106507-42-0

Basic information

• Product Name: 5-METHOXYNINHYDRIN MONOHYDRATE
• Synonyms: 5-METHOXYNINHYDRIN MONOHYDRATE
• CAS NO: 106507-42-0
• Molecular Formula: C₁₀H₈O₅
• Molecular Weight: 208.16752
• Mol File: 106507-42-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 489°Cat760mmHg
• Flash Point: 203.2°C
• Appearance: /
• Density: 1.627g/cm³
• Vapor Pressure: 2.23E-10mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: 5-METHOXYNINHYDRIN MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYNINHYDRIN MONOHYDRATE(106507-42-0)
• EPA Substance Registry System: 5-METHOXYNINHYDRIN MONOHYDRATE(106507-42-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 106507-42-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 21, p. 2231, 1991 DOI: 10.1080/00397919108055457

InChI:InChI=1/C10H8O5/c1-15-5-2-3-6-7(4-5)9(12)10(13,14)8(6)11/h2-4,13-14H,1H3

Upstream product

• 17666-95-4 5-methoxy-1H-indene-1,3(2H)-dione 
• 5111-70-6 5-methoxy-1-indanone 
• 17666-97-6 5-Methoxy-1,3-dioxo-indan-2-carboxylic acid ethyl ester 
• 188179-82-0 5-Methoxyninhydrin 
• 138485-79-7 2,2-dibromo-5-methoxy-1,3-indanedione 
• 138485-80-0 3-bromo-6-methoxy-1-indenone 

Downstream Products

• 166760-67-4 7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one 

Relevant articles and documents

Ninhydrins inhibit carbonic anhydrases directly binding to the metal ion

Ninhydrins show extensive application in organic chemistry and agriculture whereas they have been poorly investigated as bioactive molecules for medicinal chemistry purposes. A series of ninhydrin derivatives was here investigated for the inhibition of human carbonic anhydrases (CAs, EC 4.2.1.1), based on earlier evidence that gem diols are able to coordinate the metal ion from the CA active site. Ninhydrins demonstrated a micromolar inhibitory action against CA I and IX (KIs in the range 0.57–68.2 μM) and up to a nanomolar efficacy against CA II and VII (KIs in the range 0.025–78.2 μM), validated isoforms as targets in several CNS-related diseases. CA IV was instead weakly or poorly inhibited. A computational protocol based on docking, MM-GBSA and metadynamics calculations was used to elucidate the putative binding mode of this type of inhibitors to CA II and CA VII. The findings of this study testify that such pharmacologically underestimated ligands may represent interesting lead compounds for the development of CA inhibitors possessing an innovative mechanism of action, i.e., mono- or bis-coordination to the zinc ion through the diol moiety.

Synthesis and inhibition study of monoamine oxidase, indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by 3,8-substituted 5H-indeno[1,2-c]pyridazin-5-one derivatives

Previous studies on 5H-indeno[1,2-c]pyridazin-5-one derivatives as inhibitors of MAO-B revealed that it was possible to increase the MAO-B inhibitory potency of 5H-indeno[1,2-c]pyridazin-5-ones by substituting the central heterocycle in the 3-position or

Synthetic routes to ninhydrins. Preparation of ninhydrin, 5-methoxyninhydrin, and 5-(methylthio)ninhydrin

Two syntheses of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione) are described. One method employs a novel and efficient two step route, which begins with commercially available 6-methoxy-1-indanone. The application of this strategy for the preparation of a new ninhydrin derivative, 5-(methylthio)ninhydrin, and ninhydrin is also presented.