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MedKoo Cat#: 585227 | Name: Trilobolide

Description:

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

Trilobolide is a natural counterpart of thapsigargin and an activator of cytokine secretion.

Chemical Structure

Trilobolide
Trilobolide
CAS#50657-07-3

Theoretical Analysis

MedKoo Cat#: 585227

Name: Trilobolide

CAS#: 50657-07-3

Chemical Formula: C27H38O10

Exact Mass: 522.2465

Molecular Weight: 522.59

Elemental Analysis: C, 62.06; H, 7.33; O, 30.61

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
Trilobolide; Silerin; Trilobolid
IUPAC/Chemical Name
2-Butenoic acid, 2-methyl-, 6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-4-(2-methyl-1-oxobutoxy)-2-oxoazuleno(4,5-b)furan-8-yl ester, (3S-(3alpha,3abeta,4alpha(R*),6beta,6abeta,8alpha(Z),9balpha))-
InChi Key
FIAZIVNRHQWTPY-FKPRSPSXSA-N
InChi Code
InChI=1S/C27H38O10/c1-9-13(3)22(29)34-18-11-17-20(15(18)5)21-27(33,26(8,32)24(31)36-21)19(35-23(30)14(4)10-2)12-25(17,7)37-16(6)28/h9,14,17-19,21,32-33H,10-12H2,1-8H3/b13-9-/t14?,17-,18+,19-,21-,25-,26+,27+/m1/s1
SMILES Code
C/C=C(C)\C(O[C@H](C(C)=C12)C[C@@]1([H])[C@](C)(OC(C)=O)C[C@@H](OC(C(C)CC)=O)[C@]([C@]3(O)C)(O)[C@]2([H])OC3=O)=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 522.59 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: Huml L, Jurášek M, Mikšátková P, Zimmermann T, Tomanová P, Buděšínský M, Rottnerová Z, Šimková M, Harmatha J, Kmoníčková E, Lapčík O, Drašar PB. Immunoassay for determination of trilobolide. Steroids. 2017 Jan;117:105-111. doi: 10.1016/j.steroids.2016.08.019. Epub 2016 Sep 4. PubMed PMID: 27600788. 2: Škorpilová L, Rimpelová S, Jurášek M, Buděšínský M, Lokajová J, Effenberg R, Slepička P, Ruml T, Kmoníčková E, Drašar PB, Wimmer Z. BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide. Beilstein J Org Chem. 2017 Jul 4;13:1316-1324. doi: 10.3762/bjoc.13.128. eCollection 2017. PubMed PMID: 28781697; PubMed Central PMCID: PMC5530629. 3: Jurášek M, Džubák P, Rimpelová S, Sedlák D, Konečný P, Frydrych I, Gurská S, Hajdúch M, Bogdanová K, Kolář M, Müller T, Kmoníčková E, Ruml T, Harmatha J, Drašar PB. Trilobolide-steroid hybrids: Synthesis, cytotoxic and antimycobacterial activity. Steroids. 2017 Jan;117:97-104. doi: 10.1016/j.steroids.2016.08.011. Epub 2016 Aug 17. PubMed PMID: 27543674. 4: Tomanová P, Rimpelová S, Jurášek M, Buděšínský M, Vejvodová L, Ruml T, Kmoníčková E, Drašar PB. Trilobolide-porphyrin conjugates: on synthesis and biological effects evaluation. Steroids. 2015 May;97:8-12. doi: 10.1016/j.steroids.2014.08.024. Epub 2014 Sep 6. PubMed PMID: 25204594. 5: Harmatha J, Buděšínský M, Vokáč K, Kostecká P, Kmoníčková E, Zídek Z. Trilobolide and related sesquiterpene lactones from Laser trilobum possessing immunobiological properties. Fitoterapia. 2013 Sep;89:157-66. doi: 10.1016/j.fitote.2013.05.025. Epub 2013 Jun 5. PubMed PMID: 23747321. 6: Jurášek M, Rimpelová S, Kmoníčková E, Drašar P, Ruml T. Tailor-made fluorescent trilobolide to study its biological relevance. J Med Chem. 2014 Oct 9;57(19):7947-54. doi: 10.1021/jm500690j. Epub 2014 Sep 17. PubMed PMID: 25197766. 