Cyanocobalamin | CAS#68-19-9 | cobalt-containing coordination compound

MedKoo Cat#: 599059 | Name: Cyanocobalamin

Featured

Description:

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

Cyanocobalamin is a cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.

Chemical Structure

Cyanocobalamin

CAS#68-19-9

Theoretical Analysis

MedKoo Cat#: 599059

Name: Cyanocobalamin

CAS#: 68-19-9

Chemical Formula: C63H88CoN14O14P

Exact Mass: 0.0000

Molecular Weight: 1355.39

Elemental Analysis: C, 55.83; H, 6.54; Co, 4.35; N, 14.47; O, 16.53; P, 2.29

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
2g	USD 550.00	2 Weeks
5g	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Cyanocobalamin; Vitamin B12; Docigram; NSC 80365; NSC-80365; NSC80365;

IUPAC/Chemical Name

cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,7S,12S,13S,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] phosphate;cyanide

InChi Key

SOTXWUBWSAORPH-WDAIGIHHSA-M

InChi Code

InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,74,76,84H,12-19,22,24-27H2,1-11H3,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);;/q2*-1;+3/p-1/b38-23-,50-32-,51-33-;;/t31-,34-,35-,36-,37+,41+,52+,53+,56-,57-,59-,60+,61+,62+;;/m1../s1

SMILES Code

CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)C(=C7[C@@]([C@@H](C(=N7)C=C8C([C@@H](C(=N8)C(=C4[N-]5)C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[C-]#N.[Co+3]

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Vitamin B12 plays a key role in the normal functioning of the brain and nervous system, and for the formation of blood.

In vitro activity:

The results indicated that vitamin B12 interacts with tau protein and prevents fibrillization of tau protein. Blocking the cysteine residues of tau confirmed the cysteine-mediated binding of vitamin B12 to tau and showed that binding to cysteine is essential for inhibitory effect of vitamin B12 on tau aggregation. Reference: ACS Chem Neurosci. 2017 Dec 20;8(12):2676-2682. https://pubmed.ncbi.nlm.nih.gov/28841372/

In vivo activity:

The parameters indicating diastolic function including E-wave deceleration rate (EWDR), isovolumic relaxation time (IVRT), and E’ were also normalized by B12 (Fig. 1f–h). Taken together, these data demonstrate that high-dose oral supplements of B12 prevent development of diabetic cardiomyopathy in the Elmo1H/H Ins2Akita/+ mice. Reference: Commun Biol. 2021; 4: 775. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8222371/

	Solvent	mg/mL	mM
Solubility
	DMSO	62.5	45.98
	Ethanol	100.0	73.56
	Water	11.7	8.58

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 1,355.39 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.

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. Rafiee S, Asadollahi K, Riazi G, Ahmadian S, Saboury AA. Vitamin B12 Inhibits Tau Fibrillization via Binding to Cysteine Residues of Tau. ACS Chem Neurosci. 2017 Dec 20;8(12):2676-2682. doi: 10.1021/acschemneuro.7b00230. Epub 2017 Sep 6. PMID: 28841372. 2. Alam P, Siddiqi MK, Chaturvedi SK, Zaman M, Khan RH. Vitamin B12 offers neuronal cell protection by inhibiting Aβ-42 amyloid fibrillation. Int J Biol Macromol. 2017 Jun;99:477-482. doi: 10.1016/j.ijbiomac.2017.03.001. Epub 2017 Mar 4. PMID: 28267610. 3. Kakoki M, Ramanathan PV, Hagaman JR, Grant R, Wilder JC, Taylor JM, Charles Jennette J, Smithies O, Maeda-Smithies N. Cyanocobalamin prevents cardiomyopathy in type 1 diabetes by modulating oxidative stress and DNMT-SOCS1/3-IGF-1 signaling. Commun Biol. 2021 Jun 23;4(1):775. doi: 10.1038/s42003-021-02291-y. PMID: 34163008; PMCID: PMC8222371. 4. Khastar H, Garmabi B, Zare Mehrjerdi F, Rahimi MT, Shamsaei N, Ali AH, Khorsand N, Khaksari M. Cyanocobalamin improves memory impairment via inhibition of necrosis and apoptosis of hippocampal cell death after transient global ischemia/reperfusion. Iran J Basic Med Sci. 2021 Feb;24(2):160-166. doi: 10.22038/IJBMS.2020.48447.11126. PMID: 33953854; PMCID: PMC8061327.

