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03920590

Oleanolic acid

primary reference standard

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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:
85151701
PubChem Substance ID:
329747839
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

mp

>300 °C (lit.)

application(s)

food and beverages

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

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General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference Standard in the analysis of herbal medicinal products

Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
HWI01611-2
HWI01611-1
HWI01611

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Sigma-Aldrich

U6753

Ursolic acid

Fei Yu et al.
Journal of medicinal chemistry, 56(11), 4300-4319 (2013-05-15)
Development of hepatitis C virus (HCV) entry inhibitors represents an emerging approach that satisfies a tandem mechanism for use with other inhibitors in a multifaceted cocktail. By screening Chinese herbal extracts, oleanolic acid (OA) was found to display weak potency
Min Song et al.
Journal of pharmaceutical and biomedical analysis, 40(1), 190-196 (2005-08-30)
A highly selective and sensitive HPLC-ESI-MS-MS method was developed for the determination of oleanolic acid in human plasma. The oleanolic acid and glycyrrhetinic acid (internal standard) were recovered from plasma with ethyl acetate liquid-liquid extraction. The organic extracts were dried
Liangfeng Fu et al.
Organic letters, 15(7), 1622-1625 (2013-03-28)
Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial
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
Jacob Pollier et al.
Phytochemistry, 77, 10-15 (2012-03-02)
Oleanolic acid (3β-hydroxyolean-12-en-28-oic acid) is a pentacyclic triterpenoid compound with a widespread occurrence throughout the plant kingdom. In nature, the compound exists either as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be
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