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MilliporeSigma

222429

5-Methylisatin

95%

Synonym(s):

5-Methylindole-2,3-dione, NSC 9398

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
608-05-9
Molecular Weight:
161.16
NACRES:
NA.22
PubChem Substance ID:
24853331
UNSPSC Code:
12352100
EC Number:
210-152-1
MDL number:
MFCD00005721
Assay:
95%
Form:
solid

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InChI key

VAJCSPZKMVQIAP-UHFFFAOYSA-N

InChI

1S/C9H7NO2/c1-5-2-3-7-6(4-5)8(11)9(12)10-7/h2-4H,1H3,(H,10,11,12)

SMILES string

Cc1ccc2NC(=O)C(=O)c2c1

assay

95%

form

solid

mp

180 °C (dec.) (lit.)

solubility

methanol: soluble 25 mg/mL, clear to slightly hazy, orange to red

functional group

ketone

Quality Level

100

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This Item
N17807143510663190
5-Methylisatin 95%

Sigma-Aldrich

222429

5-Methylisatin

5-Nitroisatin 97%

Sigma-Aldrich

N17807

5-Nitroisatin

5-Hydroxyindole-2-carboxylic acid ≥96.5%

Sigma-Aldrich

143510

5-Hydroxyindole-2-carboxylic acid

Ethyl 5-methylindole-2-carboxylate 97%

Sigma-Aldrich

663190

Ethyl 5-methylindole-2-carboxylate

assay

95%

assay

97%

assay

≥96.5%

assay

97%

solubility

methanol: soluble 25 mg/mL, clear to slightly hazy, orange to red

solubility

-

solubility

chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown

solubility

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

form

solid

form

powder

form

powder

form

solid

mp

180 °C (dec.) (lit.)

mp

251 °C (dec.) (lit.)

mp

249 °C (dec.) (lit.)

mp

160-164 °C

functional group

ketone

functional group

-

functional group

carboxylic acid

functional group

ester

General description

5-Methylisatin is an inhibitor of atrial natriuretic peptide (ANP) receptor coupled with guanylyl cyclase (GC)[1].

Application

5-Methylisatin was used as an internal standard during the determination of isatin (indole-2, 3-
dione) in body fluids by capillary column gas chromatography-mass spectrometry (GC—MS)[2].
Reactant for preparation of:
  • Antimycobacterial agents
  • Promoters of central nervous system (CNS) depression in mice
  • Inhibitors of TAK1 kinase
  • Anti-human immunodeficiency virus (HIV) agent
  • Potent herpes simplex virus (HSV) inhibitors
  • Antimicrobial agents
  • IKKβ inhibitors
  • Potential drug to combat human immunodeficiency virus-tuberculosis (HIV-TB) coinfection
  • Cyclooxygenase 1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) inhibitors
  • Antibacterial and anticancer agents

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT8670
MKCR7988
MKCN9106
MKCJ2013
MKCG6296

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A E Medvedev et al.
Biochemical pharmacology, 57(8), 913-915 (1999-03-23)
Isatin is an endogenous indole and an inhibitor of atrial natriuretic peptide (ANP) receptors coupled with particulate guanylyl cyclase (GC). In this study, several isatin analogues were tested as inhibitors of ANP-stimulated GC in rat brain and heart membranes. None
Yong Wang et al.
Bioorganic chemistry, 97, 103710-103710 (2020-03-09)
Moenomycin A, the well-known natural product inhibitor of peptidoglycan glycosyltransferase (PGT), is a large amphiphilic molecule of molecular mass of 1583 g/mol and its bioavailablity as a drug is relatively poor. In searching for small-molecule ligands with high inhibition ability targeting
M Dorneanu et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 100(1-2), 167-171 (1996-01-01)
This paper presents the synthesis of six hydrazones obtained by treating 5-methyl-isatin or 1-morpholino methyl-5-methyl-isatin with 3-(R-phenyl)-6-hydrazino-pyridazine (R = OCH3, Cl, Br) and two complex combination with copper, derived from 3-(p-anisyl-pyridazinyl)-hydrazone-5-methyl-indoline-2- one. The structure of the new compounds was confirmed
J M Halket et al.
Journal of chromatography, 562(1-2), 279-287 (1991-01-02)
A simple procedure based upon capillary column gas chromatography-mass spectrometry (GC-MS) is described for the detection and determination of isatin (indole-2,3-dione) in body fluids and tissues. After addition of 5-methylisatin as internal standard to urine or tissue homogenates, organic extracts

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