6659-45-6

6659-45-6 structure

Name: Dihydrorotenone
Chemical Name: Dihydrorotenone (VAN)
CAS Number: 6659-45-6
Molecular Formula: C₂₃H₂₄O₆
Molecular Weight: 396.433
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2018-05-22 08:00:00
Modify Date: 2024-01-03 09:09:19
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].

Name	Dihydrorotenone (VAN)
Synonyms	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

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.

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

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

83-79-4

~91%

6659-45-6

Literature: O'Neil, James P.; VanBrocklin, Henry F.; Morimoto, Hiromi; Williams, Philip G. Journal of Labelled Compounds and Radiopharmaceuticals, 1997 , vol. 39, # 3 p. 215 - 221

34487-52-0

6659-45-6

Literature: Carson, David; Crombie, Leslie; Kilbee, Geoffrey W.; Moffatt, Frank; Whiting, Donald A. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982 , p. 779 - 788

Precursor 2
83-79-4 34487-52-0
DownStream 0

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