Eupalinolide A | CAS#877822-40-7 | Cellular chaperone-inducer

MedKoo Cat#: 464683 | Name: Eupalinolide A

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Description:

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

Eupalinolide A is a sesquiterpene lactone that has been found in E. lindleyanum and has cellular chaperone-inducing activity. It activates heat shock factor 1 (Hsf1) and induces the expression and increases the protein levels of heat shock protein 70 (Hsp70) in B16 cells when used at concentrations of 5, 7.5, and 10 µg/ml.

Chemical Structure

Eupalinolide A

CAS#877822-40-7

Theoretical Analysis

MedKoo Cat#: 464683

Name: Eupalinolide A

CAS#: 877822-40-7

Chemical Formula: C24H30O9

Exact Mass: 462.1890

Molecular Weight: 462.50

Elemental Analysis: C, 62.33; H, 6.54; O, 31.13

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 650.00	2 Weeks
100mg	USD 1,150.00	2 Weeks

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Related CAS #

No Data

Synonym

Eupalinolide A; Eupalinolide-A; Eupalinolide G; Eupalinolide-G;

IUPAC/Chemical Name

4-hydroxy-2-methyl-2-butenoic acid, (2E)-(3aR,4R,6Z,9S,10Z,11aR)-9-(acetyloxy)-6-[(acetyloxy)methyl]-2,3,3a,4,5,8,9,11a-octahydro-10-methyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester

InChi Key

HPWMABTYJYZFLK-IAQZCCQJSA-N

InChi Code

InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10-,18-6+/t19-,20+,21+,22-/m0/s1

SMILES Code

O=C(O[C@@H]1C/C(COC(C)=O)=C\C[C@H](OC(C)=O)/C(C)=C\[C@@]([C@]1([H])C2=C)([H])OC2=O)/C(C)=C/CO

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

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	64.87
	DMSO	30.0	64.87
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.71
	Ethanol	15.0	32.43

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 462.50 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: Zhang Y, Dong F, Cao Z, Wang T, Pan L, Luo W, Ding W, Li J, Jin L, Liu H, Zhang H, Mu J, Han M, Wei Y, Deng X, Liu D, Hao P, Zeng G, Pang Y, Liu G, Zhen C. Eupalinolide A induces autophagy via the ROS/ERK signaling pathway in hepatocellular carcinoma cells in vitro and in vivo. Int J Oncol. 2022 Nov;61(5):131. doi: 10.3892/ijo.2022.5421. Epub 2022 Sep 16. PMID: 36111510; PMCID: PMC9507091. 2: Li Y, Liu X, Li L, Zhang T, Gao Y, Zeng K, Wang Q. Characterization of the metabolism of eupalinolide A and B by carboxylesterase and cytochrome P450 in human liver microsomes. Front Pharmacol. 2023 Jan 25;14:1093696. doi: 10.3389/fphar.2023.1093696. PMID: 36762117; PMCID: PMC9905117. 3: Zhang J, Zhao F, Yu X, Lu X, Zheng G. Pharmacokinetics of eupalinolide A, eupalinolide B and hyperoside from Eupatorium lindleyanum in rats by LC/MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jul 15;995-996:1-7. doi: 10.1016/j.jchromb.2015.04.038. Epub 2015 May 16. PMID: 26011510. 4: Huang L, Xu DQ, Yue SJ, Chen YY, Fu RJ, Lu Z, Tang YP. [Research on Q-markers of Eupatorium lindleyanum based on analytic hierarchy process-entropy weight method and network pharmacology]. Zhongguo Zhong Yao Za Zhi. 2021 Nov;46(21):5545-5554. Chinese. doi: 10.19540/j.cnki.cjcmm.20210813.201. PMID: 34951205. 5: Yang NY, Qian SH, Duan JA, Li P, Tian LJ. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Asian Nat Prod Res. 2007 Apr-Aug;9(3-5):339-45. doi: 10.1080/10286020600727673. PMID: 17613619. 6: Yan G, Ji L, Luo Y, Hu Y. Preparative isolation and purification of three sesquiterpenoid lactones from Eupatorium lindleyanum DC. by high-speed counter- current chromatography. Molecules. 2012 Jul 27;17(8):9002-9. doi: 10.3390/molecules17089002. PMID: 22842644; PMCID: PMC6268613. 7: Yamashita Y, Ikeda T, Matsuda M, Maji D, Hoshino T, Mizushima T. Purification and characterization of HSP-inducers from Eupatorium lindleyanum. Biochem Pharmacol. 2012 Apr 1;83(7):909-22. doi: 10.1016/j.bcp.2011.12.040. Epub 2012 Jan 8. PMID: 22245466. 8: Huang L, Xu DQ, Chen YY, Fu RJ, Yue SJ, Yin JF, Tang YP. Qualitative and quantitative analysis of chemical components in Eupatorium lindleyanum DC. by ultra-performance liquid chromatography-mass spectrometry integrated with anti- inflammatory activity research. J Sep Sci. 2021 Sep;44(17):3174-3187. doi: 10.1002/jssc.202100208. Epub 2021 Jul 8. PMID: 34184412.