| Identification | More | [Name]
6-Nitroveratraldehyde | [CAS]
20357-25-9 | [Synonyms]
2-NITRO-4,5-BIS(METHYLOXY)BENZALDEHYDE
2-Nitro-4,5-dimethoxybenzaldehyde
3,4-DIMETHOXY-6-NITROBENZALDEHYDE
4,5-DIMETHOXY-2-NITROBENZALDEHYDE
6-NITROVERATRALDEHYDE
ASISCHEM R27925
DMNB
TIMTEC-BB SBB000505
Benzaldehyde, 4,5-dimethoxy-2-nitro-
4,5-DIMETHOXY-6-NITROBENZALDEHYDE
6-NITROVERATRALDEHYDE, TECH., 80%
6-NITROVERATRALDEHYDE 80%
3,4-Dimethoxy-6-nitrobenzaldehyde, 6-Nitroveratraldehyde, DMNB
DNA-K Inhibitor
6-Nitroveratraldehyde, 85%,tech | [EINECS(EC#)]
243-762-1 | [Molecular Formula]
C9H9NO5 | [MDL Number]
MFCD00007134 | [Molecular Weight]
211.17 | [MOL File]
20357-25-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow fluffy powder | [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. ]
2-8°C
| [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 | [InChI]
1S/C9H9NO5/c1-14-8-3-6(5-11)7(10(12)13)4-9(8)15-2/h3-5H,1-2H3 | [InChIKey]
YWSPWKXREVSQCA-UHFFFAOYSA-N | [SMILES]
COc1cc(C=O)c(cc1OC)[N+]([O-])=O | [CAS DataBase Reference]
20357-25-9(CAS DataBase Reference) | [NIST Chemistry Reference]
6-Nitroveratraldehyde(20357-25-9) |
| Hazard Information | Back Directory | [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.] |
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