ChemicalBook > CAS DataBase List > BROMOENOL LACTONE

BROMOENOL LACTONE

Product Name
BROMOENOL LACTONE
CAS No.
88070-98-8
Chemical Name
BROMOENOL LACTONE
Synonyms
BEL;HELSS;HALOENOL LACTONE;BROMOENOL LACTONE;(6E)-Bromoenol lactone;Bromoenol lactone (BEL);Bromoenol Lactone Solution;HALOENOL LACTONE SUICIDE SUBSTRATE;(6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one;E-6-(BROMOETHYLENE)TETRAHYDRO-3-(1-NAPHTHYL)-2H-PYRAN-2-ONE
CBNumber
CB2471725
Molecular Formula
C16H13BrO2
Formula Weight
317.18
MOL File
88070-98-8.mol
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BROMOENOL LACTONE Property

Melting point:
103-106℃
Boiling point:
467.0±45.0 °C(Predicted)
Density 
1.538±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: Dilute in aqueous medium immediately prior to use and store on ice for no more than 12 hours.soluble
form 
White solid.
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B1552
Product name
Bromoenol lactone
Purity
≥98% (TLC)
Packaging
5mg
Price
$221
Updated
2024/03/01
Alfa Aesar
Product number
J63728
Product name
Haloenol Lactone Suicide Substrate, 98+%
Packaging
10mg
Price
$291
Updated
2021/12/16
Alfa Aesar
Product number
J63728
Product name
Haloenol Lactone Suicide Substrate, 98+%
Packaging
5mg
Price
$171
Updated
2021/12/16
Cayman Chemical
Product number
70700
Product name
Bromoenol lactone
Purity
≥95%
Packaging
5mg
Price
$120
Updated
2024/03/01
Cayman Chemical
Product number
70700
Product name
Bromoenol lactone
Purity
≥95%
Packaging
10mg
Price
$228
Updated
2024/03/01
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BROMOENOL LACTONE Chemical Properties,Usage,Production

Uses

HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone) is an inhibitor of Ca-independent PLA2 and Mg-dependent PAP.

Definition

ChEBI: Bromoenol lactone is a member of naphthalenes.

Biological Activity

bromoenol lactone is a potent and irreversible inhibitor of myocardial cytosolic calcium-independent phospholipase a2 (ipla2) [1].the ipla2 has been involved in stimulus-induced arachidonic acid release and lysophospholipid generation. the catalytic action of ipla2 is responsible for phospholipid remodeling as a housekeeping function. arachidonic acid and lysophospholipid generated by ipla2 act as a signaling molecule in cellular functions, including eicosanoid production, glucose-induced insulin secretion, fas-induced apoptosis, cellular proliferation, membrane traffic in fusion, contribution to myocardial ischemia, and others [2].bel promoted apoptosis in a variety of cell lines, including u937, thp-1, and monomac (human phagocyte), raw264.7 (murine macrophage), jurkat (human t lymphocyte), and gh3 (human pituitary). long term treatment with bel (up to 24 h) increased annexin-v binding to the cell surface and nuclear dna damage. bel induced the proteolysis of procaspase-9 and procaspase-3 and increased cleavage of poly (adp-ribose) polymerase [1]. bel inhibited cellular phosphatidic acid phosphohydrolase (pap) activity in intact p388d1 macrophages with an ic50 of ～8 μm. bel blocked triacylglycerol biosynthesis in p388d1 cells by decreasing diacylglycerol availability [3].

Biochem/physiol Actions

Potent, irreversible inhibitor of calcium-independent phospholipase A2 and of magnesium-dependent phosphatidate phosphohydrolase from P388D macrophages (IC50 = 8?μM); enzyme activated irreversible chymotrypsin inhibitor (Ki = 636 nM).

References

[1] fuentes l, pérez r, nieto m l, et al. bromoenol lactone promotes cell death by a mechanism involving phosphatidate phosphohydrolase-1 rather than calcium-independent phospholipase a2[j]. journal of biological chemistry, 2003, 278(45): 44683-44690.
[2] akiba s, sato t. cellular function of calcium-independent phospholipase a2[j]. biological and pharmaceutical bulletin, 2004, 27(8): 1174-1178.
[3] balsinde j, dennis e a. bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse p388d1 macrophages[j]. journal of biological chemistry, 1996, 271(50): 31937-31941.

BROMOENOL LACTONE Preparation Products And Raw materials

Raw materials

Preparation Products

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BROMOENOL LACTONE Suppliers

China 41 Germany 1 India 1 Switzerland 3 Ukraine 1 United Kingdom 3 United States 13 Global 63
3B Pharmachem (Wuhan) International Co.,Ltd.
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88070-98-8, BROMOENOL LACTONERelated Search:

U-73343 Phosphatidylinositol (Soy) SodiuM 2-Heptadecanone Citicoline sodium UMBELLIFERYL ARACHIDONATE LUFFARIELLOLIDE OLEYLOXYETHYL PHOSPHORYLCHOLINE Thioetheramide PC Ethyl 1-naphthaleneacetate 2-Naphthaleneethanol Methyl naphthalene-1-acetate 1-BROMO-1-BUTENE 2-Methyl-5-hydroxypentanoic acid lactone VINYL PHENYL ACETATE (S)-BROMOENOL LACTONE BROMOENOL LACTONE (R)-BROMOENOL LACTONE NAPHTHYL ACETIC ACID

  • E-6-(BROMOETHYLENE)TETRAHYDRO-3-(1-NAPHTHYL)-2H-PYRAN-2-ONE
  • (E)-6-(BROMOMETHYLENE)TETRAHYDRO-3-(1-NAPHTHALENYL)-2H-PYRAN-2-ONE
  • (E)-6-(BROMOMETHYLENE)TETRAHYDRO-3-(1-NAPTHALENYL)-2H-PYRAN-2-ONE
  • HELSS
  • HALOENOL LACTONE
  • HALOENOL LACTONE SUICIDE SUBSTRATE
  • BEL
  • BROMOENOL LACTONE
  • 6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one
  • BEL, E-6-(Bromoethylene)tetrahydro-3-(1-naphthyl)-2H-pyran-2-one
  • Bromoenol Lactone Solution
  • HELSS (Haloenol lactone suicide substrate, BEL, Bromoenol lactone)
  • Bromoenol lactone (BEL)
  • (6E)-6-(bromomethylidene)-3-naphthalen-1-yloxan-2-one
  • (6E)-Bromoenol lactone
  • 2H-Pyran-2-one, 6-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-, (6E)-
  • 88070-98-8
  • A to C
  • Biochemicals and Reagents
  • BioChemical
  • Chymotrypsin, alpha-
  • Enzyme Inhibitors
  • Enzyme Inhibitors by Enzyme
  • Enzymes, Inhibitors, and Substrates