3β-Hydroxyolean-12-en-28-oic acid 3β-羟基齐墩果-12-烯-28-酸

CAS 508-02-1 MFCD00064914

化学结构图

508-02-1
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

化学属性

Mol. FormulaC30 H48 O3
Mol. Weight456.7
Melting Point>300°C
Density1.1
Boiling Point553.5°C at 760 mmHg

别名和识别编码

Chemical Name3β-Hydroxyolean-12-en-28-oic acid
MDL NumberMFCD00064914
CAS Number508-02-1
EC Number208-081-6
Reaxys-RN2228570
Beilstein Registry Number2228570
PubChem Substance ID87558857
Merck Number6827
Synonym (3-beta)-olean-12-en-28-oicaci (3beta)-olean-12-en-28-oicaci (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 3-HYDROXYOLEAN-12-EN-28-OIC ACID 3-beta-hydroxy-olean-12-en-28-oicaci CARYOPHYLLIN(SH) Caryophyllin Oleanol Oleanolic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Chemical Name Translation3β-羟基齐墩果-12-烯-28-酸
LabNetwork Molecule IDLN01292246
Canonical SMILESC[C@]([C@@]1([H])[C@]2(CC[C@@H]3O)C)(CC[C@@]2([H])C3(C)C)[C@@](C4=CC1)(CC[C@]5(C(O)=O)[C@@]4([H])CC(C)(C)CC5)C
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分类

  • {SNA} Allium cepa (Onion), Allium sativum (Garlic),
  • {SNA} Acacia, Additional Standards, Alphabetical Index of Phytochemical Standards, Analytical Standards, Calendula, Chromatography, Crataegus, Eleutherococcus, Epilobium, Foeniculum, Hedera, Isoprenoids, Lavandula, Life Sciences Standards, Melissa, N - R, Natural Compounds, Nerium, Olea, Passiflora, Phytochemical Standards, Phytochemical Standards by Plant Genus, Rosmarinus, Salvia, Sambucus,

产品应用

  • 适用于各种类型肝炎,具有促进肝细胞再生,加速受损肝细胞的修复,并有强心、利尿和抗炎作用。

相关文献及参考

  • [2]. Liu J, et al. Oleanolic acid inhibits proliferation and invasiveness of Kras-transformed cells via autophagy. J Nutr Biochem. 2014 Nov;25(11):1154-60.
  • [3]. Liu J, et al. p38 MAPK signaling mediates mitochondrial apoptosis in cancer cells induced by oleanolic acid. Asian Pac J Cancer Prev. 2014;15(11):4519-25.
  • [4]. Martín R, et al. Oleanolic acid modulates the immune-inflammatory response in mice with experimental autoimmune myocarditis and protects from cardiac injury. Therapeutic implications for the human disease. J Mol Cell Cardiol. 2014 Jul;72:250-62.
  • Merck: 14,6827
  • Merck: 14,6827 Beilstein:10(4)1164
  • [1]. Zhao X, et al. Oleanolic acid suppresses the proliferation of lung carcinoma cells by miR-122/Cyclin G1/MEF2D axis. Mol Cell Biochem. 2015 Feb;400(1-2):1-7.
  • [1]. Zhao X, et al. Oleanolic acid suppresses the proliferation of lung carcinoma cells by miR-122/Cyclin G1/MEF2D axis. Mol Cell Biochem. 2015 Feb;400(1-2):1-7.

安全信息

GHS Symbol
RTECSRK0177965
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P302+P352
  • P305+P351+P338
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P405 Store locked up. 上锁保管。
  • P501a
Signal word Warning
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
WGK Germany2
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xi
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S37 Wear suitable gloves 戴适当手套;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition +4°C 2-8°C 4℃ 储存温度2-8°C
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JPPMAB Journal of Pharmacy and Pharmacology.  (Pharmaceutical Soc. of Great
   Britain, 1 Lambeth High St., London SEI 7JN, UK)  V.1-    1949-
   Volume(issue)/page/year: 44,456,1992

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JPPMAB Journal of Pharmacy and Pharmacology.  (Pharmaceutical Soc. of Great
   Britain, 1 Lambeth High St., London SEI 7JN, UK)  V.1-    1949-
   Volume(issue)/page/year: 44,456,1992

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JPPMAB Journal of Pharmacy and Pharmacology.  (Pharmaceutical Soc. of Great
   Britain, 1 Lambeth High St., London SEI 7JN, UK)  V.1-    1949-
   Volume(issue)/page/year: 44,456,1992

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   DRFUD4 Drugs of the Future.  (J.R. Prous, S.A., Apartado de Correos 540,
   08080 Barcelona, Spain) V.1-    1975/76-  Volume(issue)/page/year:
   19,450,1994

