1616618-82-6

Basic information

• Product Name: (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid
• Synonyms: (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid
• CAS NO: 1616618-82-6
• Molecular Weight: 632.045
• Mol File: 1616618-82-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid(1616618-82-6)
• EPA Substance Registry System: (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid(1616618-82-6)

Safety Data

• Hazardous Substances Data: 1616618-82-6(Hazardous Substances Data)

Upstream product

• 21481-56-1 (2S,3R)-2-octadecanoylaminooctadecane-1,3-diol 

Relevant articles and documents

Synthesis of the rosette-inducing factor RIF-1 and analogs

Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.