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SML0949

Sigma-Aldrich

4μ8C

≥98% (HPLC)

Synonym(s):

7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-carboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C11H8O4
CAS Number:
14003-96-4
Molecular Weight:
204.18
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

InChI

1S/C11H8O4/c1-6-4-10(14)15-11-7(6)2-3-9(13)8(11)5-12/h2-5,13H,1H3

InChI key

RTHHSXOVIJWFQP-UHFFFAOYSA-N

Biochem/physiol Actions

4μ8C is a potent inhibitor of the ER transmembrane protein IRE1, which mediates the unfolded protein response. 4μ8C inhibits regulated IRE1-dependent degradation (RIDD) and unconventional spicing of XBP1 mRNA in response to endopasmic reticulum (ER) stress, but has no affect on the kinase activity of IRE1.
4μ8C is a salicylaldehyde derivative and its inhibitory action targets the K907 lysine residue in RNase (ribonuclease) domain and affects IRE1α (endoplasmic reticulum to nucleus signaling 1) RNase activity. In vitro analysis proved that 4μ8C was able to inhibit the release of insulin at high glucose levels.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

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’.

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4μ8C inhibits insulin secretion independent of IRE1α RNase activity.
Sato H, et al.
Cell Structure and Function, 42(1), 61-70 (2017)
Su Xian et al.
EMBO reports, 22(12), e52509-e52509 (2021-10-27)
Aneuploidy is a chromosomal abnormality associated with poor prognosis in many cancer types. Here, we tested the hypothesis that the unfolded protein response (UPR) mechanistically links aneuploidy and local immune dysregulation. Using a single somatic copy number alteration (SCNA) score
Jirka Peschek et al.
EMBO reports, 16(12), 1688-1698 (2015-10-21)
The kinase/endonuclease IRE1 is the most conserved signal transducer of the unfolded protein response (UPR), an intracellular signaling network that monitors and regulates the protein folding capacity of the endoplasmic reticulum (ER). Upon sensing protein folding perturbations in the ER
Targeting the IRE1α?XBP1 branch of the unfolded protein response in human diseases.
Jiang D, et al.
Seminars in Cancer Biology, 33, 48-56 (2015)
Zhiyuan Fang et al.
Journal of dairy science, 105(8), 6895-6908 (2022-07-16)
Endoplasmic reticulum (ER) stress can be induced by various stimuli and triggers the unfolded protein response to activate intracellular signaling pathways that are mediated by 3 ER-resident sensors: inositol requiring protein-1α (IRE1α), PKR-like ER kinase (PERK), and activating transcription factor-6
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