Rotenone

Modify Date: 2026-07-01 16:41:39

Rotenone Structure
Rotenone structure
Common Name Rotenone
CAS Number 83-79-4 Molecular Weight 394.417
Density 1.3±0.1 g/cm3 Boiling Point 559.8±50.0 °C at 760 mmHg
Molecular Formula C23H22O6 Melting Point 159-164 °C(lit.)
MSDS Chinese USA Flash Point 244.6±30.2 °C
Symbol GHS06 GHS09
GHS06, GHS09
Signal Word Danger

 Use of Rotenone


Rotenone is an mitochondrial electron transport chain complex I inhibitor.

 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name rotenone
Synonym More Synonyms

 Rotenone Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

Description Rotenone is an mitochondrial electron transport chain complex I inhibitor.
Related Catalog
In Vitro Mitogen Activated Protein Kinase (MAPK), Toll-like receptor, Wnt, and Ras signaling pathways are intensively involved in the effect of rotenone on the ENS[2]. Rotenone-induced cell death is reduced by treatment as measured by decline in the levels of pro-apoptotic proteins. Moreover, treatment significantly augments the levels of anti-apoptotic Bcl2 and blocks the release of cytochrome c, thereby alleviating the rotenone-induced dopaminergic neuronal loss, as evidenced by tyrosine hydroxylase (TH) immunostaining in the striatum[3].
In Vivo Rotenone causes a significant increase in the excitatory amino acid neurotransmitters; glutamate and aspartate together with a significant decrease in the inhibitory amino acids, GABA, glycine and taurine are observed in the cerebellum of rat model of PD[1]. Rotenone (1.5, 2, or 2.5 mg/kg) causes a dose-dependent increase in α-synuclein in the substantia nigra. Furthermore, at 2 and 2.5 mg/kg, rotenone causes a significant decrease in the number of tyrosine hydroxylase-immunoreactive neurons in the substantia nigra, and dopamine in the striatum in rats[4].
References

[1]. Khadrawy YA, et al. Cerebellar neurochemical and histopathological changes in rat model of Parkinson's disease induced by intrastriatal injection of rotenone. Gen Physiol Biophys. 2016 Nov 30

[2]. Guan Q, et al. RNA-Seq Expression Analysis of Enteric Neuron Cells with Rotenone Treatment and Prediction of Regulated Pathways. Neurochem Res. 2016 Nov 30

[3]. Kishore Kumar SN, et al. Morinda citrifolia mitigates rotenone-induced striatal neuronal loss in male Sprague-Dawley rats by preventing mitochondrial pathway of intrinsic apoptosis. Redox Rep. 2016 Nov 24:1-12

[4]. Zhang ZN, et al. Subcutaneous rotenone rat model of Parkinson's disease: dose exploration study. Brain Res. 2016 Nov 19. pii: S0006-8993(16)30776-4

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

Density 1.3±0.1 g/cm3
Boiling Point 559.8±50.0 °C at 760 mmHg
Melting Point 159-164 °C(lit.)
Molecular Formula C23H22O6
Molecular Weight 394.417
Flash Point 244.6±30.2 °C
Exact Mass 394.141632
PSA 63.22000
LogP 4.65
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.591
InChIKey JUVIOZPCNVVQFO-HBGVWJBISA-N
SMILES C=C(C)C1Cc2c(ccc3c2OC2COc4cc(OC)c(OC)cc4C2C3=O)O1
Stability Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.

