Rocaglamide
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MedKoo CAT#: 406598

CAS#: 84573-16-0

Description: Rocaglamide is the first cyclopenta[b]benzofuran derivative (flavagline), isolated from Aglaia elliptifolia in 1982 by King and colleagues based on its antileukemic activity. Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.


Price and Availability

Size Price Shipping out time Quantity
2mg USD 350 Same day
5mg USD 650 Same day
10mg USD 1150 Same day
25mg USD 2150 Same day
50mg USD 3750 Same day
100mg USD 5950 Same day
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

Rocaglamide, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406598
Name: Rocaglamide
CAS#: 84573-16-0
Chemical Formula: C29H31NO7
Exact Mass: 505.21005
Molecular Weight: 505.56
Elemental Analysis: C, 68.90; H, 6.18; N, 2.77; O, 22.15


Synonym: Rocaglamide; Rocaglamide A; RocA; NSC 326408.

IUPAC/Chemical Name: (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide

InChi Key: DAPAQENNNINUPW-IDAMAFBJSA-N

InChi Code: InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

SMILES Code: O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=CC(OC)=CC(OC)=C35)N(C)C


Technical Data

Appearance:
White to off- white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

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, not in water

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


Additional Information

  
 
 
 


References

1: Luan Z, He Y, He F, Chen Z. Rocaglamide overcomes tumor necrosis factor-related apoptosis-inducing ligand resistance in hepatocellular carcinoma cells by attenuating the inhibition of caspase-8 through cellular FLICE-like-inhibitory protein downregulation. Mol Med Rep. 2015 Jan;11(1):203-11. doi: 10.3892/mmr.2014.2718. Epub 2014 Oct 21. PubMed PMID: 25333816; PubMed Central PMCID: PMC4237083.

2: Duong NT, Edrada-Ebel R, Ebel R, Lin W, Duong AT, Dang XQ, Nguyen NH, Proksch P. New rocaglamide derivatives from Vietnamese Aglaia species. Nat Prod Commun. 2014 Jun;9(6):833-4. PubMed PMID: 25115092.

3: Pan L, Woodard JL, Lucas DM, Fuchs JR, Kinghorn AD. Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species. Nat Prod Rep. 2014 Jul;31(7):924-39. doi: 10.1039/c4np00006d. Epub 2014 May 2. Review. PubMed PMID: 24788392; PubMed Central PMCID: PMC4091845.

4: Becker MS, Schmezer P, Breuer R, Haas SF, Essers MA, Krammer PH, Li-Weber M. The traditional Chinese medical compound Rocaglamide protects nonmalignant primary cells from DNA damage-induced toxicity by inhibition of p53 expression. Cell Death Dis. 2014 Jan 16;5:e1000. doi: 10.1038/cddis.2013.528. PubMed PMID: 24434508; PubMed Central PMCID: PMC4040689.

5: Neumann J, Boerries M, Köhler R, Giaisi M, Krammer PH, Busch H, Li-Weber M. The natural anticancer compound rocaglamide selectively inhibits the G1-S-phase transition in cancer cells through the ATM/ATR-mediated Chk1/2 cell cycle checkpoints. Int J Cancer. 2014 Apr 15;134(8):1991-2002. doi: 10.1002/ijc.28521. Epub 2013 Oct 21. PubMed PMID: 24150948.

6: El-Neketi M, Ebrahim W, Duong NT, Gedara S, Badria F, Saad HE, Müller WE, Proksch P. Cytotoxic rocaglamide derivatives from Aglaia duppereana. Z Naturforsch C. 2013 Jul-Aug;68(7-8):269-74. PubMed PMID: 24066511.

7: Sadlish H, Galicia-Vazquez G, Paris CG, Aust T, Bhullar B, Chang L, Helliwell SB, Hoepfner D, Knapp B, Riedl R, Roggo S, Schuierer S, Studer C, Porco JA Jr, Pelletier J, Movva NR. Evidence for a functionally relevant rocaglamide binding site on the eIF4A-RNA complex. ACS Chem Biol. 2013 Jul 19;8(7):1519-27. doi: 10.1021/cb400158t. Epub 2013 May 7. PubMed PMID: 23614532; PubMed Central PMCID: PMC3796129.

