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MedKoo Cat#: 531012 | Name: Cinchonidine
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Description:

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

Cinchonidine is an cinchona alkaloid with antimalarial activity. Cinchonidine adsorbed onto a platinum metal catalyst leads to rate acceleration and induces strong stereocontrol in the asymmetric hydrogenation of trifluoroacetophenone. In the hydrogenation of the heteroaromatic ring of cinchonidine in toluene, the diastereomeric excess of the (S)-hexahydrocinchonidine increased upon increasing Pt{111}/Pt{100} ratio, but this distinct shape selectivity was observed only after the oxidative removal of PAA at 473 K. The use of the as-prepared nanoparticles inverted the major diastereomer to R, and this isomer was formed also in acetic acid.

Chemical Structure

Cinchonidine
Cinchonidine
CAS#485-71-2 (free base)

Theoretical Analysis

MedKoo Cat#: 531012

Name: Cinchonidine

CAS#: 485-71-2 (free base)

Chemical Formula: C19H22N2O

Exact Mass: 294.1732

Molecular Weight: 294.40

Elemental Analysis: C, 77.52; H, 7.53; N, 9.52; O, 5.43

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
25g USD 850.00 2 Weeks
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Related CAS #
485-71-2 (free base) 524-54-9 (2HCl) 524-57-2 (HCl) 524-61-8 (sulfate)
Synonym
Cinchonan-9-ol, (8α,9R)-; α-Quinidine; (-)-Cinchonidine; Cinchovatine; L-Cinchonidine; 2-Quinuclidinemethanol, α-4-quinolyl-5-vinyl-; (8α,9R)-Cinchonan-9-ol; (8S,9R)-Cinchonidine; NSC 5364; NSC5364; NSC-5364
IUPAC/Chemical Name
(R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
InChi Key
KMPWYEUPVWOPIM-KODHJQJWSA-N
InChi Code
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
SMILES Code
C=C[C@@H](C[N@@]1CC2)[C@@H]2C[C@H]1[C@H](O)C3=CC=NC4=CC=CC=C34
Appearance
White 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 294.40 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: Deka J, Satyanarayana L, Karunakar GV, Bhattacharyya PK, Bania KK. Chiral modification of copper exchanged zeolite-Y with cinchonidine and its application in the asymmetric Henry reaction. Dalton Trans. 2015 Dec 28;44(48):20949-63. doi: 10.1039/c5dt03630e. Epub 2015 Nov 18. PubMed PMID: 26579982. 2: Zhang T, Li D. Influences of urea and pH on the interaction of cinchonidine with bovine serum albumin by steady state fluorescence spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Aug;112:15-20. doi: 10.1016/j.saa.2013.04.032. Epub 2013 Apr 11. PubMed PMID: 23651774. 3: Nawaz SA, Ayaz M, Brandt W, Wessjohann LA, Westermann B. Cation-π and π-π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids. Biochem Biophys Res Commun. 2011 Jan 28;404(4):935-40. doi: 10.1016/j.bbrc.2010.12.084. Epub 2010 Dec 23. PubMed PMID: 21185266. 4: Keunchkarian S, Grisales JO, Padró JM, Boeris S, Castells CB. Development of a chiral stationary phase based on cinchonidine. Comparison with a quinine-based chiral column. Chirality. 2012 Jul;24(7):512-8. doi: 10.1002/chir.22046. Epub 2012 May 10. PubMed PMID: 22573362. 5: Meemken F, Baiker A, Schenker S, Hungerbühler K. Chiral modification of platinum by co-adsorbed cinchonidine and trifluoroacetic acid: origin of enhanced stereocontrol in the hydrogenation of trifluoroacetophenone. Chemistry. 2014 Jan 27;20(5):1298-309. doi: 10.1002/chem.201303261. Epub 2013 Dec 30. PubMed PMID: 24382788. 