Dihydrorotenone

Modify Date: 2024-01-03 09:09:19

Dihydrorotenone Structure
Dihydrorotenone structure
Common Name Dihydrorotenone
CAS Number 6659-45-6 Molecular Weight 396.433
Density 1.3±0.1 g/cm3 Boiling Point 553.9±50.0 °C at 760 mmHg
Molecular Formula C23H24O6 Melting Point 216 °C
MSDS N/A Flash Point 241.6±30.2 °C

 Use of Dihydrorotenone


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].

 Names

Name Dihydrorotenone (VAN)
Synonym More Synonyms

 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
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

~91%

Dihydrorotenone Structure

Dihydrorotenone

CAS#: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

~%

Dihydrorotenone Structure

Dihydrorotenone

CAS#: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 & DownStream

Precursor  2

DownStream  0

 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