(2S)-Isoxanthohumol

Base Information

• Chemical Name: (2S)-Isoxanthohumol
• CAS No.: 70872-29-6
• Molecular Formula: C21H22O5
• Molecular Weight: 354.39600
• Hs Code.: 29329990
• UNII: X4YHZ98N7Q
• DSSTox Substance ID: DTXSID101045280
• Nikkaji Number: J1.661.185I
• Wikidata: Q72486654
• ChEMBL ID: CHEMBL4160626
• Mol file: 70872-29-6.mol

Synonyms:70872-29-6;(2S)-Isoxanthohumol;(-)-Isoxanthohumol;(S)-7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one;(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one;Isoxanthohumol, (-)-;Isoxanthohumol (sophora);X4YHZ98N7Q;CHEMBL4160626;SCHEMBL14092988;YKGCBLWILMDSAV-SFHVURJKSA-N;DTXSID101045280;HY-N2584;s9070;AKOS032949010;CCG-268085;AC-35040;MS-25528;CS-0022926;FT-0645062;I1065;(2S)-4',7-Dihydroxy-5-methoxy-8-prenylflavanone;(2s)-7,4'-dihydroxy-5-methoxy-8-(gamma,gamma-dimethylallyl)-flavanone;(2S)-2-(4-Hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-7-oxidanyl-2,3-dihydrochromen-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-, (2S)-;4H-1-Benzopyran-4-one,2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-, (2S)-

Chemical Property of (2S)-Isoxanthohumol

Chemical Property:

• Melting Point: 196-208℃
• Boiling Point: 585.8±50.0 °C(Predicted)
• PKA: 7.90±0.40(Predicted)
• PSA: 75.99000
• Density: 1.245±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 4.32160
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 354.14672380
• Heavy Atom Count: 26
• Complexity: 519

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-Isoxanthohumol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C
• Isomeric SMILES: CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
• Uses: (-)-Isoxanthohumol is a structural analog of xanthohumol that possesses anti-microbial activity. Also, it exhibits diverse biological activities, e.g. antitumor, antiiflammatory, antioxidant and antiangiogenic.

Technology Process of (2S)-Isoxanthohumol

There total 12 articles about (2S)-Isoxanthohumol 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: 99.0%

4-(7-acetoxy-5-methoxy-8-(3-methylbut-2-en-1-yl)-4-oxochroman-2-yl)phenyl acetate → isoxanthohumol (521-48-2,70872-29-6)

Guidance literature:

With potassium hydroxide; In methanol; for 1h;

DOI:10.1039/d1ra05443k

Reference yield: 83.8%

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

Guidance literature:

With sodium hydroxide;

DOI:10.1016/j.tet.2008.07.072

Reference yield: 18.3%

dimethylallyl diphosphate (358-72-5) + 7,4′-dihydroxy-5-methoxyflavanone (61775-19-7) → Isoxanthohumol (70872-29-6)

Guidance literature:

With recombinant Sophora flavescens flavonoid prenyltransferase; magnesium chloride; In aq. buffer; at 40 ℃; for 2h; pH=9; stereospecific reaction; Kinetics; Enzymatic reaction;

DOI:10.1002/adsc.201300196

upstream raw materials:

xanthoarnol

xanthohumol

desmethylxanthohumol

2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate

Downstream raw materials:

2'',3''-dihydroisoxanthohumol

Refernces

• 1、 Andrusiak, Joanna,Mylkie, Kinga,Wysocka, Ma?gorzata,?cianowski, Jacek,Wolan, Andrzej,Budny, Marcin. "Synthesis of xanthohumol and xanthohumol-d3from naringenin". . p. 28934 - 28939. Retrieved 2021/09/22.
• 2、 -. "Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders". Page/Page column 39. . Retrieved 2017/01/23.