1-(2,3-Dihydroxy-3H-indol-3-yl)acetone

Names

[ Name ]:
1-(2,3-Dihydroxy-3H-indol-3-yl)acetone

[Synonym ]:
3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one
1-(2,3-Dihydroxy-3H-indol-3-yl)acetone
2H-Indol-2-one, 1,3-dihydro-3-hydroxy-3-(2-oxopropyl)-
2-propanone, 1-(2,3-dihydroxy-3H-indol-3-yl)-
3-Hydroxy-3-acetonyl-2-oxindole
3-hydroxy-3-acetonyloxindole
3-hydroxy-3-acetonylisatin

Biological Activity

[Description]:

3-Acetonyl-3-hydroxyoxindole (AHO) is a potent systemic acquired resistance (SAR) inducer in plants. 3-Acetonyl-3-hydroxyoxindole induces resistance in tobacco plants against infection with tobacco mosaic virus (TMV) and the fungal pathogen Erysiphe cichoracearum. 3-Acetonyl-3-hydroxyoxindole increases the level of pathogenesis-related gene 1 (PR-1) expression, salicylic acid (SA) accumulation and phenylalanine ammonia-lyase activity[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[In Vitro]

3-Acetonyl-3-hydroxyoxindole (AHO) (500-700 nM) increases in endogenous SA levels and phenylalanine ammonia-lyase (PAL) activity[1]. 3-Acetonyl-3-hydroxyoxindole (0-500 nM) increases the expression of pathogenesis-related gene 1 (PR-1) in tobacco[1].

[References]

[1]. Li Y, et al. 3-Acetonyl-3-hydroxyoxindole: a new inducer of systemic acquired resistance in plants. Plant Biotechnol J. 2008 Apr;6(3):301-8.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
450.2±45.0 °C at 760 mmHg

[ Melting Point ]:
167-168℃ (Decomposition)

[ Molecular Formula ]:
C₁₁H₁₁NO₃

[ Molecular Weight ]:
205.210

[ Flash Point ]:
226.1±28.7 °C

[ Exact Mass ]:
205.073898

[ PSA ]:
66.40000

[ LogP ]:
0.09

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.584

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM3289480

CHEMICAL NAME :: 2H-Indol-2-one, 1,3-dihydro-3-hydroxy-3-(2-oxopropyl)-

CAS REGISTRY NUMBER :: 33417-17-3

BEILSTEIN REFERENCE NO. :: 0182807

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H11-N-O3

MOLECULAR WEIGHT :: 205.23

WISWESSER LINE NOTATION :: T56 BMV DHJ DQ D1V1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 19,562,1985

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%