オレウロペイン

Oleuropein

HCID 5281544CAS 32619-42-4

基本情報

標準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
分子式
C25H32O13
平均分子量
540.5 g/mol
単同位体質量
540.18429108

概要

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.

名称と識別子

優先名称
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
現地名
オレウロペイン
英語名
Oleuropein
分子式
C25H32O13
分子量
540.51

名称と別名

Oleuropein32619-42-4OleoeuropeinoleoeuropeineCHEBI:7747DTXSID609051032-(3,4-Dihydroxyphenyl)ethyl (2S-(2alpha,3E,4beta))-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetatemethyl (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-carboxylate2O4553545Lmethyl (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-carboxylateRefChem:168112DTXCID401334206
名称をさらに表示
(2S)-3-[(E)-エチリデン]-2-(β-D-グルコピラノシルオキシ)-3,4-ジヒドロ-5-(メトキシカルボニル)-2H-ピラン-4α-酢酸2-(3,4-ジヒドロキシフェニル)エチルオロイロペインオロイロペイングルコシドオロイロペオシドオレウロペイン(2S,3E,4S)-2-(β-D-グルコピラノシルオキシ)-3-エチリデン-5-(メトキシカルボニル)-3,4-ジヒドロ-2H-ピラン-4-酢酸2-(3,4-ジヒドロキシフェニル)エチルオリーブ葉エキスオレウロペイン, >95%オレウロペイン, 75%メチル (2S,3E,4S)-4-{2-[2-(3,4-ジヒドロキシフェニル)エトキシ]-2-オキソエチル}-3-エチリデン-2-{[(2S,3R,4S,5S,6R)-3,4,5-トリヒドロキシ-6-(ヒドロキシメチル)オキサン-2-イル]オキシ}-3,4-ジヒドロ-2H-ピラン-5-カルボキシラートOlive Leaf Extracthydroxy complex alcohol2-(3,4-dihydroxyphenyl)ethyl [2S-(2alpha,3E,4beta)]-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetate2H-Pyran-4-acetic acid, 3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(3,4-dihydroxyphenyl)ethyl ester, [2S-(2alpha,3E,4beta)]A688A-688Oleuropein ext
methyl (4S,5Z,6R)-4-(2-(2-(3,4-dihydroxyphenyl)ethoxy)-2-oxo-ethyl)-5-ethylidene-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-4H-pyran-3-carboxylate251-129-6OleuropeineOleuroperinOleuropein CRSOleuropein, 75%Oleuropein, >95%Oleuropein (Standard)

データベース識別子

CAS
32619-42-4
PubChem CID
5281544
DTXSID
DTXSID60905103
ChEMBL
CHEMBL1911053
ChEBI
CHEBI:7747
UNII
2O4553545L
EC Number
251-129-6
Nikkaji
J17.724E

物性

構造計算による物性

XLogP
-0.4
極性表面積
202 Ų
水素結合供与体数
6
水素結合受容体数
13
回転可能結合数
11
重原子数
38

実験および物理化学的性質

Melting Point89 - 91 °C
Physical DescriptionSolid

物理化学的性質

融点
89 · 89-90°C
比旋光度
20 · D20 -147° (H2O, alcohol, or acetone); D20 -127°
沸点
772.9 · 772.9±60.0 °C(Predicted)
比重(密度)
1.5 · 1.50±0.1 g/cm3(Predicted)
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
DMSO(微量)、エタノール(微量、超音波処理)、メタノール(微量)

化学的性質

化学的特性Brown Solid

安全と法規制

GHS分類

GHS Classification · 3 件

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.

危険有害性情報

Hazard Classes and CategoriesNot Classified

安全データ

wgk
3
hs_code
29389090
safety_code
24/25
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological Classification · 3 件

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.

Cellular LocationsCytoplasm
応用分野 · 2 件

説明Oleuropein 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 .

来歴The 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.

上流・下流製品情報

下流製品

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Shaanxi Huike Botanical Development Co., Ltd+86-29-62663046 · [email protected]
補足説明 · 2 件

定義本品は、オリーブOlea europaeaの葉のエキスである。

定義ChEBI: 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.

関連反応

4 件

関連ノート

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