Vindorosine

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MedKoo CAT#: 585391

CAS#: 5231-60-7

Description: Vindorosine is extracted from Catharanthus roseus, and reduces KCl-stimulated Ca(2+) influx in the smooth muscles of rat renal arteries.


Price and Availability

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Pricing updated 2020-02-28. Prices are subject to change without notice.

Vindorosine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 585391
Name: Vindorosine
CAS#: 5231-60-7
Chemical Formula: C24H30N2O5
Exact Mass: 426.2155
Molecular Weight: 426.513
Elemental Analysis: C, 67.59; H, 7.09; N, 6.57; O, 18.76


Synonym: Vindorosine

IUPAC/Chemical Name: methyl 11-acetyloxy-12-ethyl-10-hydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

InChi Key: SASWULSUPROHRT-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H30N2O5/c1-5-22-11-8-13-26-14-12-23(18(22)26)16-9-6-7-10-17(16)25(3)19(23)24(29,21(28)30-4)20(22)31-15(2)27/h6-11,18-20,29H,5,12-14H2,1-4H3

SMILES Code: O=C(C1(O)C2N(C)C3=CC=CC=C3C(C45)2CCN5CC=CC4(CC)C1OC(C)=O)OC


Technical Data

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


References

1: Chen W, Yang XD, Tan WY, Zhang XY, Liao XL, Zhang H. Total Synthesis of (-)-Vindorosine. Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12327-12331. doi: 10.1002/anie.201707249. Epub 2017 Aug 24. PubMed PMID: 28782228.

2: Wu XL, Cheang WS, Zhang DM, Li Y, Lau CW, Wang GC, Huang Y, Ye WC. Antagonism of Ca2+ influx via L-type Ca2+ channels mediates the vasorelaxant effect of Catharanthus roseus-derived vindorosine in rat renal artery. Planta Med. 2014 Dec;80(18):1672-7. doi: 10.1055/s-0034-1383220. Epub 2014 Oct 23. PubMed PMID: 25340466.

3: Wang Y, Lin J, Wang X, Wang G, Zhang X, Yao B, Zhao Y, Yu P, Lin B, Liu Y, Cheng M. Brønsted Acid-Catalyzed Tandem Cyclizations of Tryptamine-Ynamides Yielding 1H-Pyrrolo[2,3-d]carbazole Derivatives. Chemistry. 2018 Mar 15;24(16):4026-4032. doi: 10.1002/chem.201705189. Epub 2018 Jan 10. PubMed PMID: 29168592.

4: Qu Y, Easson ML, Froese J, Simionescu R, Hudlicky T, De Luca V. Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proc Natl Acad Sci U S A. 2015 May 12;112(19):6224-9. doi: 10.1073/pnas.1501821112. Epub 2015 Apr 27. PubMed PMID: 25918424; PubMed Central PMCID: PMC4434687.

5: Sasaki Y, Kato D, Boger DL. Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues. J Am Chem Soc. 2010 Sep 29;132(38):13533-44. doi: 10.1021/ja106284s. PubMed PMID: 20809620; PubMed Central PMCID: PMC2944909.

6: Sears JE, Boger DL. Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications. Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27. PubMed PMID: 26813287; PubMed Central PMCID: PMC4755904.

7: Elliott GI, Velcicky J, Ishikawa H, Li Y, Boger DL. Total synthesis of (-)- and ent-(+)-vindorosine: tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles. Angew Chem Int Ed Engl. 2006 Jan 16;45(4):620-2. PubMed PMID: 16355429.

8: Büchi G, Matsumoto KE, Nishimura H. The total synthesis of (plus or minus)-vindorosine. J Am Chem Soc. 1971 Jun 30;93(13):3299-301. PubMed PMID: 5559600.

9: Deluca V, Balsevich J, Tyler RT, Kurz WG. Characterization of a novel N-methyltransferase (NMT) from Catharanthus roseus plants : Detection of NMT and other enzymes of the indole alkaloid biosynthetic pathway in different cell suspension culture systems. Plant Cell Rep. 1987 Dec;6(6):458-61. doi: 10.1007/BF00272782. PubMed PMID: 24248932.

10: Matsuoka J, Kumagai H, Inuki S, Oishi S, Ohno H. Construction of the Pyrrolo[2,3-d]carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide. J Org Chem. 2019 Jul 19;84(14):9358-9363. doi: 10.1021/acs.joc.9b01149. Epub 2019 Jun 17. PubMed PMID: 31244165.

11: Khoronenko VE, Malanova AS, Baskakov DS, Ryabov AB, Pikin OV. [Regional and peripheral blockades for prevention of chronic post-thoracotomy pain syndrome in oncosurgical practice]. Khirurgiia (Mosk). 2017;(8):58-63. doi: 10.17116/hirurgia2017858-63. Russian. PubMed PMID: 28805780.

12: Zhong XZ, Wang GC, Wang Y, Zhang XQ, Ye WC. [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus]. Yao Xue Xue Bao. 2010 Apr;45(4):471-4. Chinese. PubMed PMID: 21355212.

13: Ishikawa H, Elliott GI, Velcicky J, Choi Y, Boger DL. Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids. J Am Chem Soc. 2006 Aug 16;128(32):10596-612. PubMed PMID: 16895428; PubMed Central PMCID: PMC2531198.

14: Heureux N, Wouters J, Markó IE. Sequential acid/base-catalyzed polycyclization of tryptamine derivatives. A rapid access to Büchi's ketone. Org Lett. 2005 Nov 10;7(23):5245-8. PubMed PMID: 16268549.