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MedKoo Cat#: 581167 | Name: Rotenone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rotenone is a botanical insecticide that is an inhibitor of mitochondrial electron transport. Rotenone is an inhibitor of NDUFS.

Chemical Structure

Rotenone
Rotenone
CAS#83-79-4

Theoretical Analysis

MedKoo Cat#: 581167

Name: Rotenone

CAS#: 83-79-4

Chemical Formula: C23H22O6

Exact Mass: 394.1416

Molecular Weight: 394.42

Elemental Analysis: C, 70.04; H, 5.62; O, 24.34

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
10g USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Rotenone; Cube root; bCube-Pulver; Ronone; HSDB 1762; Ro-KO;
IUPAC/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-
InChi Key
JUVIOZPCNVVQFO-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3
SMILES Code
O=C1C2C(COC3=CC(OC)=C(OC)C=C32)OC4=C1C=CC5=C4CC(C(C)=C)O5
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# T23C07I30
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Rotenone inhibits NAD-linked substrate oxidation of NADH dehydrogenase with an EC50=10 pmol/mg. Studies indicate that rotenone inhibits mammalian cell proliferation via suppressing microtubule assembly by binding to tubulin. Rotenone can inhibit the effects of N-methyl-4-phenylpyridinium on mitochondrial swelling and cytochrome c release.
In vitro activity:
Rotenone may promote the activation of THP-1 monocytes contributing to enhanced neurodegeneration. After 2 hours of Rotenone incubation, increased reactive oxygen species production and altered mitochondrial activity and transmembrane potential were observed, which later resulted in DNA oxidative damage and apoptosis. Reference: Mol Biol Rep. 2023 Feb;50(2):1241-1252. https://pubmed.ncbi.nlm.nih.gov/36446982/
In vivo activity:
In a mouse model of ferroptosis, single Rotenone administration markedly inhibited neuronal viability, promoted iron accumulation, increased malondialdehyde contents, decreased total superoxide dismutase activity, and downregulated ferroptosis-related proteins in primary neurons. Rotenone exacerbated the intracerebral hemorrhage-induced hemorrhagic volumes, brain edema, and neurological deficits. Reference: ACS Chem Neurosci. 2023 Mar 15;14(6):1071-1079. https://pubmed.ncbi.nlm.nih.gov/36848438/
Solvent mg/mL mM
Solubility
DMSO 50.0 126.77
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 394.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Currò M, Saija C, Trainito A, Trovato-Salinaro A, Bertuccio MP, Visalli G, Caccamo D, Ientile R. Rotenone-induced oxidative stress in THP-1 cells: biphasic effects of baicalin. Mol Biol Rep. 2023 Feb;50(2):1241-1252. doi: 10.1007/s11033-022-08060-2. Epub 2022 Nov 29. PMID: 36446982. 2. da Cruz IBM, de Afonso Bonotto NC, Turra BO, Teixeira CF, Azzolin VF, Ribeiro EAM, Piccoli JDCE, Barbisan F. Rotenone-exposure as cytofunctional aging model of human dermal fibroblast prior replicative senescence. Toxicol In Vitro. 2023 Sep;91:105637. doi: 10.1016/j.tiv.2023.105637. Epub 2023 Jun 30. PMID: 37394047. 3. Cheng Y, Zhang Z, Tang H, Chen B, Cai Y, Wei Y, Zhao W, Wu ZB, Shang H. Mitochondrial Inhibitor Rotenone Triggers and Enhances Neuronal Ferroptosis Following Intracerebral Hemorrhage. ACS Chem Neurosci. 2023 Mar 15;14(6):1071-1079. doi: 10.1021/acschemneuro.2c00308. Epub 2023 Feb 27. PMID: 36848438. 4. Inoue-Yanagimachi M, Himori N, Uchida K, Tawarayama H, Sato K, Yamamoto M, Namekata K, Harada T, Nakazawa T. Changes in glial cells and neurotrophic factors due to rotenone-induced oxidative stress in Nrf2 knockout mice. Exp Eye Res. 2023 Jan;226:109314. doi: 10.1016/j.exer.2022.109314. Epub 2022 Nov 16. PMID: 36400285.
