138749-63-0

Basic information

• Product Name: rubroflavin
• Synonyms: rubroflavin
• CAS NO: 138749-63-0
• Molecular Formula: C₉H₁₁N₃O₃S₂
• Molecular Weight: 273.33194
• Mol File: 138749-63-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.59g/cm³
• Refractive Index: 1.714
• CAS DataBase Reference: rubroflavin(CAS DataBase Reference)
• NIST Chemistry Reference: rubroflavin(138749-63-0)
• EPA Substance Registry System: rubroflavin(138749-63-0)

Safety Data

• Hazardous Substances Data: 138749-63-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11N3O3S2/c1-16-6-3-5(13)4-7(17(2)15)8(6)11-12-9(10)14/h3-4H,1-2H3,(H3,10,12,14)/b11-8-/t17-/m0/s1

Upstream product

• 1028295-44-4 rubroflavin (+)-3-bromocamphor-10-sulfonic acid ester 

Relevant articles and documents

Pigments from the puffball Calvatia rubro-flava - Isolation, structural elucidation and synthesis

The orange pigment rubroflavin (1) from the dried fruit bodies of Calvatia rubro-flava (Lycoperdaceae) owes its high optical rotation to a methanesulfinyl group directly attached to a 1,4-benzoquinone semicarbazone chromophore. Rubroflavin is present in fresh fungi in its leuco form 4, which is easily oxidized to 1. Thermal fragmentation of 1 yields (-)-3-methanesulfinyl-5-(methylthio)phenol (6), whose configuration was assigned as (S) by quantum mechanical calculations. This result is supported by CD comparison of 6 with (S)-4-(methanesulfinyl)toluene, and the synthesis of (S)-1 from esters of deoxyrubroflavin (8) by stereoselective sulfoxidation. In the same manner, optically active (S,S)-oxyrubroflavin (2) and (S)-craniformin (3) were obtained. NMR measurements in different solvents indicate that 1 and the related 1,4-benzoquinone semicarbazones are in equilibrium with their azophenol tautomers.