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MedKoo Cat#: 146124 | Name: Helveticoside

Description:

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

Helveticoside is a natural glycoside found in plants such as Helvetia species, known for its potential pharmacological properties, including anti-inflammatory and antioxidant effects. It has been studied for its ability to alleviate symptoms associated with oxidative stress and inflammatory diseases. Helveticoside works by modulating the activity of enzymes involved in oxidative pathways and reducing the production of pro-inflammatory cytokines.

Chemical Structure

Helveticoside
Helveticoside
CAS#630-64-8

Theoretical Analysis

MedKoo Cat#: 146124

Name: Helveticoside

CAS#: 630-64-8

Chemical Formula: C15H26O2

Exact Mass: 238.1933

Molecular Weight: 238.37

Elemental Analysis: C, 75.58; H, 10.99; O, 13.42

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
Helveticoside; Erysimin;
IUPAC/Chemical Name
(3R,3aS,6S,7S,8aR)-3-isopropyl-6,8a-dimethyloctahydro-1H-3a,6-epoxyazulen-7-ol
InChi Key
QBILRDAMJUPXCX-AGAUEGNUSA-N
InChi Code
1S/C29H42O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h11,15-16,18-22,24-25,31,33-35H,3-10,12-14H2,1-2H3/t16-,18+,19-,20+,21-,22+,24+,25-,26-,27+,28+,29+/m1/s1
SMILES Code
[H][C@@]1(C[C@H](O)[C@H](O)[C@@H](C)O1)O[C@H]2CC[C@]3(C=O)[C@@]4([H])CC[C@]5(C)[C@H](CC[C@]5(O)[C@]4([H])CC[C@]3(O)C2)C6=CC(=O)OC6
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 238.37 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: An N, Sun Y, Ma L, Shi S, Zheng X, Feng W, Shan Z, Han Y, Zhao L, Wu H. Helveticoside Exhibited p53-dependent Anticancer Activity Against Colorectal Cancer. Arch Med Res. 2020 Apr;51(3):224-232. doi: 10.1016/j.arcmed.2020.02.007. Epub 2020 Mar 6. PMID: 32147288. 2: Wen W, Wu P, Zhang Y, Chen Z, Sun J, Chen H. Comprehensive Analysis of NAFLD and the Therapeutic Target Identified. Front Cell Dev Biol. 2021 Sep 20;9:704704. doi: 10.3389/fcell.2021.704704. PMID: 34616724; PMCID: PMC8488166. 3: Kim BY, Lee J, Kim NS. Helveticoside is a biologically active component of the seed extract of Descurainia sophia and induces reciprocal gene regulation in A549 human lung cancer cells. BMC Genomics. 2015 Sep 18;16(1):713. doi: 10.1186/s12864-015-1918-1. PMID: 26384484; PMCID: PMC4575430. 4: Grosa G, Allegrone G, Del Grosso E. LC-ESI-MS/MS characterization of strophanthin-K. J Pharm Biomed Anal. 2005 Jun 1;38(1):79-86. doi: 10.1016/j.jpba.2004.12.008. Epub 2005 Jan 19. PMID: 15907623. 5: Bao H, Wang J, Zhou D, Han Z, Su L, Zhang Y, Ye X, Xu C, Wang Y, Li Q. Protein-protein interaction network analysis in chronic obstructive pulmonary disease. Lung. 2014 Feb;192(1):87-93. doi: 10.1007/s00408-013-9509-x. Epub 2013 Nov 17. Retraction in: Lung. 2015 Oct;193(5):869. doi: 10.1007/s00408-015-9786-7. PMID: 24241792. 6: Wu Y, Wu Z, Jin Q, Liu J, Xu P. Identification and Analysis of Biomarkers Associated with Lipophagy and Therapeutic Agents for COVID-19. Viruses. 2024 Jun 7;16(6):923. doi: 10.3390/v16060923. PMID: 38932215; PMCID: PMC11209609. 7: Schaumann W, Wegerle R. Verbesserung der Resorption von Helveticosid und Helveticosol durch Substitution der Hydroxylwasserstoffe an der Digitoxose [Improvement in the absorption of helveticoside and helveticosol by substitution of the hydroxyl hydrogen on digitoxose]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1969;262(1):73-86. German. PMID: 4237043. 8: Chen C, Lan B, Xie G, Liu Z. Analysis and identification of ferroptosis- related genes in ulcerative colitis. Scand J Gastroenterol. 2023 Jul- Dec;58(12):1422-1433. doi: 10.1080/00365521.2023.2240927. Epub 2023 Aug 2. PMID: 37530128. 