6-Nitroveratraldehyde Chemical Properties

Melting point:

131-133 °C (lit.)

Boiling point:

350.84°C (rough estimate)

Density 

1.4194 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO: 22 mg/mL

form 

solid

color 

yellow

Water Solubility 

Insoluble in water. Soluble to 25 mM in ethanol with gentle warming and to 100 mM in DMSO.

Sensitive 

Air & Light Sensitive

BRN 

395599

CAS DataBase Reference

20357-25-9(CAS DataBase Reference)

NIST Chemistry Reference

6-Nitroveratraldehyde(20357-25-9)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

RTECS 

GY8410000

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

• Language:English Provider:6-Nitroveratraldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Nitroveratraldehyde Usage And Synthesis

Chemical Properties

yellow fluffy powder

Uses

6-Nitroveratraldehyde has been used in the preparation of no-carrier-added 6-18F-fluoro-L-dopa, fundamental tracer for cerebral positron emission tomography studies of dopaminergic system in humans and o-nitroaryl-bis(5-methylfur-2-yl)methanes, versatile synthons for the synthesis of nitrogen-containing heterocycles. DMNB is also an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair. It is also used for synthesizing analogs of alpha-asarone.

Definition

ChEBI: 4,5-dimethoxy-2-nitrobenzaldehyde is a C-nitro compound and an aromatic ether.

General Description

A cell-permeable vanillin derivative that acts as a potent and selective inhibitor of DNA-dependent protein kinase (DNA-PK) activity (IC₅₀ = 15 μM) and DNA-PK-mediated double strand break (DSB) DNA repair by non-homologous DNA-end-joining (NHEJ). Reported to effectively sensitize cells to Cisplatin (Cat. No. 232120). Does not affect the activities of PKC or Chk2.

Biological Activity

Inhibitor of DNA-dependent protein kinase (DNA-PK) (IC 50 = 15 μ M), an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair in human cells. Displays 100-fold higher potency than its analog vanillin and does not affect PKC activity. Produces lethal effects on cisplatin-treated D5037 cells upon continuous exposure.

Biochem/physiol Actions

Cell permeable: yes

Purification Methods

The aldehyde is purified by dissolving 9g in 200mL of boiling 95% EtOH, and set aside overnight to crystallise. It is then dried in vacuo at 50o and recrystallised from 110mL of 95% EtOH to give 6-7g of aldehyde with m 132-133o. Crystallisation from aqueous EtOH provides light yellow needles. It is light sensitive and should be stored in the dark [Fetscher Org Synth Coll Vol 4 735 1963]. [Beilstein 8 H 262, 8 I 610, 8 II 290, 6 III 2065, 6 IV 1785.]

6-Nitroveratraldehyde (20357-25-9)Related Product Information

• 4-Dimethylaminobenzaldehyde
• Dimethyldimethoxysilane
• 3,5-Dimethoxybenzaldehyde
• 2,6-Dimethoxybenzaldehyde
• 3,4-Dimethoxybenzoic acid
• 2-Nitrobenzaldehyde
• 2,5-Dimethoxybenzaldehyde
• Dimethoxymethane
• p-Anisaldehyde
• 3-Phenoxybenzaldehyde
• 2,4-Dimethoxybenzaldehyde
• Veratraldehyde
• 2,3-Dimethoxybenzaldehyde
• o-Anisaldehyde
• NITROGEN DIOXIDE
• 2,6-DINITROPHENOL
• VERATRINE
• Methyl 2-nitro-3,4,5-trimethoxybenzoate