Vicine

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

MedKoo CAT#: 585374

CAS#: 152-93-2

Description: Vicine is an alkaloid glycoside found mainly in fava beans (Vicia faba). Vicine is toxic in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. It causes hemolytic anemia, called favism.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-02-28. Prices are subject to change without notice.

Vicine 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#: 585374
Name: Vicine
CAS#: 152-93-2
Chemical Formula: C10H16N4O7
Exact Mass: 304.1019
Molecular Weight: 304.259
Elemental Analysis: C, 39.48; H, 5.30; N, 18.41; O, 36.81


Synonym: Vicine

IUPAC/Chemical Name: InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1

InChi Key: KGNGTSCIQCLKEH-SYCVNHKBSA-N

InChi Code: InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1

SMILES Code: O=C1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C(N)N=C(N)N1


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: Arbid MS, Koriem KM, Asaad GF, Megahed HA. Effect of the antibiotic neomycin on the toxicity of the glycoside vicine in rats. J Toxicol. 2013;2013:913128. doi: 10.1155/2013/913128. Epub 2013 Jun 12. PubMed PMID: 23840205; PubMed Central PMCID: PMC3694484.

2: Lessire M, Gallo V, Prato M, Akide-Ndunge O, Mandili G, Marget P, Arese P, Duc G. Effects of faba beans with different concentrations of vicine and convicine on egg production, egg quality and red blood cells in laying hens. Animal. 2017 Aug;11(8):1270-1278. doi: 10.1017/S1751731116002688. Epub 2016 Dec 29. PubMed PMID: 28031067; PubMed Central PMCID: PMC5523731.

3: Rizzello CG, Losito I, Facchini L, Katina K, Palmisano F, Gobbetti M, Coda R. Degradation of vicine, convicine and their aglycones during fermentation of faba bean flour. Sci Rep. 2016 Aug 31;6:32452. doi: 10.1038/srep32452. PubMed PMID: 27578427; PubMed Central PMCID: PMC5006014.

4: Farran MT, Darwish AH, Uwayjan MG, Sleiman FT, Ashkarian VM. Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks. Int J Toxicol. 2002 May-Jun;21(3):201-9. PubMed PMID: 12055021.

5: Arbid MS, Madhyastha MS, Marquardt RR, Frohlich AA. Effect of neomycin on the hydrolysis and toxicity of vicine and convicine in rats. Food Chem Toxicol. 1993 Nov;31(11):835-40. PubMed PMID: 8258412.

6: Pulkkinen M, Zhou X, Lampi AM, Piironen V. Determination and stability of divicine and isouramil produced by enzymatic hydrolysis of vicine and convicine of faba bean. Food Chem. 2016 Dec 1;212:10-9. doi: 10.1016/j.foodchem.2016.05.077. Epub 2016 May 13. PubMed PMID: 27374500.

7: Luzzatto L, Arese P. Favism and Glucose-6-Phosphate Dehydrogenase Deficiency. N Engl J Med. 2018 Jan 4;378(1):60-71. Review. PubMed PMID: 29298156.

8: Naber EC, Vogt H, Harnish S, Krieg R, Ueberschaer KH, Rauch HW. Reproductive performance of hens fed field beans and potential relationships to vicine metabolism. Poult Sci. 1988 Mar;67(3):455-62. PubMed PMID: 3405925.

9: Abd Allah MA, Foda YH, Abu Salem FM, Abd Allah ZS. Treatments for reducing total vicine in Egyptian faba bean (Giza 2 variety). Plant Foods Hum Nutr. 1988;38(3):201-10. PubMed PMID: 3237624.

10: Muduuli DS, Marquardt RR, Guenter W. Effect of dietary vicine and vitamin E supplementation on the productive performance of growing and laying chickens. Br J Nutr. 1982 Jan;47(1):53-60. PubMed PMID: 7059568.

11: Getachew F, Vandenberg A, Smits J. A practical toxicity bioassay for vicine and convicine levels in faba bean (Vicia faba). J Sci Food Agric. 2018 Oct;98(13):5105-5111. doi: 10.1002/jsfa.9049. Epub 2018 May 17. PubMed PMID: 29611201.

12: Pedersen JZ, Musci G, Rotilio G. Electron spin resonance characterization of the radicals produced by enzymatic or chemical cleavage of vicine. Biochemistry. 1988 Nov 15;27(23):8534-6. PubMed PMID: 19177687.

13: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK532498/ PubMed PMID: 30372002.

14: Purves RW, Khazaei H, Vandenberg A. Quantification of vicine and convicine in faba bean seeds using hydrophilic interaction liquid chromatography. Food Chem. 2018 Feb 1;240:1137-1145. doi: 10.1016/j.foodchem.2017.08.040. Epub 2017 Aug 15. PubMed PMID: 28946235.

15: Gallo V, Skorokhod OA, Simula LF, Marrocco T, Tambini E, Schwarzer E, Marget P, Duc G, Arese P. No red blood cell damage and no hemolysis in G6PD-deficient subjects after ingestion of low vicine/convicine Vicia faba seeds. Blood. 2018 Apr 5;131(14):1621-1625. doi: 10.1182/blood-2017-09-806364. Epub 2018 Feb 21. PubMed PMID: 29467185.

16: Monteiro HP, Winterbourn CC. Release of iron from ferritin by divicine, isouramil, acid-hydrolyzed vicine, and dialuric acid and initiation of lipid peroxidation. Arch Biochem Biophys. 1989 Jun;271(2):536-45. PubMed PMID: 2730003.

17: Purves RW, Khazaei H, Vandenberg A. Toward a high-throughput method for determining vicine and convicine levels in faba bean seeds using flow injection analysis combined with tandem mass spectrometry. Food Chem. 2018 Aug 1;256:219-227. doi: 10.1016/j.foodchem.2018.02.104. Epub 2018 Feb 21. PubMed PMID: 29606441.

18: Burbano C, Cuadrado C, Muzquiz M, Cubero JI. Variation of favism-inducing factors (vicine, convicine and L-DOPA) during pod development in Vicia faba L. Plant Foods Hum Nutr. 1995 Apr;47(3):265-75. PubMed PMID: 7659704.

19: Winterbourn CC, Cowden WB, Sutton HC. Auto-oxidation of dialuric acid, divicine and isouramil. Superoxide dependent and independent mechanisms. Biochem Pharmacol. 1989 Feb 15;38(4):611-8. PubMed PMID: 2537083.

20: Olaboro G, Marquardt RR, Campbell LD, Fröhlich AA. Purification, Identification and quantification of an Egg-weight-depressing factor (vicine) in fababeans (Vicia faba L.). J Sci Food Agric. 1981 Dec;32(12):1163-71. PubMed PMID: 7321530.