9: DITTERTOVA V, BURAN L, BABULOVA A, SELECKY FV. [Effect of oxyphylline on the cardiotoxic activity of convallatoxin and helveticoside and on their action on the heart-lung preparation of the cat]. Cesk Farm. 1963 Feb 5;12:104-7. Czech. PMID: 14028075. 10: BABULOVA A, BURAN L, SELECKY FV. [The cardiotoxic activity of helveticoside, a cardiac glycoside from Erysimum canescens Roth]. Arzneimittelforschung. 1963 May;13:412-4. German. PMID: 13965884. 11: Kaiser F, Schaumann W. Stoffwechsel von Derivaten des Helveticosids und Helveticosols [Metabolism of helveticoside and helveticosol derivatives]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1969;262(1):87-96. German. PMID: 4237044. 12: Kopp B, Krenn L, Kubelka E, Kubelka W. Cardenolides from Adonis aestivalis. Phytochemistry. 1992 Sep;31(9):3195-8. doi: 10.1016/0031-9422(92)83473-c. PMID: 1368415. 13: Kasavi C. Idiopathic Pulmonary Arterial Hypertension: Network-Based Integration of Multi-Omics Data Reveals New Molecular Signatures and Candidate Drugs. OMICS. 2023 Jul;27(7):315-326. doi: 10.1089/omi.2023.0066. Epub 2023 Jul 6. PMID: 37410515. 14: Kim SJ, Kim HY, Lee YJ, Cui HZ, Jang JY, Kang DG, Lee HS. Ethanol Extract of Lepidium apetalum Seed Elicits Contractile Response and Attenuates Atrial Natriuretic Peptide Secretion in Beating Rabbit Atria. Evid Based Complement Alternat Med. 2013;2013:404713. doi: 10.1155/2013/404713. Epub 2013 Oct 29. PMID: 24288558; PMCID: PMC3830812. 15: Zhong D, Wu C, Bai J, Xu D, Zeng X, Wang Q. Co-expression network analysis reveals the pivotal role of mitochondrial dysfunction and interferon signature in juvenile dermatomyositis. PeerJ. 2020 Feb 18;8:e8611. doi: 10.7717/peerj.8611. PMID: 32110496; PMCID: PMC7034382. 16: FOERSTER W, PAVEK K. UBER STRUKTUR-WIRKUNGSBEZIEHUNGEN UND QUALITATIVE WIRKUNGSUNTERSCHIEDE ZWISCHEN G-STROPHANTHIN, CONVALLATOXIN, HELVETICOSID UND CYMARIN [ON STRUCTURE-ACTIVITY RELATIONS AND QUALITATIVE DISTINCTIONS OF EFFICACY BETWEEN G-STROPHANTHIN, CONVALLATOXIN, HELVETICOSIDE AND CYMARINE]. Arch Int Pharmacodyn Ther. 1964 Apr 1;148:471-86. German. PMID: 14181242. 17: Graebner R, Geisel B. Pharmakologische Wirksamkeit substituiter Helveticosid- und Helveticosolderivate, insbesonere des Cyclopentanonhelveticosid sowie der unter Lichteinfluss entstehenen Umwandlungsprodukte ds Strophanthidins [Pharmacological effect of substituted helveticoside and helveticosol derivatives with special reference to cyclopentanonehelveticoside and light-induced transformation products of strophantidine]. Arzneimittelforschung. 1972 Nov;22(11):1854-64. German. PMID: 4679055. 18: ZATHURECKY L, BAUEROVA O, SOMOSKEOEY G, MOLNAR L, SUCHY S. STABILITA KARDENOLIDOV STROFANTID'INOV'EHO TYPU V INJEK CN'YCH PR'IPRAVKOCH. III. PR'IPRAVA STABILN'YCH INJEK CN'YCH ROZTOKOV HELVETIKOZIDU [STABILITY OF CARDENOLIDES OF THE STROPHANTHIDIN TYPE IN INJECTABLE PREPARATIONS. III. PREPARATIONS OF STABLE INJECTABLE SOLUTIONS OF HELVETICOSIDE]. Cesk Farm. 1963 May;12:171-7. Czech. PMID: 14073570. 19: Li G, Zhang C, Liang W, Zhang Y, Shen Y, Tian X. Berberine regulates the Notch1/PTEN/PI3K/AKT/mTOR pathway and acts synergistically with 17-AAG and SAHA in SW480 colon cancer cells. Pharm Biol. 2021 Dec;59(1):21-30. doi: 10.1080/13880209.2020.1865407. PMID: 33417512; PMCID: PMC7808376. 20: Mirzaei M, Züst T, Younkin GC, Hastings AP, Alani ML, Agrawal AA, Jander G. Less Is More: a Mutation in the Chemical Defense Pathway of Erysimum cheiranthoides (Brassicaceae) Reduces Total Cardenolide Abundance but Increases Resistance to Insect Herbivores. J Chem Ecol. 2020 Dec;46(11-12):1131-1143. doi: 10.1007/s10886-020-01225-y. Epub 2020 Nov 12. PMID: 33180277.

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