In vitro protocol:
1. Currò M, Saija C, Trainito A, Trovato-Salinaro A, Bertuccio MP, Visalli G, Caccamo D, Ientile R. Rotenone-induced oxidative stress in THP-1 cells: biphasic effects of baicalin. Mol Biol Rep. 2023 Feb;50(2):1241-1252. doi: 10.1007/s11033-022-08060-2. Epub 2022 Nov 29. PMID: 36446982. 2. da Cruz IBM, de Afonso Bonotto NC, Turra BO, Teixeira CF, Azzolin VF, Ribeiro EAM, Piccoli JDCE, Barbisan F. Rotenone-exposure as cytofunctional aging model of human dermal fibroblast prior replicative senescence. Toxicol In Vitro. 2023 Sep;91:105637. doi: 10.1016/j.tiv.2023.105637. Epub 2023 Jun 30. PMID: 37394047.
In vivo protocol:
1. Cheng Y, Zhang Z, Tang H, Chen B, Cai Y, Wei Y, Zhao W, Wu ZB, Shang H. Mitochondrial Inhibitor Rotenone Triggers and Enhances Neuronal Ferroptosis Following Intracerebral Hemorrhage. ACS Chem Neurosci. 2023 Mar 15;14(6):1071-1079. doi: 10.1021/acschemneuro.2c00308. Epub 2023 Feb 27. PMID: 36848438. 2. Inoue-Yanagimachi M, Himori N, Uchida K, Tawarayama H, Sato K, Yamamoto M, Namekata K, Harada T, Nakazawa T. Changes in glial cells and neurotrophic factors due to rotenone-induced oxidative stress in Nrf2 knockout mice. Exp Eye Res. 2023 Jan;226:109314. doi: 10.1016/j.exer.2022.109314. Epub 2022 Nov 16. PMID: 36400285.
1: Johnson ME, Bobrovskaya L. An update on the rotenone models of Parkinson's disease: their ability to reproduce the features of clinical disease and model gene-environment interactions. Neurotoxicology. 2015 Jan;46:101-16. doi: 10.1016/j.neuro.2014.12.002. Epub 2014 Dec 13. Review. PubMed PMID: 25514659. 2: Yuan YH, Yan WF, Sun JD, Huang JY, Mu Z, Chen NH. The molecular mechanism of rotenone-induced α-synuclein aggregation: emphasizing the role of the calcium/GSK3β pathway. Toxicol Lett. 2015 Mar 4;233(2):163-71. doi: 10.1016/j.toxlet.2014.11.029. Epub 2014 Nov 26. PubMed PMID: 25433145. 3: Rohan M, Fairweather A, Grainger N. Using gamma distribution to determine half-life of rotenone, applied in freshwater. Sci Total Environ. 2015 Sep 15;527-528:246-51. doi: 10.1016/j.scitotenv.2015.04.059. Epub 2015 May 14. PubMed PMID: 25965037. 4: Dalu T, Wasserman RJ, Jordaan M, Froneman WP, Weyl OL. An Assessment of the Effect of Rotenone on Selected Non-Target Aquatic Fauna. PLoS One. 2015 Nov 5;10(11):e0142140. doi: 10.1371/journal.pone.0142140. eCollection 2015. PubMed PMID: 26540301; PubMed Central PMCID: PMC4634929. 5: Knaryan VH, Samantaray S, Park S, Azuma M, Inoue J, Banik NL. SNJ-1945, a calpain inhibitor, protects SH-SY5Y cells against MPP(+) and rotenone. J Neurochem. 2014 Jul;130(2):280-90. doi: 10.1111/jnc.12629. Epub 2013 Dec 16. PubMed PMID: 24341912; PubMed Central PMCID: PMC4038676. 6: Verma DK, Joshi N, Raju KS, Wahajuddin M, Singh RK, Singh S. Metabolic enhancer piracetam attenuates rotenone induced oxidative stress: a study in different rat brain regions. Acta Neurobiol Exp (Wars). 2015;75(4):399-411. PubMed PMID: 26994419. 7: Badaboina S, Bai HW, Na YH, Park CH, Kim TH, Lee TH, Chung BY. Novel Radiolytic Rotenone Derivative, Rotenoisin B with Potent Anti-Carcinogenic Activity in Hepatic Cancer Cells. Int J Mol Sci. 2015 Jul 24;16(8):16806-15. doi: 10.3390/ijms160816806. PubMed PMID: 26213921; PubMed Central PMCID: PMC4581171. 8: Estrella-Parra EA, Gomez-Verjan JC, González-Sánchez I, Vázquez-Martínez ER, Vergara-Castañeda E, Cerbón MA, Alavez-Solano D, Reyes-Chilpa R. Rotenone isolated from Pachyrhizus erosus displays cytotoxicity and genotoxicity in K562 cells. Nat Prod Res. 2014;28(20):1780-5. doi: 10.1080/14786419.2014.939081. Epub 2014 Jul 23. PubMed PMID: 25055205. 