Ursolic Acid

Modify Date: 2024-01-02 14:12:34

Ursolic Acid Structure
Ursolic Acid structure
 Common Name Ursolic Acid
CAS Number 77-52-1 Molecular Weight 456.700
Density 1.1±0.1 g/cm3 Boiling Point 556.9±50.0 °C at 760 mmHg
Molecular Formula C30H48O3 Melting Point 292 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 304.7±26.6 °C

 Use of Ursolic Acid


Ursolic acid(Bungeolic acid) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. IC50 value:Target:in vitro: UA induced phosphorylation of AMP-activated protein kinase alpha (AMPKα) and suppressed the protein expression of DNA methyltransferase 1 (DNMT1) in the dose-dependent manner [1]. The combination of ursolic acid (0.5 μM) and leucine (10 μM) proved to be the most effective in promoting myogenic differentiation. The combination of ursolic acid and leucine significantly increased CK activity than treatment with either agent alone. The level of myosin heavy chain, a myogenic differentiation marker protein, was also enhanced by the combination of ursolic acid and leucine [2]. Ursolic acid efficiently induced apoptosis, possibly via the downregulation of B-cell lymphoma 2 (Bcl-2), the upregulation of Bcl-2-associated X protein and the proteolytic activation of caspase-3. Furthermore, the activation of p38 mitogen-activated protein kinase and c-Jun N-terminal kinase was increased by the administration of ursolic acid. In addition, ursolic acid significantly suppressed the invasive phenotype of the SNU-484 cells and significantly decreased the expression of matrix metalloproteinase (MMP)-2 [3]. ursolic acid (UA) potently induces the apoptosis of gastric cancer SGC-7901 cells. Further mechanistic studies revealed that the ROCK1/PTEN signaling pathway plays a critical role in UA-mediated mitochondrial translocation of cofilin-1 and apoptosis [4].in vivo: UA treatment markedly improved the survival of septic rats, and attenuated CLP-induced lung injury, including reduction of lung wet/dry weight ratio, infiltration of leukocytes and proteins, myeloperoxidase activity, and malondialdehyde content. In addition, UA significantly decreased the serum levels of tumor necrosis factor-α, interleukin-6, and interleukin-1β, inhibited the expression of inducible nitric oxide synthase and cyclooxygenase-2 in the lung, which are involved in the productions of nitric oxide and prostaglandin E2 [5].

 Names

Name ursolic acid
Synonym More Synonyms

 Ursolic Acid Biological Activity

Description Ursolic acid(Bungeolic acid) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. IC50 value:Target:in vitro: UA induced phosphorylation of AMP-activated protein kinase alpha (AMPKα) and suppressed the protein expression of DNA methyltransferase 1 (DNMT1) in the dose-dependent manner [1]. The combination of ursolic acid (0.5 μM) and leucine (10 μM) proved to be the most effective in promoting myogenic differentiation. The combination of ursolic acid and leucine significantly increased CK activity than treatment with either agent alone. The level of myosin heavy chain, a myogenic differentiation marker protein, was also enhanced by the combination of ursolic acid and leucine [2]. Ursolic acid efficiently induced apoptosis, possibly via the downregulation of B-cell lymphoma 2 (Bcl-2), the upregulation of Bcl-2-associated X protein and the proteolytic activation of caspase-3. Furthermore, the activation of p38 mitogen-activated protein kinase and c-Jun N-terminal kinase was increased by the administration of ursolic acid. In addition, ursolic acid significantly suppressed the invasive phenotype of the SNU-484 cells and significantly decreased the expression of matrix metalloproteinase (MMP)-2 [3]. ursolic acid (UA) potently induces the apoptosis of gastric cancer SGC-7901 cells. Further mechanistic studies revealed that the ROCK1/PTEN signaling pathway plays a critical role in UA-mediated mitochondrial translocation of cofilin-1 and apoptosis [4].in vivo: UA treatment markedly improved the survival of septic rats, and attenuated CLP-induced lung injury, including reduction of lung wet/dry weight ratio, infiltration of leukocytes and proteins, myeloperoxidase activity, and malondialdehyde content. In addition, UA significantly decreased the serum levels of tumor necrosis factor-α, interleukin-6, and interleukin-1β, inhibited the expression of inducible nitric oxide synthase and cyclooxygenase-2 in the lung, which are involved in the productions of nitric oxide and prostaglandin E2 [5].
Related Catalog
References

[1]. Yie Y, et al. Ursolic acid inhibited growth of hepatocellular carcinoma HepG2 cells through AMPKα-mediated reduction of DNA methyltransferase 1. Mol Cell Biochem. 2014 Dec 30.

