2,4-Dihydroxychalcone

Base Information

• Chemical Name: 2,4-Dihydroxychalcone
• CAS No.: 1776-30-3
• Molecular Formula: C15H12 O3
• Molecular Weight: 240.258
• Nikkaji Number: J608.557A
• Wikidata: Q76325161
• Metabolomics Workbench ID: 48597
• ChEMBL ID: CHEMBL373249
• Mol file: 1776-30-3.mol

Synonyms:2,4-dihydroxychalcone;NSC 401492;(E)-3-(2,4-dihydroxyphenyl)-1-phenylprop-2-en-1-one;BRN 2052485;3-(2,4-Dihydroxyphenyl)-1-phenyl-2-propen-1-one;CHEMBL373249;CHEBI:174241;LS-52902;J-011299;(2E)-3-(2,4-dihydroxyphenyl)-1-phenylprop-2-en-1-one;(E)-3-(2,4-dihydroxyphenyl)-1-phenyl-prop-2-en-1-one

Chemical Property of 2,4-Dihydroxychalcone

Chemical Property:

• Melting Point: 170°C
• Boiling Point: 453.5±38.0 °C(Predicted)
• PKA: 7.42±0.35(Predicted)
• Flash Point: 242.2oC
• PSA: 57.53000
• Density: 1.286±0.06 g/cm3(Predicted)
• LogP: 2.99390
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 240.078644241
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

99% ^*data from raw suppliers

1-(2,4-Dihydroxyphenyl)-3-phenylprop-2-en-1-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=CC2=C(C=C(C=C2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)/C=C/C2=C(C=C(C=C2)O)O
• Uses: anthelmintic, antiulcer, antineoplastic

Technology Process of 2,4-Dihydroxychalcone

There total 50 articles about 2,4-Dihydroxychalcone 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: 100.0%

(E)-1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-phenylprop-2-en-1-one (126686-32-6) → (E)-2',4'-dihydroxychalcone (1776-30-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 0 - 40 ℃; for 3h;

DOI:10.3390/molecules27020463

Reference yield: 87.0%

2',4'-dihydroxy-4-acetophenone (89-84-9) + benzaldehyde (100-52-7) → 2',4'-dihydroxychalcone (1776-30-3,25515-43-9)

Guidance literature:

With calcium hydroxide; In methanol; for 12h; Temperature; Time; Reflux; Green chemistry;

DOI:10.1080/15533174.2012.752392

Reference yield: 78.0%

benzaldehyde (100-52-7) + 2',4'-bis(tetrahydropyran-2-yloxy)acetophenone (136258-01-0) → (E)-2',4'-dihydroxychalcone (1776-30-3)

Guidance literature:

With barium hydroxide octahydrate; toluene-4-sulfonic acid; In methanol; at 40 ℃; for 12h; stirring; evapg; water adding; netralizing with 1 M HCl; extg. with EtOAc;

DOI:10.1111/j.2042-7158.1997.tb06837.x

upstream raw materials:

cinnamoyl chloride

recorcinol

Cinnamic acid

1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one

Downstream raw materials:

benzoic acid methyl ester

4-hydroxysalicylic acid

benzoic acid

7-hydroxy-2-phenyl-chroman-4-one

Refernces

• 1、 Morsingh. "". . p. 355. Retrieved 1969.
• 2、 Passalacqua, Thais G.,Torres, Fábio A.E.,Nogueira, Camila T.,De Almeida, Leticia,Del Cistia, Mayara L.,Dos Santos, Mariana B.,Regasini, Luis O.,Graminha, Márcia A.S.,Marchetto, Reinaldo,Zottis, Aderson. "The 2′,4′-dihydroxychalcone could be explored to develop new inhibitors against the glycerol-3-phosphate dehydrogenase from Leishmania species". . p. 3564 - 3568. Retrieved 2015.
• 3、 Abdpour, Shahin,Jalili-Baleh, Leili,Nadri, Hamid,Forootanfar, Hamid,Bukhari, Syed Nasir Abbas,Ramazani, Ali,Ebrahimi, Seyed Esmaeil Sadat,Foroumadi, Alireza,Khoobi, Mehdi. "Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer's disease". . . Retrieved 2021/03/14.
• 4、 Zhong, Hui,Zhou, Jia,An, Xiao-Hong,Hua, Ying-Rong,Lai, Yi-Fan,Zhang, Rui,Ahmad, Owais,Zhang, Ye,Shang, Jing. "Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents". . p. 523 - 533. Retrieved 2019/04/01.