6: Fukiya K, Itoh K, Yamaguchi S, Kishiba A, Adachi M, Watanabe N, Tanaka Y. A single amino acid substitution confers high cinchonidine oxidation activity comparable with that of rabbit to monkey aldehyde oxidase 1. Drug Metab Dispos. 2010 Feb;38(2):302-7. doi: 10.1124/dmd.109.030064. Epub 2009 Nov 12. PubMed PMID: 19910515. 7: Karczmarzyk Z, Lipińska TM, Wysocki W, Denisiuk M, Piechocka K. Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases. Acta Crystallogr C. 2011 Sep;67(Pt 9):o346-9. doi: 10.1107/S0108270111027272. Epub 2011 Aug 5. PubMed PMID: 21881184. 8: Schmidt E, Kleist W, Krumeich F, Mallat T, Baiker A. Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine. Chemistry. 2010 Feb 15;16(7):2181-92. doi: 10.1002/chem.200902517. PubMed PMID: 20039346. 9: Maeda N, Hungerbühler K, Baiker A. Asymmetric hydrogenation on chirally modified Pt: origin of hydrogen in the N-H-O interaction between cinchonidine and ketone. J Am Chem Soc. 2011 Dec 14;133(49):19567-9. doi: 10.1021/ja2054918. Epub 2011 Nov 15. PubMed PMID: 22084835. 10: Liu Y, Hoshina K, Haginaka J. Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. Talanta. 2010 Mar 15;80(5):1713-8. doi: 10.1016/j.talanta.2009.10.011. Epub 2009 Oct 14. PubMed PMID: 20152401. 11: Vargas A, Bonalumi N, Ferri D, Baiker A. Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study. J Phys Chem A. 2006 Jan 26;110(3):1118-27. PubMed PMID: 16420016. 12: Xu QM, Wang D, Wan LJ, Bai CL, Wang Y. Adsorption mode of cinchonidine on Cu(111) surface. J Am Chem Soc. 2002 Dec 4;124(48):14300-1. PubMed PMID: 12452692. 13: Ferri D, Bürgi T. An in situ attenuated total reflection infrared study of a chiral catalytic solid-liquid interface: cinchonidine adsorption on pt. J Am Chem Soc. 2001 Dec 5;123(48):12074-84. PubMed PMID: 11724616. 14: Behzadi B, Vargas A, Ferri D, Ernst KH, Baiker A. Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study. J Phys Chem B. 2006 Aug 31;110(34):17082-9. PubMed PMID: 16928003. 15: Matsui J, Minamimura N, Nishimoto K, Tamaki K, Sugimoto N. Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 May 5;804(1):223-9. PubMed PMID: 15093176. 16: KING H. Conversion of hydroquinidine into hydrocinchonine and of cupreine into cinchonidine. J Chem Soc. 1946 Jun;(6):523. PubMed PMID: 20280697. 17: Wang W, Ma X, Wan J, Cao J, Tang Q. Preparation and confinement effect of a heterogeneous 9-amino-9-deoxy-epi-cinchonidine organocatalyst for asymmetric aldol addition in aqueous medium. Dalton Trans. 2012 May 14;41(18):5715-26. doi: 10.1039/c2dt12390h. Epub 2012 Mar 27. PubMed PMID: 22451074. 18: You Y, Wu ZJ, Wang ZH, Xu XY, Zhang XM, Yuan WC. Enantioselective Synthesis of 3,3-Disubstituted Oxindoles Bearing Two Different Heteroatoms at the C3 Position by Organocatalyzed Sulfenylation and Selenenylation of 3-Pyrrolyl-oxindoles. J Org Chem. 2015 Aug 21;80(16):8470-7. doi: 10.1021/acs.joc.5b01491. Epub 2015 Aug 12. PubMed PMID: 26252841. 19: Olsen RA, Borchardt D, Mink L, Agarwal A, Mueller LJ, Zaera F. Effect of protonation on the conformation of cinchonidine. J Am Chem Soc. 2006 Dec 13;128(49):15594-5. PubMed PMID: 17147361. 20: Kraynov A, Suchopar A, D'Souza L, Richards R. Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS. Phys Chem Chem Phys. 2006 Mar 21;8(11):1321-8. Epub 2006 Feb 17. PubMed PMID: 16633613.