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MedKoo Cat#: 596845 | Name: Santonin
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Description:

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

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

Santonin
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: 246.31

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

Price and Availability

Size Price Availability Quantity
5g USD 375.00
10g USD 775.00
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Related CAS #
No Data
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 and DMF
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Santonin has been used as a building block in the synthesis of terpenoids. Santonin is an anthelmintic that induces paralysis of A. lumbricoides.
In vitro activity:
Dysidea avara extracts, which contain α-Santonin, may selectively induce apoptosis in malignant pediatric lymphocytes. Treatment of ALL B-lymphocytes with the Dysidea avara extract caused augmentation in ROS generation, decline in mitochondrial membrane potential, mitochondrial swelling, release of cytochrome c from mitochondria and activation of caspase-3 only in mitochondria isolated from B-ALL lymphocytes. Reference: Asian Pac J Cancer Prev. 2018 Aug 24;19(8):2149-2154. https://pubmed.ncbi.nlm.nih.gov/30139218/
In vivo activity:
To be determined
Solvent mg/mL mM
Solubility
DMF 5.0 20.30
DMSO 5.0 20.30
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 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.

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
Formulation protocol:
1. Aghvami M, Keshavarz A, Nazemi M, Zarei MH, Pourahmad J. Selective Cytotoxicity of α-Santonin from the Persian Gulf Sponge Dysidea Avara on Pediatric ALL B-lymphocytes via Mitochondrial Targeting. Asian Pac J Cancer Prev. 2018 Aug 24;19(8):2149-2154. doi: 10.22034/APJCP.2018.19.8.2149. PMID: 30139218; PMCID: PMC6171380. 2. Singh B, Srivastava JS, Khosa RL, Singh UP. Individual and combined effects of berberine and santonin on spore germination of some fungi. Folia Microbiol (Praha). 2001;46(2):137-42. doi: 10.1007/BF02873592. PMID: 11501401.
In vitro protocol:
1. Aghvami M, Keshavarz A, Nazemi M, Zarei MH, Pourahmad J. Selective Cytotoxicity of α-Santonin from the Persian Gulf Sponge Dysidea Avara on Pediatric ALL B-lymphocytes via Mitochondrial Targeting. Asian Pac J Cancer Prev. 2018 Aug 24;19(8):2149-2154. doi: 10.22034/APJCP.2018.19.8.2149. PMID: 30139218; PMCID: PMC6171380. 2. Singh B, Srivastava JS, Khosa RL, Singh UP. Individual and combined effects of berberine and santonin on spore germination of some fungi. Folia Microbiol (Praha). 2001;46(2):137-42. doi: 10.1007/BF02873592. PMID: 11501401.
In vivo protocol:
To be determined
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.

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