Helenalin
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MedKoo CAT#: 573413

CAS#: 6754-13-8

Description: 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

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Helenalin
CAS# 6754-13-8

Theoretical Analysis

MedKoo Cat#: 573413
Name: Helenalin
CAS#: 6754-13-8
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
1.0mg USD 595.0 2 Weeks
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Synonym: Helenalin, Helenalin A, HSDB 3490, PF 56

IUPAC/Chemical Name: Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone

InChi Key: ZVLOPMNVFLSSAA-XEPQRQSNSA-N

InChi Code: 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: C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2

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

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

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1: Widen JC, Kempema AM, Baur JW, Skopec HM, Edwards JT, Brown TJ, Brown DA, Meece FA, Harki DA. Helenalin Analogues Targeting NF-κB p65: Thiol Reactivity and Cellular Potency Studies of Varied Electrophiles. ChemMedChem. 2018 Feb 20;13(4):303-311. doi: 10.1002/cmdc.201700752. Epub 2018 Jan 19. PubMed PMID: 29349898; PubMed Central PMCID: PMC5894512.

2: Widen JC, Kempema AM, Villalta PW, Harki DA. Targeting NF-κB p65 with a Helenalin Inspired Bis-electrophile. ACS Chem Biol. 2017 Jan 20;12(1):102-113. doi: 10.1021/acschembio.6b00751. Epub 2016 Nov 28. PubMed PMID: 28103680; PubMed Central PMCID: PMC5357558.

3: Zwicker P, Schultze N, Niehs S, Albrecht D, Methling K, Wurster M, Wachlin G, Lalk M, Lindequist U, Haertel B. Differential effects of Helenalin, an anti-inflammatory sesquiterpene lactone, on the proteome, metabolome and the oxidative stress response in several immune cell types. Toxicol In Vitro. 2017 Apr;40:45-54. doi: 10.1016/j.tiv.2016.12.010. Epub 2016 Dec 18. PubMed PMID: 27998807.

4: Kordi S, Zarghami N, Akbarzadeh A, Rahmati YM, Ghasemali S, Barkhordari A, Tozihi M. A comparison of the inhibitory effect of nano-encapsulated helenalin and free helenalin on telomerase gene expression in the breast cancer cell line, by real-time PCR. Artif Cells Nanomed Biotechnol. 2016;44(2):695-703. doi: 10.3109/21691401.2014.981270. Epub 2014 Dec 1. PubMed PMID: 25435410.

5: Lin X, Zhang S, Huang R, Wei L, Tan S, Liang S, Tian Y, Wu X, Lu Z, Huang Q. Helenalin attenuates alcohol-induced hepatic fibrosis by enhancing ethanol metabolism, inhibiting oxidative stress and suppressing HSC activation. Fitoterapia. 2014 Jun;95:203-13. doi: 10.1016/j.fitote.2014.03.020. Epub 2014 Apr 2. PubMed PMID: 24704336.

6: Jang JH, Iqbal T, Min KJ, Kim S, Park JW, Son EI, Lee TJ, Kwon TK. Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma. Toxicol In Vitro. 2013 Mar;27(2):588-96. doi: 10.1016/j.tiv.2012.10.014. Epub 2012 Oct 30. PubMed PMID: 23123298.