[2]. Kim M, et al. The combination of ursolic acid and leucine potentiates the differentiation of C2C12 murine myoblasts through the mTOR signaling pathway. Int J Mol Med. 2015 Mar;35(3):755-62.

[3]. Kim ES, et al. Ursolic acid inhibits the invasive phenotype of SNU-484 human gastric cancer cells. Oncol Lett. 2015 Feb;9(2):897-902.

[4]. Li R, et al. Ursolic Acid Promotes Apoptosis of SGC-7901 Gastric Cancer Cells through ROCK/PTEN Mediated Mitochondrial Translocation of Cofilin-1. Asian Pac J Cancer Prev. 2014;15(22):9593-7.

[5]. Hu Z, et al. Ursolic acid improves survival and attenuates lung injury in septic rats induced by cecal ligation and puncture. J Surg Res. 2014 Oct 22. pii: S0022-4804(14)00967-6.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 556.9±50.0 °C at 760 mmHg
Melting Point 292 °C (dec.)(lit.)
Molecular Formula C30H48O3
Molecular Weight 456.700
Flash Point 304.7±26.6 °C
Exact Mass 456.360352
PSA 57.53000
LogP 9.01
Vapour Pressure 0.0±3.4 mmHg at 25°C
Index of Refraction 1.555
Storage condition 2~8°C
Water Solubility insoluble

 Safety Information

Hazard Statements H413
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany -
RTECS YU9520000
HS Code 2942000000

 Synthetic Route

N/A structure

N/A

CAS#:1381876-19-2

~75%

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Literature: Yan, Shiqiang; Ding, Ning; Zhang, Wei; Wang, Peng; Li, Yingxia; Li, Ming Carbohydrate Research, 2012 , vol. 354, p. 6 - 20
3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER structure

3-HYDROXY-(3ALP...

CAS#:915-32-2

~71%

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Literature: Sengupta, Pasupati; Sen, Manju; Das, Saktipada Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980 , vol. 19, # 8 p. 721 - 722
3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate structure

3'-methyl-2'-bu...

CAS#:1198208-27-3

~%

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Literature: Synthetic Communications, , vol. 43, # 1 p. 26 - 33
phenyl-3β-acetoxy-urs-12-en-28-oate structure

phenyl-3β-aceto...

CAS#:104668-95-3

~1%

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Literature: Meksuriyen, Duangdeun; Nanayakkara, N. P. Dhammika; Phoebe, Charles H.; Cordell, Geoffrey A. Phytochemistry (Elsevier), 1986 , vol. 25, # 7 p. 1685 - 1690
3-O-β-D-glucopyranosylursolic acid 28-O-β-D-glucopyranoside ester structure

3-O-β-D-glucopy...

CAS#:28288-99-5

~%

D-(+)-Glucose structure

D-(+)-Glucose

CAS#:50-99-7

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Literature: Egyptian Journal of Chemistry, , vol. 54, # 1 p. 99 - 113
Sodium acetate structure

Sodium acetate

CAS#:127-09-3

~%

Ursolic Acid Structure

Ursolic Acid

CAS#:77-52-1

Oleanic acid structure

Oleanic acid

CAS#:508-02-1

Literature: Journal of the Chemical Society, Chemical Communications, , # 14 p. 1141 - 1143

 Customs

HS Code 2942000000

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 Synonyms

Masterin
URSON
Merotaine
Neoage UR
EINECS 201-034-0
PRUNOL
MICROMEROL
Ursolicacid
Ursolic acid
MALOL
MFCD00009621
Ursolic
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