9: Kavitha M, Manivasagam T, Essa MM, Tamilselvam K, Selvakumar GP, Karthikeyan S, Thenmozhi JA, Subash S. Mangiferin antagonizes rotenone: induced apoptosis through attenuating mitochondrial dysfunction and oxidative stress in SK-N-SH neuroblastoma cells. Neurochem Res. 2014 Apr;39(4):668-76. doi: 10.1007/s11064-014-1249-7. Epub 2014 Feb 4. PubMed PMID: 24493626. 10: Deng Y, Lu J. [Role of rotenone in mitochondrial oxidative damage and the underlying mechanisms]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2014 Oct;39(10):1093-9. doi: 10.11817/j.issn.1672-7347.2014.10.019. Chinese. PubMed PMID: 25355263. 11: Ai Q, Jing Y, Jiang R, Lin L, Dai J, Che Q, Zhou D, Jia M, Wan J, Zhang L. Rotenone, a mitochondrial respiratory complex I inhibitor, ameliorates lipopolysaccharide/D-galactosamine-induced fulminant hepatitis in mice. Int Immunopharmacol. 2014 Jul;21(1):200-7. doi: 10.1016/j.intimp.2014.04.028. Epub 2014 May 13. PubMed PMID: 24830863. 12: Finlayson BJ, Eilers JM, Huchko HA. Fate and behavior of rotenone in Diamond Lake, Oregon, USA following invasive tui chub eradication. Environ Toxicol Chem. 2014 Jul;33(7):1650-5. doi: 10.1002/etc.2608. Epub 2014 May 27. PubMed PMID: 24733691. 13: Qin PW, Wang J, Wang H, Wen YJ, Lu ML, Li YF, Xu YS, Xu HH. Synthesis of rotenone-O-monosaccharide derivatives and their phloem mobility. J Agric Food Chem. 2014 May 21;62(20):4521-7. doi: 10.1021/jf500197k. Epub 2014 May 9. PubMed PMID: 24780074. 14: Sasajima H, Miyazono S, Noguchi T, Kashiwayanagi M. Intranasal administration of rotenone in mice attenuated olfactory functions through the lesion of dopaminergic neurons in the olfactory bulb. Neurotoxicology. 2015 Dec;51:106-15. doi: 10.1016/j.neuro.2015.10.006. Epub 2015 Oct 19. PubMed PMID: 26493152. 15: Ding W, Xu C, Wang B, Zhang M. Rotenone Attenuates Renal Injury in Aldosterone-Infused Rats by Inhibiting Oxidative Stress, Mitochondrial Dysfunction, and Inflammasome Activation. Med Sci Monit. 2015 Oct 17;21:3136-43. PubMed PMID: 26474533; PubMed Central PMCID: PMC4614375. 16: Rahimmi A, Khosrobakhsh F, Izadpanah E, Moloudi MR, Hassanzadeh K. N-acetylcysteine prevents rotenone-induced Parkinson's disease in rat: An investigation into the interaction of parkin and Drp1 proteins. Brain Res Bull. 2015 Apr;113:34-40. doi: 10.1016/j.brainresbull.2015.02.007. Epub 2015 Feb 28. PubMed PMID: 25732239. 17: Park SE, Sapkota K, Choi JH, Kim MK, Kim YH, Kim KM, Kim KJ, Oh HN, Kim SJ, Kim S. Rutin from Dendropanax morbifera Leveille protects human dopaminergic cells against rotenone induced cell injury through inhibiting JNK and p38 MAPK signaling. Neurochem Res. 2014 Apr;39(4):707-18. doi: 10.1007/s11064-014-1259-5. Epub 2014 Feb 19. PubMed PMID: 24549762. 18: Meinel J, Radad K, Rausch WD, Reichmann H, Gille G. Cabergoline protects dopaminergic neurons against rotenone-induced cell death in primary mesencephalic cell culture. Folia Neuropathol. 2015;53(1):29-40. PubMed PMID: 25909873. 19: Feng Y, Liu T, Dong SY, Guo YJ, Jankovic J, Xu H, Wu YC. Rotenone affects p53 transcriptional activity and apoptosis via targeting SIRT1 and H3K9 acetylation in SH-SY5Y cells. J Neurochem. 2015 Aug;134(4):668-76. doi: 10.1111/jnc.13172. Epub 2015 Jun 26. PubMed PMID: 25991017. 20: Hong Y, Nie H, Wu D, Wei X, Ding X, Ying W. NAD(+) treatment prevents rotenone-induced apoptosis and necrosis of differentiated PC12 cells. Neurosci Lett. 2014 Feb 7;560:46-50. doi: 10.1016/j.neulet.2013.11.039. Epub 2013 Dec 1. PubMed PMID: 24304867.

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