Genistein-2',3',5',6'-d4

Base Information

• Chemical Name: Genistein-2',3',5',6'-d4
• CAS No.: 187960-08-3
• Molecular Formula: C15H6 D4 O5
• Molecular Weight: 274.263
• DSSTox Substance ID: DTXSID40473830
• Nikkaji Number: J899.253C
• Wikidata: Q82303473
• Mol file: 187960-08-3.mol

Synonyms:187960-08-3;Genistein-2',3',5',6'-d4;Genistein-d4;Genistein-2',3',5',6'-d4 (Major);5,7-dihydroxy-3-(2,3,5,6-tetradeuterio-4-hydroxyphenyl)chromen-4-one;DTXSID40473830;HY-14596S;AKOS030241667;MS-23891;CS-0091916;F90926;J-012104;5,7-dihydroxy-3-[4-hydroxy(2,3,5,6-?H?)phenyl]-4H-chromen-4-one;Genistein-2 inverted exclamation mark ,3 inverted exclamation mark ,5 inverted exclamation mark ,6 inverted exclamation mark -d4 (Major)

Chemical Property of Genistein-2',3',5',6'-d4

Chemical Property:

• Melting Point: 290-292°C (dec.)
• PSA: 90.90000
• LogP: 2.57680
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 274.07793040
• Heavy Atom Count: 20
• Complexity: 411

Purity/Quality:

4-Hydroxyphenyl-2,3,5,6-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
• Isomeric SMILES: [2H]C1=C(C(=C(C(=C1C2=COC3=CC(=CC(=C3C2=O)O)O)[2H])[2H])O)[2H]
• Uses: Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol

Technology Process of Genistein-2',3',5',6'-d4

There total 3 articles about Genistein-2',3',5',6'-d4 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: 91.0%

C15H4(2)H6O5 → 5,7-dihydroxy-3-(4-hydroxyphenyl-2,3,5,6-d4)-4H-1-benzopyran-4-one (187960-08-3)

Guidance literature:

With acetyl chloride; In methanol; for 0.5h; Heating;

DOI:10.1016/S0040-4039(97)01693-6

Reference yield:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 5,7-dihydroxy-3-(4-hydroxyphenyl-2,3,5,6-d4)-4H-1-benzopyran-4-one (187960-08-3)

Guidance literature:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on; With water-d2; In acetone;

With trifluoroacetic acid-d₁; at 180 ℃; for 15h; under 9000.9 Torr; microwave irradiation;

With methanol; acetyl chloride; for 2h; Further stages.;

DOI:10.1002/jlcr.1114

Reference yield:

C15H7(2)H3O5 (136466-46-1) → 5,7-dihydroxy-3-(4-hydroxyphenyl-2,3,5,6-d4)-4H-1-benzopyran-4-one (187960-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1: P₂O₅, D₂O, BF₃ / 72 h / 55 °C

2: 91 percent / 1percent CH₃COCl / methanol / 0.5 h / Heating

With boron trifluoride; water-d2; phosphorus pentoxide; acetyl chloride; In methanol;

DOI:10.1016/S0040-4039(97)01693-6

upstream raw materials:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

C₁₅H₇⁽²⁾H₃O₅

Refernces

• 1、 Waehaelae, Kristiina,Rasku, Sirpa. "Synthesis of D4-Genistein, a Stable Deutero Labeled Isoflavone, by a Perdeuteration - Selective Dedeuteration Approach". . p. 7287 - 7290. Retrieved 2007/10/03.