1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

Base Information

• Chemical Name: 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
• CAS No.: 569-83-5
• Molecular Formula: C21H22O5
• Molecular Weight: 354.403
• DSSTox Substance ID: DTXSID301117926
• Mol file: 569-83-5.mol

Synonyms:1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;MFCD00210576;2',4,4'-Trihydroxy-3'-prenyl-6'-methoxychalcone;DTXSID301117926;HMS3872D13;SY288787;FT-0645055

Chemical Property of 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

Chemical Property:

• Vapor Pressure: 6.82E-14mmHg at 25°C
• Refractive Index: 1.641
• Boiling Point: 576.5°C at 760 mmHg
• PKA: 7.47±0.45(Predicted)
• Flash Point: 203.4°C
• PSA: 86.99000
• Density: 1.244g/cm³
• LogP: 4.21680
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.14672380
• Heavy Atom Count: 26
• Complexity: 515

Purity/Quality:

99%, ^*data from raw suppliers

Xanthohumol(RandomConfiguration) 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
• Use Description: Xanthohumol, a natural compound found in hops and beer, has diverse applications in different fields. In the realm of health and nutrition, it is gaining attention for its potential health benefits, including antioxidant and anti-inflammatory properties. Xanthohumol has been studied for its role in reducing oxidative stress and inflammation, which can be beneficial in preventing chronic diseases such as cancer and cardiovascular disorders. In the food and beverage industry, it contributes to the flavor and aroma of beer, serving as a bittering and aromatic agent. Moreover, in the field of cosmetics and skincare, xanthohumol is utilized for its anti-aging and skin-protective properties, as it can help combat UV-induced skin damage. Its multifaceted utility underscores its significance in promoting health, enhancing culinary experiences, and contributing to skincare, where it plays a pivotal role in improving well-being, flavor profiles, and cosmetic formulations.

Technology Process of 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

There total 23 articles about 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

isoxanthohumol (521-48-2,70872-29-6) → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.04.060

Reference yield: 64.0%

2′,4,4′-trimethoxymethoxy-6′-methoxy-3′-prenylchalcone → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With hydrogenchloride; In methanol; for 0.25h; Heating;

DOI:10.1016/j.bmc.2008.02.079

Reference yield: 50.0%

2',4',4-trihydroxy-6'methoxy-3-(3-methylbut-2-en-1-yloxy)chalcone → xanthohumol (569-83-5,6754-58-1)

Guidance literature:

With hydrogenchloride; In methanol; water; for 0.5h; Inert atmosphere; Reflux;

DOI:10.1021/jm5016507

upstream raw materials:

isoxanthohumol

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

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

3,5-dihydroxyphenol

Downstream raw materials:

isoxanthohumol

α,β-dihydroxanthohumol

5-methoxy-8-(3-methyl-but-2-enyl)-7-(4-nitro-benzoyloxy)-2-[4-(4-nitro-benzoyloxy)-phenyl]-chroman-4-one

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one

Refernces

• 1、 Han, Pei-Pei,Liu, Ke-Xiong,Su, Liang,Wang, Qiu-An. "Synthesis and Antiproliferative Activity of Prenylated Chalcone Mannich Base Derivatives". . p. 425 - 431. Retrieved 2021/05/29.
• 2、 Yao, Juan,Zhang, Baoxin,Ge, Chunpo,Peng, Shoujiao,Fang, Jianguo. "Xanthohumol, a polyphenol chalcone present in hops, activating nrf2 enzymes to confer protection against oxidative damage in pc12 cells". . p. 1521 - 1531. Retrieved 2015/03/05.