In vitro protocol:

In vivo protocol:

1. Kakoki M, Ramanathan PV, Hagaman JR, Grant R, Wilder JC, Taylor JM, Charles Jennette J, Smithies O, Maeda-Smithies N. Cyanocobalamin prevents cardiomyopathy in type 1 diabetes by modulating oxidative stress and DNMT-SOCS1/3-IGF-1 signaling. Commun Biol. 2021 Jun 23;4(1):775. doi: 10.1038/s42003-021-02291-y. PMID: 34163008; PMCID: PMC8222371. 2. Khastar H, Garmabi B, Zare Mehrjerdi F, Rahimi MT, Shamsaei N, Ali AH, Khorsand N, Khaksari M. Cyanocobalamin improves memory impairment via inhibition of necrosis and apoptosis of hippocampal cell death after transient global ischemia/reperfusion. Iran J Basic Med Sci. 2021 Feb;24(2):160-166. doi: 10.22038/IJBMS.2020.48447.11126. PMID: 33953854; PMCID: PMC8061327.

1: Prakasan V, Sanyal B, Pritamdas Chawla S, Chander R, Sharma A. Cyanocobalamin solutions as potential dosimeters in low-dose food irradiations. Appl Radiat Isot. 2014 Apr;86:97-101. doi: 10.1016/j.apradiso.2014.01.015. Epub 2014 Jan 30. PubMed PMID: 24530977. 2: Bito T, Ohishi N, Hatanaka Y, Takenaka S, Nishihara E, Yabuta Y, Watanabe F. Production and characterization of cyanocobalamin-enriched lettuce (Lactuca sativa L.) grown using hydroponics. J Agric Food Chem. 2013 Apr 24;61(16):3852-8. doi: 10.1021/jf305033s. Epub 2013 Apr 12. PubMed PMID: 23578327. 3: Pugliese RS, Slagle EJ, Oettinger GR, Neuburger KJ, Ambrose TM. Subacute combined degeneration of the spinal cord in a patient abusing nitrous oxide and self-medicating with cyanocobalamin. Am J Health Syst Pharm. 2015 Jun 1;72(11):952-7. doi: 10.2146/ajhp140583. PubMed PMID: 25987690. 4: Ahmad I, Qadeer K, Hafeez A, Bano R, Vaid FH. Multicomponent spectrometric assay of cyanocobalamin and its photoproduct hydroxocobalamin in the presence of ascorbic acid in photolyzed solutions. Pak J Pharm Sci. 2014 Mar;27(2):209-15. PubMed PMID: 24577904. 5: Goto Y, Masuda A, Aiba T. In vivo application of chitosan to improve bioavailability of cyanocobalamin, a form of vitamin B12, following intraintestinal administration in rats. Int J Pharm. 2015 Apr 10;483(1-2):250-5. doi: 10.1016/j.ijpharm.2015.02.016. Epub 2015 Feb 11. PubMed PMID: 25681732. 6: Ghazanfari S, Imenshahidi M, Etemad L, Moshiri M, Hosseinzadeh H. Effect of cyanocobalamin (vitamin B12) in the induction and expression of morphine tolerance and dependence in mice. Drug Res (Stuttg). 2014 Mar;64(3):113-7. doi: 10.1055/s-0033-1355364. Epub 2013 Oct 8. PubMed PMID: 24105105. 7: Ahmad I, Qadeer K, Zahid S, Sheraz MA, Ismail T, Hussain W, Ansari IA. Effect of ascorbic acid on the degradation of cyanocobalamin and hydroxocobalamin in aqueous solution: a kinetic study. AAPS PharmSciTech. 2014 Oct;15(5):1324-33. doi: 10.1208/s12249-014-0160-5. Epub 2014 Jun 12. PubMed PMID: 24920523; PubMed Central PMCID: PMC4179674. 8: Pereira RA, Silveira PA, Montagner P, Schneider A, Schmitt E, Rabassa VR, Pfeifer LF, Del Pino FA, Pulga ME, Corrêa MN. Effect of butaphosphan and cyanocobalamin on postpartum metabolism and milk production in dairy cows. Animal. 2013 Jul;7(7):1143-7. doi: 10.1017/S1751731113000013. Epub 2013 Jan 29. PubMed PMID: 23360824. 9: Thakkar K, Billa G. Treatment of vitamin B12 deficiency-methylcobalamine? Cyancobalamine? Hydroxocobalamin?