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E2895

Sigma-Aldrich

(±)-(E)-4-Ethyl-2-[(E)-hydroxyimino]-5-nitro-3-hexenamide

≥98%

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Synonym(s):
NOR-3
Empirical Formula (Hill Notation):
C8H13N3O4
CAS Number:
138472-01-2
Molecular Weight:
215.21
UNSPSC Code:
12352200
PubChem Substance ID:
329799038
NACRES:
NA.77

Quality Level

100

Assay

≥98%

form

powder

solubility

DMSO: 10 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

CC\C(=C/C(=N\O)C(N)=O)C(C)[N+]([O-])=O

InChI

1S/C8H13N3O4/c1-3-6(5(2)11(14)15)4-7(10-13)8(9)12/h4-5,13H,3H2,1-2H3,(H2,9,12)/b6-4+,10-7+

InChI key

MZAGXDHQGXUDDX-AGLLBGTNSA-N

Application

Cell-permeable NO donor; releases nitric oxide spontaneously in a rate-controlled manner. Half-life in solution = 30 min.

Biochem/physiol Actions

Activates intracellular guanylyl cyclase.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Y Kita et al.
European journal of pharmacology, 257(1-2), 123-130 (1994-05-12)
(+-)-(E)-Ethyl-2-[(E)-hydroxyimino]-5-nitro-3-hexeneamide (FK409), which was isolated from microbial products, has been reported to show a vasorelaxant effect through a mechanism similar to that of the organic nitrates such as isosorbide dinitrate. In solution at pH 7.4, FK409 decomposed and released nitric
Tomáš Macháček et al.
Parasites & vectors, 13(1), 426-426 (2020-08-21)
Avian schistosomes, the causative agents of human cercarial dermatitis (or swimmer's itch), die in mammals but the mechanisms responsible for parasite elimination are unknown. Here we examined the role of reactive nitrogen species, nitric oxide (NO) and peroxynitrite, in the
Elsa Cortés-Montero et al.
Antioxidants & redox signaling, 31(7), 503-520 (2019-05-16)
Aims: Histidine triad nucleotide-binding protein 1 (HINT1) exhibits proapoptotic and tumor-suppressive activity. HINT1 binds to transcription factors such as

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