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MedKoo Cat#: 573413 | Name: Helenalin
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Description:

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

Helenalin is a sesquiterpene lactone with anti-inflammatory effects. Helenalin inhibits gene expression mediated by NF-κB and can modify sulfhydryl groups of cysteine residues. It also suppresses the proliferation of cancer cells through the prevention of signaling through NF-κB.

Chemical Structure

Helenalin
Helenalin
CAS#6754-13-8 (free base)

Theoretical Analysis

MedKoo Cat#: 573413

Name: Helenalin

CAS#: 6754-13-8 (free base)

Chemical Formula: C15H18O4

Exact Mass: 262.1205

Molecular Weight: 262.31

Elemental Analysis: C, 68.69; H, 6.92; O, 24.40

Price and Availability

Size Price Availability Quantity
1mg USD 750.00 2 Weeks
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Related CAS #
10180-86-6 (acetate) 6754-13-8 (free base) 68798-43-6 (methacrylate)
Synonym
Helenalin; Helenalin A; (-)-Helenalin; PF 56; PF56; PF-56; NSC 85236; NSC 85236; NSC 85236
IUPAC/Chemical Name
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
InChi Key
ZVLOPMNVFLSSAA-XEPQRQSNSA-N
InChi Code
InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
SMILES Code
O[C@H]1[C@@]2(C(C(O[C@]2([H])C[C@@H](C)[C@@]([C@]13C)(C=CC3=O)[H])=O)=C)[H]
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 262.31 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: Li Y, Zeng Y, Huang Q, Wen S, Wei Y, Chen Y, Zhang X, Bai F, Lu Z, Wei J, Lin X. Retraction notice to "Helenalin from Centipeda minima ameliorates acute hepatic injury by protecting mitochondria function, activating Nrf2 pathway and inhibiting NF-κB activation" [Biomed. Pharmacother. 119 (2019) 109435]. Biomed Pharmacother. 2024 Dec;181:117697. doi: 10.1016/j.biopha.2024.117697. Epub 2024 Dec 9. PMID: 39658430. 2: Lin X, Zhang S, Huang R, Wei L, Tan S, Liang S, Tian Y, Wu X, Lu Z, Huang Q. Retraction notice to "Helenalin attenuates alcohol-induced hepatic fibrosis by enhancing ethanol metabolism, inhibiting oxidative stress and suppressing HSC activation" [Fitoterapia 95 (2014) 203-213]. Fitoterapia. 2024 Oct;178:106195. doi: 10.1016/j.fitote.2024.106195. Epub 2024 Aug 31. PMID: 39217083. 3: Deng Y, Shen L, Zhu H, Zhou Y, Hu X. Network pharmacology analysis of the Huangqi-Gancao herb pair reveals quercetin as a therapeutics for allergic rhinitis via the RELA-regulated IFNG/IRF1 axis response. Naunyn Schmiedebergs Arch Pharmacol. 2025 Feb;398(2):1597-1612. doi: 10.1007/s00210-024-03353-8. Epub 2024 Aug 12. PMID: 39133272; PMCID: PMC11825621. 4: Petrova M, Miladinova-Georgieva K, Geneva M. Influence of Abiotic and Biotic Elicitors on Organogenesis, Biomass Accumulation, and Production of Key Secondary Metabolites in Asteraceae Plants. Int J Mol Sci. 2024 Apr 10;25(8):4197. doi: 10.3390/ijms25084197. PMID: 38673783; PMCID: PMC11050642. 5: Ng D, Altamirano-Vallejo JC, Navarro-Partida J, Sanchez-Aguilar OE, Inzunza A, Valdez-Garcia JE, Gonzalez-de-la-Rosa A, Bustamante-Arias A, Armendariz- Borunda J, Santos A. Enhancing Ocular Surface in Dry Eye Disease Patients: A Clinical Evaluation of a Topical Formulation Containing Sesquiterpene Lactone Helenalin. Pharmaceuticals (Basel). 2024 Jan 30;17(2):175. doi: 10.3390/ph17020175. PMID: 38399390; PMCID: PMC10892869. 6: Schmidt TJ. Arnica montana L.: Doesn't Origin Matter? Plants (Basel). 2023 Oct 11;12(20):3532. doi: 10.3390/plants12203532. PMID: 37895999; PMCID: PMC10609804. 7: Parafiniuk A, Kromer K, Fleszar MG, Kreitschitz A, Wiśniewski J, Gamian A. Localization of Sesquiterpene Lactones Biosynthesis in Flowers of Arnica Taxa. Molecules. 2023 May 27;28(11):4379. doi: 10.3390/molecules28114379. PMID: 37298857; PMCID: PMC10254538. 