3433-15-6

Basic information

• Product Name: Barbarin
• Synonyms: 5-Phenyl-2-oxazolidinethione;Barbarin;Resedinine;Resedinine Barbarin
• CAS NO: 3433-15-6
• Molecular Formula: C₉H₉NOS
• Molecular Weight: 179.23886
• Mol File: 3433-15-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 123-124 °C
• Boiling Point: 272.009°C at 760 mmHg
• Flash Point: 118.307°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.647
• PKA: 13.30±0.40(Predicted)
• CAS DataBase Reference: Barbarin(CAS DataBase Reference)
• NIST Chemistry Reference: Barbarin(3433-15-6)
• EPA Substance Registry System: Barbarin(3433-15-6)

Safety Data

• Hazardous Substances Data: 3433-15-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 1985, 1982 DOI: 10.1021/jo00132a001

InChI:InChI=1/C9H9NOS/c12-9-10-6-8(11-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,12)

Upstream product

• 191043-23-9 (5R)-5-phenyl-1,3-oxazolidine-2-thione 
• 75-15-0 carbon disulfide 
• 7568-93-6 2-Amino-1-phenylethanol 
• 18293-48-6 (trimethylsilyl)methyl isothiocyanate 
• 100-52-7 benzaldehyde 
• 37394-53-9 ω-aminoacetophenone hydrobromide 
• 3306-05-6 N-(2-hydroxy-2-phenylethyl)acetamide 
• 1846-33-9 N-phenacylacetamide 

Downstream Products

• 81316-61-2 N-(β-hydroxy-2-phenylethyl)bis(4-methoxyphenyl)methylimine 
• 51096-49-2 2-benzylamino-1-phenyl-ethanol 
• 75626-12-9 4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 22020-69-5 oxytriphine 
• 7693-77-8 5-phenyloxazolidin-2-one 
• 81316-48-5 2-(methylthio)-5-phenyl-2-oxazoline 

Relevant articles and documents

Two goitrogenic 1,3-oxazolidine-2-thione derivatives from Brassicales taxa: Challenging identification, occurrence and immunomodulatory effects

1,3-Oxazolidine-2-thione derivatives are glucosinolate-related food constituents known to impart (thyreo)toxic properties to some cruciferous vegetables. In this work, 5,5-dimethyl-1,3-oxazolidine-2-thione and (-)-(R)-5-phenyl-1,3-oxazolidine-2-thione, known goitrogens, were isolated from Draba lasiocarpa Rochel (Brassicaceae) and Reseda luteola L. (Resedaceae), respectively, and were fully spectrally characterized. Subsequently, the occurrence of the two 1,3-oxazolidine-2-thiones was verified in six additional taxa out of in total 78 screened Serbian Brassicales taxa. The stereochemistry of 5-phenyl-1,3-oxazolidine-2-thione was inferred from nuclear magnetic resonance experiments with a chiral lanthanide-shift reagent, employed in this work for the first time for this type of compounds. Unexpectedly, during gas chromatography, 5-phenyl-1,3-oxazolidine-2-thione underwent an unreported thermal core isomerization (1,3-oxazolidine-2-thione to 1,3-thiazolidine-2-one). These goitrogenic volatile glucosinolate products were tested for their effect on rat macrophage viability (three assays) and nitric oxide production. It was shown that the compounds displayed different levels of cytotoxicity. All tested compounds caused a significant lactate dehydrogenase leakage, but only (R)-5-phenyl-1,3-oxazolidine-2-thione statistically significantly reduced macrophage mitochondrial activity, whereas the racemic 5-phenyl-1,3-oxazolidine-2-thione and 5,5-dimethyl-1,3-oxazolidine-2-thione had little or no effect. Again only (R)-5-phenyl-1,3-oxazolidine-2-thione exerted nitric oxide production-inhibiting properties, suggesting the higher immunomodulatory potential of this enantiomer compared with its antipode and racemic mixture.

Total Synthesis of (+/-) Resedine and (+/-)Resedinine Alkaloids from Reseda luteola

Total synthesis of racemic alkaloids: resedine and resedinine is described.

Trimethylsilyl-methylisothiocyanat, ein Isothiocyanatomethanid-Aequivalent

-