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Merck

U6753

Sigma-Aldrich

Ursolic acid

≥90%

Sinónimos:

3β-Hydroxy-12-ursen-28-ic acid

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100 MG
$86.310
500 MG
$242.000

$86.310


Fecha estimada de envío21 de mayo de 2025


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100 MG
$86.310
500 MG
$242.000

About This Item

Fórmula empírica (notación de Hill):
C30H48O3
Número de CAS:
Peso molecular:
456.70
Beilstein:
2228563
Número CE:
Número MDL:
Código UNSPSC:
12352002
ID de la sustancia en PubChem:
NACRES:
NA.22

$86.310


Fecha estimada de envío21 de mayo de 2025


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Ensayo

≥90%

mp

292 °C (dec.) (lit.)

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

WCGUUGGRBIKTOS-GPOJBZKASA-N

Información sobre el gen

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Descripción general

Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial,[1] anti-cancer,[2] anti-oxidative and anti-inflammatory effects.[3] It can also promote neuroregeneration after peripheral nerve injury.[3] UA can enhance sleep duration by activating the GABAergic neurotransmitter system.[4] [GABA= γ-aminobutyric acid]

Aplicación

Ursolic acid can be used as a starting material to synthesize ethoxycarbonylmethyl ursolate (ECU) by reacting with ethyl chloroacetate. ECU is further used as a key intermediate in the total synthesis of a biologically important compound 3-acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-Me 3-O-acetylursolate.[5] Ursolic acid can also be used to prepare novel heterocyclic derivatives for various activity studies.[6]

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

580.5 °F

Punto de inflamabilidad (°C)

304.7 °C

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Certificados de análisis (COA)

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Ursolic acid induces neural regeneration after sciatic nerve injury.
Liu B, et al.
Neural Regeneration Research, 8(27), 2510-2510 (2013)
Aljawharah AlQathama et al.
Biomolecules, 10(6) (2020-06-18)
We evaluate how 3-acetylation modulates the in vitro activity of ursolic acid in melanoma cells alone or in combination treatments with quercetin. Anti-proliferative studies on A375 cells and adult human dermal fibroblasts included analyses on cell cycle distribution, caspase activity
Ursolic acid enhances pentobarbital-induced sleeping behaviors via GABAergic neurotransmission in mice.
Jeon, SJ, et al.
European Journal of Pharmacology, 762, 443-448 (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
Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells
Leal AS, et al.
Bioorganic & Medicinal Chemistry, 20(19), 5774-5786 (2012)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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