其他信息

  • 临床应用:齐墩果酸为抗肝炎药,临床上主要用于治疗急性黄疸型肝炎,疗效显著,对慢性肝炎
  • 齐墩果酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 O0317 齐墩果酸水合物 Oleanolic Acid Hydrate 5G 693元
  • color:light yellow
  • 图谱信息:齐墩果酸(508-02-1)红外图谱(IR1) 齐墩果酸(508-02-1)红外图谱(IR2) 齐墩果酸(508-02-1)质谱(MS)
  • TCI Shanghai:齐墩果酸水合物 Oleanolic Acid Hydrate,>;95.0%(LC)(508-02-1)
  • 女贞子提取物:齐墩果酸是从龙胆科植物獐牙菜属的青叶胆全草或女贞子的果实中分离提取而得一种五环三萜类化合物,以游离体和配糖体存在于多种植物中,已成为临床上常用的保肝药物,对四氯化碳引起的大鼠急性和慢性肝损害有明显保护作用,可使升高的ALT和AST下降,炎症、坏死和间质炎症反应减轻,阻止纤维化形成,促进肝细胞的再生,加速坏死组织的恢复作用。电镜显示经齐墩果酸治疗后,肿大的线粒体和粗面内质网恢复。其琥珀酸酯可使小鼠肝微粒体细胞色素P450酶活力降低。此外齐墩果酸尚有纠正蛋白代谢障碍、消炎、强心、利尿、升高白细胞、降血糖和促进免疫功能、抑制S-180瘤株生长等作用。下图为从木犀科植物女贞子的干燥成熟果实中提取齐墩果酸、乌索酸的工艺流程: 女贞子成熟果实中提取齐墩果酸工艺流程图 【注1】95%乙醇回流提取4次,合并提取液,减压浓缩。 【注2】稀醇溶解后,分别以石油醚,乙酸乙酯和正丁醇萃取。 【注3】低压硅胶柱层析,石油醚-乙酸乙酯梯度洗脱。 以上信息由Chemicalbook的小刚编辑整理。
  • 齐墩果:齐墩果又称“油橄榄”是地中海地区非常典型的一种木本油料植物。属于木犀科。古代希腊人和犹太人把齐墩果作为和平的标志。在西斑牙、意大利和阿根廷,齐墩果林占据着巨大的面积。其它地方分布较少。齐墩果是一种高达3—7米的乔木,叶片常绿,核果,长达1—3厘米,中果皮含有25—40%的齐墩果油,含丰富的维生素,易被有机体消化。在医药上这种油用以预防动脉硬化。目前主要是以栽培或者野生状态生长着。油橄榄属总共约有60个种,如金叶齐墩果(olea chrysophylla)、齐墩果(O.europaea)和栽培齐墩果(oleaeuropaea var. communis)等。 齐墩果植物图
  • MOL 文件:508-02-1.mol
  • 理化性质:齐墩果酸在植物中存在很广泛,一般含量0.2%~2%。葫芦科植物罗锅底含量较高为1.5%~2%,女贞子果实含量0.6%~0.7%。齐墩果酸为白色针状结晶 (乙醇),无臭、无味。对酸、碱不稳定。熔点308~310℃,[α]20D+73.3° (c=0.15,氯仿),不溶于水,可溶于甲醇、乙醇、乙醚、丙酮和氯仿,结构为: 齐墩果酸结构式
  • MSDS 信息:3beta-Hydroxyolean-12-en-28-oic acid(508-02-1).msds
  • 齐墩果酸的作用:1,齐墩果酸具有消炎、镇静,强心、利尿、降血脂、降血糖以及护肝降酶、增强免疫和抑制S180瘤株生长等作用,是开发治疗肝病和降血糖等药物有效成分。 2,齐墩果酸对染色体损伤有保护作用,对实验性动脉粥样硬化有预防作用。临床用于治疗传染性急性黄疸型肝炎,慢性病毒性肝炎,具有明显的降低谷丙转氨酶及退黄效果。 3,齐墩果酸具有抑制肝纤维增生的作用,经齐墩果酸治疗的肝纤维化的大鼠,肝纤维增生严重并明显减轻,肝胶原蛋白含量减少,提示具有防治肝硬化的作用。 4,降低肝硬化大鼠脑匀浆酷氨酸水平:由于脑匀浆酷氨酸水平明显下降,可抑制假性神经递质的生成,故有利于肝性脑病的防治。 5,齐墩果酸胶囊为肝病辅助用药类非处方药药品,用于急慢性肝炎的辅助治疗。对肝损伤有一定的保护作用,可使升高的血清丙氨酸氨基转移酶下降,促进肝细胞再生,加速坏死组织的修复。
  • 溶于甲醇、乙醇、乙醚、丙酮和氯仿,不溶于水。
  • 用途一:适用于各种类型肝炎,具有促进肝细胞再生,加速受损肝细胞的修复,并
  • Sigma Aldrich:508-02-1(sigmaaldrich)

系列性分类


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