7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde

ChemicalBook > CAS DataBase List > 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde

7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde

Product Name: 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde
CAS No.: 14003-96-4
Chemical Name: 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde
Synonyms: 8C;4Μ8C;4u8C;4M8C;4mu8C;IRE1 INHIBITOR III;IRE1 Inhibitor III, 4μ8C;4Μ8C (IRE1 INHIBITOR III);Thioctic Acid Impurity 59;7-Hydroxy-8-formyl-4-methylcoumarin
CBNumber: CB12605899
Molecular Formula: C11H8O4
Formula Weight: 204.18
MOL File: 14003-96-4.mol

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7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde Property

Melting point:: 189-190℃ (ethanol )
Boiling point:: 398.3±42.0 °C(Predicted)
Density: 1.541
refractive index: 1.641
storage temp.: -20°C
solubility: DMSO: soluble5mg/mL, clear (warmed)
pka: 6.22±0.20(Predicted)
form: Yellow powder
color: white to beige
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey: RTHHSXOVIJWFQP-UHFFFAOYSA-N
CAS DataBase Reference: 14003-96-4

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

H350May cause cancer

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0949
Product name: 4μ8C
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $118
Updated: 2024/03/01

Sigma-Aldrich

Product number: 412512
Product name: IRE1 Inhibitor III, 4μ8C
Packaging: 25mg
Price: $201
Updated: 2024/03/01

Cayman Chemical

Product number: 22110
Product name: 4μ8C
Purity: ≥98%
Packaging: 5mg
Price: $37
Updated: 2024/03/01

Cayman Chemical

Product number: 22110
Product name: 4μ8C
Purity: ≥98%
Packaging: 10mg
Price: $68
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0949
Product name: 4μ8C
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $478
Updated: 2024/03/01

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7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde Chemical Properties,Usage,Production

Description

4μ8C (14003-96-4) is a selective inhibitor of IRE1α ribonuclease (RNase) activity (IC50?= 60 nM). Covalently binds to lysine 907 in the IRE1 endonuclease domain, blocking substrate access to the active site of IRE1α and inactivating both XBP1 splicing and IRE1α-mediated mRNA degradation but not IRE1 kinase activity.1?Inhibits IRE1α in response to hypoxia or other ER stress-inducing agents but has no effect on proliferation or clonogenic survival of hypoxic cells.2?Blocks production of IL-4, IL-5 and IL-13 production in T cells.3?4μ8C prevents the splicing of the XBP1 mRNA in response to ER stress caused by mutant proinsulin production in pancreatic β-cells.4

Uses

8-Formyl-4-methylumbelliferone is an inhibitor that blocks substrate access to the active site of IRE1 and selectively inactivates both Xbp1 splicing and IRE1-mediated mRNA degradation.

General Description

A cell-permeable coumarin o-hydroxyaldehyde compound that inhibits IRE1 RNase activity in a time- and dose-dependent manner (IC₅₀ = 550, 230, 180, 100, and 45 nM, respectively, with 0, 2, 4, 8, 16, min drug preincubation in FRET-based RNA cleavage assays) by covalently targeting IRE1 Lys907 via Schiff base formation, effectively preventing ER stress-induced site-specific mRNA splicing as well as RIDD (Regulated IRE1-Dependent Degradation) mRNA degradation (IC₅₀ = 6.9 and 4.1 μM, respectively, against Xbp1 splicing and Scara3 degradation) in MEF cultures following Tunicamycin (Cat. No. 654380) treatment. Also demonstrated to inhibit ER capacity expansion (Effective conc. 32 μM) and amylase secretion (IC₅₀<2 μM) upon stress induction by Dexamethasone (Cat. No. 265005) treatment in rat AR42J tumoral acinar pancreatic cells. Structural analysis reveals that the reduced water accessibility to Lys907 in IRE1 native conformation accounts for the unusual stability of Lys907 Schiff base formation and forms the basis of selective IRE1 RNase inhibition by 4μ8C and STF083010 (Cat. No. 412510). Although 4μ8C, but not STF083010, is also shown to inhibit IRE1 autophosphorylation by Schiff base formation with IRE1 Lys599 in the absence of ADP, cellular nucleotide prevents 4μ8C from targeting IRE1 Lys599 and inhibiting IRE1 kinase activity intracellularly.

Biochem/physiol Actions

Cell permeable: yes

storage

Store at -20°C

References

1) Cross?et al. (2012),?The molecular basis for selective inhibition of unconventional mRNA splicing by an IRE1-binding small molecule; Proc. Natl. Acad. Sci. USA,?109?E869 2) Cojocari?et al. (2013),?New small molecule inhibitors of UPR activation demonstrate that PERK, but not IRE1α signaling is essential for promoting adaptation and survival to hypoxia;? Radiother. Oncol.,?108?541 3) Kemp?et al. (2013),?The serine-threonine kinase inositol-requiring enzyme 1α (IRE1α) promotes IL-4 production in T helper cells; J. Biol. Chem.,?288?33272 4) Zhang?et al. (2014),?IRE1 inhibition perturbs the unfolded protein response in a pancreatic β-cell line expressing mutant proinsulin, but does not sensitize the cells to apoptosis;? BMC Cell Biol.,?15?29

7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde manufacturers

Career Henan Chemical Co

Product: 7-hydroxy-4-methyl-2-oxochromene-8-carbaldehyde 14003-96-4
Price: US $8.80/KG
Min. Order: 1KG
Purity: 97%-99%
Supply Ability: 100kg
Release date: 2019-07-09

14003-96-4, 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehydeRelated Search:

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2H-1-Benzopyran-8-carboxaldehyde, 7-hydroxy-4-methyl-2-oxo-

4u8C

4Μ8C

7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde

4-Methyl-7-hydroxy-8-formylcoumarin

7-Hydroxy-8-formyl-4-methylcoumarin

8-Formyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one

8-Formyl-7-hydroxy-4-methylcoumarin

IRE1 Inhibitor III, 4μ8C

4M8C

4Μ8C (IRE1 INHIBITOR III)

IRE1 INHIBITOR III

IRE1 Inhibitor III, 4μ8C - CAS 14003-96-4 - Calbiochem

7-hydroxy-4-methyl-2-oxochromene-8-carbaldehyde

4mu8C

Thioctic Acid Impurity 59

14003-96-4

Inhibitors