Indolin-2,3-dion

Bezeichnung:Indolin-2,3-dion

CAS-Nr91-56-5

Englisch Name:Isatin

CBNumberCB2447182

SummenformelC8H5NO2

Molgewicht147.13

MOL-Datei91-56-5.mol

Synonyma

Indolin-2,3-dion

Indolin-2,3-dion physikalisch-chemischer Eigenschaften

Schmelzpunkt	193-195 °C (dec.) (lit.)
Siedepunkt	267.22°C (rough estimate)
Dichte	1.3067 (rough estimate)
Dampfdruck	0Pa at 25℃
Brechungsindex	1.4700 (estimate)
Flammpunkt	220 °C
storage temp.	Store below +30°C.
Löslichkeit	soluble
Aggregatzustand	Powder
pka	10.34±0.20(Predicted)
Farbe	Orange
PH	7 (1.9g/l, H2O, 20℃)
Wasserlöslichkeit	Soluble in water (1.9 g/L at 20°C).
Decomposition	194 ºC
Merck	14,5104
BRN	383659
Stabilität	Stable. Incompatible with strong acids.
InChIKey	JXDYKVIHCLTXOP-UHFFFAOYSA-N
LogP	0.45
CAS Datenbank	91-56-5(CAS DataBase Reference)
NIST chemische Informationen	Isatin(91-56-5)
EPA chemische Informationen	1H-Indole-2,3-dione (91-56-5)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-20/21/22
S-Sätze:	26-36-24/25
RIDADR	2811
WGK Germany	1
RTECS-Nr.	NL7873000
Selbstentzündungstemperatur	220 °C
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29337900

Gefahreninformationscode (GHS)

Isatin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
orange-red powder or crystals
Verwenden
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.
Verwenden
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.
Verwenden
manufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.
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
Biologische Aktivität
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].
IC 50
15 μm
läuterung methode
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.]
Einzelnachweise
[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.

Isatin Upstream-Materialien And Downstream Produkte

Indolin-2,3-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

91-56-5, Isatin Verwandte Suche:

Send Inquriy