3β-Hydroxyurs-12-en-28-sure

Bezeichnung:3β-Hydroxyurs-12-en-28-sure

CAS-Nr77-52-1

Englisch Name:Ursolic acid

CBNumberCB7470516

SummenformelC30H48O3

Molgewicht456.71

MOL-Datei77-52-1.mol

Synonyma

3β-Hydroxyurs-12-en-28-sure

3β-Hydroxyurs-12-en-28-sure physikalisch-chemischer Eigenschaften

Schmelzpunkt	292 °C (dec.) (lit.)
alpha	59 º (c=0.3, pyridine)
Siedepunkt	502.79°C (rough estimate)
Dichte	1.0261 (rough estimate)
Brechungsindex	1.4940 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO (up to 25 mg/ml with warming)
Aggregatzustand	Crystalline Powder or Needles
pka	4.68±0.70(Predicted)
Farbe	White to off-white
Wasserlöslichkeit	insoluble
Merck	14,9890
BRN	2228563
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
LogP	8.731 (est)
CAS Datenbank	77-52-1(CAS DataBase Reference)
EPA chemische Informationen	Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)- (77-52-1)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	24/25-36-26
WGK Germany	-
RTECS-Nr.	YU9520000
F	10-23
HS Code	29181990
Giftige Stoffe Daten	77-52-1(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Ursolic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
white to light yellow crystal powde
Verwenden
Ursolic Acid is a Triterpene acid used in cosmetics, that also has STAT3 pathway inhibiting properties. It inhibits endothelial cell proliferation and migration (IC50=5 μM) and angiogenesis. Promotes skeletal muscle rejuvenation via enhanced SIRT1 expression. Induces apoptosis in malignant mesothelioma cells. Ursolic acid protects against muscle atrophy and boosts muscle growth (see also tomatidine T538500).
Application
ursolic acid helps maintain the look and feel of the skin, acts as a perfume and helps mask odor. Therapeutic benefits in skin care include anti-inflammatory activity. ursolic acid has demonstrated anti-microbial, anti-bacterial, and anti-fungal action as well.
Definition
ChEBI: Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane.
Allgemeine Beschreibung
Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial, anti-cancer, anti-oxidative and anti-inflammatory effects. It can also promote neuroregeneration after peripheral nerve injury. UA can enhance sleep duration by activating the GABAergic neurotransmitter system. [GABA= γ-aminobutyric acid]
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.
Anticancer Research
It is a triterpenoid, derived from basil, and suppresses the activation of NF-κB byinhibiting a kinase that activates NF-κB(IKK) (Aggarwal and Shishodia 2004). It suppresses tumorigenesis, tumor promotion, and angiogenesis by downregulationof the expression of lipoxygenases (LOX), MMP-9, and COX-2. It is reported toinduce apoptosis in breast cancer, melanoma, hepatoma, prostate cancer, andacute myelogenous leukemia by preventing replication of DNA, inhibition of proteintyrosine kinases, activation of caspases, induction of calcium release, anddownregulating apoptosis gene cellular inhibitor. Ursolic acid inhibits IκBαkinase activity, degradation of IκBα, phosphorylation, NF-κB-dependent reportergene expression, p65 nuclear translocation, and p65 phosphorylation. Inhibitionof NF-κB leads to the reduction of cyclin D1, COX-2, and MMP9 expression.This downregulates STAT-3 activation and its regulated gene products such ascyclin D1, Mcl-1, Bcl-xL, survivin, Bcl-2, and VEGF. It also induces the expressionof tyrosine phosphatase SHP-1 protein and of mRNA (Aggarwal et al. 2008;Hsu et al. 2004).
Nebenwirkungen
Adverse effects of Ursolic acid include reduction of sperm viability and inhibition of spermatogenesis, leading to infertility. Ursolic acid is capable of inducing endothelial cell death at concentrations above 12.5uM, and the mechanism of death is related to apoptosis. In addition, it also appears to cause DNA strand breaks.
Cytotoxicity
IC₅₀ (μg/mL): 6.7 (518A2), 5.3 (A2780), 7(A549), 6.4 (FaDu), 4.8 (HT29), 5.8(MCF-7), 8.5 (NIH3T3) (Wiemann et al.2016)
IC₅₀ (μg/mL): 12.38 (MGC-803),17.12(HCT-116), 13.39 (T24), 13.81(HepG2), 16.36 (A549), >45.7 (HL-7702)(Hua et al. 2015).

Ursolic acid Upstream-Materialien And Downstream Produkte

3β-Hydroxyurs-12-en-28-sure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

77-52-1, Ursolic acid Verwandte Suche:

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