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

Modify Date: 2025-08-24 16:24:38

1-(2,3-Dihydroxy-3H-indol-3-yl)acetone Structure
1-(2,3-Dihydroxy-3H-indol-3-yl)acetone structure
 Common Name 1-(2,3-Dihydroxy-3H-indol-3-yl)acetone
CAS Number 33417-17-3 Molecular Weight 205.210
Density 1.3±0.1 g/cm3 Boiling Point 450.2±45.0 °C at 760 mmHg
Molecular Formula C11H11NO3 Melting Point 167-168℃ (Decomposition)
MSDS N/A Flash Point 226.1±28.7 °C

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


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].

 Names

Name 3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
Synonym More Synonyms

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

isatin structure

isatin

CAS#:91-56-5

Acetone structure

Acetone

CAS#:67-64-1

Malononitrile structure

Malononitrile

CAS#:109-77-3

~8%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Detail
Literature: Kumar, Akshay; Chimni, Swapandeep Singh Beilstein Journal of Organic Chemistry, 2014 , vol. 10, p. 929 - 935
isatin structure

isatin

CAS#:91-56-5

Acetone structure

Acetone

CAS#:67-64-1

~92%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Popp; Parson; Donigan Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 10 p. 1235 - 1237
Acetoacetic Acid structure

Acetoacetic Acid

CAS#:541-50-4

isatin structure

isatin

CAS#:91-56-5

~93%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Zhong, Fangrui; Jiang, Chunhui; Yao, Weijun; Xu, Li-Wen; Lu, Yixin Tetrahedron Letters, 2013 , vol. 54, # 32 p. 4333 - 4336
3-(2-oxopropyl)-3-tert-butyldimethylsilyl-oxyindolin-2-one structure

3-(2-oxopropyl)...

CAS#:700359-40-6

~50%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Kawasaki, Tomomi; Nagaoka, Miyuki; Satoh, Tomoko; Okamoto, Ayako; Ukon, Rie; Ogawa, Atsuyo Tetrahedron, 2004 , vol. 60, # 15 p. 3493 - 3503
3-hydroxy-3-prop-2-enyl-1H-indol-2-one structure

3-hydroxy-3-pro...

CAS#:220598-39-0

~%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Kawasaki, Tomomi; Nagaoka, Miyuki; Satoh, Tomoko; Okamoto, Ayako; Ukon, Rie; Ogawa, Atsuyo Tetrahedron, 2004 , vol. 60, # 15 p. 3493 - 3503
3-allyl-3-tert-butyldimethylsilyloxyindolin-2-one structure

3-allyl-3-tert-...

CAS#:700359-39-3

~%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Kawasaki, Tomomi; Nagaoka, Miyuki; Satoh, Tomoko; Okamoto, Ayako; Ukon, Rie; Ogawa, Atsuyo Tetrahedron, 2004 , vol. 60, # 15 p. 3493 - 3503
isatin structure

isatin

CAS#:91-56-5

Diethylamine structure

Diethylamine

CAS#:109-89-7

Acetone structure

Acetone

CAS#:67-64-1

~%

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

1-(2,3-Dihydrox...

CAS#:33417-17-3

Literature: Braude; Lindwall Journal of the American Chemical Society, 1933 , vol. 55, p. 325

 Customs

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

 Synonyms

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
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