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MedKoo Cat#: 575011 | Name: Aristolone
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Description:

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

Aristolone is a sesquiterpene that has anticancer activity, and induces mesenteric vasodilation and ameliorates hypertension via activation of the KATP channel and PDK1-Akt-eNOS pathway.

Chemical Structure

Aristolone
CAS#25274-27-5

Theoretical Analysis

MedKoo Cat#: 575011

Name: Aristolone

CAS#: 25274-27-5

Chemical Formula: C15H22O

Exact Mass: 218.1671

Molecular Weight: 218.34

Elemental Analysis: C, 82.52; H, 10.16; O, 7.33

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 600.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Aristolone; (–)-Aristolone; Aristofone
IUPAC/Chemical Name
(1aR,7R,7aR,7bS)-1,1,7,7a-tetramethyl-1,1a,4,5,6,7,7a,7b-octahydro-2H-cyclopropa[a]naphthalen-2-one
InChi Key
UGVIZCBJCSXBCJ-JWFUOXDNSA-N
InChi Code
InChI=1S/C15H22O/c1-9-6-5-7-10-8-11(16)12-13(14(12,2)3)15(9,10)4/h8-9,12-13H,5-7H2,1-4H3/t9-,12-,13+,15+/m1/s1
SMILES Code
C[C@@]12[C@]3([C@]([H])(C3(C)C)C(C=C1CCC[C@H]2C)=O)[H]
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 218.34 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: Fang J, Li R, Zhang Y, Oduro PK, Li S, Leng L, Wang Z, Rao Y, Niu L, Wu HH, Wang Q. Aristolone in Nardostachys jatamansi DC. induces mesenteric vasodilation and ameliorates hypertension via activation of the KATP channel and PDK1-Akt-eNOS pathway. Phytomedicine. 2022 Sep;104:154257. doi: 10.1016/j.phymed.2022.154257. Epub 2022 Jun 9. PMID: 35738117. 2: Loumouamou AN, Bikindou K, Bitemou E, Chalard P, Silou T, Figueredo G. Optimization of the extraction of the p-menthadienol isomers and aristolone contained in the essential oil from Elyonurus hensii using a 23 full factorial design. Food Sci Nutr. 2017 Feb 9;5(3):784-792. doi: 10.1002/fsn3.459. PMID: 28572969; PMCID: PMC5448358. 3: Wang LX, Jiang XJ, Li XM, Mao MF, Wei GZ, Wang F. Aristolane-type Sesquiterpenoids from Nardostachys chinensis and Revised Structure of Aristolanhydride. Nat Prod Bioprospect. 2019 Apr;9(2):149-155. doi: 10.1007/s13659-019-0200-7. Epub 2019 Mar 8. PMID: 30848431; PMCID: PMC6426942. 4: Clericuzio M, Cassino C, Corana F, Vidari G. Terpenoids from Russula lepida and R. amarissima (Basidiomycota, Russulaceae). Phytochemistry. 2012 Dec;84:154-9. doi: 10.1016/j.phytochem.2012.07.024. Epub 2012 Aug 30. PMID: 22938994. 5: Zhang W, Nan G, Wu HH, Jiang M, Li TX, Wang M, Gao XM, Zhu Y, Song YS, Wang J, Xu YT. A Simple and Rapid UPLC-PDA Method for Quality Control of Nardostachys jatamansi. Planta Med. 2018 May;84(8):536-543. doi: 10.1055/s-0043-123655. Epub 2017 Dec 4. PMID: 29202512. 6: Priya Rani M, Padmakumari KP. HPTLC and reverse phase HPLC methods for the simultaneous quantification and in vitro screening of antioxidant potential of isolated sesquiterpenoids from the rhizomes of Cyperus rotundus. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Sep 1;904:22-8. doi: 10.1016/j.jchromb.2012.05.042. Epub 2012 Jun 12. PMID: 22877740. 7: Su S, Sun WS, Wang B, Cheng W, Liang H, Zhao YY, Zhang QY, Wu J. A novel brominated cuparene-derived sesquiterpene ether from the red alga Laurencia sp. J Asian Nat Prod Res. 2010 Oct;12(10):916-20. doi: 10.1080/10286020.2010.506190. PMID: 20924905. 