Available from stock

Betulinic acid

SKU: B0402

Category: Phytochemicals

Synonyms: 3β-Hydroxy-20(29)-lupaene-28-oic acid; 472-15-1
CAS-Number: C₃₀H₄₈O₃
Molecular Formula: 456.71
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 powder
Identity: 1H-NMR

Properties

Solvents: DMSO (20 mg/ml), DMF (15 mg/ml)

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

Transportation: Not dangerous goods

Description: Betulinic acid is a natural plant triterpenoid. It has been shown to have anticancer, apoptotic, anti-inflammatory, antiobesity, antimalarial and anti-HIC properties. It has been described as a potent DNA topoisomerase II inhibitor and proteasome activator. It is an agonist of the G protein-coupled bile acid receptor TGR5, which might be linked with its ability to alter gene expression and fatty liver development. Betulinic acid also reduces NF-?B signaling and expression of microRNA-33 in LPS-treated macrophages, increasing levels of the ATP-binding cassette (ABC) cholesterol transporter ABCA1.
Smiles: O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@@]3(C)CC[C@]5(C(O)=O)[C@]4([H])[C@H](C(C)=C)CC5)([H])C1(C)C
InChi Key: QGJZLNKBHJESQX-FZFNOLFKSA-N
References: (1) T. Fujioka, et al., J. Nat. Prod. 57, 243 (1994) , (2) E. Pisha, et al., Nat. Med. 1, 1046 (1995) , (3) Y. Kashiwada, et al., J. Med. Chem. 39, 1016 (1996) , (4) Y. Takada & B.B. Aggarwal: J. Immunol. 171, 3278 (2003) , (5) H. Kasperczyk, et al., Oncogene 24, 6945 (2005) , (6) S. Wada & R. Tanaka, Chem. Biodivers. 2, 689 (2005) , (7) L. Huang, et al., FEBS Lett. 581, 4955 (2007) , (8) M.S. de Sa, et al., Parasitol. Res. 105, 275 (2009) , (9) F.B. Mullauer, et al., Anticancer Drugs 21, 215 (2010) , (10) C. Genet, et al., J. Med. Chem. 53, 178 (2010) , (11) Y. Wan, et al., Intern. Immunopharmacol. 17, 184 (2013) , (12) G.J. Zhao, et al., PLoS One 8, e474782 (2013) , (13) K.D. Kim, et al., Nutr. Metab. Cardiovasc. Dis. 29, 409 (2019) , (14) Y. Zheng, et al., Oxid. Med. Cell Longev. 2019, 8781690 (2019) , (15) W. Liu, et al., Am. J. Transl. Res. 11, 6952 (2019)
InChi: InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

Betulinic acid is a natural plant triterpenoid. It has been shown to have anticancer, apoptotic, anti-inflammatory, antiobesity, antimalarial and anti-HIC properties. It has been described as a potent DNA topoisomerase II inhibitor and proteasome activator. It is an agonist of the G protein-coupled bile acid receptor TGR5, which might be linked with its ability to alter gene expression and fatty liver development. Betulinic acid also reduces NF-?B signaling and expression of microRNA-33 in LPS-treated macrophages, increasing levels of the ATP-binding cassette (ABC) cholesterol transporter ABCA1.

SKU: B0402 Category: Phytochemicals

Additional information

Additional information

Synonyms	3β-Hydroxy-20(29)-lupaene-28-oic acid
Purity	≥98% (HPLC)
Appearance	White powder
CAS-Number	472-15-1
Molecular Formula	C30H48O3
Molecular Weight	456.71
Identity	1H-NMR
Solvents	DMSO (20 mg/ml), DMF (15 mg/ml)
Smiles	O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@@]3(C)CC[C@]5(C(O)=O)[C@]4([H])[C@H](C(C)=C)CC5)([H])C1(C)C
InChi Key	QGJZLNKBHJESQX-FZFNOLFKSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Transportation	Not dangerous goods
References	(1) T. Fujioka, et al., J. Nat. Prod. 57, 243 (1994), (2) E. Pisha, et al., Nat. Med. 1, 1046 (1995), (3) Y. Kashiwada, et al., J. Med. Chem. 39, 1016 (1996), (4) Y. Takada & B.B. Aggarwal: J. Immunol. 171, 3278 (2003), (5) H. Kasperczyk, et al., Oncogene 24, 6945 (2005), (6) S. Wada & R. Tanaka, Chem. Biodivers. 2, 689 (2005), (7) L. Huang, et al., FEBS Lett. 581, 4955 (2007), (8) M.S. de Sa, et al., Parasitol. Res. 105, 275 (2009), (9) F.B. Mullauer, et al., Anticancer Drugs 21, 215 (2010), (10) C. Genet, et al., J. Med. Chem. 53, 178 (2010), (11) Y. Wan, et al., Intern. Immunopharmacol. 17, 184 (2013), (12) G.J. Zhao, et al., PLoS One 8, e474782 (2013), (13) K.D. Kim, et al., Nutr. Metab. Cardiovasc. Dis. 29, 409 (2019), (14) Y. Zheng, et al., Oxid. Med. Cell Longev. 2019, 8781690 (2019), (15) W. Liu, et al., Am. J. Transl. Res. 11, 6952 (2019)
InChi	InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
Quantity	25 mg, Bulk