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Grundinformationen
- 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- Summenformel
- C25H32O13
- Durchschnittliche Molmasse
- 540,518 g/mol
- Monoisotopische Masse
- 540,18429108
Namen und Bezeichner
- Bevorzugter Name
- Oleuropein
- IUPAC
- Methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate
- Lokaler Name
- Oleuropein
- Englischer Name
- Oleuropein
- Summenformel
- C25H32O13
- Molmasse
- 540.51
Namen und Synonyme
Datenbank-Bezeichner
- CAS
32619-42-4- PubChem CID
- 5281544
- DTXSID
DTXSID60905103- ChEMBL
CHEMBL1911053- ChEBI
CHEBI:7747- UNII
- 2O4553545L
- EC Number
- 251-129-6
- Nikkaji
- J17.724E
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 89 · 89-90°C
- Siedepunkt
- 772.9 · 772.9±60.0 °C(Predicted)
- Dichte
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- Löslichkeit
- DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
- pka
- 9.7 · 9.70±0.10(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Light Beige to Dark Brown
- Stabilität
- Hygroscopic, Light Sensitive
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 32619 · 32619-42-4(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29389090
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungOleuropein 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.
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Ergänzende Hinweise
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.
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