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Xanthohumol

  • CAS No.: 6754-58-1
  • Purity: 99%
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Factory supply good quality Xanthohumol 6754-58-1 with stock

  • Molecular Formula: C21H22O5
  • Molecular Weight: 354.403
  • Appearance/Colour: Orange powder 
  • Vapor Pressure: 6.82E-14mmHg at 25°C 
  • Melting Point: 157-159oC 
  • Refractive Index: 1.641 
  • Boiling Point: 576.5 °C at 760 mmHg 
  • PKA: 7.59±0.45(Predicted) 
  • Flash Point: 203.4 °C 
  • PSA: 86.99000 
  • Density: 1.244 g/cm3 
  • LogP: 4.21680 

Xanthohumol(Cas 6754-58-1) Usage

Biochem/physiol Actions

Xanthohumol induces apoptosis in glioma cancer by modulating microRNA based network. It exhibits anti-inflammatory property by inhibiting janus kinases (JAKs), signal transducer and activator of transcription proteins (STATs). Xanthohumol elicits antiviral functionality against bovine viral diarrhea virus (BVDV) and anti-hepatitis C virus in vitro. It also induces autophagy and has antiplatelet and neuroprotective effects. Xanthohumol also regulates various metabolic processes including the inhibition of triglyceride formation, atherosclerotic plaque and adipogenesis.

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.

Definition

ChEBI: 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 apo tosis in human malignant glioblastoma cells.

General Description

Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.

InChI:InChI=1/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+

6754-58-1 Relevant articles

Synthesis of xanthohumol and xanthohumol-d3from naringenin

?cianowski, Jacek,Andrusiak, Joanna,Budny, Marcin,Mylkie, Kinga,Wolan, Andrzej,Wysocka, Ma?gorzata

, p. 28934 - 28939 (2021/09/22)

A six-step synthesis of xanthohumol (1a)...

Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives

Han, Pei-Pei,Liu, Ke-Xiong,Su, Liang,Wang, Qiu-An

, p. 425 - 431 (2021/05/29)

Prenylated chalcones xanthohumol (1) and...

Microbial conjugation studies of licochalcones and xanthohumol

Han, Fubo,Xiao, Yina,Lee, Ik-Soo

, (2021/06/30)

Microbial conjugation studies of licocha...

Xanthohumol, a polyphenol chalcone present in hops, activating nrf2 enzymes to confer protection against oxidative damage in pc12 cells

Yao, Juan,Zhang, Baoxin,Ge, Chunpo,Peng, Shoujiao,Fang, Jianguo

, p. 1521 - 1531 (2015/03/05)

Xanthohumol (2a?2,4a?2,4-trihydroxy-6a?2...

6754-58-1 Process route

2′,4,4′-trimethoxymethoxy-6′-methoxy-3′-prenylchalcone

2′,4,4′-trimethoxymethoxy-6′-methoxy-3′-prenylchalcone

xanthohumol
569-83-5,6754-58-1

xanthohumol

Conditions
Conditions Yield
With hydrogenchloride; In methanol; for 0.25h; Heating;
64%
With hydrogenchloride; In methanol; at 40 ℃; for 1h;
57%
isoxanthohumol
521-48-2,70872-29-6

isoxanthohumol

xanthohumol
569-83-5,6754-58-1

xanthohumol

Conditions
Conditions Yield
With sodium thioethylate; In N,N-dimethyl-formamide;
98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 70 ℃; for 12h;
85%

6754-58-1 Upstream products

  • 521-48-2
    521-48-2

    isoxanthohumol

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    160624-22-6

    1-{2,4-bis(methoxymethoxy)-6-[(3-methylbut-2-en-1-yl)oxy]phenyl}ethanone

  • 90632-20-5
    90632-20-5

    1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone

  • 108-73-6
    108-73-6

    3,5-dihydroxyphenol

6754-58-1 Downstream products

  • 521-48-2
    521-48-2

    isoxanthohumol

  • 96169-02-7
    96169-02-7

    Tetrahydroxanthohumol

  • 906368-84-1
    906368-84-1

    7,4'-di-triisopropylsilyloxy-isoxanthohumol

  • 906368-85-2
    906368-85-2

    7,4'-di-triisopropylsilyloxy-8-prenylnaringenin

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