SIRTINOL

ChemicalBook > CAS DataBase List > 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

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410536-97-9, SIRTINOLRelated Search:

CYCLOPAMINE (+)-Camptothecin Troglitazone SU 4312 Aristoforin 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE AGK2 SRT1720 Veliparib BEZ235 (NVP-BEZ235, Dactolisib) Doxorubicin hydrochloride SIRTINOL 2-((O-TOLYLIMINO)METHYL)PHENOL 2-AMINO-N-(1-PHENYL-ETHYL)-BENZAMIDE 1-((PHENYLIMINO)METHYL)NAPHTHALEN-2-OL

{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