8: Barkhordari A, Jafari-Gharabaghlou D, Turk Z, Zarghami N. Potential Anti- Cancer Effect of Helenalin as a Natural Bioactive Compound on the Growth and Telomerase Gene Expression in Breast Cancer Cell Line. Asian Pac J Cancer Prev. 2023 Jan 1;24(1):133-140. doi: 10.31557/APJCP.2023.24.1.133. PMID: 36708561; PMCID: PMC10152844. 9: Jürgens FM, Robledo SM, Schmidt TJ. Evaluation of Pharmacokinetic and Toxicological Parameters of Arnica Tincture after Dermal Application In Vivo. Pharmaceutics. 2022 Nov 4;14(11):2379. doi: 10.3390/pharmaceutics14112379. PMID: 36365196; PMCID: PMC9695956. 10: Luo Y, Ge P, Wen H, Zhang Y, Liu J, Dong X, Lan B, Zhang G, Yang Q, Chen H. C/EBPβ Promotes LPS-Induced IL-1β Transcription and Secretion in Alveolar Macrophages via NOD2 Signaling. J Inflamm Res. 2022 Sep 11;15:5247-5263. doi: 10.2147/JIR.S377499. PMID: 36120185; PMCID: PMC9477153. 11: Yang CM, Yang CC, Hsu WH, Hsiao LD, Tseng HC, Shih YF. Tumor Necrosis Factor-α-Induced C-C Motif Chemokine Ligand 20 Expression through TNF Receptor 1-Dependent Activation of EGFR/p38 MAPK and JNK1/2/FoxO1 or the NF-κB Pathway in Human Cardiac Fibroblasts. Int J Mol Sci. 2022 Aug 13;23(16):9086. doi: 10.3390/ijms23169086. PMID: 36012347; PMCID: PMC9409325. 12: Yang CC, Hsiao LD, Shih YF, Hsu CK, Hu CY, Yang CM. Thrombin Induces COX-2 and PGE2 Expression via PAR1/PKCalpha/MAPK-Dependent NF-kappaB Activation in Human Tracheal Smooth Muscle Cells. Mediators Inflamm. 2022 Apr 19;2022:4600029. doi: 10.1155/2022/4600029. PMID: 35497094; PMCID: PMC9042634. 13: Jürgens FM, Herrmann FC, Robledo SM, Schmidt TJ. Dermal Absorption of Sesquiterpene Lactones from Arnica Tincture. Pharmaceutics. 2022 Mar 29;14(4):742. doi: 10.3390/pharmaceutics14040742. PMID: 35456576; PMCID: PMC9027632. 14: Greinwald A, Hartmann M, Heilmann J, Heinrich M, Luick R, Reif A. Soil and Vegetation Drive Sesquiterpene Lactone Content and Profile in Arnica montana L. Flower Heads From Apuseni-Mountains, Romania. Front Plant Sci. 2022 Jan 28;13:813939. doi: 10.3389/fpls.2022.813939. PMID: 35154225; PMCID: PMC8832060. 15: Xiong Y, Wen S, Li Y, Wei Y, Fang B, Li C, Huang Q, Lin X. Comprehensive analysis of transcriptomics and metabolomics to illustrate the underlying mechanism of helenalin against hepatic fibrosis. Eur J Pharmacol. 2022 Mar 15;919:174770. doi: 10.1016/j.ejphar.2022.174770. Epub 2022 Feb 2. PMID: 35120860. 16: Abdel Ghani L, Yusenko MV, Frank D, Moorthy R, Widen JC, Dörner W, Khandanpour C, Harki DA, Klempnauer KH. A synthetic covalent ligand of the C/EBPβ transactivation domain inhibits acute myeloid leukemia cells. Cancer Lett. 2022 Apr 1;530:170-180. doi: 10.1016/j.canlet.2022.01.024. Epub 2022 Jan 22. PMID: 35077804. 17: Jürgens FM, Behrens M, Humpf HU, Robledo SM, Schmidt TJ. In Vitro Metabolism of Helenalin Acetate and 11α,13-Dihydrohelenalin Acetate: Natural Sesquiterpene Lactones from Arnica. Metabolites. 2022 Jan 17;12(1):88. doi: 10.3390/metabo12010088. PMID: 35050210; PMCID: PMC8780470. 18: Sánchez Alberti A, Beer MF, Cerny N, Bivona AE, Fabian L, Morales C, Moglioni A, Malchiodi EL, Donadel OJ, Sülsen VP. In Vitro, In Vivo, and In Silico Studies of Cumanin Diacetate as a Potential Drug against Trypanosoma cruzi Infection. ACS Omega. 2021 Dec 20;7(1):968-978. doi: 10.1021/acsomega.1c05560. PMID: 35036760; PMCID: PMC8757452. 19: Klempnauer KH. C/EBPβ sustains the oncogenic program of AML cells by cooperating with MYB and co-activator p300 in a transcriptional module. Exp Hematol. 2022 Apr;108:8-15. doi: 10.1016/j.exphem.2022.01.003. Epub 2022 Jan 13. PMID: 35032593. 20: Šadibolová M, Juvonen RO, Auriola S, Boušová I. In vitro metabolism of helenalin and its inhibitory effect on human cytochrome P450 activity. Arch Toxicol. 2022 Mar;96(3):793-808. doi: 10.1007/s00204-021-03218-6. Epub 2022 Jan 6. PMID: 34989853.

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