Santonin
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MedKoo CAT#: 596845

CAS#: 481-06-1

Description: Santonin is an Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region.


Chemical Structure

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Santonin
CAS# 481-06-1

Theoretical Analysis

MedKoo Cat#: 596845
Name: Santonin
CAS#: 481-06-1
Chemical Formula: C15H18O3
Exact Mass: 246.1256
Molecular Weight: 246.3
Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
5.0g USD 220.0 2 Weeks
10.0g USD 350.0 2 Weeks
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Synonym: Santonin; alpha-Santonin; NSC 4900; NSC-4900; NSC4900;

IUPAC/Chemical Name: (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione

InChi Key: XJHDMGJURBVLLE-BOCCBSBMSA-N

InChi Code: InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1

SMILES Code: O=C1[C@@H](C)[C@@](CC[C@@]2(C)C=CC(C(C)=C23)=O)([H])[C@]3([H])O1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 246.3 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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1: Díaz K, Espinoza L, Madrid A, Pizarro L, Chamy R. Isolation and Identification of Compounds from Bioactive Extracts of Taraxacum officinale Weber ex F. H. Wigg. (Dandelion) as a Potential Source of Antibacterial Agents. Evid Based Complement Alternat Med. 2018 Jan 1;2018:2706417. doi: 10.1155/2018/2706417. eCollection 2018. PubMed PMID: 29507587; PubMed Central PMCID: PMC5817818.

2: Coricello A, El-Magboub A, Luna M, Ferrario A, Haworth IS, Gomer CJ, Aiello F, Adams JD. Rational drug design and synthesis of new α-Santonin derivatives as potential COX-2 inhibitors. Bioorg Med Chem Lett. 2018 Apr 1;28(6):993-996. doi: 10.1016/j.bmcl.2018.02.036. Epub 2018 Feb 22. PubMed PMID: 29501395.

3: Chen H, Yang X, Yu Z, Cheng Z, Yuan H, Zhao Z, Wu G, Xie N, Yuan X, Sun Q, Zhang W. Synthesis and biological evaluation of α-santonin derivatives as anti-hepatoma agents. Eur J Med Chem. 2018 Apr 10;149:90-97. doi: 10.1016/j.ejmech.2018.02.073. Epub 2018 Feb 23. PubMed PMID: 29499490.

4: Khan S, Tubino M, Vila MMDC, Bastos FA. First Time Determination of Important Catalyst Sodium Methoxide Used in Biodiesel by Colorimetric Method. Anal Chem. 2018 Mar 6;90(5):3550-3555. doi: 10.1021/acs.analchem.7b05445. Epub 2018 Feb 23. PubMed PMID: 29433318.

5: Hallwass F, Teles RR, Hellemann E, Griesinger C, Gil RR, Navarro-Vázquez A. Measurement of residual chemical shift anisotropies in compressed polymethylmethacrylate gels. Automatic compensation of gel isotropic shift contribution. Magn Reson Chem. 2018 May;56(5):321-328. doi: 10.1002/mrc.4711. Epub 2018 Feb 8. PubMed PMID: 29327368.

6: Zhang Z, Ratnikov M, Spraggon G, Alper PB. Photoinduced Rearrangement of Dienones and Santonin Rerouted by Amines. Angew Chem Int Ed Engl. 2018 Jan 22;57(4):904-908. doi: 10.1002/anie.201710463. Epub 2017 Dec 20. PubMed PMID: 29266649.

7: Sahu N, Meena S, Shukla V, Chaturvedi P, Kumar B, Datta D, Arya KR. Extraction, fractionation and re-fractionation of Artemisia nilagirica for anticancer activity and HPLC-ESI-QTOF-MS/MS determination. J Ethnopharmacol. 2018 Mar 1;213:72-80. doi: 10.1016/j.jep.2017.10.029. PubMed PMID: 29109061.

8: Quach HT, Kondo T, Watanabe M, Tamura R, Yajima Y, Sayama S, Ando M, Kataoka T. Eudesmane-Type Sesquiterpene Lactones Inhibit Nuclear Translocation of the Nuclear Factor κB Subunit RelB in Response to a Lymphotoxin β Stimulation. Biol Pharm Bull. 2017;40(10):1669-1677. doi: 10.1248/bpb.b17-00170. PubMed PMID: 28966239.

9: Cala A, Molinillo JMG, Fernández-Aparicio M, Ayuso J, Álvarez JA, Rubiales D, Macías FA. Complexation of sesquiterpene lactones with cyclodextrins: synthesis and effects on their activities on parasitic weeds. Org Biomol Chem. 2017 Aug 9;15(31):6500-6510. doi: 10.1039/c7ob01394a. PubMed PMID: 28745382.