8: Cheng SY, Wen ZH, Wang SK, Chiang MY, El-Gamal AA, Dai CF, Duh CY. Revision of the absolute configuration at C(23) of lanostanoids and isolation of secondary metabolites from formosan soft coral Nephthea erecta. Chem Biodivers. 2009 Jan;6(1):86-95. doi: 10.1002/cbdv.200800015. PMID: 19180458. 9: Shen SM, Yang Q, Zang Y, Li J, Liu X, Guo YW. Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa. Beilstein J Org Chem. 2022 Jul 25;18:916-925. doi: 10.3762/bjoc.18.91. PMID: 35957756; PMCID: PMC9344550. 10: Zubía E, Ortega MJ, Carballo JL. Sesquiterpenes from the sponge Axinyssa isabela. J Nat Prod. 2008 Dec;71(12):2004-10. doi: 10.1021/np800465n. PMID: 19007287. 11: Dastan D, Salehi P, Reza Gohari A, Zimmermann S, Kaiser M, Hamburger M, Reza Khavasi H, Ebrahimi SN. Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations. Phytochemistry. 2012 Jun;78:170-8. doi: 10.1016/j.phytochem.2012.02.016. Epub 2012 Mar 20. PMID: 22440297. 12: Sulyman AO, Akolade JO, Sabiu SA, Aladodo RA, Muritala HF. Antidiabetic potentials of ethanolic extract of Aristolochia ringens (Vahl.) roots. J Ethnopharmacol. 2016 Apr 22;182:122-8. doi: 10.1016/j.jep.2016.02.002. Epub 2016 Feb 16. PMID: 26899440. 13: Li R, Wang ZM, Wang Y, Dong X, Zhang LH, Wang T, Zhu Y, Gao XM, Wu HH, Xu YT. Antidepressant activities and regulative effects on serotonin transporter of Nardostachys jatamansi DC. J Ethnopharmacol. 2021 Mar 25;268:113601. doi: 10.1016/j.jep.2020.113601. Epub 2020 Nov 18. PMID: 33220358. 14: Su JH, Dai CF, Huang HH, Wu YC, Sung PJ, Hsu CH, Sheu JH. Terpenoid-related metabolites from a formosan soft coral Nephthea chabrolii. Chem Pharm Bull (Tokyo). 2007 Apr;55(4):594-7. doi: 10.1248/cpb.55.594. PMID: 17409554. 15: Zubía E, Ortega MJ, Hernández-Guerrero CJ, Carballo JL. Isothiocyanate sesquiterpenes from a sponge of the genus axinyssa. J Nat Prod. 2008 Apr;71(4):608-14. doi: 10.1021/np070593s. Epub 2008 Feb 21. PMID: 18288806. 16: Ha JH, Lee KY, Choi HC, Cho J, Kang BS, Lim JC, Lee DU. Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus. Biol Pharm Bull. 2002 Jan;25(1):128-30. doi: 10.1248/bpb.25.128. PMID: 11824542. 17: Marrelli M, Cristaldi B, Menichini F, Conforti F. Inhibitory effects of wild dietary plants on lipid peroxidation and on the proliferation of human cancer cells. Food Chem Toxicol. 2015 Dec;86:16-24. doi: 10.1016/j.fct.2015.09.011. Epub 2015 Sep 25. PMID: 26408343. 18: Huong le T, Thang TD, Ogunwande IA. Chemical constituents of essential oils from the leaves, stems, roots and fruits of Alpinia polyantha. Nat Prod Commun. 2015 Feb;10(2):367-8. PMID: 25920286. 19: Wang J, Zhao J, Liu H, Zhou L, Liu Z, Wang J, Han J, Yu Z, Yang F. Chemical analysis and biological activity of the essential oils of two valerianaceous species from China: Nardostachys chinensis and Valeriana officinalis. Molecules. 2010 Sep 14;15(9):6411-22. doi: 10.3390/molecules15096411. PMID: 20877232; PMCID: PMC6257676. 20: Memariani T, Hosseini T, Kamali H, Mohammadi A, Ghorbani M, Shakeri A, Spandidos DA, Tsatsakis AM, Shahsavand S. Evaluation of the cytotoxic effects of Cyperus longus extract, fractions and its essential oil on the PC3 and MCF7 cancer cell lines. Oncol Lett. 2016 Feb;11(2):1353-1360. doi: 10.3892/ol.2015.4050. Epub 2015 Dec 23. PMID: 26893742; PMCID: PMC4734339.