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508-02-1

508-02-1 structure
508-02-1 structure
Name oleanolic acid
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
Description Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.
Related Catalog
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.
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
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RK0177965
CHEMICAL NAME :
Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-
CAS REGISTRY NUMBER :
508-02-1
LAST UPDATED :
199701
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C30-H48-O3
MOLECULAR WEIGHT :
456.78

HEALTH HAZARD DATA

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
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
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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