Eupatolide | CAS# 6750-25-0 | anti-cancer, antineoplastic

MedKoo Cat#: 413410 | Name: Eupatolide

Description:

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

Eupatolide is a germacranolide with formula C15H20O3, isolated from several Inula species. It exhibits anti-cancer properties. It has a role as an antineoplastic agent and a plant metabolite. It is a germacranolide, a homoallylic alcohol, a secondary alcohol and a gamma-lactone.

Chemical Structure

Eupatolide

CAS#6750-25-0

Theoretical Analysis

MedKoo Cat#: 413410

Name: Eupatolide

CAS#: 6750-25-0

Chemical Formula: C15H20O3

Exact Mass: 248.1412

Molecular Weight: 248.32

Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

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

Eupatolide; NSC152861; NSC-152861; NSC 152861

IUPAC/Chemical Name

Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-4-hydroxy-6,10-dimethyl-3-methylene-, (3aR-(3aR*,4R*,6E,10E,11aR*))- (9CI)

InChi Key

PDEJECFRCJOMEN-OURLZOILSA-N

InChi Code

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1

SMILES Code

O=C(O[C@@]1([H])[C@@]2([H])[C@H](O)C/C(C)=C/CC/C(C)=C/1)C2=C

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

>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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 248.32 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.

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: Avila-Carrasco L, Majano P, Sánchez-Toméro JA, Selgas R, López-Cabrera M, Aguilera A, González Mateo G. Natural Plants Compounds as Modulators of Epithelial-to-Mesenchymal Transition. Front Pharmacol. 2019 Jul 30;10:715. doi: 10.3389/fphar.2019.00715. PMID: 31417401; PMCID: PMC6682706. 2: Ma X, Wu K, Xu A, Jiao P, Li H, Xing L. The sesquiterpene lactone eupatolide induces apoptosis in non-small cell lung cancer cells by suppressing STAT3 signaling. Environ Toxicol Pharmacol. 2021 Jan;81:103513. doi: 10.1016/j.etap.2020.103513. Epub 2020 Oct 20. PMID: 33091599. 3: Boldbaatar A, Lee S, Han S, Jeong AL, Ka HI, Buyanravjikh S, Lee JH, Lim JS, Lee MS, Yang Y. Eupatolide inhibits the TGF-β1-induced migration of breast cancer cells via downregulation of SMAD3 phosphorylation and transcriptional repression of ALK5. Oncol Lett. 2017 Nov;14(5):6031-6039. doi: 10.3892/ol.2017.6957. Epub 2017 Sep 15. Erratum in: Oncol Lett. 2018 Jun;15(6):8885. PMID: 29113242; PMCID: PMC5661662. 4: Frey M, Schmauder K, Pateraki I, Spring O. Biosynthesis of Eupatolide-A Metabolic Route for Sesquiterpene Lactone Formation Involving the P450 Enzyme CYP71DD6. ACS Chem Biol. 2018 Jun 15;13(6):1536-1543. doi: 10.1021/acschembio.8b00126. Epub 2018 May 21. PMID: 29758164. 5: Lee J, Tae N, Lee JJ, Kim T, Lee JH. Eupatolide inhibits lipopolysaccharide- induced COX-2 and iNOS expression in RAW264.7 cells by inducing proteasomal degradation of TRAF6. Eur J Pharmacol. 2010 Jun 25;636(1-3):173-80. doi: 10.1016/j.ejphar.2010.03.021. Epub 2010 Mar 28. Erratum in: Eur J Pharmacol. 2013 May 15;708(1-3):139. PMID: 20353767. 6: Boldbaatar A, Lee S, Han S, Jeong AL, Ka HI, Buyanravjikh S, Lee JH, Lim JS, Lee MS, Yang Y. Erratum: Eupatolide inhibits the TGF-β1-induced migration of breast cancer cells via downregulation of SMAD3 phosphorylation and transcriptional repression of ALK5. Oncol Lett. 2018 Jun;15(6):8885. doi: 10.3892/ol.2018.8427. Epub 2018 Apr 4. Erratum for: Oncol Lett. 2017 Nov;14 (5):6031-6039. PMID: 29809196; PMCID: PMC5950548. 7: Kim N, Hwangbo C, Lee S, Lee JH. Eupatolide inhibits PDGF-induced proliferation and migration of aortic smooth muscle cells through ROS-dependent heme oxygenase-1 induction. Phytother Res. 2013 Nov;27(11):1700-7. doi: 10.1002/ptr.4924. Epub 2013 Jan 8. PMID: 23297002. 8: Lee J, Hwangbo C, Lee JJ, Seo J, Lee JH. The sesquiterpene lactone eupatolide sensitizes breast cancer cells to TRAIL through down-regulation of c-FLIP expression. Oncol Rep. 2010 Jan;23(1):229-37. PMID: 19956887. 9: Frey M, Klaiber I, Conrad J, Spring O. CYP71BL9, the missing link in costunolide synthesis of sunflower. Phytochemistry. 2020 Sep;177:112430. doi: 10.1016/j.phytochem.2020.112430. Epub 2020 Jun 6. PMID: 32516579. 10: Lee KH, Huang HC, Huang ES, Furukawa H. Antitumor agents. II. Eupatolide, a new cytotoxic principle from Eupatorium formosanum HAY. J Pharm Sci. 1972 Apr;61(4):629-31. doi: 10.1002/jps.2600610432. PMID: 4335375.