Sirtinol

Base Information

• Chemical Name: Sirtinol
• CAS No.: 410536-97-9
• Molecular Formula: C26H22N2O2
• Molecular Weight: 394.473
• Hs Code.: 2925290090
• Nikkaji Number: J1.625.763J
• Wikidata: Q27140353,Q27215793
• Metabolomics Workbench ID: 66283
• ChEMBL ID: CHEMBL380797
• Mol file: 410536-97-9.mol

Synonyms:sirtinol

Chemical Property of Sirtinol

Chemical Property:

• Vapor Pressure: 8.88E-17mmHg at 25°C
• Melting Point: 119-120℃
• Boiling Point: 650°Cat760mmHg
• PKA: 7.85±0.50(Predicted)
• Flash Point: 211.4°C
• PSA: 61.69000
• Density: 1.276g/cm³
• LogP: 6.17790
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml).
• Water Solubility.: Soluble in water, DMSO and methanol
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 394.168127949
• Heavy Atom Count: 30
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

Sirtinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC(=O)C2=CC=CC=C2N=CC3=C(C=CC4=CC=CC=C43)O
• Description: Sirtinol (410536-97-9) is an inhibitor of sirtuin family enzymes including human SIRT1 (IC50=60 μM), human SIRT2 (IC50=58 μM), and yeast Sir2 (IC50=48 μM) with no inhibition of human HDAC1. Active in vivo and in purified enzyme studies. Cell permeable.
• Uses: Sirtinol is a known inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5 and exhibits anticancer properties. Sirtinol is a cell permeable specific inhibitor of sirtuin NAD-dependant deacetylases

Technology Process of Sirtinol

There total 2 articles about Sirtinol 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: 94.0%

2-amino-N-(1-phenylethyl)benzamide (85592-80-9) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 2-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide (410536-97-9)

Guidance literature:

With acetic acid; In ethanol; benzene; at 80 ℃;

Reference yield: 87.0%

isatoic anhydride (118-48-9) + rac-methylbenzylamine (618-36-0) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 2-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide (410536-97-9)

Guidance literature:

With water; at 20 ℃; for 3h; Green chemistry;

DOI:10.1080/00397911.2013.833627

Reference yield:

2-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide (410536-97-9) → C26H21FN2O4S

Guidance literature:

With fluorosulfonyl fluoride; triethylamine; In dimethyl sulfoxide; acetonitrile; at 20 ℃;

DOI:10.1021/jacs.7b12788

upstream raw materials:

2-amino-N-(1-phenylethyl)benzamide

2-hydroxynaphthalene-1-carbaldehyde

isatoic anhydride

rac-methylbenzylamine

Refernces

• 1、 -. "Sirtuin Inhibiting Compounds". Page/Page column 30; 32-33. . Retrieved 2009/06/27.