MedKoo Cat#: 592156 | Name: Isoalantolactone
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Description:

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

Isoalantolactone induces apoptosis through reactive oxygen species-dependent upregulation of death receptor 5 in human esophageal cancer cells.

Chemical Structure

Isoalantolactone
Isoalantolactone
CAS#470-17-7

Theoretical Analysis

MedKoo Cat#: 592156

Name: Isoalantolactone

CAS#: 470-17-7

Chemical Formula: C15H20O2

Exact Mass: 232.1463

Molecular Weight: 242.32

Elemental Analysis: C, 77.55; H, 8.68; O, 13.77

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
50mg USD 500.00 2 Weeks
100mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Isoalantolactone; NSC 601353; NSC-601353; NSC601353
IUPAC/Chemical Name
Eudesma-4(14),11(13)-dien-12-oic acid, 8-beta-hydroxy-, gamma-lactone
InChi Key
CVUANYCQTOGILD-QVHKTLOISA-N
InChi Code
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1
SMILES Code
O=C(O[C@@](C[C@@]1(C)CCC2)([H])[C@]3([H])C[C@@]1([H])C2=C)C3=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
>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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 242.32 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.

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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[Epub ahead of print] PubMed PMID: 29781054. 4: Zhou B, Ye J, Yang N, Chen L, Zhuo Z, Mao L, Liu Q, Lan G, Ning J, Ge G, Yang L, Shen Y, Wang S, Zhang W. Metabolism and pharmacokinetics of alantolactone and isoalantolactone in rats: Thiol conjugation as a potential metabolic pathway. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jan 1;1072:370-378. doi: 10.1016/j.jchromb.2017.11.039. Epub 2017 Dec 2. PubMed PMID: 29223921. 5: Li S, Shi H, Chang W, Li Y, Zhang M, Qiao Y, Lou H. Eudesmane sesquiterpenes from Chinese liverwort are substrates of Cdrs and display antifungal activity by targeting Erg6 and Erg11 of Candida albicans. Bioorg Med Chem. 2017 Oct 15;25(20):5764-5771. doi: 10.1016/j.bmc.2017.09.001. Epub 2017 Sep 9. PubMed PMID: 28935182. 6: Kalachaveedu M, Raghavan D, Telapolu S, Kuruvilla S, Kedike B. Phytoestrogenic effect of Inula racemosa Hook f - A cardioprotective root drug in traditional medicine. J Ethnopharmacol. 2018 Jan 10;210:408-416. doi: 10.1016/j.jep.2017.09.001. Epub 2017 Sep 8. PubMed PMID: 28893570. 7: Kalola J, Shah R, Patel A, Lahiri SK, Shah MB. Anti-inflammatory and immunomodulatory activities of Inula cappa roots (Compositae). J Complement Integr Med. 2017 Mar 18;14(3). pii: /j/jcim.2017.14.issue-3/jcim-2016-0083/jcim-2016-0083.xml. doi: 10.1515/jcim-2016-0083. PubMed PMID: 28889730. 8: Yang Y, Tu R, Sun W, Zhu Z, Zhang Y. Silver perchlorate in the mobile phase for rapid separation and determination of a pair of positional isomers in Inula racemosa Hook.f. with RP-HPLC. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 15;1063:25-30. doi: 10.1016/j.jchromb.2017.08.013. Epub 2017 Aug 14. PubMed PMID: 28837869. 9: Jin C, Zhang G, Zhang Y, Hua P, Song G, Sun M, Li X, Tong T, Li B, Zhang X. Isoalantolactone induces intrinsic apoptosis through p53 signaling pathway in human lung squamous carcinoma cells. PLoS One. 2017 Aug 4;12(8):e0181731. doi: 10.1371/journal.pone.0181731. eCollection 2017. PubMed PMID: 28777796; PubMed Central PMCID: PMC5544200. 