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O5504

Sigma-Aldrich

Oleanolic acid

≥97%

Synonym(s):

(+)-Oleanolic acid, 3beta-Hydroxyolean-12-en-28-oic acid, Astrantiagenin C, Caryophyllin, Oleanic acid

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About This Item

Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
508-02-1
Molecular Weight:
456.70
EC Number:
208-081-6
MDL number:
MFCD00064914
UNSPSC Code:
12352002
PubChem Substance ID:
57654491
NACRES:
NA.22

Assay

≥97%

form

powder

color

light yellow

mp

>300 °C (lit.)

storage temp.

2-8°C

SMILES string

[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O

InChI

1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

InChI key

MIJYXULNPSFWEK-GTOFXWBISA-N

Gene Information

mouse ... Ifng(15978) , Nos2(18126)

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General description

Oleanolic acid is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits antibacterial, antitumor and antileishmanial activity.

Application

Oleanolic acid has been used as a reference compound during its quantification in the roots of Cissampelos pareria Linn.var hirsuta by high performance thin layer chromatography (HPTLC).

Biochem/physiol Actions

Triterpenoid isolated from medicinal plants. Antitumor and hepatoprotective agent. Oleanolic acid has therapeutic potential for neurodegenerative diseases.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Apurva Bhave et al.
Journal of food and drug analysis, 25(3), 681-690 (2017-09-16)
In this study, an in-depth analysis of the unique set of rosehip samples from 71 Rosa genotypes was conducted with the aim to identify the most suitable ones for applications in the food and pharmaceutical industries based on the content
Oleanolic acid (OA) as an antileishmanial agent: Biological evaluation and in silico mechanistic insights.
Melo TS, et al.
Parasitology International, 65(3), 227-237 (2016)
Validated HPTLC method for qualitative and quantitative estimation of oleanolic acid in roots of Cissampelos pareira Linn. var. hirsuta, Menispermaceae.
Patel VG, et al.
Der Pharmacia Lettre, 7(5), 300-306 (2015)
Amélia M Silva et al.
Pharmaceutics, 11(8) (2019-07-28)
Oleanolic (OA) and ursolic (UA) acids are recognized triterpenoids with anti-cancer properties, showing cell-specific activity that can be enhanced when loaded into polymeric nanoparticles. The cytotoxic activity of OA and UA was assessed by Alamar Blue assay in three different
Dick de Zeeuw et al.
The New England journal of medicine, 369(26), 2492-2503 (2013-11-12)
Although inhibitors of the renin-angiotensin-aldosterone system can slow the progression of diabetic kidney disease, the residual risk is high. Whether nuclear 1 factor (erythroid-derived 2)-related factor 2 activators further reduce this risk is unknown. We randomly assigned 2185 patients with
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