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MedKoo Cat#: 461728 | Name: Salonitenolide

Description:

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

Salonitenolide is a germacranolide isolated from from Aegialophila pumila Jus. Boiss.

Chemical Structure

Salonitenolide
Salonitenolide
CAS#26931-94-2

Theoretical Analysis

MedKoo Cat#: 461728

Name: Salonitenolide

CAS#: 26931-94-2

Chemical Formula: C15H20O4

Exact Mass: 264.1362

Molecular Weight: 264.32

Elemental Analysis: C, 68.16; H, 7.63; O, 24.21

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
Salonitenolide;
IUPAC/Chemical Name
(3aR,4S,6E,10Z,11aR)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
InChi Key
BLDTUWFMPJJRPR-PNQYDXICSA-N
InChi Code
InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13+,14+/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@@]2([H])[C@@H](O)C/C(C)=C/CC/C(CO)=C/1)C2=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 264.32 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: Rosselli S, Maggio AM, Raccuglia RA, Morris-Natschke SL, Bastow KF, Lee KH, Bruno M. Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide. Nat Prod Commun. 2010 May;5(5):675-80. PubMed PMID: 20521529. 2: Trendafilova A, Jadranin M, Gorgorov R, Stanilova M. Bioactive Compounds in Wild, In vitro Obtained, Ex vitro Adapted, and Acclimated Plants of Centaurea davidovii (Asteraceae). Nat Prod Commun. 2015 Jun;10(6):839-41. PubMed PMID: 26197494. 3: Esposito A, Malafronte N, Sanogo R, D'Ambola M, Severino L. Sesquiterpene Lactones from Vernonia nigritiana. Nat Prod Commun. 2016 May;11(5):583-4. PubMed PMID: 27319122. 4: Milošević Ifantis T, Solujić S, Pavlović-Muratspahić D, Skaltsa H. Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance. Phytochemistry. 2013 Oct;94:159-70. doi: 10.1016/j.phytochem.2013.05.014. Epub 2013 Jul 1. PubMed PMID: 23827325. 5: Vanhaelen-Fastré R, Vanhaelen M. [Presence of salonitenolide in Cnicus benedictus (author's transl)]. Planta Med. 1974 Dec;26(4):375-9. French. PubMed PMID: 4465820. 6: El-Masry S, Vuilhorgne M, Evans FJ. Sesquiterpene Lactones from Aegialophila pumila. Planta Med. 1984 Feb;50(1):115. PubMed PMID: 17340274. 7: Bruno M, Rosselli S, Maggio A, Raccuglia RA, Napolitano F, Senatore F. Antibacterial evaluation of cnicin and some natural and semisynthetic analogues. Planta Med. 2003 Mar;69(3):277-81. PubMed PMID: 12677537. 8: Barrero AF, Oltra JE, Raslan DS, Saude DA. Microbial transformation of sesquiterpene lactones by the fungi cunninghamella echinulata and rhizopus oryzae . J Nat Prod. 1999 May;62(5):726-9. PubMed PMID: 10346955. 9: Zidorn C, Ellmerer-Müller EP, Dobner MJ, Stuppner H. A highly substituted germacranolide from Leontodon cichoraceus. Z Naturforsch C. 2001 Sep-Oct;56(9-10):904-8. PubMed PMID: 11724404. 10: Barrero AF, Oltra JE, Alvarez M, Raslan DS, Saúde DA, Akssira M. New sources and antifungal activity of sesquiterpene lactones. Fitoterapia. 2000 Feb;71(1):60-4. PubMed PMID: 11449472. 11: Huneck S, Jakupovic J, Schuster A. [Further Compounds from Centaurea stoebe.]. Planta Med. 1986 Oct;(5):398-9. German. PubMed PMID: 17345351. 12: Saroglou V, Karioti A, Demetzos C, Dimas K, Skaltsa H. Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. J Nat Prod. 2005 Sep;68(9):1404-7. Erratum in: J Nat Prod. 2011 Sep 23;74(9):2029. PubMed PMID: 16180824. 13: Álvarez-Calero JM, Ruiz E, López-Pérez JL, Jaraíz M, Rubio JE, Jorge ZD, Suárez M, Massanet GM. 15-Hydroxygermacranolides as Sources of Structural Diversity: Synthesis of Sesquiterpene Lactones by Cyclization and Rearrangement Reactions. Experimental and DFT Study. J Org Chem. 2018 May 18;83(10):5480-5495. doi: 10.1021/acs.joc.8b00407. Epub 2018 May 3. PubMed PMID: 29694044.