-clearing the confusion. Eur J Clin Nutr. 2015 Jan;69(1):1-2. doi: 10.1038/ejcn.2014.165. Epub 2014 Aug 13. PubMed PMID: 25117994. 10: Baskakova A, Awwad S, Jiménez JQ, Gill H, Novikov O, Khaw PT, Brocchini S, Zhilyakova E, Williams GR. Electrospun formulations of acyclovir, ciprofloxacin and cyanocobalamin for ocular drug delivery. Int J Pharm. 2016 Apr 11;502(1-2):208-18. doi: 10.1016/j.ijpharm.2016.02.015. Epub 2016 Feb 17. PubMed PMID: 26899973. 11: Castelli MC, Wong DF, Friedman K, Riley MG. Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Clin Ther. 2011 Jul;33(7):934-45. doi: 10.1016/j.clinthera.2011.05.088. Epub 2011 Jul 1. PubMed PMID: 21722960. 12: Obeid R, Fedosov SN, Nexo E. Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency. Mol Nutr Food Res. 2015 Jul;59(7):1364-72. doi: 10.1002/mnfr.201500019. Epub 2015 May 12. Review. PubMed PMID: 25820384; PubMed Central PMCID: PMC4692085. 13: Abu-Soud HM, Maitra D, Byun J, Souza CEA, Banerjee J, Saed GM, Diamond MP, Andreana PR, Pennathur S. The reaction of HOCl and cyanocobalamin: corrin destruction and the liberation of cyanogen chloride. Free Radic Biol Med. 2012 Feb 1;52(3):616-625. doi: 10.1016/j.freeradbiomed.2011.10.496. Epub 2011 Nov 10. PubMed PMID: 22138102; PubMed Central PMCID: PMC3786219. 14: Albers U, Pedrero-Chamizo R, Meléndez A, Pietrzik K, Castillo MJ, González-Gross M. Efficacy of a 28-day oral cyanocobalamin supplementation on vitamin B status in Spanish institutionalized elderly. Int J Vitam Nutr Res. 2012 Apr;82(2):104-12. doi: 10.1024/0300-9831/a000099. PubMed PMID: 23065835. 15: Djuric V, Bogic M, Popadic AP, Spiric VT, Raskovic S. Anaphylactic reaction to hydroxycobalamin with tolerance to cyanocobalamin. Ann Allergy Asthma Immunol. 2012 Mar;108(3):207-8. doi: 10.1016/j.anai.2011.12.009. Epub 2012 Jan 11. PubMed PMID: 22374207. 16: Fürll M, Deniz A, Westphal B, Illing C, Constable PD. Effect of multiple intravenous injections of butaphosphan and cyanocobalamin on the metabolism of periparturient dairy cows. J Dairy Sci. 2010 Sep;93(9):4155-64. doi: 10.3168/jds.2009-2914. PubMed PMID: 20723690. 17: Schwertner HA, Valtier S, Bebarta VS. Liquid chromatographic mass spectrometric (LC/MS/MS) determination of plasma hydroxocobalamin and cyanocobalamin concentrations after hydroxocobalamin antidote treatment for cyanide poisoning. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Sep 15;905:10-6. doi: 10.1016/j.jchromb.2012.07.012. Epub 2012 Aug 9. PubMed PMID: 22939270. 18: Kartal O, Gulec M, Demirel F, Yesillik S, Caliskaner Z, Sener O. Vitamin B12 allergy and successful desensitisation with cyanocobalamin: a case report. Allergol Immunopathol (Madr). 2012 Sep-Oct;40(5):324-5. doi: 10.1016/j.aller.2011.10.003. Epub 2012 Jan 21. PubMed PMID: 22266142. 19: Spence JD. Metabolic vitamin B12 deficiency: a missed opportunity to prevent dementia and stroke. Nutr Res. 2016 Feb;36(2):109-16. doi: 10.1016/j.nutres.2015.10.003. Epub 2015 Oct 21. Review. PubMed PMID: 26597770. 20: Matte JJ, Guay F, Le Floc'h N, Girard CL. Bioavailability of dietary cyanocobalamin (vitamin B12) in growing pigs. J Anim Sci. 2010 Dec;88(12):3936-44. doi: 10.2527/jas.2010-2979. Epub 2010 Aug 13. PubMed PMID: 20709870.