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MedKoo Cat#: 461592 | Name: Ryanodol

Description:

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

Ryanodol is a complex diterpenoid that modulates intracellular calcium-ion release at ryanodine receptors, ion channels critical for skeletal and cardiac muscle excitation-contraction coupling and synaptic transmission.

Chemical Structure

Ryanodol
Ryanodol
CAS#6688-49-9

Theoretical Analysis

MedKoo Cat#: 461592

Name: Ryanodol

CAS#: 6688-49-9

Chemical Formula: C20H32O8

Exact Mass: 400.2097

Molecular Weight: 400.46

Elemental Analysis: C, 59.98; H, 8.05; O, 31.96

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
Ryanodol;
IUPAC/Chemical Name
(1S,2R,2aS,2a1R,3S,3aS,6S,7R,7aR,9S,9aS)-1-isopropyl-3,6,9a-trimethylhexahydro-3,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-1,2,2a,2a1,3a,7,9(2H,3H)-heptaol
InChi Key
POSDEVOSMOCDHR-BPHXWNOMSA-N
InChi Code
InChI=1S/C20H32O8/c1-9(2)17(25)12(22)18(26)13(4)8-16(24)14(17,5)20(18,27)19(28-16)11(21)10(3)6-7-15(13,19)23/h9-12,21-27H,6-8H2,1-5H3/t10-,11+,12+,13-,14-,15-,16-,17+,18+,19+,20+/m0/s1
SMILES Code
CC([C@]1([C@H]([C@]2([C@]3(C[C@@]4(O[C@]5([C@]2([C@]14C)O)[C@@H]([C@H](CC[C@]35O)C)O)O)C)O)O)O)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 400.46 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: Chuang KV, Xu C, Reisman SE. A 15-step synthesis of (+)-ryanodol. Science. 2016 Aug 26;353(6302):912-5. doi: 10.1126/science.aag1028. PubMed PMID: 27563092; PubMed Central PMCID: PMC5505075. 2: Nagatomo M, Koshimizu M, Masuda K, Tabuchi T, Urabe D, Inoue M. Total synthesis of ryanodol. J Am Chem Soc. 2014 Apr 23;136(16):5916-9. doi: 10.1021/ja502770n. Epub 2014 Apr 11. PubMed PMID: 24708178. 3: Masuda K, Nagatomo M, Inoue M. Chemical Conversion of Ryanodol to Ryanodine. Chem Pharm Bull (Tokyo). 2016 Jul 1;64(7):874-9. doi: 10.1248/cpb.c16-00214. Epub 2016 Mar 23. PubMed PMID: 27010543. 4: Masuda K, Koshimizu M, Nagatomo M, Inoue M. Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine. Chemistry. 2016 Jan 4;22(1):230-6. doi: 10.1002/chem.201503641. Epub 2015 Nov 30. PubMed PMID: 26616265. 5: Koshimizu M, Nagatomo M, Inoue M. Unified Total Synthesis of 3-epi-Ryanodol, Cinnzeylanol, Cinncassiols A and B, and Structural Revision of Natural Ryanodol and Cinnacasol. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2493-7. doi: 10.1002/anie.201511116. Epub 2016 Jan 14. PubMed PMID: 26766239. 6: Ramos-Franco J, Gomez AM, Nani A, Liu Y, Copello JA, Fill M. Ryanodol action on calcium sparks in ventricular myocytes. Pflugers Arch. 2010 Sep;460(4):767-76. doi: 10.1007/s00424-010-0839-8. Epub 2010 Apr 24. PubMed PMID: 20419313; PubMed Central PMCID: PMC3315696. 7: Porta M, Diaz-Sylvester PL, Nani A, Ramos-Franco J, Copello JA. Ryanoids and imperatoxin affect the modulation of cardiac ryanodine receptors by dihydropyridine receptor Peptide A. Biochim Biophys Acta. 2008 Nov;1778(11):2469-79. doi: 10.1016/j.bbamem.2008.07.024. Epub 2008 Aug 3. PubMed PMID: 18722342; PubMed Central PMCID: PMC2738596. 8: Hui CS, Besch HR Jr, Bidasee KR. Effects of ryanoids on spontaneous and depolarization-evoked calcium release events in frog muscle. Biophys J. 2004 Jul;87(1):243-55. PubMed PMID: 15240461; PubMed Central PMCID: PMC1304347. 9: VALENTA Z, WIESNER K, BABIN DR, BOGRI T, FORREST TP, FRIED F, REINSHAGEN H. On the structure of ryanodol. Experientia. 1962 Mar 15;18:111-3. PubMed PMID: 13924329. 10: Sigalas C, Mayo-Martin MB, Jane DE, Sitsapesan R. Ca2+-calmodulin increases RyR2 open probability yet reduces ryanoid association with RyR2. Biophys J. 2009 Oct 7;97(7):1907-16. doi: 10.1016/j.bpj.2009.07.027. PubMed PMID: 19804721; PubMed Central PMCID: PMC2756350. 11: Bidasee KR, Besch HR Jr. Structure-function relationships among ryanodine derivatives. Pyridyl ryanodine definitively separates activation potency from high affinity. J Biol Chem. 1998 May 15;273(20):12176-86. PubMed PMID: 9575165. 12: Tanna B, Welch W, Ruest L, Sutko JL, Williams AJ. The interaction of a neutral ryanoid with the ryanodine receptor channel provides insights into the mechanisms by which ryanoid binding is modulated by voltage. J Gen Physiol. 2000 Jul 1;116(1):1-9. PubMed PMID: 10871634; PubMed Central PMCID: PMC2229611. 13: González-Coloma A, Gutiérrez C, Hübner H, Achenbach H, Terrero D, Fraga BM. Selective insect antifeedant and toxic action of ryanoid diterpenes. J Agric Food Chem. 1999 Oct;47(10):4419-24. PubMed PMID: 10552828. 14: Tinker A, Sutko JL, Ruest L, Deslongchamps P, Welch W, Airey JA, Gerzon K, Bidasee KR, Besch HR Jr, Williams AJ. Electrophysiological effects of ryanodine derivatives on the sheep cardiac sarcoplasmic reticulum calcium-release channel. Biophys J. 1996 May;70(5):2110-9. PubMed PMID: 9172735; PubMed Central PMCID: PMC1225186. 15: Xu C, Han A, Reisman SE. An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol. Org Lett. 2018 Jul 6;20(13):3793-3796. doi: 10.1021/acs.orglett.8b01387. Epub 2018 Jun 13. PubMed PMID: 29897247. 16: Welch W, Sutko JL, Mitchell KE, Airey J, Ruest L. The pyrrole locus is the major orienting factor in ryanodine binding. Biochemistry. 1996 Jun 4;35(22):7165-73. PubMed PMID: 8679544. 17: Waterhouse AL, Pessah IN, Francini AO, Casida JE. Structural aspects of ryanodine action and selectivity. J Med Chem. 1987 Apr;30(4):710-6. PubMed PMID: 2435905. 18: Gonzalez-Coloma A, Hernandez MG, Perales A, Fraga BM. Chemical ecology of canarian laurel forest: Toxic diterpenes fromPersea indica (Lauraceae). J Chem Ecol. 1990 Sep;16(9):2723-33. doi: 10.1007/BF00988081. PubMed PMID: 24264325. 19: Fernández-Velasco M, Ruiz-Hurtado G, Rueda A, Neco P, Mercado-Morales M, Delgado C, Napolitano C, Priori SG, Richard S, Gómez AM, Benitah JP. RyRCa2+ leak limits cardiac Ca2+ window current overcoming the tonic effect of calmodulinin mice. PLoS One. 2011;6(6):e20863. doi: 10.1371/journal.pone.0020863. Epub 2011 Jun 6. PubMed PMID: 21673970; PubMed Central PMCID: PMC3108979. 20: Tanna B, Welch W, Ruest L, Sutko JL, Williams AJ. Ryanoid modification of the cardiac muscle ryanodine receptor channel results in relocation of the tetraethylammonium binding site. J Gen Physiol. 2001 May;117(5):385-94. PubMed PMID: 11331348; PubMed Central PMCID: PMC2233661.

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