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オレアノール酸水和物

Oleanolic Acid

HCID 10494
ノート反応

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基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
508-02-1
標準SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
InChIKey
MIJYXULNPSFWEK-GTOFXWBISA-N
分子式
C30H48O3
平均分子量
456.7 g/mol
単同位体質量
456.36034539

名称と識別子

優先名称
Oleanolic Acid
IUPAC
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
現地名
オレアノール酸水和物
英語名
Oleanolic acid
分子式
C30H48O3
分子量
456.7

名称と別名

OLEANOLIC ACID508-02-1Oleanic acidCaryophyllinAstrantiagenin CGiganteumgenin CVirgaureagenin B3beta-Hydroxyolean-12-en-28-oic acidOleanololeonolic acid(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid6SMK8R7TGJ
名称をさらに表示
オレアノール酸水和物3β-ヒドロキシオレアナ-12-エン-28-酸3β-ヒドロキシ-20-メチル-29-ノルウルサ-12-エン-28-酸オレオノール酸オレアノル酸オレアノール酸カリオフィリンオレアノール酸 HYDRATEオレアノール酸, 97%オレアン酸3β-ヒドロキシ-5-メチルオレアナ-12-エン-28-酸(4aS,6aS,6bR,8aR,10S,12aR,12bS,14bS)-10-ヒドロキシ-2,2,6a,6b,8a,9,9,12a-オクタメチル-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-イコサヒドロピセン-4a-カルボン酸(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-ヒドロキシ-2,2,6a,6b,9,9,12a-ヘプタメチル-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-イコサヒドロピセン-4a-カルボン酸

物性

構造計算による物性補完中

XLogP
7.5
極性表面積
57.5 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
1
重原子数
33
形式電荷
0
複雑度
885

実験および物理化学的性質

Melting Point310 °C
Physical DescriptionSolid

物理化学的性質

融点
300 °C · >300 °C (lit.)
沸点
502.79 °C · 502.79°C (rough estimate)
比旋光度
20 · D20 +83.3° (c = 0.6 in chloroform)
比重(密度)
1.0261 · 1.0261 (rough estimate)
屈折率
1.494 · 1.4940 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
クロロホルム(微量)、DMSO(微量、加熱)、メタノール(微量、加熱)
外見
Solid
酸解離定数(Pka)
2.52 · 2.52(at 25℃)
色
ライトイエロー
Merck
14 · 14,6827
化粧品成分の機能
スキンコンディショニング
InChIKey
NZQIXFRGWXNLSP-IDYUENATSA-N
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 3 件

This chemical does not meet GHS hazard criteria for 94.4% (68 of 72) of all reports.

Not Classified;Reported as not meeting GHS hazard criteria by 68 of 72 companies (only 5.6% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 72 reports by companies from 5 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 68 of 72 reports by companies.;There are 3 notifications provided by 4 of 72 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory InformationChemical: Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-
Hazard Classes and CategoriesNot Classified

法規制情報

Regulatory InformationChemical: Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-

安全データ

wgk
2
tsca
TSCA listed
rtecs
RK0177965
hs_code
29181990
risk_code
36/37/38
hazard_code
Xi
safety_code

化学と産業

薬理情報

Cellular LocationsExtracellular;Membrane

用途と製造

General Manufacturing InformationOlean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-: ACTIVE
応用分野 · 7 件

解説C30H48O3(456.68).オレアノール酸,オレアナン骨格をもつトリテルペン系カルボン酸.モクセイ科オリーブOlea europaeaの葉に遊離の状態で含まれているほか,配糖体などとして多種類の植物に含まれている.融点310 ℃.[α]D+83.3°(クロロホルム).有機溶媒に易溶.森北出版「化学辞典(第2版)

用途医薬品及び化粧品添加物研究用。

説明Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid with the formula of C30H48O3. It was found in the non-glyceride fraction of olive pomace oil and is widely distributed in food and plants where it exists as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be linked to one or more sugar chains. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. Oleanolic acid and its derivatives possess several promising pharmacological activities, such as hepatoprotective effects, and anti-inflammatory, antioxidant, or anticancer activities.

天然物の起源The ingredient is mainly extracted from the leaves of Olea europaea and Viscum album L. Besides, it is found in the fruit of ligustrum lucidum ait, the whole grass of swertia mileensis t.n.he et w.l.shi, s. mussotii franch, the leaves and roots of astrantia major, the root bark and stem bark of aralia chinensis, the roots of hemsleya macrosperma c.y.wu , the roots of hemsleya amabilis diels, and the roots of hemsleya chinensis cogn. There is a long history in the herb and fruit which contain oleanolic acid. They play an important role in the treatment of various diseases. Oleanolic acid may be the most effective component in various Chinese medicines.

来歴The chemical formula was first identified in 1918. In 1960, Khastgir purified the compound for the first time. Corey identified the structure of oleanolic acid in 1993.Now the compound has been made into a drug and is being marketed in China. As early as 2002, the tablet form of oleanolic acid was listed. In 2010, capsule preparations came into the market, and to date, there is no other listed preparation. Sanofi treated it as antiulcer and NSAIDs candidate in abroad.Although it has anti-inflammatory and anti-ulcer effects, Sanofi stopped the study of developing oleanolic acid into a drug in 1989.

関連反応

3 件
反応記録を作成
HRID 580310 の反応式
HRID 580310反応物としてuspto-grants-1988_06
HRID 2190248 の反応式
HRID 2190248反応物としてuspto-grants-2012_12
HRID 2190252 の反応式
HRID 2190252反応物としてuspto-grants-2012_12

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
パナキスサポゲニン
Oleanolic
Oleanoic Acid
Oleanlic Acid
OLEANOLIC ACID HYDRATE
(3-beta)-olean-12-en-28-oicaci
3-HYDROXYOLEAN-12-EN-28-OIC ACID
(3-beta)-3-hydroxyolean-12-en-28-oicacid
eanoL
NSC-114945Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-DTXSID50858790CHEBI:37659Triterpenes, OleananeRefChem:6084DTXCID701474453208-081-6

データベース識別子

CAS
508-02-1
PubChem CID
10494
DTXSID
DTXSID50858790
ChEMBL
CHEMBL168
ChEBI
CHEBI:37659
UNII
6SMK8R7TGJ
EC Number
208-081-6
Nikkaji
J6.235I
LogP
8.576 · 8.576 (est)
CAS データベース
508 · 508-02-1(CAS DataBase Reference)
EPAの化学物質情報
Oleanolic acid (508-02-1)
26-36-37/39-60-37
ストレージクラス
11 - Combustible Solids

使用Oleanolic acid is a triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. It can Inhibits secretory phospholipase A2 that is mainly used for the treatment of acute jaundiced hepatitis with remarkable efficacy, and also has good effect on chronic hepatitis.

一般的な説明Oleanolic acid is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits antibacterial, antitumor and antileishmanial activity. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.

上流・下流製品情報

下流製品

バルドキソロンメチルEthyl (3beta)-3-hydroxyolean-12-en-28-oate3-オキソオレアナ-12-エン-28-酸バルドキソロンOleanolic acid benzoate

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補足説明 · 2 件

定義本品は、次の化学式で表される有機酸である。

定義ChEBI: Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane.