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Dihydrorotenone

Names

[ CAS No. ]:
6659-45-6

[ Name ]:
Dihydrorotenone

[Synonym ]:
1',2'-dihydrorotenone
1-Dihydrorotenon
Furo[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethyl)-, (2R,6aS,12aS)-
Dihydrorotenone
6'.7'-Dihydro-rotenon
(2R,6aS,12aS)-2-Isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
6',7'-dihydrorotenone

Biological Activity

[Description]:

Dihydrorotenone, a natural pesticide, is a potent mitochondrial inhibitor. Dihydrorotenone probably induces Parkinsonian syndrome. Dihydrorotenone induces human plasma cell apoptosis by triggering endoplasmic reticulum stress and activating p38 signaling pathway[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Signaling Pathways >> Metabolic Enzyme/Protease >> Mitochondrial Metabolism
Research Areas >> Neurological Disease

[References]

[1]. Zhang J, et al. The natural pesticide dihydrorotenone induces human plasma cell apoptosis by triggering endoplasmic reticulum stress and activating p38 signaling pathway. PLoS One. 2013 Jul 26;8(7):e69911.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
553.9±50.0 °C at 760 mmHg

[ Melting Point ]:
216 °C

[ Molecular Formula ]:
C23H24O6

[ Molecular Weight ]:
396.433

[ Flash Point ]:
241.6±30.2 °C

[ Exact Mass ]:
396.157288

[ PSA ]:
63.22000

[ LogP ]:
4.82

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.580

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ2623100
CHEMICAL NAME :
(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a-al phah)-one, 1,2,12,12a-alpha-tetrahydro- 2-alpha-isopropyl-8,9-dimethoxy-
CAS REGISTRY NUMBER :
6659-45-6
LAST UPDATED :
199512
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C23-H24-O6
MOLECULAR WEIGHT :
396.47

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - other changes
REFERENCE :
JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 42,364,1953
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
IECHAD Industrial and Engineering Chemistry. (Washington, DC) V.15-62, 1923-70. For publisher information, see CHMTBL. Volume(issue)/page/year: 29,429,1937 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4616 mg/kg/57W-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 42,364,1953

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream