| Identification | More | [Name]
Isatin | [CAS]
91-56-5 | [Synonyms]
1H-Indole-2,3-dione
2,3-DIHYDROINDOLE-2,3-DIONE
2,3-DIKETOINDOLINE
2,3-INDOLEDIONE
2,3-INDOLINEDIONE
2,3-KETOINDOLINE
AKOS BBS-00003223
INDOLE-2,3-DIONE
ISATIC ANHYDRIDE
ISATIN
O-AMINOBENZOYLFORMIC ACID
O-AMINOBENZOYLFORMIC ANHYDRIDE
O-AMINOPHENYLGLYOXALIC LACTIM
TIMTEC-BB SBB009100
,3-Dihydro-1H-indole-2,3-dione
2,3-Didetonindoline
2,3-Dioxo-2,3-dihydroindole
2,3-Dioxoindoline
Indoquinone
Isatic acid lactam | [EINECS(EC#)]
202-077-8 | [Molecular Formula]
C8H5NO2 | [MDL Number]
MFCD00005718 | [Molecular Weight]
147.13 | [MOL File]
91-56-5.mol |
| Chemical Properties | Back Directory | [Appearance]
orange-red powder or crystals | [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) | [Fp ]
220 °C
| [storage temp. ]
Store at RT. | [solubility ]
soluble | [form ]
Powder | [pka]
10.34±0.20(Predicted) | [color ]
Orange | [PH]
7 (1.9g/l, H2O, 20℃) | [Stability:]
Stable. Incompatible with strong acids. | [Water Solubility ]
Soluble in water (1.9 g/L at 20°C). | [Decomposition ]
194 ºC | [Merck ]
14,5104 | [BRN ]
383659 | [InChIKey]
JXDYKVIHCLTXOP-UHFFFAOYSA-N | [LogP]
0.45 | [CAS DataBase Reference]
91-56-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Isatin(91-56-5) | [EPA Substance Registry System]
91-56-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
2811 | [WGK Germany ]
1
| [RTECS ]
NL7873000
| [Autoignition Temperature]
220 °C | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29337900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Indigo-->2,2,2-Trichloroacetamide | [Preparation Products]
Indole-->7-Hydroxygranisetron-->1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE-->Solvent Yellow 114-->1-Methylindazole-3-carboxylic acid-->Lonidamine-->3-(HYDROXYMETHYL)INDAZOLE-->6-BROMO-2-METHYL-QUINOLINE-4-CARBOXYLIC ACID-->CINCHOPHEN-->Indirubin-->3-ACETYL-2-METHYL-QUINOLINE-4-CARBOXYLIC ACID-->1-(2,6-Dichlorophenyl)indole-2,3-dione-->3,3-Bis(3-methyl-4-hydroxyphenyl)indoline-2-on-->1H-INDAZOLE-3-CARBOXYLIC ACID ETHYL ESTER-->5-IODOISATIN-->5H-Pyrido[4,3-b]carbazole-5,11(6H)-dione-->1-Acetyl-1H-indole-2,3-dione-->3,3-BIS(P-HYDROXYPHENYL)OXINDOLE-->3,3-dichloro-2-oxoindoline-5-sulphonyl chloride-->5-Bromoisatoic anhydride |
| Questions And Answer | Back Directory | [Isatin]
Isatin, is also known as indenedione, indole quinone. Its chemical name is indol(o)-2,3-dione,it is orange-red monoclinic prism crystal at room temperature. Bitter. The molecular weight is147.13. Melting point 203.5 ℃ (Part sublimation). Dissolved in water, hot ethanol, benzene, acetone, ether-soluble. Soluble in boiling alcohol, soluble in ether and boiling water and it is reddish brown , soluble in caustic and solution is purple, it changes to yellow after placement. Its alcohol solution has a very unpleasant odor. Weakly alkaline, it can salify with a perchlorate.
Above information of is edited by Andy from ChemicalBook (2016-11-19). | [Chemical Properties]
Orange-red monoclinic prism crystals. Melting point 203.5 ℃ (Part sublimation). Soluble in hot ethanol, ethyl ether-soluble, soluble in hot water, benzene, acetone, dissolved in alkali metal hydroxide oxide. The solution is purple, it turns yellow after placement, alkaline activity is extremely weak. Bitter. | [Uses]
(1) The product is used as medicine and dye intermediates ,and it is used for the production of drug quinophan, dye disperse Yellow E-3G ; in chemical analysis,it is used as reagents for the determination of copper ions, mercaptans, thiophene, indoxyl-beta-glucoside.
(2) Isatin as a reference material for the preparation of indigo and Maya blue; for the preparation of phthalazinone derivatives, spirooxindole derivatives, the expression of P-glycoprotein for multi-drug resistant cells; The ketone is fused to form indole-2-one as a tubercular mycobacterial protein tyrosine phosphatase B, a potent selective inhibitor, as a powerful antimicrobial and antifungal triazole-isatine complex, And the Knoevenagel enrichment reaction; the isatin is activated by the direct sp2/sp3C-H bond, and undergoes a reaction with the cyclopentadienyl-Pd (II) catalyzes the CH addition reaction to form 3-substituted-3-hydroxy 2-oxindole. | [production method]
Condensation of chloral and aniline can generate oximide-acetanilide, and then by cyclization, hydrolysis , isatin is obtained. |
| Hazard Information | Back Directory | [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]
Nonflammable | [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]. | [IC 50]
15 μm | [storage]
Store at -20°C | [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. |
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