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-
  • 8C
  • 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