Helenalin Acetate

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

MedKoo CAT#: 526407

CAS#: 10180-86-6

Description: Helenalin Acetate is an anti-inflammatory and anti-cancer agent, disrupting the cooperation of CCAAT-box/enhancer-binding protein beta (C/EBPß) and co-activator p300.


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Helenalin Acetate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526407
Name: Helenalin Acetate
CAS#: 10180-86-6
Chemical Formula: C17H20O5
Exact Mass: 304.1311
Molecular Weight: 304.342
Elemental Analysis: C, 67.09; H, 6.62; O, 26.28


Synonym: Helenalin Acetate

IUPAC/Chemical Name: [(3aR,5R,5aR,8aR,9S,9aR)-5,8a-Dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate

InChi Key: DCNRYQODUSSOKC-HKHYKUHTSA-N

InChi Code: InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12-,14-,15+,17+/m1/s1

SMILES Code: C[C@H]1[C@H](C=CC2=O)[C@]2(C)[C@@H](OC(C)=O)[C@H](C3=C)[C@H](OC3=O)C1


Technical Data

Appearance:
Solid powder

Purity:
>95% (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:
>2 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).

Harmonized System Code:
293490


References

1: Wulsten IF, Costa-Silva TA, Mesquita JT, Lima ML, Galuppo MK, Taniwaki NN, Borborema SET, Da Costa FB, Schmidt TJ, Tempone AG. Investigation of the Anti-Leishmania (Leishmania) infantum Activity of Some Natural Sesquiterpene Lactones. Molecules. 2017 Apr 25;22(5). pii: E685. doi: 10.3390/molecules22050685. PubMed PMID: 28441357.

2: Jakobs A, Steinmann S, Henrich SM, Schmidt TJ, Klempnauer KH. Helenalin Acetate, a Natural Sesquiterpene Lactone with Anti-inflammatory and Anti-cancer Activity, Disrupts the Cooperation of CCAAT Box/Enhancer-binding Protein β (C/EBPβ) and Co-activator p300. J Biol Chem. 2016 Dec 9;291(50):26098-26108. Epub 2016 Nov 1. PubMed PMID: 27803164; PubMed Central PMCID: PMC5207079.

3: Schomburg C, Schuehly W, Da Costa FB, Klempnauer KH, Schmidt TJ. Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships. Eur J Med Chem. 2013 May;63:313-20. doi: 10.1016/j.ejmech.2013.02.018. Epub 2013 Feb 26. PubMed PMID: 23501116.

4: Ramanandraibe V, Martin MT, Rakotondramanana DL, Mambu L, Ramanitrahasimbola D, Labaïed M, Grellier P, Rasoanaivo P, Frappier F. Pseudoguanolide sesquiterpene lactones from Vernoniopsis caudata and their in vitro antiplasmodial activities. J Nat Prod. 2005 May;68(5):800-3. PubMed PMID: 15921436.

5: Wagner S, Suter A, Merfort I. Skin penetration studies of Arnica preparations and of their sesquiterpene lactones. Planta Med. 2004 Oct;70(10):897-903. PubMed PMID: 15490315.

6: Wagner S, Kratz F, Merfort I. In vitro behaviour of sesquiterpene lactones and sesquiterpene lactone-containing plant preparations in human blood, plasma and human serum albumin solutions. Planta Med. 2004 Mar;70(3):227-33. PubMed PMID: 15114499.

7: Gertsch J, Sticher O, Schmidt T, Heilmann J. Influence of helenanolide-type sesquiterpene lactones on gene transcription profiles in Jurkat T cells and human peripheral blood cells: anti-inflammatory and cytotoxic effects. Biochem Pharmacol. 2003 Dec 1;66(11):2141-53. PubMed PMID: 14609739.

8: Schmidt TJ, Brun R, Willuhn G, Khalid SA. Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones. Planta Med. 2002 Aug;68(8):750-1. PubMed PMID: 12221603.

9: 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.

10: Heilmann J, Wasescha MR, Schmidt TJ. The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells. Bioorg Med Chem. 2001 Aug;9(8):2189-94. PubMed PMID: 11504656.

11: 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.

12: Beekman AC, Woerdenbag HJ, van Uden W, Pras N, Konings AW, Wikström HV, Schmidt TJ. Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones. J Nat Prod. 1997 Mar;60(3):252-7. PubMed PMID: 9090867.

13: Malarz J, Stojakowska A, Dohnal B, Kisiel W. Helenalin Acetate in in vitro Propagated Plants of Arnica montana. Planta Med. 1993 Feb;59(1):51-3. PubMed PMID: 17230337.

14: Hausen BM. [Arnica allergy]. Hautarzt. 1980 Jan;31(1):10-7. Review. German. PubMed PMID: 6993423.

15: Hausen BM, Herrmann HD, Willuhn G. The sensitizing capacity of Compositae plants. I. Occupational contact dermatitis from Arnica longifolia Eaton. Contact Dermatitis. 1978 Feb;4(1):3-10. PubMed PMID: 148995.

16: Lee KH, Kim SH, Furukawa H, Piantadosi C. Antitumor agents. 11. Synthesis and cytotoxic activity of epoxides of helenalin related derivatives. J Med Chem. 1975 Jan;18(1):59-63. PubMed PMID: 1109577.