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MedKoo Cat#: 526407 | Name: Helenalin Acetate
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Description:

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

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.

Chemical Structure

Helenalin Acetate
Helenalin Acetate
CAS#10180-86-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 526407

Name: Helenalin Acetate

CAS#: 10180-86-6 (acetate)

Chemical Formula: C17H20O5

Exact Mass: 304.1311

Molecular Weight: 304.34

Elemental Analysis: C, 67.09; H, 6.62; O, 26.28

Price and Availability

Size Price Availability Quantity
1mg USD 850.00 2 Weeks
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Related CAS #
10180-86-6 (acetate) 6754-13-8 (free base) 68798-43-6 (methacrylate)
Synonym
Helenalin Acetate; 6-O-Acetylhelenalin; Angustibalin; NSC 166124; NSC166124; NSC-166124;
IUPAC/Chemical Name
(3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-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
CC(O[C@@H]1[C@]2([C@](C=CC2=O)([H])[C@@H](C[C@]3([H])[C@@]1([H])C(C(O3)=O)=C)C)C)=O
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 304.34 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: 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.