Merck
CN
All Photos(1)

Documents

SML2239

Sigma-Aldrich

INF39

≥98% (HPLC)

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
2-Chloro-α-methylene-benzenepropanoic acid ethyl ester, Ethyl 2-(2-chlorobenzyl)acrylate
Empirical Formula (Hill Notation):
C12H13ClO2
CAS Number:
866028-26-4
Molecular Weight:
224.68
MDL number:
MFCD27930542
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

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.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Mattia Cocco et al.
Journal of medicinal chemistry, 60(9), 3656-3671 (2017-04-15)
Pharmacological inhibition of NLRP3 inflammasome activation may offer a new option in the treatment of inflammatory bowel disease. In this work, we report the design, synthesis, and biological screening of a series of acrylate derivatives as NLRP3 inhibitors. The in
Mattia Cocco et al.
ChemMedChem, 11(16), 1790-1803 (2016-03-19)
NLRP3 inflammasome plays a key role in the intracellular activation of caspase-1, processing of pro-inflammatory interleukin-1β (IL-1β), and pyroptotic cell death cascade. The overactivation of NLRP3 is implicated in the pathogenesis of autoinflammatory diseases, known as cryopyrin-associated periodic syndromes (CAPS)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service