Oleanic acid

Modify Date: 2024-01-02 21:10:54

Oleanic acid Structure
Oleanic acid structure
 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 Chinese USA Flash Point 302.6±26.6 °C

 Use of Oleanic acid


Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

 Names

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
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
Storage condition 2-8°C

 Toxicological Information

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

 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

 Synthetic Route

 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%

 Articles150

More Articles
Analysis of triterpenoids and phytosterols in vegetables by thin-layer chromatography coupled to tandem mass spectrometry.

J. Chromatogr. A. 1381 , 229-38, (2015)

Three TLC methods were used for an initial screening of some common plant triterpenoids and phytosterols in cuticular wax extracts of different vegetables (zucchini, eggplant, tomato, red pepper, mang...
Functional Characterization of Cucurbitadienol Synthase and Triterpene Glycosyltransferase Involved in Biosynthesis of Mogrosides from Siraitia grosvenorii.

Plant Cell Physiol. 56 , 1172-82, (2015)

Mogrosides, the major bioactive components isolated from the fruits of Siraitia grosvenorii, are a family of cucurbitane-type tetracyclic triterpenoid saponins that are used worldwide as high-potency ...
Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities.

Phytochemistry 108 , 157-70, (2014)

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, tw...

 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
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