Dihydrorotenone

Names

[ 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

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.