 MSDS

This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ2800000
CHEMICAL NAME :
(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6ah)- one, 1,2,12,12a-tetrahydro-2-alpha- isopropenyl-8,9-dimethoxy-
CAS REGISTRY NUMBER :
83-79-4
LAST UPDATED :
199803
DATA ITEMS CITED :
71
MOLECULAR FORMULA :
C23-H22-O6
MOLECULAR WEIGHT :
394.45
WISWESSER LINE NOTATION :
T G5 D6 B666 CV HO MO POT&TT&J IY1&U1 SO1 TO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
143 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
294 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
500 mg/m3/30M
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>940 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
132 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2650 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
650 ug/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
650 ug/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
350 ug/kg
TOXIC EFFECTS :
Behavioral - ataxia Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - pig
DOSE/DURATION :
3700 ug/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - chronic pulmonary edema Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Bird - pigeon
DOSE/DURATION :
1 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - duck
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
4 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1505 mg/kg/14D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5460 mg/kg/13W-C
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
54600 mg/kg/13W-C
TOXIC EFFECTS :
Liver - changes in liver weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
180 mg/kg/9D-C
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - chronic pulmonary edema Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3245 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
71 mg/kg/42D-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
68 mg/kg/40D-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3285 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - thyroid tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2960 ug/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
98 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)

MUTATION DATA

TYPE OF TEST :
Sex chromosome loss and nondisjunction
TEST SYSTEM :
Rodent - hamster Lung
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 263,173,1991 *** REVIEWS *** ACGIH TLV-Not classifiable as a human carcinogen DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-TWA 5 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 MSHA STANDARD-air:TWA 5 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: 3,224,1971 OSHA PEL (Gen Indu):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1910.1000,1994 OSHA PEL (Construc):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1926.55,1994 OSHA PEL (Shipyard):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1915.1000,1993 OSHA PEL (Fed Cont):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 41,50-204.50,1994 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 5 mg/m3 JAN 1993 OEL-BELGIUM:TWA 5 mg/m3 JAN 1993 OEL-DENMARK:TWA 5 mg/m3 JAN 1993 OEL-FINLAND:TWA 5 mg/m3;STEL 10 mg/m3 JAN 1993 OEL-GERMANY:TWA 5 mg/m3 JAN 1993 OEL-THE NETHERLANDS:TWA 5 mg/m3 JAN 1993 OEL-THE PHILIPPINES:TWA 5 mg/m3 JAN 1993 OEL-SWITZERLAND:TWA 5 mg/m3 JAN 1993 OEL-TURKEY:TWA 5 mg/m3 JAN 1993 OEL-UNITED KINGDOM:TWA 5 mg/m3;STEL 10 mg/m3 JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO ROTENONE-air:10H TWA 5 mg/m3 REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 67530 No. of Facilities: 70 (estimated) No. of Industries: 3 No. of Occupations: 4 No. of Employees: 2937 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 67530 No. of Facilities: 913 (estimated) No. of Industries: 3 No. of Occupations: 3 No. of Employees: 8100 (estimated) No. of Female Employees: 2470 (estimated)

 Safety Information

This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.

Symbol GHS06 GHS09
GHS06, GHS09
Signal Word Danger
Hazard Statements H301-H315-H319-H335-H410
Precautionary Statements P273-P280-P301 + P310 + P330-P337 + P313-P391-P501
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic;N:Dangerousfortheenvironment;
Risk Phrases R25;R36/37/38;R50/53
Safety Phrases 22-24/25-36-45-60-61
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS DJ2800000
Packaging Group III
Hazard Class 6.1(b)

 Synthetic Route

This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.

~81%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Bhandari, Prabha; Crombie, Leslie; Kilbee, Geoffrey W.; Pegg, Stephen J.; Proudfoot, Geoffrey; et al. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992 , # 7 p. 851 - 864

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Singhal, Ashok Kumar; Sharma, Ram Prakash; Baruah, Jogendra Nath; Govindan, Serengolam V.; Herz, Werner Phytochemistry (Elsevier), 1982 , vol. 21, # 4 p. 949 - 951

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 21 p. 2605 - 2614

~59%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
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

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 21 p. 2605 - 2614

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 7 p. 851 - 864

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 204 - 205

~%

Rotenone Structure

Rotenone

CAS#:83-79-4

Learn More
Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 7 p. 851 - 864

 Articles312

More Articles

This table lists relevant public references with title, journal and publication metadata for this compound.

High fat, high sucrose diet causes cardiac mitochondrial dysfunction due in part to oxidative post-translational modification of mitochondrial complex II.

