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O5504

Sigma-Aldrich

Oleanolic acid

≥97%

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Synonym(s):
(+)-Oleanolic acid, 3beta-Hydroxyolean-12-en-28-oic acid, Astrantiagenin C, Caryophyllin, Oleanic acid
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
Molecular Weight:
456.70
EC Number:
MDL number:
PubChem Substance ID:
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

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This Item
M6699SMB00119G10105
vibrant-m

O5504

Oleanolic acid

vibrant-m

M6699

Maslinic acid

vibrant-m

SMB00119

Arjunolic acid

vibrant-m

G10105

18β-Glycyrrhetinic acid

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

form

powder

form

powder

form

solid

form

-

mp

>300 °C (lit.)

mp

-

mp

-

mp

292-295 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

color

light yellow

color

white to off-white

color

-

color

-

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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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
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
Ursolic, oleanolic and betulinic acids: antibacterial spectra and selectivity indexes.
Fontanay S, et al.
Journal of Ethnopharmacology, 120(2), 272-276 (2008)

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