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SIRTINOL

Product Name
SIRTINOL
CAS No.
410536-97-9
Chemical Name
SIRTINOL
Synonyms
SIRTINOL;SIRTINOL USP/EP/BP;SIR TWO INHIBITOR NAPHTHOL;Sirtinol - CAS 410536-97-9 - Calbiochem;2-{[(2-hydroxy-1-naphthyl)methylene]amino}-N-(1-phenylethyl)benzamide;2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE;2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide;2-(((2-Hydroxynaphthalen-1-yl)methylene)amino)-N-(1-phenylethyl)benzamide;2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide;(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide
CBNumber
CB7748565
Molecular Formula
C26H22N2O2
Formula Weight
394.47
MOL File
410536-97-9.mol
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SIRTINOL Property

Melting point:
119-120℃
Boiling point:
659.2±50.0 °C(Predicted)
Density 
1.16
storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 30 mg/ml).
form 
Yellow solid
pka
7.85±0.50(Predicted)
color 
Pale yellow
Water Solubility 
Soluble in water, DMSO and methanol
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S7942
Product name
Sirtinol
Purity
≥95% (HPLC)
Packaging
1mg
Price
$106
Updated
2024/03/01
Sigma-Aldrich
Product number
S7942
Product name
Sirtinol
Purity
≥95% (HPLC)
Packaging
5mg
Price
$144
Updated
2024/03/01
Sigma-Aldrich
Product number
566320
Product name
Sirtinol
Packaging
5mg
Price
$289
Updated
2024/03/01
Alfa Aesar
Product number
J64486
Product name
Sirtinol
Packaging
10mg
Price
$202
Updated
2023/06/20
Cayman Chemical
Product number
10523
Product name
Sirtinol
Purity
≥98%
Packaging
5mg
Price
$68
Updated
2024/03/01
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SIRTINOL Chemical Properties,Usage,Production

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 cell permeable specific inhibitor of sirtuin NAD-dependant deacetylases

Uses

Sirtinol is a known inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5 and exhibits anticancer properties.

Definition

ChEBI: Sirtinol is a benzamide obtained by formal condensation of the carboxy group of 2-{[(2-hydroxy-1-naphthyl)methylene]amino}benzoic acid with the amino group of 1-phenylethylamine. It has a role as an anti-inflammatory agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and a Sir2 inhibitor. It is a member of benzamides, an aldimine and a member of naphthols. It is functionally related to an anthranilic acid.

General Description

A cell-permeable 2-hydroxy-1-naphthaldehyde derivative that acts as a specific and direct inhibitor of the sirtuin class of deacetylase activity with no affect on human HDAC1 (IC50 = 48 μM, 131 μM and 58 μM for ySir2, hSIRT1 and hSIRT2, respectively). Reported to inhibit Sir2p transcriptional silencing activity in vivo (IC50 = 25 μM), and NAD-dependent histone deacetylase activity of purified recombinant yeast Sir2p and human SIRT2 in vitro (IC50 = 70 μM and 40 μM, respectively). A 10 mM (1 mg/254 μl) solution of Sirtinol (Cat. No. 566321) in DMSO is also available.

Biological Activity

Cell-permeable, selective sirtuin deacetylase inhibitor (IC 50 values are 38, 68 and 131 μ M at SIRT2, Sir2p and SIRT1 respectively) that has no effect on HDAC1 activity. Significantly decreases growth and viability of PCa and HEK293T cells in vitro .

Biochem/physiol Actions

Cell permeable: yes

storage

Store at -20°C

References

1) Ota et al. (2006) SIRT1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells; Oncogene, 25 176 2) Mai et al. (2005) Design, synthesis and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (Sirtuin) inhibitors; J. Med. Chem. 48 7789 3) Grozinger et al. (2001) Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening; J. Biol. Chem. 276 38837 4) Koering et al. (2002) Human telomeric position effect is determined by chromosomal context and telomeric chromatin integrity; EMBO Rep. 3 1055

SIRTINOL Preparation Products And Raw materials

Raw materials

Preparation Products

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SIRTINOL Suppliers

Canada 1 China 81 India 3 Japan 1 Russia 1 Switzerland 2 United Kingdom 7 United States 25 Global 121
VDM Biochemicals
Tel
0330-2528181
Fax
0330-2528171
Email
sales@vdmbio.com
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United States
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ApexBio Technology LLC
Tel
+1-832-696-8203
Fax
+1-832-641-3177
Email
info@apexbt.com
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United States
ProdList
477
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EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8449
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60
Target molecule Corp.
Tel
857-239-0968
Fax
857-239-8801
Email
service1@targetmol.com
Country
United States
ProdList
2559
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Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
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United States
ProdList
4662
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60
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6393
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58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63711
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Aladdin Scientific
Tel
+1-833-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57511
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TargetMol Chemicals Inc.
Tel
+1-781-999-5354
Email
support@targetmol.com
Country
United States
ProdList
19973
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58

410536-97-9, SIRTINOLRelated Search:

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  • {2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]}-N-(1-phenethyl)benzamide (Sirtinol)
  • 2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE
  • SIRTINOL
  • SIR TWO INHIBITOR NAPHTHOL
  • (E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide
  • 2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide
  • 2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide
  • Sirtinol - CAS 410536-97-9 - Calbiochem
  • 2-{[(2-hydroxy-1-naphthyl)methylene]amino}-N-(1-phenylethyl)benzamide
  • N-(1-ethyl-1-cyclohexa-2,4-dienyl)-2-[(2-oxo-1-naphthalenylidene)methylamino]benzamide
  • Benzamide, 2-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)-
  • Sirtinol,2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide
  • SIRTINOL USP/EP/BP
  • 2-(((2-Hydroxynaphthalen-1-yl)methylene)amino)-N-(1-phenylethyl)benzamide
  • 410536-97-9
  • C26H22N2O2
  • DNA-RNA Transcription Regulators
  • Gene Regulation and Expression
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Inhibitors
  • Inhibitor
  • Other Enzyme Inhibitors.
  • Other enzyme inhibitors and activators