Available from stock

Ursolic acid

SKU: U0400

Category: Phytochemicals

Synonyms: 3β-Hydroxy-12-ursen-28-oic acid , Bungeolic Acid , Maerotaine , Malol , NSC 4060 , NSC 167406; 77-52-1
CAS-Number: C₃₀H₄₈O₃
Molecular Formula: 456.711
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: DMSO (10 mg/ml), DMF (10 mg/ml)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Transportation: Not dangerous goods

Description: Ursolic acid is a pentacyclic triterpenoid that has been isolated from M. pumila. Ursolic acid has diverse biological effects, including anti-inflammatory, anticancer, antidiabetic, antiobesity, neuroprotective, cardioprotective, hepatoprotective, antioxidant and antiviral and antibacterial effects. Effects relevant to its anticancer properties include, apoptosis and autophagy induction, preventing angiogenesis, microtubule-destabilizing, induction of cell cycle arrest and inhibition of tumor growth. Ursolic acid inhibits NF-?B signaling through suppression of IkappaBalpha kinase and p65 phosphorylation. It has been shown to enhance pancreatic beta-cell function in diabetic mice and activates the TGR5 receptor to enhance GLP-1 secretion. Its antiobesity potential is related to inhibiting pancreatic lipase and adipogenesis and increasing insulin sensitivity and inhibiting α,-glucosidase. Ursolic acid is also liver X receptor α, (LXRα,) antagonist inhibiting ligand-induced Nnnalcoholic fatty liver and drug-induced lipogenesis. Ursolic acid also scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and inhibits the growth of several strains of Gram-positive and Gram-negative bacteria in vitro.
Smiles: C[C@@H]1CC[C@]2(C(O)=O)CC[C@@]3([H])[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])[C@H]1C
InChi Key: NZFQEZMPDNBQMO-PBILNHPASA-N
References: (1) Z. Kowalewski, et al., Arch. Immunol. Ther. Exp. 24, 115 (1976) , (2) D.K. Kim, et al., Int. J. Cancer 87, 629 (2000) , (3) L. Novotny, et al., Neoplasma 48, 241 (2001) (Review) , (4) F. Abe, et al., Biol Pharm Bull. 25, 1485 (2002) , (5) S. Shishodia, et al., Cancer Res. 63, 4375 (2003) , (6) M.S. Ali, et al., Phytother. Res. 21, 558 (2007) , (7) A. Nataraju, et al., Curr. Top Med. Chem. 7, 801 (2007) , (8) S.M. Jang, et al., Int. Immunopharmacol. 9, 113 (2009) , (9) M. Kanjoormana & G. Kuttan, Integr. Cancer Ther. 9, 224 (2010) , (10) I. Kazmi, et al., Eur. J. Pharmacol. 709, 28 (2013) , (11) Y. He, et al., PLoS One 8, e70135 (2013) , (12) L. Wozniak, et al., Molecules 20, 20614 (2015) (Review) , (13) D. Kashyap, et al., Recent Pat. Inflamm. Allergy Drug Discov. 10, 21 (2016) (Review) , (14) C.K. Katashima, et al., Obes. Rev. 18, 700 (2017) (Review) , (15) A.M. Ramirez-Rodriguez, et al., J. Med. Food. 20, 882 (2017) , (16) S.H. Lo, et al., Naunyn Schmiedebergs Arch. Pharmacol. 390, 1097 (2017) , (17) Y.N. Lin, et al., J. Agric. Food Chem. 66, 11647 (2018) , (18) S. Habtemariam, Oxid. Med. Cell Longev. 2019, 8512048 (2019) (Review) , (18) S. Mlala, et al., Molecules 24, E2751 (2019) (Review) , (20) J. Wang, et al., J. Sci. Food Agric. 100, 986 (2020)
InChi: InChI=1S/C29H46O3/c1-17-9-15-29(25(31)32)16-10-20-19(24(29)18(17)2)7-8-22-27(20,5)13-11-21-26(3,4)23(30)12-14-28(21,22)6/h7,17-18,20-24,30H,8-16H2,1-6H3,(H,31,32)/t17-,18+,20-,21+,22+,23+,24+,27+,28+,29?/m1/s1

