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Xanthohumol

Xanthohumol Struktur
6754-58-1
CAS-Nr.
6754-58-1
Englisch Name:
Xanthohumol
Synonyma:
XanthohuMo;XANTHOHUMOL;Xantho-Flav;Xanthohumol-RM;prop-2-en-1-one;Xantho Flav-Pure;Xanthohumol, >99%;Xanthohumol 99.8%;Xanthohumol Standard;Xanthohumol (6CI, 7CI)
CBNumber:
CB5128899
Summenformel:
C21H22O5
Molgewicht:
354.4
MOL-Datei:
6754-58-1.mol

Xanthohumol Eigenschaften

Schmelzpunkt:
157-159℃
Siedepunkt:
576.5±50.0 °C(Predicted)
Dichte
1.244
storage temp. 
2-8°C
L?slichkeit
ethanol: soluble10mg/mL
Aggregatzustand
powder
pka
7.59±0.45(Predicted)
Farbe
Yellow
Stabilit?t:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChI
InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChIKey
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
SMILES
C(C1=C(OC)C=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1
LogP
5.172 (est)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher N,Xi
R-S?tze: 50/53-43
S-S?tze: 60-61-45-22
RIDADR  UN 3077 9/PG 3
WGK Germany  3
RTECS-Nr. UD5574117
HS Code  29145090
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H400 Sehr giftig für Wasserorganismen. Kurzfristig (akut) gew?ssergef?hrdend Kategorie 1 Warnung GHS hazard pictogramssrc="/GHS09.jpg" width="20" height="20" /> P273, P391, P501
Sicherheit
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Xanthohumol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R50/53:Sehr giftig für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.

S-S?tze Betriebsanweisung:

S60:Dieses Produkt und sein Beh?lter sind als gef?hrlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.

Beschreibung

Xanthohumol(XH, 6754-58-1) binds to the N-terminal domain of valosin-containing protein (VCP), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of VCP thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II) Impairs prostate cancer cell growth and proliferation Cell permeable.

Chemische Eigenschaften

Xanthohumol is a Light yellow to Brown powder to crystal. It can dissolve in ethanol. This compound is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.

Verwenden

Xanthohumol from hop (Humulus lupulus) has been used:
to treat glioblastoma cells to test its effect on inducing apoptosis
to test its protective effect in renal ischemia/reperfusion (I/R) injury
as a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system

Definition

ChEBI: Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as a metabolite, an apoptosis inducer, an antineoplastic agent, an antiviral agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor and an anti-HIV-1 agent. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).

Application

Xanthohumol is the prenylated chalcone isolated from the female inflorescences of the hop plant (Humulus lupulus L.), an ingredient of beer, have long been used in traditional medicine. Xanthohumol is one of the bioactive substances, and has been reported that it has various pharmacological activities, including antioxidant, anti-inflammatory, anti-proliferative, and osteogenic effects. 

Allgemeine Beschreibung

Xanthohumol (XN), a prenylated chalcone present in Hop (Humulus lupulus), has been found to possess prominent activities against aging, diabetes, inflammation, microbial infection, and cancer.

Einzelnachweise

[1] YUKIKO SASAZAWA. Xanthohumol Impairs Autophagosome Maturation through Direct Inhibition of Valosin-Containing Protein[J]. ACS Chemical Biology, 2012, 7 5: 892-900. DOI:10.1021/cb200492h.
[2] ROBERTA VENè. Xanthohumol impairs human prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice.[J]. Molecular Medicine, 2012, 18: 1292-1302. DOI:10.2119/molmed.2012.00174.
[3] VIOLETTA KRAJKA-KU?NIAK  Wanda B D Jaros?aw Paluszczak. Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro[J]. Toxicology in Vitro, 2013, 27 1: Pages 149-156. DOI:10.1016/j.tiv.2012.10.008.
[4] BIRGIT M. DIETZ  Judy L B. Biological reactive intermediates (BRIs) formed from botanical dietary supplements[J]. Chemico-Biological Interactions, 2011, 192 1: Pages 72-80. DOI:10.1016/j.cbi.2010.10.007.
[5] SOSMITHA GIRISA. Xanthohumol from Hop: Hope for cancer prevention and treatment[J]. IUBMB Life, 2021, 73 8: 1016-1044. DOI:10.1002/iub.2522.

Xanthohumol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Xanthohumol Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 274)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.
+86-0086-025-69916489 +86-18852044786
tongyuansales@vip.sina.com China 323 58
ZhenYiBio Technology Inc
+8615309206328
alexxue@zhenyibio.com China 296 58
Hebei Kingfiner Technology Development Co.Ltd
+86-15532196582 +86-15373005021
lisa@kingfinertech.com China 2990 58
Henan Fengda Chemical Co., Ltd
+86-371-86557731 +86-13613820652
info@fdachem.com China 20288 58
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714
fandachem@gmail.com China 9220 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3619 58
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29886 58
Chengdu GLP biotechnology Co Ltd
028-87075086 13350802083
scglp@glp-china.com CHINA 1824 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897
sales@biopurify.com China 3772 58
Nanjing Dolon Biotechnology Co.,Ltd.
18905173768
sales@dolonchem.com CHINA 2972 58

6754-58-1()Verwandte Suche:


  • XANTHOHUMOL
  • XANTHOHUMOL, HUMULUS LU PULUS
  • 2',4',4-TRIHYDROXY-6'-METHOXY-3'-PRENYLCHALCONE
  • (2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
  • XanthohuMo
  • Xanthohumol from hop (Humulus lupulus)
  • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  • 2-Propen-1-one,1-[2,4-dihydroxy-6-Methoxy-3-(3-Methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)-
  • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)
  • prop-2-en-1-one
  • 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propenone
  • Xanthohumol, >99%
  • Humulus Lupulus Extract Xanthohumol 6754-58-1 HPLC 95% 98% Yellow Powder
  • large stock Xanthohumol 6754-58-1
  • Xantho Flav-Pure
  • Xantho-Flav
  • Hops Flower Extract (Standard)
  • Xanthohumol Standard
  • (E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  • (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone
  • (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
  • Xanthohumol ex. Hop (Humulus Lupulus), 94%
  • Xanthohumol Hops Extract
  • Xanthohumol (6CI, 7CI)
  • Xanthohumol 99.8%
  • Xanthohumol-RM
  • 6754-58-1
  • Flavaniods
  • standard material,plant extracts
  • SiChem
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