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Ursolic acid

analytical standard

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Synonym(s):
3β-Hydroxy-12-ursen-28-ic acid
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
77-52-1
Molecular Weight:
456.70
Beilstein:
2228563
EC Number:
201-034-0
MDL number:
MFCD00009621
UNSPSC Code:
85151701
PubChem Substance ID:
329769543
NACRES:
NA.24

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.

WGK

WGK 3

Flash Point(F)

580.5 °F

Flash Point(C)

304.7 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
MinKyun Na et al.
Journal of natural products, 69(11), 1572-1576 (2006-11-28)
Inhibition of protein tyrosine phosphatase-1B (PTP1B) has been proposed as a therapy for treatment of type-2 diabetes and obesity. Bioassay-guided fractionation of an EtOAc-soluble extract of the root bark of Erythrina mildbraedii, using an in vitro PTP1B inhibitory assay, resulted
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
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
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