Ursolic acid is a pentacyclic triterpenoid that has been isolated from M. pumila. Ursolic acid has diverse biological effects, including anti-inflammatory, anticancer, antidiabetic, antiobesity, neuroprotective, cardioprotective, hepatoprotective, antioxidant and antiviral and antibacterial effects. Effects relevant to its anticancer properties include, apoptosis and autophagy induction, preventing angiogenesis, microtubule-destabilizing, induction of cell cycle arrest and inhibition of tumor growth. Ursolic acid inhibits NF-?B signaling through suppression of IkappaBalpha kinase and p65 phosphorylation. It has been shown to enhance pancreatic beta-cell function in diabetic mice and activates the TGR5 receptor to enhance GLP-1 secretion. Its antiobesity potential is related to inhibiting pancreatic lipase and adipogenesis and increasing insulin sensitivity and inhibiting α,-glucosidase. Ursolic acid is also liver X receptor α, (LXRα,) antagonist inhibiting ligand-induced Nnnalcoholic fatty liver and drug-induced lipogenesis. Ursolic acid also scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and inhibits the growth of several strains of Gram-positive and Gram-negative bacteria in vitro.

SKU: U0400 Category: Phytochemicals

Additional information

Additional information

Synonyms	3β-Hydroxy-12-ursen-28-oic acid, Bungeolic Acid, Maerotaine, Malol, NSC 4060, NSC 167406
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	77-52-1
Molecular Formula	C30H48O3
Molecular Weight	456.711
Identity	1H-NMR
Solvents	DMSO (10 mg/ml), DMF (10 mg/ml)
Smiles	C[C@@H]1CC[C@]2(C(O)=O)CC[C@@]3([H])[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])[C@H]1C
InChi Key	NZFQEZMPDNBQMO-PBILNHPASA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Transportation	Not dangerous goods
References	(1) Z. Kowalewski, et al., Arch. Immunol. Ther. Exp. 24, 115 (1976), (2) D.K. Kim, et al., Int. J. Cancer 87, 629 (2000), (3) L. Novotny, et al., Neoplasma 48, 241 (2001) (Review), (4) F. Abe, et al., Biol Pharm Bull. 25, 1485 (2002), (5) S. Shishodia, et al., Cancer Res. 63, 4375 (2003), (6) M.S. Ali, et al., Phytother. Res. 21, 558 (2007), (7) A. Nataraju, et al., Curr. Top Med. Chem. 7, 801 (2007), (8) S.M. Jang, et al., Int. Immunopharmacol. 9, 113 (2009), (9) M. Kanjoormana & G. Kuttan, Integr. Cancer Ther. 9, 224 (2010), (10) I. Kazmi, et al., Eur. J. Pharmacol. 709, 28 (2013), (11) Y. He, et al., PLoS One 8, e70135 (2013), (12) L. Wozniak, et al., Molecules 20, 20614 (2015) (Review), (13) D. Kashyap, et al., Recent Pat. Inflamm. Allergy Drug Discov. 10, 21 (2016) (Review), (14) C.K. Katashima, et al., Obes. Rev. 18, 700 (2017) (Review), (15) A.M. Ramirez-Rodriguez, et al., J. Med. Food. 20, 882 (2017), (16) S.H. Lo, et al., Naunyn Schmiedebergs Arch. Pharmacol. 390, 1097 (2017), (17) Y.N. Lin, et al., J. Agric. Food Chem. 66, 11647 (2018), (18) S. Habtemariam, Oxid. Med. Cell Longev. 2019, 8512048 (2019) (Review), (18) S. Mlala, et al., Molecules 24, E2751 (2019) (Review), (20) J. Wang, et al., J. Sci. Food Agric. 100, 986 (2020)
InChi	InChI=1S/C29H46O3/c1-17-9-15-29(25(31)32)16-10-20-19(24(29)18(17)2)7-8-22-27(20,5)13-11-21-26(3,4)23(30)12-14-28(21,22)6/h7,17-18,20-24,30H,8-16H2,1-6H3,(H,31,32)/t17-,18+,20-,21+,22+,23+,24+,27+,28+,29?/m1/s1
Quantity	500 mg, 1 g, Bulk