2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromen

Bezeichnung:2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromen

CAS-Nr490-46-0

Englisch Name:L-Epicatechin

CBNumberCB0454852

SummenformelC15H14O6

Molgewicht290.27

MOL-Datei490-46-0.mol

Synonyma

2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromen

2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromen physikalisch-chemischer Eigenschaften

Schmelzpunkt	240 °C (dec.)(lit.)
alpha	-55～-65゜(D/20℃)(c=1,CH3OH)
Siedepunkt	629.2 °C
Dichte	1.593±0.06 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	insoluble in H2O; insoluble in EtOH; ≥14.5 mg/mL in DMSO
Aggregatzustand	Solid
pka	9.54±0.10(Predicted)
Farbe	White to Light yellow to Light orange
Wasserlöslichkeit	Soluble in water or alcohol
Merck	13,1912
BRN	92760
Stabilität	Hygroscopic
InChIKey	PFTAWBLQPZVEMU-UKRRQHHQSA-N
LogP	0.490 (est)
CAS Datenbank	490-46-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	KB3745000
F	10-23
HS Code	29329990

Gefahreninformationscode (GHS)

L-Epicatechin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities. It scavenges DPPH radicals in a cell-free assay when used at a concentration of 5 μM. (−)-Epicatechin inhibits COX-1 (IC₅₀ = 3.2 μM). It acts synergistically with epigallocatechin gallate to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 μM. (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.
Chemische Eigenschaften
white to light yellow crystal powde
Verwenden
An antioxidant and natural product from green tea
Verwenden
Catechin is a polyphenolic flavonoid that has been isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany. Catechin is a more potent antioxidant than ascorbate or α-tocopherol in certain in vitro lipid peroxidation assays. (?)-Epicatechin is a 2R,3R stereoisomer of catechin. Like catechin, (?)-epicatechin is a powerful antioxidant. It inhibits cyclooxygenase 1 (IC50 = 3.2 μM). Also, at 100 μM, (?)-epicatechin induces apoptosis in human adenocarcinoma PC-9 cells and stimulates the inhibition of tumor necrosis factor-α release from BALB-c/3T3 cells treated with epigallocatechin gallate.
Verwenden
Potent antioxidant and antineoplastic agent.
Definition
ChEBI: A catechin with (2R,3R)-configuration.
Allgemeine Beschreibung
(?)-Epicatechin (EC) belongs to the group of flavanols and is abundantly present in cacao and cacao products. The chemical structure of EC includes an oxygenated heterocycle with a 4-hydroxyl group linked with two aromatic rings.
Biochem/physiol Actions
This antioxidant is found in chocolate. (-)-Epicatechin is linked with cardiovascular effects. It is considered as a dependable standard due to its availability in cacao seeds and cocoa products. The halogenating activity of myeloperoxidase can be restored by (-)-epicatechin.
Einzelnachweise
[1]. chakravarthy bk, gupta s, gambhir ss, et al. pancreatic beta-cell regeneration in rats by (-)-epicatechin. lancet, 1981, 2(8249): 759-760.
[2]. wippel r, rehn m, gorren ac, et al. interference of the polyphenol epicatechin with the biological chemistry of nitric oxide- and peroxynitrite-mediated reactions. biochem pharmacol, 2004, 67(7): 1285-1295.
[3]. brossette t, hundsdörfer c, kröncke kd, et al. direct evidence that (-)-epicatechin increases nitric oxide levels in human endothelial cells. eur j nutr, 2011, 50(7): 595-599.
[4]. okushio k, suzuki m, matsumoto n, et al. identification of (-)-epicatechin metabolites and their metabolic fate in the rat. drug metab dispos, 1999, 27(2): 309-316.

L-Epicatechin Upstream-Materialien And Downstream Produkte

2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

490-46-0, L-Epicatechin Verwandte Suche:

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