J. Mol. Cell. Cardiol. 78 , 165-73, (2014)

Diet-induced obesity leads to metabolic heart disease (MHD) characterized by increased oxidative stress that may cause oxidative post-translational modifications (OPTM) of cardiac mitochondrial protei...

Thermogenic activity of UCP1 in human white fat-derived beige adipocytes.

Mol. Endocrinol. 29(1) , 130-9, (2014)

Heat-producing beige/brite (brown-in-white) adipocytes in white adipose tissue have the potential to suppress metabolic disease in mice and hold great promise for the treatment of obesity and type 2 d...

The catalytic subunit of DNA-dependent protein kinase is required for cellular resistance to oxidative stress independent of DNA double-strand break repair.

Free Radic. Biol. Med. 76 , 278-85, (2014)

DNA-dependent protein kinase catalytic subunit (DNA-PKcs) and ataxia telangiectasia mutated (ATM) are the two major kinases involved in DNA double-strand break (DSB) repair, and are required for cellu...

 RotenoneBioassay

View more

This table contains target information, in‑vitro & in‑vivo assay data for this compound.

Name: Primary qHTS assay for inhibitors of alpha-synuclein gene (SNCA) expression
Source: NCGC
External Id: SNCA-p-activity-luciferase
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-keats_OPM1-m4-1
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-OC1MY5-m4-1
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-KMS_34-m4-1
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-keats_L363-m4-1
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-keats_OCIMY7-m4-1
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-MM1R-m4-1
Name: Larvicidal activity against Aedes aegypti fourth instar larvae after 24 hrs
Source: ChEMBL
Target: Aedes aegypti
External Id: CHEMBL1113717
Name: Quantitative High-Throughput drug screen in 47 multiple myeloma cell lines against th...
Source: NCGC
Target: N/A
External Id: s-my-mm1s-m4-1
Total 885, Current Page 1 of 89
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 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

(-)-rotenone
derris
(2R,6aS,12aS)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
protax
(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Derris root
[2R-(2a,6aa,12aa)]-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Rotacide E.C.
(2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one
MFCD09025614
5'-b-Rotenone
TUBATOXIN
(2R,6aS,12aS)-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Foliafume E.C.
paraderil
Dermostatin A
Rotenone,(2R,6aS,12aS)-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
(-)-cis-rotenone
(2R,6aS,12aS)-2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Noxfire
EINECS 201-501-9
Tubotoxine
Canex

 Rotenone | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the SMILES notation of rotenone?
A: SMILES notation of rotenone is C=C(C)C1Cc2c(ccc3c2OC2COc4cc(OC)c(OC)cc4C2C3=O)O1.
Q: What are the downstream products of rotenone?
A: Related downstream products(CAS) of rotenone: 522-17-8;34487-52-0;3466-09-9;3466-23-7;6659-45-6.
Q: What are the uses of rotenone?
A: Main uses of rotenone: Rotenone is an mitochondrial electron transport chain complex I inhibitor.
Q: What is the CAS number of rotenone?
A: CAS number of rotenone is 83-79-4.
Q: What is the polar surface area (PSA) of rotenone?
A: Polar surface area (PSA) of rotenone is 63.22000.
Q: What is the melting point of rotenone?
A: Melting point of rotenone is 159-164 °C(lit.).
Q: What is the boiling point of rotenone?
A: Boiling point of rotenone is 559.8±50.0 °C at 760 mmHg.
Q: What are the upstream materials of rotenone?
A: Related upstream materials(CAS) of rotenone: 23355-70-6;3466-09-9;186581-53-3;34487-52-0;23295-59-2.
Q: What is the English name of rotenone?
A: The English name of rotenone is rotenone.
Q: What is the InChIKey of rotenone?
A: InChIKey of rotenone is JUVIOZPCNVVQFO-HBGVWJBISA-N.

 Rotenonefactory

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

Shanghai Nianxing Industrial Co., Ltd
BioBioPha
Dayang Chem (Hangzhou) Co., Ltd.
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