Isobavachalcone

Base Information

• Chemical Name: Isobavachalcone
• CAS No.: 20784-50-3
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• UNII: ZWO2SC993A
• ChEMBL ID: CHEMBL253467
• DSSTox Substance ID: DTXSID601317123
• Metabolomics Workbench ID: 26516
• Nikkaji Number: J1.041.729E,J19.902H
• Wikidata: Q27103503
• Mol file: 20784-50-3.mol

Synonyms:isobavachalcone

Chemical Property of Isobavachalcone

Chemical Property:

• Vapor Pressure: 1.15E-12mmHg at 25°C
• Melting Point: 156.8-157.8 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 549°Cat760mmHg
• PKA: 7.99±0.40(Predicted)
• Flash Point: 299.9°C
• PSA: 77.76000
• Density: 1.243g/cm³
• LogP: 4.20820
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Soluble in DMSO
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.13615911
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

more than 97% ^*data from raw suppliers

Isobavachalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)C
• Isomeric SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
• Uses: Isobavachalcone is an inhibitor of platelet aggregation.

Technology Process of Isobavachalcone

There total 18 articles about Isobavachalcone 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: 89.0%

(E)-1-(2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1449202-18-9) → isobavachalcone (54676-49-2,20784-50-3) + 2',4-dihydroxy-4'-methoxymethoxy-3'-prenylchalcone

Guidance literature:

With hydrogenchloride; In methanol; water; for 3h; Reflux;

DOI:10.1002/ejoc.201201063

Reference yield: 75.0%

(E)-1-(2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1449202-18-9) → isobavachalcone (54676-49-2,20784-50-3)

Guidance literature:

With hydrogenchloride; methanol; In water; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.12.044

Reference yield: 72.0%

4,4'-bis(methoxymethoxy)-2'-hydroxyl-3'-prenylchalcone → isobavachalcone (54676-49-2,20784-50-3)

Guidance literature:

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

DOI:10.1016/j.tet.2011.04.104

upstream raw materials:

2',4'-dihydroxy-4-acetophenone

2'-prenyloxy-4'-methoxymethoxyacetophenone

4,4'-bis(methoxymethoxy)-2'-prenyloxychalcone

4-methoxymethoxy-benzaldehyde

Downstream raw materials:

(E)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Refernces

• 1、 Wang, Ruishan,Chen, Ridao,Li, Jianhua,Liu, Xiao,Xie, Kebo,Chen, Dawei,Peng, Ying,Dai, Jungui. "Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase". . p. 2143 - 2147. Retrieved 2016/09/09.
• 2、 Wang, Haomeng,Yan, Zhihong,Lei, Yanan,Sheng, Kai,Yao, Qingwei,Lu, Kui,Yu, Peng. "Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions". . p. 897 - 899. Retrieved 2014/02/14.