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MedKoo Cat#: 461426 | Name: Amorphigenin

Description:

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

Amorphigenin is a rotenoid compound which exhibits a strong larvicidal activity.

Chemical Structure

Amorphigenin
Amorphigenin
CAS#4208-09-7

Theoretical Analysis

MedKoo Cat#: 461426

Name: Amorphigenin

CAS#: 4208-09-7

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 #
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Synonym
Amorphigenin; 3'-Hydroxyrotenone; 8'-Hydroxyrotenone;
IUPAC/Chemical Name
(2R,6aS,12aS)-2-(3-hydroxyprop-1-en-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
InChi Key
ZJMLELXRQUXRIU-HBGVWJBISA-N
InChi Code
InChI=1S/C23H22O7/c1-11(9-24)16-7-14-15(29-16)5-4-12-22(25)21-13-6-18(26-2)19(27-3)8-17(13)28-10-20(21)30-23(12)14/h4-6,8,16,20-21,24H,1,7,9-10H2,2-3H3/t16-,20-,21+/m1/s1
SMILES Code
O=C1[C@]2([H])[C@](COC3=C2C=C(OC)C(OC)=C3)([H])OC4=C1C=CC5=C4C[C@H](C(CO)=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
2934.99.03.00
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: Ji M, Liang Y, Gu Z, Li X. Inhibitory Effects of Amorphigenin on the Mitochondrial Complex I of Culex pipiens pallens Coquillett (Diptera: Culicidae). Int J Mol Sci. 2015 Aug 20;16(8):19713-27. doi: 10.3390/ijms160819713. PubMed PMID: 26307964; PubMed Central PMCID: PMC4581321. 2: Liang Y, Li X, Gu Z, Qin P, Ji M. Toxicity of amorphigenin from the seeds of Amorpha fruticosa against the larvae of Culex pipiens pallens (Diptera: Culicidae). Molecules. 2015 Feb 16;20(2):3238-54. doi: 10.3390/molecules20023238. PubMed PMID: 25690287. 3: Zhong H, Zuo Y, Wu X, Peng Y, He H, Yang J, Guan C, Xu Z. [Synergistic Antitumor Effect of Amorphigenin Combined with Cisplatin in Human Lung Adenocarcinoma A549/DDP Cells]. Zhongguo Fei Ai Za Zhi. 2016 Dec 20;19(12):805-812. Chinese. PubMed PMID: 27978865; PubMed Central PMCID: PMC5973453. 4: Kim BG, Kwak HB, Choi EY, Kim HS, Kim MH, Kim SH, Choi MK, Chun CH, Oh J, Kim JJ. Amorphigenin inhibits Osteoclast differentiation by suppressing c-Fos and nuclear factor of activated T cells. Anat Cell Biol. 2010 Dec;43(4):310-6. doi: 10.5115/acb.2010.43.4.310. Epub 2010 Dec 31. PubMed PMID: 21267405; PubMed Central PMCID: PMC3026183. 5: Gyémánt N, Tanaka M, Antus S, Hohmann J, Csuka O, Mándoky L, Molnár J. In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. In Vivo. 2005 Mar-Apr;19(2):367-74. PubMed PMID: 15796199. 6: Crombie L, Whiting DA. Review article number 135 biosynthesis in the rotenoid group of natural products: applications of isotope methodology. Phytochemistry. 1998 Nov 20;49(6):1479-1507. PubMed PMID: 11711058. 7: Sariaslani FS, Rosazza JP. Microbial Transformations of Natural Antitumor Agents: Products of Rotenone and Dihydrorotenone Transformation by Cunninghamella blakesleeana. Appl Environ Microbiol. 1983 Feb;45(2):616-21. PubMed PMID: 16346210; PubMed Central PMCID: PMC242333. 8: Earley FG, Ragan CI. Photoaffinity labelling of mitochondrial NADH dehydrogenase with arylazidoamorphigenin, an analogue of rotenone. Biochem J. 1984 Dec 1;224(2):525-34. PubMed PMID: 6517863; PubMed Central PMCID: PMC1144461. 9: Li L, Wang HK, Chang JJ, McPhail AT, McPhail DR, Terada H, Konoshima T, Kokumai M, Kozuka M, Estes JR, et al. Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa. J Nat Prod. 1993 May;56(5):690-8. PubMed PMID: 8326318. 10: Kloutek E, Popov A, Drenska D, Uzunov P. [Experimental research on the hepatoprotective activity of flavonoids isolated from Amorpha fructiosa]. Eksp Med Morfol. 1985;24(2):50-4. Bulgarian. PubMed PMID: 4065006. 11: Chin YW, Mdee LK, Mbwambo ZH, Mi Q, Chai HB, Cragg GM, Swanson SM, Kinghorn AD. Prenylated flavonoids from the root bark of Berchemia discolor, a Tanzanian medicinal plant. J Nat Prod. 2006 Nov;69(11):1649-52. PubMed PMID: 17125241; PubMed Central PMCID: PMC2471879. 12: Muharini R, Díaz A, Ebrahim W, Mándi A, Kurtán T, Rehberg N, Kalscheuer R, Hartmann R, Orfali RS, Lin W, Liu Z, Proksch P. Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa. J Nat Prod. 2017 Jan 27;80(1):169-180. doi: 10.1021/acs.jnatprod.6b00809. Epub 2017 Jan 11. PubMed PMID: 28075580. 13: Konoshima T, Terada H, Kokumai M, Kozuka M, Tokuda H, Estes JR, Li L, Wang HK, Lee KH. Studies on inhibitors of skin tumor promotion, XII. Rotenoids from Amorpha fruticosa. J Nat Prod. 1993 Jun;56(6):843-8. PubMed PMID: 8350086. 14: Wongrattanakamon P, Lee VS, Nimmanpipug P, Sirithunyalug B, Chansakaow S, Jiranusornkul S. Insight into the molecular mechanism of P-glycoprotein mediated drug toxicity induced by bioflavonoids: an integrated computational approach. Toxicol Mech Methods. 2017 May;27(4):253-271. doi: 10.1080/15376516.2016.1273428. Epub 2017 Feb 15. PubMed PMID: 27996361.