Basic information
- CAS
32619-42-4- Standard SMILES
C/C=C1/[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1- InChIKey
RFWGABANNQMHMZ-ZCHJGGQASA-N- Molecular formula
- C25H32O13
- Average molar mass
- 540.5 g/mol
- Monoisotopic mass
- 540.18429108
Overview
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 an antioxidant, an antineoplastic agent, an antihypertensive agent, a radical scavenger, a nutraceutical, an anti-inflammatory agent, an apoptosis inducer, a NF-kappaB inhibitor and a plant metabolite. It is a beta-D-glucoside, a methyl ester, a member of pyrans, a member of catechols, a secoiridoid glycoside and a diester.
Names & identifiers
- Preferred name
- Oleuropein
- IUPAC
- 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
- English name
- Oleuropein
- Molecular formula
- C25H32O13
- Molecular weight
- 540.51
Names & synonyms
Show more names
Database identifiers
- CAS
32619-42-4- PubChem CID
- 5281544
- DTXSID
DTXSID60905103- ChEMBL
CHEMBL1911053- ChEBI
CHEBI:7747- UNII
- 2O4553545L
- EC Number
- 251-129-6
- Nikkaji
- J17.724E
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 202 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 11
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 873
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 89 · 89-90°C
- alpha
- 20 · D20 -147° (H2O, alcohol, or acetone); D20 -127°
- Boiling point
- 772.9 · 772.9±60.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
- pka
- 9.7 · 9.70±0.10(Predicted)
- form
- Solid
- color
- Light Beige to Dark Brown
- Stability
- Hygroscopic, Light Sensitive
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- Cosmetics Ingredients Functions
- ANTIOXIDANTHAIR WAVING OR STRAIGHTENINGHAIR CONDITIONINGHAIR FIXING
- InChIKey
- RFWGABANNQMHMZ-JUVTZQQOSA-N
- SMILES
- C([C@@H]1C(=CO[C@@H](O[C@@]2([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)/C/1=C/C)C(=O)OC)C(=O)OCCC1C=CC(O)=C(O)C=1 |&1:1,5,7,9,10,12,14,r|
- LogP
- -0.865 · -0.865 (est)
- CAS DataBase Reference
- 32619 · 32619-42-4(CAS DataBase Reference)
- FDA UNII
- 2 O4553545L · 2O4553545L
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29389090 · 29389090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Safety data
- wgk
- 3
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs used to cause dilation of the blood vessels.
Applications
DescriptionOleuropein is a phenolic compound extracted from olive (Canarium album (Lour.) Raeusch., Gan Lan) leaves mainly. The olive tree belongs to family Oleaceae Olea genus of evergreen trees, and it is the world famous fruit and woody species. There is highly edible value for cultivating trees. Affiliated to famous economic forest and subtropical fruit trees, they are rich in olive oil which is considered as high-quality edible oil .
HistoryThe usage of olive ramification (including olive oil) in human health dates back to several centuries ago. For centuries, olive oil has been added to cosmetics and pharmacological agent. However, the unrefined mixture is applied primarily, and later studies have found that the main component of it which can be absorbed is olive polyphenols . Olive polyphenol, which gives a unique bitter taste, is mainly from the seeds, leaves, and immature bark of the olive (14% of dry weight). The content and purity are affected by fruit ripening stage, production, and extraction technology. In 1959, oleuropein was isolated, and the chemical structure was identified . In addition, oleuropein can be found in other kinds of plants, such as Lauraceae, Syringa, Ligustrum, Hibiscus and Jasminum. Up to now, the amount of Oleaceae containing oleuropein is 25 at least, including jasmine, cloves, lobular lilac, etc. Based on the molecular structure, pharmacological effects have been studied further. Clinical and experiment statistics demonstrated it is beneficial to human health. People gradually realized the function of its antioxidative, anti-inflammatory, and antitumor effects, atherosclerosis prevention, blood glucose hypoglycemia reduction, and nerve protection.
UsesOleuropein is a tyrosol ester derivative of elenolic acid and phenolic glycoside found in olive oil. Oleuropein shows antioxidant, anti-ischemic and hypolipidemic activity. Oleuropein has also been used as an immunomodulator .
Usesolive leaf extract is astringent and anti-septic. It also has vasodialating capacities, as well as being perfuming and skin-conditioning. olive leaf extract has demonstrated some anti-oxidant and freeradical scavenger activities. olive leaves contain both bioflavonoids and polyphenols. The extract generally found in anti-aging products.
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: 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.
Related reactions
Compound notes
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