8: Malona JA, Cariou K, Spencer WT 3rd, Frontier AJ. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization. J Org Chem. 2012 Feb 17;77(4):1891-908. doi: 10.1021/jo202366c. Epub 2012 Jan 26. PubMed PMID: 22283818; PubMed Central PMCID: PMC3306619.

9: Rodrigo CM, Cencic R, Roche SP, Pelletier J, Porco JA. Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies. J Med Chem. 2012 Jan 12;55(1):558-62. doi: 10.1021/jm201263k. Epub 2011 Dec 19. PubMed PMID: 22128783; PubMed Central PMCID: PMC3263355.

10: Giaisi M, Köhler R, Fulda S, Krammer PH, Li-Weber M. Rocaglamide and a XIAP inhibitor cooperatively sensitize TRAIL-mediated apoptosis in Hodgkin's lymphomas. Int J Cancer. 2012 Aug 15;131(4):1003-8. doi: 10.1002/ijc.26458. Epub 2011 Nov 8. PubMed PMID: 21952919.

11: Cai XH, Xie B, Guo H. Progress in the total synthesis of rocaglamide. ISRN Org Chem. 2011 Apr 4;2011:239817. doi: 10.5402/2011/239817. Review. PubMed PMID: 24052818; PubMed Central PMCID: PMC3767207.

12: Bleumink M, Köhler R, Giaisi M, Proksch P, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL resistance in HTLV-1-associated adult T-cell leukemia/lymphoma by translational suppression of c-FLIP expression. Cell Death Differ. 2011 Feb;18(2):362-70. doi: 10.1038/cdd.2010.99. Epub 2010 Aug 13. PubMed PMID: 20706274; PubMed Central PMCID: PMC3131883.

13: Malona JA, Cariou K, Frontier AJ. Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide. J Am Chem Soc. 2009 Jun 10;131(22):7560-1. doi: 10.1021/ja9029736. PubMed PMID: 19445456; PubMed Central PMCID: PMC2732401.

14: Zhu JY, Giaisi M, Köhler R, Müller WW, Mühleisen A, Proksch P, Krammer PH, Li-Weber M. Rocaglamide sensitizes leukemic T cells to activation-induced cell death by differential regulation of CD95L and c-FLIP expression. Cell Death Differ. 2009 Sep;16(9):1289-99. doi: 10.1038/cdd.2009.42. Epub 2009 Apr 17. PubMed PMID: 19373244.

15: Giese MW, Moser WH. Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence. Org Lett. 2008 Oct 2;10(19):4215-8. doi: 10.1021/ol801435j. Epub 2008 Aug 28. PubMed PMID: 18754622.

16: Zhu JY, Lavrik IN, Mahlknecht U, Giaisi M, Proksch P, Krammer PH, Li-Weber M. The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities. Int J Cancer. 2007 Oct 15;121(8):1839-46. PubMed PMID: 17565740.

17: Chumkaew P, Kato S, Chantrapromma K. Potent cytotoxic rocaglamide derivatives from the fruits of Amoora cucullata. Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1344-6. PubMed PMID: 16946551.

18: Proksch P, Giaisi M, Treiber MK, Palfi K, Merling A, Spring H, Krammer PH, Li-Weber M. Rocaglamide derivatives are immunosuppressive phytochemicals that target NF-AT activity in T cells. J Immunol. 2005 Jun 1;174(11):7075-84. PubMed PMID: 15905551.

19: Bringmann G, Mühlbacher J, Messer K, Dreyer M, Ebel R, Nugroho BW, Wray V, Proksch P. Cyclorocaglamide, the first bridged cyclopentatetrahydrobenzofuran, and a related "open chain" rocaglamide derivative from Aglaia oligophylla. J Nat Prod. 2003 Jan;66(1):80-5. PubMed PMID: 12542350.

20: Baumann B, Bohnenstengel F, Siegmund D, Wajant H, Weber C, Herr I, Debatin KM, Proksch P, Wirth T. Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells. J Biol Chem. 2002 Nov 22;277(47):44791-800. Epub 2002 Sep 16. PubMed PMID: 12237314.