4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid
- Product Name
- 4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid
- CAS No.
- 215030-90-3
- Chemical Name
- 4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid
- Synonyms
- BMS 493;BMS204, 493;BMS493,BMS-493;(E)-4-(2-(5,5-Dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalen-2-yl)vinyl)benzoic acid;4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid;4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid;(E)-4-[2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)naphthalen-2-yl]ethen-1-yl]benzoic acid;Benzoic acid, 4-[(1E)-2-[5,6-dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]-
- CBNumber
- CB22518846
- Molecular Formula
- C29H24O2
- Formula Weight
- 404.5
- MOL File
- 215030-90-3.mol
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid Property
- Boiling point:
- 605.4±55.0 °C(Predicted)
- Density
- 1.21±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO: ≥20mg/mL
- pka
- 4.27±0.10(Predicted)
- form
- powder
- color
- light yellow to yellow
Safety
- WGK Germany
- 2
N-Bromosuccinimide Price
- Product number
- B6688
- Product name
- BMS 493
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $198.64
- Updated
- 2025/07/31
- Product number
- B6688
- Product name
- BMS 493
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $782.39
- Updated
- 2025/07/31
- Product number
- 17418
- Product name
- BMS 493
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $44
- Updated
- 2024/03/01
- Product number
- 17418
- Product name
- BMS 493
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $109
- Updated
- 2024/03/01
- Product number
- 17418
- Product name
- BMS 493
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $193
- Updated
- 2024/03/01
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid Chemical Properties,Usage,Production
Description
Nuclear retinoic acid receptors (RARs) are transcriptional regulators with roles in cell proliferation and differentiation. BMS 493 is a pan-RAR inverse agonist that blocks RARα activity with an IC50 value of 114 nM. In all RAR types (RARα, RARβ, and RARγ), BMS493 prevents the recruitment of transcriptional coactivators to RARs while stabilizing corepressor interactions. BMS 493 has been used to elucidate the critical roles of RARs in development and immune response.
Uses
BMS 493 has been used:
- as an inhibitor for the dietary and pharmacologic manipulation of retinoic acid (RA) activity in vivo and in vitro
- for human induced pluripotent stem cells (iPSCs) culture and ventricular cardiomyocytes (VCMs) differentiation
- to inhibit retinoic acid (RA) signaling in explants
- as a retinoic acid receptor (RAR) inhibitor for the induction of synaptonemal complex protein 3 (SCP3) and ATP-dependent RNA helicase (DDX4) in primordial germ cells (PGCs)
Definition
ChEBI: BMS-493 is a member of the class of dihydronaphthalenes that is 1,2-dihydronaphthalene which is substituted at positions 1, 1, 4, and 6 by methyl, methyl, phenylethynyl, and 2-(p-carboxyphenyl)vinyl groups, respectively (the E isomer). It has a role as a retinoic acid receptor antagonist. It is a member of benzoic acids, a stilbenoid, a member of dihydronaphthalenes and an acetylenic compound.
General Description
BMS 493 inhibits the formation of neuritic processes and plasmenyethanolamine -phospholipase A2 (PLA2) activity.
Biochem/physiol Actions
BMS 493 is an inverse pan-RAR agonist. Retinoic acid receptors (RARs) are ligand-dependent transcription factors that control a number of physiological processes. RARs exert their functions by regulating gene networks controlling cell growth, differentiation, survival, and death.
storage
Store at +4°C
References
[1] C CHAZAUD P D P Chambon. Retinoic acid is required in the mouse embryo for left-right asymmetry determination and heart morphogenesis.[J]. Development, 1999, 126 12: 2589-2596. DOI: 10.1242/dev.126.12.2589
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] ALBANE LE MAIRE. A unique secondary-structure switch controls constitutive gene repression by retinoic acid receptor[J]. Nature Structural & Molecular Biology, 2010, 17 7: 801-807. DOI: 10.1038/nsmb.1855
[4] PIERRE GERMAIN. Differential action on coregulator interaction defines inverse retinoid agonists and neutral antagonists.[J]. Chemistry & biology, 2009: 479-489. DOI: 10.1016/j.chembiol.2009.03.008
[5] R MOLLARD. Stage-dependent responses of the developing lung to retinoic acid signaling.[J]. International Journal of Developmental Biology, 2000, 44 5: 457-462.
[6] CLAIRE CHAZAUD . Retinoic acid signaling regulates murine bronchial tubule formation[J]. Mechanisms of Development, 2003, 120 6: Pages 691-700. DOI: 10.1016/s0925-4773(03)00048-0
[7] FRéDéRIC GEISSMANN. Retinoids regulate survival and antigen presentation by immature dendritic cells.[J]. Journal of Experimental Medicine, 2003, 198 4: 623-634. DOI: 10.1084/jem.20030390
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid Preparation Products And Raw materials
Raw materials
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