10: Chen H, Wu G, Gao S, Guo R, Zhao Z, Yuan H, Liu S, Wu J, Lu X, Yuan X, Yu Z, Zu X, Xie N, Yang N, Hu Z, Sun Q, Zhang W. Discovery of Potent Small-Molecule Inhibitors of Ubiquitin-Conjugating Enzyme UbcH5c from α-Santonin Derivatives. J Med Chem. 2017 Aug 24;60(16):6828-6852. doi: 10.1021/acs.jmedchem.6b01829. Epub 2017 Aug 2. PubMed PMID: 28696694.

11: PLOS ONE Staff. Correction: Quantification of santonin in eight species of Artemisia from Kazakhstan by means of HPLC-UV: Method development and validation. PLoS One. 2017 Mar 28;12(3):e0175088. doi: 10.1371/journal.pone.0175088. eCollection 2017. PubMed PMID: 28350868; PubMed Central PMCID: PMC5370136.

12: Sakipova Z, Wong NS, Bekezhanova T, Sadykova, Shukirbekova A, Boylan F. Quantification of santonin in eight species of Artemisia from Kazakhstan by means of HPLC-UV: Method development and validation. PLoS One. 2017 Mar 16;12(3):e0173714. doi: 10.1371/journal.pone.0173714. eCollection 2017. Erratum in: PLoS One. 2017 Mar 28;12 (3):e0175088. PubMed PMID: 28301522; PubMed Central PMCID: PMC5354383.

13: Chinthakindi PK, Singh J, Gupta S, Nargotra A, Mahajan P, Kaul A, Ahmed Z, Koul S, Sangwan PL. Synthesis of α-santonin derivatives for diminutive effect on T and B-cell proliferation and their structure activity relationships. Eur J Med Chem. 2017 Feb 15;127:1047-1058. doi: 10.1016/j.ejmech.2016.11.018. Epub 2016 Nov 9. PubMed PMID: 27847171.

14: Liu YJ, Liu YH, Zhang ZZ, Yan SY, Chen K, Shi BF. Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C-H Bonds. Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13859-13862. doi: 10.1002/anie.201607766. Epub 2016 Sep 28. PubMed PMID: 27678130.

15: Dangroo NA, Singh J, Dar AA, Gupta N, Chinthakindi PK, Kaul A, Khuroo MA, Sangwan PL. Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation. Eur J Med Chem. 2016 Sep 14;120:160-9. doi: 10.1016/j.ejmech.2016.05.018. Epub 2016 May 10. PubMed PMID: 27191613.

16: Masnyk M, Butkiewicz A, Górecki M, Luboradzki R, Bannwarth C, Grimme S, Frelek J. Synthesis and Comprehensive Structural and Chiroptical Characterization of Enones Derived from (-)-α-Santonin by Experiment and Theory. J Org Chem. 2016 Jun 3;81(11):4588-600. doi: 10.1021/acs.joc.6b00416. Epub 2016 May 12. PubMed PMID: 27115057.

17: Hoshino M, Khutia A, Xing H, Inokuma Y, Fujita M. The crystalline sponge method updated. IUCrJ. 2016 Feb 12;3(Pt 2):139-51. doi: 10.1107/S2052252515024379. eCollection 2016 Mar 1. PubMed PMID: 27006777; PubMed Central PMCID: PMC4775162.

18: Ramamurthy V. Photochemistry within a water-soluble organic capsule. Acc Chem Res. 2015 Nov 17;48(11):2904-17. doi: 10.1021/acs.accounts.5b00360. Epub 2015 Oct 21. PubMed PMID: 26488308.

19: Yan X, Ren F, Liu W, Dong D, Zhang J, Zhang D, Bai J, Lyu Y. [Gastrostomy in dogs with magnetic compression technique combined with endoscopy]. Zhonghua Wei Chang Wai Ke Za Zhi. 2015 Aug;18(8):832-4. Chinese. PubMed PMID: 26303697.

20: Khazir J, Riley DL, Chashoo G, Mir BA, Liles D, Islam MA, Singh SK, Vishwakarma RA, Pilcher LA. Design, synthesis and anticancer activity of Michael-type thiol adducts of α-santonin analogue with exocyclic methylene. Eur J Med Chem. 2015 Aug 28;101:769-79. doi: 10.1016/j.ejmech.2015.07.022. Epub 2015 Jul 17. PubMed PMID: 26222449.