEIN [USP-RS]

Common Name

English

OLEOEUROPEIN

Common Name

English

2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER, (2S,3E,4S)-

Common Name

English

2H-PYRAN-4-ACETIC ACID, 5-CARBOXY-3-ETHYLIDENE-2-(.BETA.-D-GLUCOSYLOXY)-3,4-DIHYDRO-, 3,4-DIHYDROXYPHENETHYL 5-METHYL ESTER

Common Name

English

Oleuropein [WHO-DD]

Common Name

English

OLEOEUROPEINE

Common Name

English

OLEUROPEIN [VANDF]

Common Name

English

OLEUROPEIN [MI]

Common Name

English

Classification Tree Code System Code

DSLD

2487 (Number of products:27)