Xanthatin | CAS#26791-73-1

MedKoo Cat#: 333126 | Name: Xanthatin

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Description:

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

Xanthatin, a sesquiterpene lactone isolated primarily from Xanthium species, exhibits a range of bioactivities with a strong focus on anticancer properties. It induces apoptosis and cell cycle arrest in various human cancer cell lines, including breast (MCF-7), lung (A549), liver (HepG2), and colon (HT-29) cancers, with reported IC₅₀ values typically in the low micromolar range (e.g., ~2–10 μM depending on the cell type and exposure time). Mechanistically, xanthatin inhibits NF-κB signaling, suppresses STAT3 activation, and induces oxidative stress by generating reactive oxygen species (ROS). It has also shown antibacterial, anti-inflammatory, and antiangiogenic effects in vitro.

Chemical Structure

Xanthatin

CAS#26791-73-1

Theoretical Analysis

MedKoo Cat#: 333126

Name: Xanthatin

CAS#: 26791-73-1

Chemical Formula: C15H18O3

Exact Mass: 246.1256

Molecular Weight: 246.31

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks

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Related CAS #

No Data

Synonym

Xanthatin; CID 5281511; CID-5281511; CID5281511;

IUPAC/Chemical Name

(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

InChi Key

RBRPTFMVULVGIC-ZTIIIDENSA-N

InChi Code

InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1

SMILES Code

O=C(O[C@]1([H])[C@]2([H])CC=C(/C=C/C(C)=O)[C@@H](C)C1)C2=C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 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.

