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Key Documents

SML2239

Sigma-Aldrich

INF39

≥98% (HPLC)

Synonym(s):

2-Chloro-α-methylene-benzenepropanoic acid ethyl ester, Ethyl 2-(2-chlorobenzyl)acrylate

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About This Item

Empirical Formula (Hill Notation):
C12H13ClO2
CAS Number:
Molecular Weight:
224.68
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

oil

color

colorless to light brown

storage temp.

−20°C

SMILES string

ClC1=C(CC(C(OCC)=O)=C)C=CC=C1

InChI

1S/C12H13ClO2/c1-3-15-12(14)9(2)8-10-6-4-5-7-11(10)13/h4-7H,2-3,8H2,1H3

InChI key

VTAOWWAFBSFWSG-UHFFFAOYSA-N

Biochem/physiol Actions

INF39 is an orally active acrylate derivative and a non-cytotoxic INF4E analog (no toxicity at 100 μM in THP-1 cultures vs. TC50 = 65 μM with INF4E) that acts as an irreversible inhibitor against NLRP3 (NACHT, LRR and PYD domains-containing protein 3) ATPase activity (52% inhibition in 15 min by 100 μM INF39; 105 ng human NLP3 & 250 μM ATP) essential for the NLRP3 inflammasome assembly and activation. INF39 effectively decreases 5 mM (30 min) ATP-induced interleukin-1β (IL-1β) release and pyroptosis of murine bone marrow-derived macrophages in cultures (by 55-58% and 43-65%, respectively, with 1-hr 10 μM INF39 pretreatment of LPS-primed BMDM) and alleviates gut-associated inflammation in a rat model of 2,4-dinitrobenzenesulfonic acid (DNBS)-induced colitis in vivo (12.5-50 mg/kg/day in 0.2 mL olive oil p.o.).
Orally active irreversible NLRP3 inhibitor that suppresses ATP-dependent macrophage activation and alleviates DNBS-induced colitis in rats.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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