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Urolithin A

HCID 5488186
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Grundinformationen

CAS
1143-70-0
Standard-SMILES
O=c1oc2cc(O)ccc2c2ccc(O)cc12
InChIKey
RIUPLDUFZCXCHM-UHFFFAOYSA-N
Summenformel
C13H8O4
Durchschnittliche Molmasse
228,203 g/mol
Monoisotopische Masse
228,04225874

Namen und Bezeichner

Bevorzugter Name
Urolithin A
IUPAC
3,8-Dihydroxy-6H-dibenzo[b,d]pyran-6-one
Englischer Name
Urolithin A
Summenformel
C13H8O4
Molmasse
228.2

Namen und Synonyme

UA3,8-dihydroxybenzo[c]chromen-6-oneUro-AC13H8O4Urolith ANeolithicAUrolithin AUrolithan Aurolithin-A(UAJACS-1143-70-0

Datenbank-Bezeichner

CAS
1143-70-0
PubChem CID
5488186
DTXSID
DTXSID40150694
ChEMBL
CHEMBL1836264
ChEBI
CHEBI:168442
UNII
ILJ8NEF6DT
EC Number
881-478-5
Nikkaji
J12.496F

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
340 · 340-345 °C
Siedepunkt
527.9 · 527.9±43.0 °C(Predicted)
Dichte
1.516 · 1.516±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
DMSO (Slightly), Methanol (Very Slightly)
Aggregatzustand
powder
pka
9.07 · 9.07±0.20(Predicted)
Farbe
white to beige
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING - MISCELLANEOUS
InChI
InChI=1S/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H
InChIKey
RIUPLDUFZCXCHM-UHFFFAOYSA-N
SMILES
C12=CC(O)=CC=C1C1=CC=C(O)C=C1C(=O)O2
LogP
2.311 · 2.311 (est)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungUrolithin A is a metabolite of ellagic acid. It is produced by the body after you ingest compounds found in particularly high concentration in pomegranates (particularly the bitter components such as the skin and seeds) and can help recycle defective mitochondria. Since it is a metabolite that results from the transformation of the tannins in pomegranate by gut bacteria, it can be classified as a postbiotic.It has been demonstrated to stimulate mitophagy and improve muscle health in old animals and in preclinical models of aging.

VerwendenUrolithin A(UA) is a major metabolite of ellagitannin and exhibits anti-inflammatory and antioxidant properties. UA also has the ability to induce autophagy and apoptosis, inhibit cell cycle progression, and inhibit DNA synthesis. At the physiological level, UA improved muscle function in nematodes, young rodents, old mice, and muscle-wasting disorders such as Duchenne muscle dystrophy (DMD). Long-term intake of UA improves muscle endurance. In vitro studies, it has also been shown to inhibit the growth of human cancer cells in the colon, prostate and breast.

Darstellung · 1 Eintrag

synthetische2-bromo-5-methoxybenzoic acid is coupled with resorcinol to yield the intermediate “methoxy” product (Intermediate A), which is then isolated via filtration and dried for use in step 2. The solvent methanol is utilized in this step.the intermediate product, "Intermediate A", is treated with the Lewis acid, AlCl3, in order to obtain a crude urolithin A. The ether cleavage of Intermediate A is accomplished by activation of the methyl ether through the addition of the Lewis acid, AlCl3, in toluene. The activated species is then hydrolyzed by the addition of water. Following hydrolysis, the crude product is filtered and dried.crude urolithin A is dissolved in dimethyl sulfoxide (DMSO) for a polish filtration and subsequently precipitated from this DMSO solution by the addition of water. The filter cake is rinsed by water, followed by methanol. The raw urolithin A is then triturated with acetic acid (HOAc) to further purify the product and then collected by filtration. Following filtration, the purified product is rinsed with HOAc followed by tert-butyl-methyl ether (TBME), then dried to yield the final product, urolithin A.Synthesis of Urolithin A

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Ergänzende Hinweise

DefinitionChEBI: Urolithin A is a member of coumarins. It has a role as a geroprotector.