7: Harmatha J, Vokáč K, Buděšínský M, Zídek Z, Kmoníčková E. Immunobiological properties of sesquiterpene lactones obtained by chemically transformed structural modifications of trilobolide. Fitoterapia. 2015 Dec;107:90-99. doi: 10.1016/j.fitote.2015.10.002. Epub 2015 Oct 22. PubMed PMID: 26474674. 8: Wictome M, Holub M, East JM, Lee AG. The importance of the hydroxyl moieties for inhibition of the Ca(2+)-ATPase by trilobolide and 2,5-di(tert-butyl)-1,4-benzohydroquinone. Biochem Biophys Res Commun. 1994 Mar 15;199(2):916-21. PubMed PMID: 8135840. 9: Kmoníčková E, Harmatha J, Vokáč K, Kostecká P, Farghali H, Zídek Z. Sesquiterpene lactone trilobolide activates production of interferon-γ and nitric oxide. Fitoterapia. 2010 Dec;81(8):1213-9. doi: 10.1016/j.fitote.2010.08.005. Epub 2010 Aug 19. PubMed PMID: 20727953. 10: Harmatha J, Buděšínský M, Jurášek M, Zimmermann T, Drašar P, Zídek Z, Kmoníčková E, Vejvodová L. Structural modification of trilobolide for upgrading its immunobiological properties and reducing its cytotoxic action. Fitoterapia. 2019 Apr;134:88-95. doi: 10.1016/j.fitote.2019.02.002. Epub 2019 Feb 4. PubMed PMID: 30731148. 11: Oliver SF, Högenauer K, Simic O, Antonello A, Smith MD, Ley SV. A route to the thapsigargins from (S)-carvone providing a substrate-controlled total synthesis of trilobolide, nortrilobolide, and thapsivillosin F. Angew Chem Int Ed Engl. 2003 Dec 15;42(48):5996-6000. PubMed PMID: 14679553. 12: Rimpelová S, Jurášek M, Peterková L, Bejček J, Spiwok V, Majdl M, Jirásko M, Buděšínský M, Harmatha J, Kmoníčková E, Drašar P, Ruml T. Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica. Beilstein J Org Chem. 2019 Aug 13;15:1933-1944. doi: 10.3762/bjoc.15.189. eCollection 2019. PubMed PMID: 31501660; PubMed Central PMCID: PMC6720059. 13: Huang X, Ou S, Tang S, Fu L, Wu J. Simultaneous determination of trilobolide-6-O-isobutyrates A and B in Wedelia trilobata by gas chromatography. Se Pu. 2006 Sep;24(5):499-502. PubMed PMID: 17165548. 14: Wictome M, Khan YM, East JM, Lee AG. Binding of sesquiterpene lactone inhibitors to the Ca(2+)-ATPase. Biochem J. 1995 Sep 15;310 ( Pt 3):859-68. PubMed PMID: 7575419; PubMed Central PMCID: PMC1135975. 15: Rasmussen U, Christensen SB, Sandberg F. Phytochemistry of the genus Thapsia. Planta Med. 1981 Dec;43(4):336-41. PubMed PMID: 17402057. 16: Søhoel H, Jensen AM, Møller JV, Nissen P, Denmeade SR, Isaacs JT, Olsen CE, Christensen SB. Natural products as starting materials for development of second-generation SERCA inhibitors targeted towards prostate cancer cells. Bioorg Med Chem. 2006 Apr 15;14(8):2810-5. Epub 2006 Jan 10. PubMed PMID: 16412648. 17: Andrews SP, Ball M, Wierschem F, Cleator E, Oliver S, Högenauer K, Simic O, Antonello A, Hünger U, Smith MD, Ley SV. Total synthesis of five thapsigargins: guaianolide natural products exhibiting sub-nanomolar SERCA inhibition. Chemistry. 2007;13(20):5688-712. 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