6-Nitroveratraldehyde
Synonym(s):DMNB, 4,5- Di methoxy-2- nitro benzaldehyde, DNA-Dependent Protein Kinase Inhibitor;DMNB, 4,5-Dimethoxy-2-nitrobenzaldehyde, DNA-Dependent Protein Kinase Inhibitor;DNA-PK Inhibitor - CAS 20357-25-9 - Calbiochem
- CAS NO.:20357-25-9
- Empirical Formula: C9H9NO5
- Molecular Weight: 211.17
- MDL number: MFCD00007134
- EINECS: 243-762-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-09 19:38:33
What is 6-Nitroveratraldehyde ?
Chemical properties
yellow fluffy powder
The Uses of 6-Nitroveratraldehyde
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.
What are the applications of Application
DMNB is a vanillin derivative and potent inhibitor of DNA-PK
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.]
Properties of 6-Nitroveratraldehyde
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 for 6-Nitroveratraldehyde
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 6-Nitroveratraldehyde
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REDDY N REDDY PHARMACEUTICALS
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ALUMINIUM IODIDE 100 GM BUFFER CAPSULE PH 7.0 - 10 CAP BUFFER SOLUTION PH 9.5 (BORATE) EZEE BLUE GEL STAINER BORAX CARMINE (GRENACHERS ALCOHOLIC) POTASSIUM IODATE - IODIDE SOLN 0.1 N Dabigatran Acyl-O3-D-Glucuronide Trifluoroacetic Acid Salt Isofolic Acid Dabigatran 2-O-acylglucuronide metabolite Dabigatran Acyl-?-D- glucuronide Trifluroacetic Acid Erythromycin EP Impurity A Desloratidine Related Compound ARelated products of tetrahydrofuran
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