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MedKoo Cat#: 592860 | Name: Amphidinolide F

Description:

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

Amphidinolide F is a new cytotoxic macrolide

Chemical Structure

Amphidinolide F
Amphidinolide F
CAS#139594-87-9

Theoretical Analysis

MedKoo Cat#: 592860

Name: Amphidinolide F

CAS#: 139594-87-9

Chemical Formula: C35H52O9

Exact Mass: 616.3611

Molecular Weight: 616.79

Elemental Analysis: C, 68.16; H, 8.50; O, 23.35

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
Amphidinolide F
IUPAC/Chemical Name
3,26,27-Trioxatricyclo(21.2.1.16,9)heptacos-13-ene-4,18,21-trione, 10,11,16-trihydroxy-7,14,15,19-tetramethyl-12-methylene-2-(4-methyl-1,3-pentadienyl)-
InChi Key
VLOUARUYJFXXNO-VMHIOKEMSA-N
InChi Code
InChI=1S/C35H52O9/c1-19(2)9-8-10-29-30-12-11-26(42-30)16-25(36)14-21(4)27(37)17-28(38)24(7)20(3)13-23(6)34(40)35(41)32-15-22(5)31(43-32)18-33(39)44-29/h8-10,13,21-22,24,26,28-32,34-35,38,40-41H,6,11-12,14-18H2,1-5,7H3/b10-8+,20-13+
SMILES Code
O=C(CC1C(C)CC(O1)C(O)C(O)C(/C=C(C)/C(C)C(O)CC(C(C)C2)=O)=C)OC(/C=C/C=C(C)/C)C(O3)CCC3CC2=O
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 616.79 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: Valot G, Regens CS, O'Malley DP, Godineau E, Takikawa H, Fürstner A. Total synthesis of amphidinolide F. Angew Chem Int Ed Engl. 2013 Sep 2;52(36):9534-8. doi: 10.1002/anie.201301700. Epub 2013 Apr 22. PubMed PMID: 23610047. 2: Mahapatra S, Carter RG. Enantioselective total synthesis of amphidinolide F. Angew Chem Int Ed Engl. 2012 Aug 6;51(32):7948-51. doi: 10.1002/anie.201203935. Epub 2012 Jul 5. PubMed PMID: 22767517; PubMed Central PMCID: PMC3419500. 3: Roy S, Spilling CD. Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F. Org Lett. 2010 Nov 19;12(22):5326-9. doi: 10.1021/ol102345v. Epub 2010 Oct 28. PubMed PMID: 21028791; PubMed Central PMCID: PMC2981351. 4: Mahapatra S, Carter RG. Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F. J Am Chem Soc. 2013 Jul 24;135(29):10792-803. doi: 10.1021/ja404796n. Epub 2013 Jul 11. PubMed PMID: 23845005; PubMed Central PMCID: PMC3786714. 5: Morra NA, Pagenkopf BL. Gram scale synthesis of the C(18)-C(34) fragment of amphidinolide C. Org Lett. 2011 Feb 18;13(4):572-5. doi: 10.1021/ol1030074. Epub 2011 Jan 21. PubMed PMID: 21254755. 6: Kobayashi J, Tsuda M, Ishibashi M, Shigemori H, Yamasu T, Hirota H, Sasaki T. Amphidinolide F, a new cytotoxic macrolide from the marine dinoflagellate Amphidinium sp. J Antibiot (Tokyo). 1991 Nov;44(11):1259-61. PubMed PMID: 1761423. 7: Valot G, Mailhol D, Regens CS, O'Malley DP, Godineau E, Takikawa H, Philipps P, Fürstner A. Concise total syntheses of amphidinolides C and F. Chemistry. 2015 Feb 2;21(6):2398-408. doi: 10.1002/chem.201405790. Epub 2014 Dec 17. PubMed PMID: 25521077. 8: Shotwell JB, Roush WR. Synthesis of the C11-C29 fragment of amphidinolide F. Org Lett. 2004 Oct 14;6(21):3865-8. PubMed PMID: 15469369. 9: Clark JS, Yang G, Osnowski AP. Synthesis of the C-18-C-34 fragment of amphidinolides C, C2, and C3. Org Lett. 2013 Apr 5;15(7):1464-7. doi: 10.1021/ol400482j. Epub 2013 Mar 25. PubMed PMID: 23527614. 10: Ferrié L, Fenneteau J, Figadère B. Total Synthesis of the Marine Macrolide Amphidinolide F. Org Lett. 2018 Jun 1;20(11):3192-3196. doi: 10.1021/acs.orglett.8b01020. Epub 2018 May 15. PubMed PMID: 29762038. 11: Ferrié L, Figadère B. Efficient synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F. Org Lett. 2010 Nov 5;12(21):4976-9. doi: 10.1021/ol1021228. PubMed PMID: 20882983. 12: Mahapatra S, Carter RG. Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F. Org Biomol Chem. 2009 Nov 21;7(22):4582-5. doi: 10.1039/b916744g. Epub 2009 Sep 16. PubMed PMID: 19865690; PubMed Central PMCID: PMC2830907. 13: Fürstner A. From understanding to prediction: gold- and platinum-based π-acid catalysis for target oriented synthesis. Acc Chem Res. 2014 Mar 18;47(3):925-38. doi: 10.1021/ar4001789. Epub 2013 Nov 26. PubMed PMID: 24279341.