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MedKoo Cat#: 592857 | Name: Amphidinolide C

Description:

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

Amphidinolide C is a potent cytotoxic 25-membered macrolide from marine dinoflagellate Amphidinium sp.

Chemical Structure

Amphidinolide C
Amphidinolide C
CAS#112945-21-8

Theoretical Analysis

MedKoo Cat#: 592857

Name: Amphidinolide C

CAS#: 112945-21-8

Chemical Formula: C41H62O10

Exact Mass: 714.4343

Molecular Weight: 714.94

Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 68.88; H, 8.74; O, 22.38

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
Amphidinolide C
IUPAC/Chemical Name
(1S,2R,6S,7R,9R,10R,11R,15R,16S,19S,23R,E)-10,11,16-trihydroxy-2-((S,1E,3E)-5-hydroxy-4-methyl-6-methylenedeca-1,3-dien-1-yl)-7,14,15,19-tetramethyl-12-methylene-3,26,27-trioxatricyclo[21.2.1.16,9]heptacos-13-ene-4,18,21-trione
InChi Key
RNKCEFQNDOJBLW-IEBOKVSHSA-N
InChi Code
InChI=1S/C41H62O10/c1-9-10-12-23(2)39(46)24(3)13-11-14-34-35-16-15-31(49-35)20-30(42)18-26(5)32(43)21-33(44)29(8)25(4)17-28(7)40(47)41(48)37-19-27(6)36(50-37)22-38(45)51-34/h11,13-14,17,26-27,29,31,33-37,39-41,44,46-48H,2,7,9-10,12,15-16,18-22H2,1,3-6,8H3/b14-11+,24-13+,25-17+/t26-,27+,29+,31+,33-,34+,35-,36-,37+,39-,40+,41-/m0/s1
SMILES Code
O[C@H](\C(=C\C=C\[C@H]1OC(C[C@@H]2O[C@H](C[C@H]2C)[C@H](O)[C@H](O)C(C=C([C@H]([C@H](CC([C@@H](C)CC(C[C@H]2CC[C@@H]1O2)=O)=O)O)C)C)=C)=O)C)C(CCCC)=C
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 714.94 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: 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. 2: 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. 3: Wu D, Forsyth CJ. Syntheses of the C1-C14 and C15-C25 fragments of amphidinolide C. Org Lett. 2013 Mar 15;15(6):1178-81. doi: 10.1021/ol303515h. Epub 2013 Feb 26. PubMed PMID: 23441846. 4: 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. 5: Clark JS, Yang G, Osnowski AP. Synthesis of the C-1-C-17 fragment of amphidinolides C, C2, C3, and F. Org Lett. 2013 Apr 5;15(7):1460-3. doi: 10.1021/ol4004838. Epub 2013 Mar 25. PubMed PMID: 23527702. 6: Bates RH, Shotwell JB, Roush WR. Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C. Org Lett. 2008 Oct 2;10(19):4343-6. doi: 10.1021/ol801852j. Epub 2008 Sep 11. PubMed PMID: 18783230; PubMed Central PMCID: PMC2650083. 7: 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. 8: Kubota T, Tsuda M, Kobayashi J. Absolute stereochemistry of amphidinolide C. Org Lett. 2001 May 3;3(9):1363-6. PubMed PMID: 11348235. 9: 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. 10: Paudyal MP, Rath NP, Spilling CD. A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction. Org Lett. 2010 Jul 2;12(13):2954-7. doi: 10.1021/ol100959a. PubMed PMID: 20527780; PubMed Central PMCID: PMC2896498. 11: 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. 12: 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.