Isatin
Synonym(s):Isatin;2,3-Indolinedione;Isatine;Isatinic acid anhydride;Isatic acid lactam
- CAS NO.:91-56-5
- Empirical Formula: C8H5NO2
- Molecular Weight: 147.13
- MDL number: MFCD00005718
- EINECS: 202-077-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-20 11:41:24
What is Isatin?
Chemical properties
orange-red powder or crystals
The Uses of Isatin
Isatin is an endogenous monoamine oxidize (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes. Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles. It is used as chromatographic spray reagent for amino acid detection.
The Uses of Isatin
manufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.
The Uses of Isatin
Isatin can be used as a reactant to prepare:
- Phthalazinone derivatives.
- Spirooxindole derivatives.
- Agents against multidrug-resistant cells expressing P-glycoprotein.
- Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.
- Triazole-isatine compounds as potential antibacterial and antifungal agents.
- Biologically relevant scaffolds such as spiro[indole-thiazolidinones].
It can be a reactant for:
- Cascade reactions with heterocyclic ketene aminals.
- Knoevenagel condensation reactions.
Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.
What are the applications of Application
Isatin is an endogenous monoamine oxidase inhibitor
Definition
ChEBI: An indoledione that is the 2,3-diketo derivative of indole.
Synthesis Reference(s)
The Journal of Organic Chemistry, 55, p. 197, 1990 DOI: 10.1021/jo00288a033
Flammability and Explosibility
Non flammable
Biological Activity
isatin is a monoamine oxidase inhibitor.monoamine oxidase inhibitors have been used as therapies for the treatment of depression, particularly in treating atypical depression. monoamine oxidase inhibitors are also used in the treatment of parkinson's disease and other disorders.
in vitro
previous study found that isatin treatment at 1-400 μm for 24h could induce a significant dose-dependent increase in mtt metabolism by sh-sy5y cells, which was not due to the increase in cell division. in addition, isatin at the higher concentrations was able to trigger cell death, though mtt metabolism was still increased, indicating that the surviving cells were hypermetabolic. with a longer treatment, isatin was found to cause cell death in a dose-dependent manner, and the predominant mode of cell death was apoptosis at lower concentrations, while at the highest concentration increasing numbers of necrotic cells were also observed [1].
in vivo
animal study showed that the motor activity of japanese encephalitis virus (jev)-induced rats receiving isatin was improved significantly when compared with that of untreated jev-infected rats. in addition, isatin was able to prevent the decrease in striatal da levels in jev-rats and the increased turnover of dopamine (da) (dopac/da) induced by jev was significantly inhibited by isatin. such results indicated that the exogenously administered isatin was able to improve jev-induced parkinsonism via increasing the striatum da concentrations [2].
Purification Methods
Crystallise isatin from amyl alcohol and sublime it at 180o/1mm. In aqueous NaOH the ring opens to yield sodium o-aminobenzoylformate. [Beilstein 21 II 327, 567, 21 III/IV 4981, 21/10 V 221.]
References
[1] igosheva n,lorz c,o'conner e,glover v,mehmet h. isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. neurochem int.2005 aug;47(3):216-24.
[2] hamaue n,minami m,terado m,hirafuji m,endo t,machida m,hiroshige t,ogata a,tashiro k,saito h,parvez sh. comparative study of the effects of isatin, an endogenous mao-inhibitor, and selegiline on bradykinesia and dopamine levels in a rat model of parkinson's disease induced by the japanese encephalitis virus. neurotoxicology.2004 jan;25(1-2):205-13.
Properties of Isatin
Melting point: | 193-195 °C (dec.) (lit.) |
Boiling point: | 267.22°C (rough estimate) |
Density | 1.3067 (rough estimate) |
vapor pressure | 0Pa at 25℃ |
refractive index | 1.4700 (estimate) |
Flash point: | 220 °C |
storage temp. | Store below +30°C. |
solubility | soluble |
form | Powder |
pka | 10.34±0.20(Predicted) |
color | Orange |
PH | 7 (1.9g/l, H2O, 20℃) |
Water Solubility | Soluble in water (1.9 g/L at 20°C). |
Decomposition | 194 ºC |
Merck | 14,5104 |
BRN | 383659 |
Stability: | Stable. Incompatible with strong acids. |
CAS DataBase Reference | 91-56-5(CAS DataBase Reference) |
NIST Chemistry Reference | Isatin(91-56-5) |
EPA Substance Registry System | 1H-Indole-2,3-dione (91-56-5) |
Safety information for Isatin
Signal word | Warning |
Pictogram(s) |
Flame Flammables GHS02 |
GHS Hazard Statements |
H226:Flammable liquids |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P242:Use only non-sparking tools. P243:Take precautionary measures against static discharge. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for Isatin
InChIKey | JXDYKVIHCLTXOP-UHFFFAOYSA-N |
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