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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 873
実験および物理化学的性質
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)
- 酸解離定数(Pka)
- 9.7 · 9.70±0.10(Predicted)
- 外見
- Solid
- 色
- ライトベージュ~ダークブラウン
- 安定性
- 吸湿性、光感受性
- 主な用途
- メタボロミクスビタミン、栄養補助食品、天然製品
- 化粧品成分の機能
- 抗酸化物質ヘアウェーブとヘアストレートヘアコンディショニングヘアフィックス
- 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 データベース
- 32619 · 32619-42-4(CAS DataBase Reference)
化学的性質
化学的特性Brown Solid
安全と法規制
GHS分類
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.
危険有害性情報
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
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.
応用分野
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
補足説明
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
関連ノート
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