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: Berenguer Roque A, Zgheib A, Salomon-Izquierdo S, Manso Peña A, Osoria Alfonso LA, Piloto-Ferrer J, Annabi B. Xanthatin nanocrystals exert anti- inflammatory properties against TNFα-primed 2D monolayers and in 3D spheroids of human HT29 colorectal cancer cells. Discov Nano. 2025 May 19;20(1):83. doi: 10.1186/s11671-025-04257-z. PMID: 40388049; PMCID: PMC12089583. 2: Gao X, Li Y, Xu H, Ni S, Pan H, Ma C, Zhao X, Zhang H. Xanthatin induces apoptosis through ROS-mediated c-FLIP inhibition in human retinoblastoma cells. Front Med (Lausanne). 2025 Apr 16;12:1554934. doi: 10.3389/fmed.2025.1554934. PMID: 40309730; PMCID: PMC12041067. 3: Yuan H, Wu R, Hu Y, Zhang J, Zhang Y, Wang Z, Huo J, Tang L, Zhao B, Fan Z. Fungicidal Activity of Carboxamides Containing Spiropiperidinyl-α-methylene-γ- butyrolactones Targeting Oxysterol Binding Protein. J Agric Food Chem. 2025 Apr 16;73(15):8852-8864. doi: 10.1021/acs.jafc.5c00121. Epub 2025 Apr 1. PMID: 40170001. 4: Feng L, Xu L, Huang J, Wang Y, Xia Q, Meng J, Wang R, Liu K. Cardiotoxicity induced by xanthatin via activating apoptosis and ERS pathways in zebrafish. Drug Chem Toxicol. 2025 Mar 24:1-12. doi: 10.1080/01480545.2025.2481863. Epub ahead of print. PMID: 40125983. 5: Lee E, Yang D, Hong JH. Prominent Naturally Derived Oxidative-Stress- Targeting Drugs and Their Applications in Cancer Treatment. Antioxidants (Basel). 2025 Jan 3;14(1):49. doi: 10.3390/antiox14010049. PMID: 39857383; PMCID: PMC11760868. 6: Amin N, Wu CH, Malak N, Khan A, Ullah S, Ahmad I, Khan MA, Naveed M, Ullah Z, Naz S, Khan A, Chen CC. In vitro Bioassay and In silico Pharmacokinetic Characteristics of Xanthium strumarium Plant Extract as Possible Acaricidal Agent. Curr Pharm Des. 2025;31(12):992-1005. doi: 10.2174/0113816128317849241108064144. PMID: 39694964. 7: Li C, Li Y, Wang J, Lu F, Zheng L, Yang L, Sun W, Ro DK, Qu X, Wu Y, Zhang Y. An independent biosynthetic route to frame a xanthanolide-type sesquiterpene lactone in Asteraceae. Plant J. 2025 Jan;121(2):e17199. doi: 10.1111/tpj.17199. Epub 2024 Dec 6. PMID: 39642193. 8: Liu Y, Chen W, Gao Y, Wei K. Anti-inflammatory dressing based on hyaluronic acid and hydroxyethyl starch for wound healing. Int J Biol Macromol. 2024 Dec;282(Pt 6):137078. doi: 10.1016/j.ijbiomac.2024.137078. Epub 2024 Oct 29. PMID: 39481723. 9: Yuan H, Yang H, Gao Y, Zhang J, Ren J, Liu X, Li Y, Li Z, Zhao B, Fan Z. Discovery of Novel Spiropiperidinyl-α-methylene-γ-butyrolactones as Antifungal and Antitoxin Agents Targeting Oxysterol Binding Protein. J Agric Food Chem. 2024 Jul 17;72(28):15474-15486. doi: 10.1021/acs.jafc.4c02848. Epub 2024 Jul 1. PMID: 38949855. 10: Xu L, Shi Y, Huang J, Feng L, Wang Y, Sik AG, Chen X, Liu K, Wang R, Jin M. Developmental toxicity assay of xanthatin in zebrafish embryos. Comp Biochem Physiol C Toxicol Pharmacol. 2024 Sep;283:109957. doi: 10.1016/j.cbpc.2024.109957. Epub 2024 Jun 8. PMID: 38857669. 11: Zhao B, Liu J, Zhao Y, Geng S, Zhao R, Li J, Cao Z, Liu Y, Dong J. FvOshC Is a Key Global Regulatory Target in Fusarium verticillioides for Fumonisin Biosynthesis and Disease Control. J Agric Food Chem. 2024 Jul 17;72(28):15463-15473. doi: 10.1021/acs.jafc.4c01953. Epub 2024 May 28. PMID: 38805181. 12: Luo L, Xiong J, Tang Y, Chen X, Zhang H. Protein Target Prediction and Validation of Small Molecule Compound. J Vis Exp. 2024 Feb 23;(204). doi: 10.3791/66564. PMID: 38598255. 13: Xu Y, Chen Z, Lu X, Zheng J, Liu X, Zhang T, Yang W, Qian Y. Targeted inhibition of STAT3 (Tyr705) by xanthatin alleviates osteoarthritis progression through the NF-κB signaling pathway. Biomed Pharmacother. 2024 May;174:116451. doi: 10.1016/j.biopha.2024.116451. Epub 2024 Mar 22. PMID: 38520869. 14: Wetten PA, Arismendi Sosa AC, Mariani ML, Vargas PM, Michaut MA, Penissi AB. Dehydroleucodine and xanthatin, two natural anti-inflammatory lactones, inhibit mast cell degranulation by affecting the actin cytoskeleton. Cytoskeleton (Hoboken). 2024 Apr-May;81(4-5):215-226. doi: 10.1002/cm.21805. Epub 2023 Nov 6. PMID: 37929805. 15: Geng Y, Liu P, Xie Y, Liu Y, Zhang X, Hou X, Zhang L. Xanthatin suppresses pancreatic cancer cell growth via the ROS/RBL1 signaling pathway: In vitro and in vivo insights. Phytomedicine. 2023 Oct;119:155004. doi: 10.1016/j.phymed.2023.155004. Epub 2023 Aug 3. PMID: 37562091. 16: Yang C, Li Y, Zhang Y, Hu Q, Liu Y, Li YF, Shi HC, Song LL, Cao H, Hao XJ, Zhi XY. Natural Sesquiterpene Lactone as Source of Discovery of Novel Fungicidal Candidates: Structural Modification and Antifungal Activity Evaluation of Xanthatin Derived from Xanthium strumarium L. J Agric Food Chem. 2023 Jul 26;71(29):11239-11251. doi: 10.1021/acs.jafc.3c02435. Epub 2023 Jul 14. PMID: 37449982. 17: Liu Y, Zhang X, Cheng F, Cao W, Geng Y, Chen Z, Wei W, Zhang L. Xanthatin induce DDP-resistance lung cancer cells apoptosis through regulation of GLUT1 mediated ROS accumulation. Drug Dev Res. 2023 Sep;84(6):1266-1278. doi: 10.1002/ddr.22084. Epub 2023 Jun 1. PMID: 37260173. 18: Gligor O, Clichici S, Moldovan R, Decea N, Vlase AM, Fizeșan I, Pop A, Virag P, Filip GA, Vlase L, Crișan G. An In Vitro and In Vivo Assessment of Antitumor Activity of Extracts Derived from Three Well-Known Plant Species. Plants (Basel). 2023 Apr 29;12(9):1840. doi: 10.3390/plants12091840. PMID: 37176897; PMCID: PMC10180766. 19: Zhao WS, Chen KF, Liu M, Jia XL, Huang YQ, Hao BB, Hu H, Shen XY, Yu Q, Tan MJ. Investigation of targets and anticancer mechanisms of covalently acting natural products by functional proteomics. Acta Pharmacol Sin. 2023 Aug;44(8):1701-1711. doi: 10.1038/s41401-023-01072-z. Epub 2023 Mar 17. PMID: 36932232; PMCID: PMC10374574. 20: Han J, Wang J, Wang Y, Zhu Z, Zhang S, Wu B, Meng M, Zhao J, Wang D. Sesquiterpene lactones-enriched fractions from Xanthium mongolicum Kitag alleviate RA by regulating M1 macrophage polarization via NF-κB and MAPK signaling pathway. Front Pharmacol. 2023 Jan 26;14:1104153. doi: 10.3389/fphar.2023.1104153. PMID: 36778009; PMCID: PMC9909009.