CAS 508-02-1|Oleanic acid
| Common Name | Oleanic acid | ||
|---|---|---|---|
| CAS Number | 508-02-1 | Molecular Weight | 456.700 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 553.5±50.0 °C at 760 mmHg |
| Molecular Formula | C30H48O3 | Melting Point | >300 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 302.6±26.6 °C |
Names
| Name | oleanolic acid |
|---|---|
| Synonym | More Synonyms |
Oleanic acid BiologicalActivity
| Description | Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. |
|---|---|
| Related Catalog | Signaling Pathways >>Autophagy >>AutophagyNatural Products >>Terpenoids and GlycosidesResearch 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - 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
- 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 :
- 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
Safety Information
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
|---|---|
| Hazard Codes | Xi:Irritant |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 2 |
| RTECS | RK0177965 |
| HS Code | 2918199090 |
Customs
| HS Code | 2918199090 |
|---|---|
| Summary | 2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0% |
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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 |
