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Merck

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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grade

analytical standard

Quality Level

100

assay

≥98.5% (HPLC)

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

292 °C (dec.) (lit.)

application(s)

food and beverages

format

neat

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

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

InChI key

WCGUUGGRBIKTOS-GPOJBZKASA-N

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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.

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.

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)
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
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
Yasutaka Ikeda et al.
Molecular nutrition & food research, 52(1), 26-42 (2008-01-19)
There is growing interest in the elucidation of the biological functions of triterpenoids, ubiquitously distributed throughout the plant kingdom, some of which are used as anticancer and anti-inflammatory agents in Asian countries. Ursolic acid (UA), a natural pentacyclic triterpenoid carboxylic
Simone Angeloni et al.
Plants (Basel, Switzerland), 10(2) (2021-01-27)
Leonurus cardiaca L. (Lamiaceae) is a perennial herb distributed in Asia and Southeastern Europe and has been used in traditional medicine since antiquity for its role against cardiac and gynecological disorders. The polar extracts obtained from L. cardiaca aerial parts
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