B6688 Sigma-Aldrich

BMS 493

≥98% (HPLC)

Synonym: (E)-4-[2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)naphthalen-2-yl]ethen-1-yl]benzoic acid, 4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid, BMS204, 493

  • CAS Number 215030-90-3

  • Empirical Formula (Hill Notation) C29H24O2

  • Molecular Weight 404.50

  •  MDL number MFCD17215944

  •  PubChem Substance ID 329773282

  •  NACRES NA.77



Related Categories Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
assay   ≥98% (HPLC)
form   powder
color   light yellow to yellow
solubility   DMSO: ≥20 mg/mL
originator   Bristol-Myers Squibb
storage temp.   2-8°C
SMILES string   CC1(C)CC=C(C#Cc2ccccc2)c3cc(\C=C\c4ccc(cc4)C(O)=O)ccc13
InChI   1S/C29H24O2/c1-29(2)19-18-24(14-10-21-6-4-3-5-7-21)26-20-23(13-17-27(26)29)9-8-22-11-15-25(16-12-22)28(30)31/h3-9,11-13,15-18,20H,19H2,1-2H3,(H,30,31)/b9-8+


General description

BMS 493 inhibits the formation of neuritic processes and plasmenyethanolamine -phospholipase A2 (PLA2) activity.


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)


5, 25 mg in glass bottle

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.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

Hazard statements 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Protocols & Articles


Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Nuclear Receptors (Non-Steroids)

The receptors for several classes of non-steroidal compounds, including retinoids, thyroid hormones and vitamin D, also act as ligand-dependent transcription factors. In addition, a large number of r...
Keywords: Absorption, Apoptosis, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell proliferation, Clinical, Detoxification, Diabetes, Diseases, Gene expression, Hormones, Ligands, Lipid Metabolism, Metabolism, Metabolites, Obesity, Transcription, Transduction, Vitamins

Peer-Reviewed Papers


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