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Merck
CN

89797

Ursolic acid

analytical standard

Synonym(s):

3β-Hydroxy-12-ursen-28-ic acid

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About This Item

Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
77-52-1
Molecular Weight:
456.70
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329769543
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
MFCD00009621

Key Documents

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Product Name

Ursolic acid, analytical standard

InChI key

WCGUUGGRBIKTOS-GPOJBZKASA-N

InChI

1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

SMILES string

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)CC[C@H](O)C2(C)C

grade

analytical standard

assay

≥98.5% (HPLC)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

292 °C (dec.) (lit.)

application(s)

food and beverages

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Triterpenoid found in a variety of fruits, including apples. Cardioprotective and anti-tumor agent. Under study as a potential Alzheimer′s disease therapeutic due to its inhibitory effect on the interactions between amyloid-β and the CD36 receptor.

General description

Ursolic acid belongs to the class of triterpenoid compounds that occurs widely in medicinal herbs, food and other plants. It may possess pharmacological properties like hepta-protection, analgesic, cardiotonic, sedative and tonic effects.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

580.5 °F

flash_point_c

304.7 °C

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6885
BCCL0153
BCCJ2895
BCCH6396
BCCG7683

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Pharmacology of oleanolic acid and ursolic acid
Liu J
Journal of Ethnopharmacology, 49, 57-68 (1995)
Jing-Wei Shao et al.
European journal of medicinal chemistry, 46(7), 2652-2661 (2011-04-26)
Twenty-three ursolic acid (1) derivatives 2-24 (ten novel compounds 8-10, 14-17 and 22-24) modified at the C-3 and the C-28 positions were synthesized, and their structures were confirmed by IR, (1)H NMR, MS, and elemental analysis. The single crystals of
Jin-Feng Hu et al.
Journal of natural products, 69(1), 118-120 (2006-01-31)
One new (1) and four known (2-5) ursene triterpenes with potent inhibition of the formation of the bacterial biofilm Pseudomonas aeruginosa PA01 were obtained from Diospyros dendo using a high-throughput natural products chemistry procedure. These compounds were isolated as mass-limited
Huang-Yao Tu et al.
Bioorganic & medicinal chemistry, 17(20), 7265-7274 (2009-09-18)
Twenty-three ursolic acid (1) derivatives 2-24 including nine new 1 derivatives 5, 7-11, 20-22 were synthesized and evaluated for cytotoxicities against NTUB1 cells (human bladder cancer cell line). Compounds 5 and 17 with an isopropyl ester moiety at C-17-COOH and
Hao Zhang et al.
International journal of pharmaceutics, 441(1-2), 261-268 (2012-12-01)
It has been demonstrated that ursolic acid (UA) could effectively induces apoptosis of cancer cells by inhibiting the expression of cyclooxygenase 2 (COX-2), which constitutively expresses in gastric cancer. However, the hydrophobicity of UA increases the difficulty in its potential
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