CAS Number508-02-1
Synonymsoleanoic acid; Oleanol; CARYOPHYLLIN; Oleanic acid; 3-beta-Hydroxyolean-12-en-28-oic acid; Oleanolicacid; Taraligenin; Guagenin; Araligenin; Oleanolic Acid Hydrate; MoMorgenin; MFCD00064914; Taragenin; Gledigeni; Oleanolic; Oleanolic Acid; EINECS 208-081-6
Molecular FormulaC30H48O3
Molecular Weight456.70
Purity≥97%
Density1.1±0.1 g/cm3
Boiling Point553.5±50.0 °C at 760 mmHg
Melting Point>300 °C (lit.)
Appearancepowder
EINECS208-081-6
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 508-02-1 |
| Catalog No. | 2A-9011751 |
| Chinese Name | 齐墩果酸 |
| Synonyms | oleanoic acid; Oleanol; CARYOPHYLLIN; Oleanic acid; 3-beta-Hydroxyolean-12-en-28-oic acid; Oleanolicacid; Taraligenin; Guagenin; Araligenin; Oleanolic Acid Hydrate; MoMorgenin; MFCD00064914; Taragenin; Gledigeni; Oleanolic; Oleanolic Acid; EINECS 208-081-6 |
| Molecular Formula | C30H48O3 |
| Molecular Weight | 456.70 |
| Purity | ≥97 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 553.5±50.0 °C at 760 mmHg |
| Melting Point | >300 °C (lit.) |
| Appearance | powder |
| Water Solubility | Soluble in: chloroform |
| Storage Condition | Light-sealed packaging in brown glass bottles. Sto |
| Application | Oleanolic acid is a natural compound with anti-cancer activity. |
| EINECS | 208-081-6 |
| HTC | 2918199090 |
| PubChem ID | 57654491 |
| MDL Number | MFCD00064914 |
| 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 |
| InChI | 1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1 |
| InChI Key | MIJYXULNPSFWEK-GTOFXWBISA-N |
| NACRES Code | NA.22 |
| UNSPSC | 12352002 |
| MSDS | msds/11751_1_508_02_1.pdf |
| Bioactivity | Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Target Human Endogenous Metabolite In Vitro Oleanolic acid (OA) suppresses the proliferation of lung cancer cells in both dose- and time-dependent manners, along with an increase in miR-122 abundance. CCNG1 and MEF2D, two putative miR-122 targets, are found to be downregulated by OA treatment [1]. OA induces autophagy in normal tissue-derived cells without cytotoxicity. OA-induced autophagy is shown to decrease the proliferation of KRAS-transformed normal cells and to impair their invasion and anchorage-independent growth[2]. In Vivo Mouse model experiments also demonstrat that OA suppresses the growth of KRAS-transformed breast epithelial cell MCF10A-derived tumor xenograft by inducing autophagy [2]. Activation of MAPK pathways, including p-38 MAPK, JNK and ERK, is triggered by OA in both a dose and time-dependent fashion in all the tested cancer cells. OA induces p38 MAPK activation promoted mitochondrial translocation of Bax and Bim, and inhibits Bcl-2 function by enhancing their phosphorylation. OA can induce reactive oxygen species (ROS)-dependent ASK1 activation, and this event is indispensable for p38 MAPK-dependent apoptosis in cancer cells[3].It is also proved that p38 MAPK knockdown A549 tumors are resistant to the growth-inhibitory effect of OA[3]. In OA-treated EAM mice the number of Treg cells and the production of IL-10 and IL-35 are markedly increased, while proinflammatory and profibrotic cytokines are significantly reduced[4]. References [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. [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. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 553.5±50.0 °C at 760 mmHg Melting Point >300 °C(lit.) Molecular Formula C30H48O3 Molecular Weight 456.700 Flash Point 302.6±26.6 °C Exact Mass 456.360352 PSA 57.53000 LogP 9.06 Vapour Pressure 0.0±3.4 mmHg at 25°C Index of Refraction 1.557 InChIKey MIJYXULNPSFWEK-GTOFXWBISA-N SMILES CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C2C1 Storage condition 2-8°C |
| Use of | Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Properties Articles150 Name oleanolic acid Synonym More Synonyms Oleanic acid Biological Activity Description Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Human Endogenous Metabolite In Vitro Oleanolic acid (OA) suppresses the proliferation of lung cancer cells in both dose- and time-dependent manners, along with an increase in miR-122 abundance. CCNG1 and MEF2D, two putative miR-122 targets, are found to be downregulated by OA treatment [1]. OA induces autophagy in normal tissue-derived cells without cytotoxicity. OA-induced autophagy is shown to decrease the proliferation of KRAS-transformed normal cells and to impair their invasion and anchorage-independent growth[2]. In Vivo Mouse model experiments also demonstrat that OA suppresses the growth of KRAS-transformed breast epithelial cell MCF10A-derived tumor xenograft by inducing autophagy [2]. Activation of MAPK pathways, including p-38 MAPK, JNK and ERK, is triggered by OA in both a dose and time-dependent fashion in all the tested cancer cells. OA induces p38 MAPK activation promoted mitochondrial translocation of Bax and Bim, and inhibits Bcl-2 function by enhancing their phosphorylation. OA can induce reactive oxygen species (ROS)-dependent ASK1 activation, and this event is indispensable for p38 MAPK-dependent apoptosis in cancer cells[3].It is also proved that p38 MAPK knockdown A549 tumors are resistant to the growth-inhibitory effect of OA[3]. In OA-treated EAM mice the number of Treg cells and the production of IL-10 and IL-35 are markedly increased, while proinflammatory and profibrotic cytokines are significantly reduced[4]. References [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. Chemical & Physical Properties Molecular Formula C30H48O3 Exact Mass 456.360352 PSA 57.53000 Index of Refraction 1.557 InChIKey MIJYXULNPSFWEK-GTOFXWBISA-N |
| Tax Rebate | 9.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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