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6-Nitroveratraldehyde

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CAS:20357-25-9
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6-Nitroveratraldehyde Basic information
Product Name:6-Nitroveratraldehyde
Synonyms:TIMTEC-BB SBB000505;ASISCHEM R27925;DMNB;3,4-DIMETHOXY-6-NITROBENZALDEHYDE;2-Nitro-4,5-dimethoxybenzaldehyde;2-NITRO-4,5-BIS(METHYLOXY)BENZALDEHYDE;Benzaldehyde, 4,5-dimethoxy-2-nitro-;6-NITROVERATRALDEHYDE
CAS:20357-25-9
MF:C9H9NO5
MW:211.17
EINECS:243-762-1
Product Categories:Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C9;Carbonyl Compounds
Mol File:20357-25-9.mol
6-Nitroveratraldehyde Structure
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 Reference20357-25-9(CAS DataBase Reference)
NIST Chemistry Reference6-Nitroveratraldehyde(20357-25-9)
Safety Information
Hazard Codes Xi
Safety Statements 24/25
WGK Germany 3
RTECS GY8410000
HazardClass IRRITANT
HS Code 29130000
MSDS Information
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6-Nitroveratraldehyde Usage And Synthesis
Chemical Propertiesyellow fluffy powder
Uses6-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.
DefinitionChEBI: 4,5-dimethoxy-2-nitrobenzaldehyde is a C-nitro compound and an aromatic ether.
General DescriptionA 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 ActivityInhibitor 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 ActionsCell permeable: yes
Purification MethodsThe 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.]
Tag: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