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Oleuropein

HCID 5281544CAS 32619-42-4

기본 정보

표준 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
분자식
C25H32O13
평균 분자량
540.5 g/mol
단동위원소 질량
540.18429108

개요

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.

이름 및 식별자

우선 이름
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
현지명
올레우로페인
영어명
Oleuropein
분자식
C25H32O13
분자량
540.51

이름 및 동의어

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
이름 더 보기
올레우로페인Olive 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)

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-0.4
극성 표면적
202 Ų
수소 결합 공여자 수
6
수소 결합 수용자 수
13
회전 가능 결합 수
11
무거운 원자 수
38

실험 및 물리화학적 성질

Melting Point89 - 91 °C
Physical DescriptionSolid

물리화학적 성질

녹는점
89 · 89-90°C
끓는 점
772.9 · 772.9±60.0 °C(Predicted)
밀도
1.5 · 1.50±0.1 g/cm3(Predicted)
저장 조건
2 · Inert atmosphere,2-8°C
용해도
DMSO (약간 용해됨), 에탄올 (약간 용해됨,초음파처리), 메탄올 (약간 용해됨)
산도 계수 (pKa)
9.7 · 9.70±0.10(Predicted)

화학적 성질

Brown Solid

안전 및 규제

GHS 분류

GHS Classification · 3건

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.

유해성 정보

Hazard Classes and CategoriesNot Classified

안전 데이터

wgk
3
HS 번호
29389090
safety_code
24/25
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 3건

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
응용 분야 · 2건

개요Oleuropein 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 .

역사The 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.

상·하류 제품 정보

하류 제품

공급사50 곳

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]
추가 설명 · 1건

정의ChEBI: 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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