MedKoo Cat#: 461424 | Name: Rotenolone

Description:

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

Rotenolone is a rotenoid.

Chemical Structure

Rotenolone
Rotenolone
CAS#509-96-6

Theoretical Analysis

MedKoo Cat#: 461424

Name: Rotenolone

CAS#: 509-96-6

Chemical Formula: C23H22O7

Exact Mass: 410.1366

Molecular Weight: 410.42

Elemental Analysis: C, 67.31; H, 5.40; O, 27.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rotenolone; Rotenolone I;
IUPAC/Chemical Name
(2R,6aS,12aR)-6a-hydroxy-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
InChi Key
JFVKWCYZKMUTLH-LQNXUBFPSA-N
InChi Code
InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23+/m1/s1
SMILES Code
O=C1[C@@]2(O)[C@](COC3=C2C=C(OC)C(OC)=C3)([H])OC4=C1C=CC5=C4C[C@H](C(C)=C)O5
Appearance
Solid powder
Purity
>98% (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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 410.42 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
1: Melo KM, Oliveira R, Grisolia CK, Domingues I, Pieczarka JC, de Souza Filho J, Nagamachi CY. Short-term exposure to low doses of rotenone induces developmental, biochemical, behavioral, and histological changes in fish. Environ Sci Pollut Res Int. 2015 Sep;22(18):13926-38. doi: 10.1007/s11356-015-4596-2. Epub 2015 May 7. PubMed PMID: 25948382. 2: 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. 3: Nirma C, Rodrigues AM, Basset C, Chevolot L, Girod R, Moretti C, Stien D, Dusfour I, Eparvier V. Larvicidal activity of isoflavonoids from Muellera frutescens extracts against Aedes aegypti. Nat Prod Commun. 2012 Oct;7(10):1319-22. PubMed PMID: 23156998. 4: Vasquez ME, Rinderneck J, Newman J, McMillin S, Finlayson B, Mekebri A, Crane D, Tjeerdema RS. Rotenone formulation fate in Lake Davis following the 2007 treatment. Environ Toxicol Chem. 2012 May;31(5):1032-41. doi: 10.1002/etc.1795. Epub 2012 Mar 23. PubMed PMID: 22407799. 5: Harinantenaina L, Brodie PJ, Slebodnick C, Callmander MW, Rakotobe E, Randrianasolo S, Randrianaivo R, Rasamison VE, Tendyke K, Shen Y, Suh EM, Kingston DG. Antiproliferative compounds from Pongamiopsis pervilleana from the Madagascar Dry Forest. J Nat Prod. 2010 Sep 24;73(9):1559-62. doi: 10.1021/np100430r. PubMed PMID: 20804165; PubMed Central PMCID: PMC2945424. 6: Cao S, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG. Cytotoxic compounds from Mundulea chapelieri from the Madagascar Rainforest. J Nat Prod. 2004 Mar;67(3):454-6. PubMed PMID: 15043430. 7: Cabizza M, Angioni A, Melis M, Cabras M, Tuberoso CV, Cabras P. Rotenone and rotenoids in cubè resins, formulations, and residues on olives. J Agric Food Chem. 2004 Jan 28;52(2):288-93. PubMed PMID: 14733510. 8: Fang N, Casida JE. Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents. J Agric Food Chem. 1999 May;47(5):2130-6. PubMed PMID: 10552508. 9: Newsome WH, Shields JB. Residues of rotenone and rotenolone on lettuce and tomato fruit after treatment in the field with rotenone formulations. J Agric Food Chem. 1980 Jul-Aug;28(4):722-4. PubMed PMID: 7462491. 10: Bushway RJ, Engdahl BS, Colvin BM, Hanks AR. Separation of rotenoids and the determination of rotenone in pesticide formulations by high-performance liquid chromatography. J Assoc Off Anal Chem. 1975 Sep;58(5):965-70. PubMed PMID: 1158840. 11: Fukami JI, Yamamoto I, Casida JE. Metabolism of rotenone in vitro by tissue homogenates from mammals and insects. Science. 1967 Feb 10;155(3763):713-6. PubMed PMID: 4381128.