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MedKoo Cat#: 585051 | Name: Plenolin

Description:

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

Plenolin, from Helenium microcephalum, is an anti-tumor agent.

Chemical Structure

Plenolin
Plenolin
CAS#34257-95-9

Theoretical Analysis

MedKoo Cat#: 585051

Name: Plenolin

CAS#: 34257-95-9

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
Plenolin; Dihydrohelenalin; 11alpha,13-dihydrohelenalin; 11,13-Dihyrdrohelenalin
IUPAC/Chemical Name
(3S,3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-3,4a,8-trimethyl-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
InChi Key
ICKWITMQEROMDG-ZIXXKTFOSA-N
InChi Code
InChI=1S/C15H20O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7-10,12-13,17H,6H2,1-3H3/t7-,8+,9+,10-,12-,13+,15+/m1/s1
SMILES Code
C[C@@H]1C[C@]2([H])[C@@]([C@H](O)[C@@]3(C)[C@@]1([H])C=CC3=O)([H])[C@H](C)C(O2)=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 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: Staneva J, Denkova P, Todorova M, Evstatieva L. Quantitative analysis of sesquiterpene lactones in extract of Arnica montana L. by 1H NMR spectroscopy. J Pharm Biomed Anal. 2011 Jan 5;54(1):94-9. doi: 10.1016/j.jpba.2010.08.018. Epub 2010 Aug 21. PubMed PMID: 20837387. 2: Tekko IA, Bonner MC, Bowen RD, Williams AC. Permeation of bioactive constituents from Arnica montana preparations through human skin in-vitro. J Pharm Pharmacol. 2006 Sep;58(9):1167-76. PubMed PMID: 16945174. 3: Bilia AR, Bergonzi MC, Mazzi G, Vincieri FF. Development and stability of semisolid preparations based on a supercritical CO2 Arnica extract. J Pharm Biomed Anal. 2006 May 3;41(2):449-54. Epub 2006 Feb 2. PubMed PMID: 16457981. 4: Klaas CA, Wagner G, Laufer S, Sosa S, Della Loggia R, Bomme U, Pahl HL, Merfort I. Studies on the anti-inflammatory activity of phytopharmaceuticals prepared from Arnica flowers. Planta Med. 2002 May;68(5):385-91. PubMed PMID: 12058311. 5: Tornhamre S, Schmidt TJ, Näsman-Glaser B, Ericsson I, Lindgren JA. Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells. Biochem Pharmacol. 2001 Oct 1;62(7):903-11. PubMed PMID: 11543725. 6: García-Piñeres AJ, Castro V, Mora G, Schmidt TJ, Strunck E, Pahl HL, Merfort I. Cysteine 38 in p65/NF-kappaB plays a crucial role in DNA binding inhibition by sesquiterpene lactones. J Biol Chem. 2001 Oct 26;276(43):39713-20. Epub 2001 Aug 10. PubMed PMID: 11500489. 7: Schmidt TJ. Glutathione adducts of helenalin and 11 alpha,13-dihydrohelenalin acetate inhibit glutathione S-transferase from horse liver. Planta Med. 2000 Mar;66(2):106-9. PubMed PMID: 10763580. 8: Lyss G, Schmidt TJ, Merfort I, Pahl HL. Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB. Biol Chem. 1997 Sep;378(9):951-61. PubMed PMID: 9348104. 9: Schmidt TJ. Helenanolide-type sesquiterpene lactones--III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules. Bioorg Med Chem. 1997 Apr;5(4):645-53. PubMed PMID: 9158862. 10: Grippo AA, Wyrick SD, Lee KH, Shrewsbury RP, Hall IH. Disposition of an antineoplastic sesquiterpene lactone, [3H]-plenolin, in BDF1 mice. Planta Med. 1991 Aug;57(4):309-14. PubMed PMID: 1723209. 11: Wu JB, Chun YT, Ebizuka Y, Sankawa U. Biologically active constituents of Centipeda minima: isolation of a new plenolin ester and the antiallergy activity of sesquiterpene lactones. Chem Pharm Bull (Tokyo). 1985 Sep;33(9):4091-4. PubMed PMID: 2418993. 12: Imakura Y, Lee KH, Sims D, Wu RY, Hall IH, Furukawa H, Itoigawa M, Yonaha K. Antitumor agents XXXVI: Structural elucidation of sesquiterpene lactones microhelenins-A, B, and C, microlenin acetate, and plenolin from Helenium microcephalum. J Pharm Sci. 1980 Sep;69(9):1044-9. PubMed PMID: 7411405.