10: Arha D, Ramakrishna E, Gupta AP, Rai AK, Sharma A, Ahmad I, Riyazuddin M, Gayen JR, Maurya R, Tamrakar AK. Isoalantolactone derivative promotes glucose utilization in skeletal muscle cells and increases energy expenditure in db/db mice via activating AMPK-dependent signaling. Mol Cell Endocrinol. 2018 Jan 15;460:134-151. doi: 10.1016/j.mce.2017.07.015. Epub 2017 Jul 20. PubMed PMID: 28736255. 11: He G, Zhang X, Chen Y, Chen J, Li L, Xie Y. Isoalantolactone inhibits LPS-induced inflammation via NF-κB inactivation in peritoneal macrophages and improves survival in sepsis. Biomed Pharmacother. 2017 Jun;90:598-607. doi: 10.1016/j.biopha.2017.03.095. Epub 2017 Apr 11. PubMed PMID: 28407580. 12: Seo JY, Lim SS, Kim J, Lee KW, Kim JS. Alantolactone and Isoalantolactone Prevent Amyloid β(25-35) -induced Toxicity in Mouse Cortical Neurons and Scopolamine-induced Cognitive Impairment in Mice. Phytother Res. 2017 May;31(5):801-811. doi: 10.1002/ptr.5804. Epub 2017 Mar 21. PubMed PMID: 28326625. 13: Mohan S, Gupta D. Phytochemical analysis and differential in vitro cytotoxicity assessment of root extracts of Inula racemosa. Biomed Pharmacother. 2017 May;89:781-795. doi: 10.1016/j.biopha.2017.02.053. Epub 2017 Mar 6. PubMed PMID: 28273640. 14: Guan YH, Zhang XD, Cai H, Yang CH. [Isoalantolactone Inhibits Proliferation of K562/A02 Cells through Caspase-Dependent Apoptotic Pathway]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2017 Feb;25(1):110-114. doi: 10.7534/j.issn.1009-2137.2017.01.019. Chinese. PubMed PMID: 28245385. 15: Gao S, Wang Q, Tian XH, Li HL, Shen YH, Xu XK, Wu GZ, Hu ZL, Zhang WD. Total sesquiterpene lactones prepared from Inula helenium L. has potentials in prevention and therapy of rheumatoid arthritis. J Ethnopharmacol. 2017 Jan 20;196:39-46. doi: 10.1016/j.jep.2016.12.020. Epub 2016 Dec 15. PubMed PMID: 27988396. 16: Kaur M, Kumar R, Upendrabhai DP, Singh IP, Kaur S. Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae). Pest Manag Sci. 2017 May;73(5):1031-1038. doi: 10.1002/ps.4429. Epub 2016 Oct 27. PubMed PMID: 27607232. 17: Li Z, Qin B, Qi X, Mao J, Wu D. Isoalantolactone induces apoptosis in human breast cancer cells via ROS-mediated mitochondrial pathway and downregulation of SIRT1. Arch Pharm Res. 2016 Oct;39(10):1441-1453. Epub 2016 Sep 6. PubMed PMID: 27600429. 18: Yao D, Wang Y, Huo C, Wu Y, Zhang M, Li L, Shi Q, Kiyota H, Shi X. Study on the metabolites of isoalantolactone in vivo and in vitro by ultra performance liquid chromatography combined with Triple TOF mass spectrometry. Food Chem. 2017 Jan 1;214:328-338. doi: 10.1016/j.foodchem.2016.07.100. Epub 2016 Jul 15. PubMed PMID: 27507482. 19: Wang J, Cui L, Feng L, Zhang Z, Song J, Liu D, Jia X. Isoalantolactone inhibits the migration and invasion of human breast cancer MDA-MB-231 cells via suppression of the p38 MAPK/NF-κB signaling pathway. Oncol Rep. 2016 Sep;36(3):1269-76. doi: 10.3892/or.2016.4954. Epub 2016 Jul 20. PubMed PMID: 27461575. 20: Wu M, Li T, Chen L, Peng S, Liao W, Bai R, Zhao X, Yang H, Wu C, Zeng H, Liu Y. Essential oils from Inula japonica and Angelicae dahuricae enhance sensitivity of MCF-7/ADR breast cancer cells to doxorubicin via multiple mechanisms. J Ethnopharmacol. 2016 Mar 2;180:18-27. doi: 10.1016/j.jep.2016.01.015. Epub 2016 Jan 18. PubMed PMID: 26795076.