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95200

Sigma-Aldrich

Vitamin B12a hydrochloride

≥96% (UV), ≥96% (HPLC)

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Synonym(s):
Hydroxocobalamin hydrochloride
Empirical Formula (Hill Notation):
C62H89CoN13O15P · HCl
CAS Number:
59461-30-2
Molecular Weight:
1382.82
EC Number:
261-772-4
MDL number:
MFCD00167463
UNSPSC Code:
12352205
PubChem Substance ID:
57653658
NACRES:
NA.79

biological source

fermentation/recombinant

Quality Level

100

Assay

≥96% (HPLC)
≥96% (UV)

form

powder or crystals

loss

≤12% loss on drying, 20 °C (HV)

color

red to dark red

solubility

methanol: 10 mg/mL at 20 °C, clear, dark red

storage temp.

2-8°C

SMILES string

Cl.C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)[C@H]2N([Co+]O)C1=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O)OP([O-])(=O)O[C@H]6[C@@H](O)[C@H](O[C@@H]6CO)n7cnc8cc(C)c(C)cc78

InChI

1S/C62H90N13O14P.ClH.Co.H2O/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;;;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);1H;;1H2/q;;+3;/p-3/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;;/m1.../s1

InChI key

KEHNCSYXYMMUCO-BXSGNKEGSA-K

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Application

Vitamin B12a hydrochloride has been used as an antidote for cyanide poisoning.

Biochem/physiol Actions

Vitamin B12 (cobalamin) refers to a group of chemically-related cobalt containing molecules involved in cell processes such as DNA synthesis, fatty acid synthesis, energy production and regulation. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms. Bacteria-derived hydroxocobalamin (OHCbl) and CNCbl are converted in humans to useful coenzyme forms to support metabolic processes such as mitochondrial methylmalonylcoenzyme A mutase conversion of methylmalonic acid (MMA) to succinate to link lipid and carbohydrate metabolism, and activation of methionine synthase, the rate limiting step in the synthesis of methionine.

Other Notes

Review

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S. Fukui et al.
Antibiotics, Vitamins and Hormones, 101-101 (1977)
Cisplatin analogs confer protection against cyanide poisoning
Nath AK, et al.
Cell Chemical Biology, 24(5), 565-575 (2017)
Jasmin Federizon et al.
Pharmaceutics, 13(1) (2021-01-21)
Cobalt porphyrin phospholipid (CoPoP) can incorporate within bilayers to enable non-covalent surface-display of antigens on liposomes by mixing with proteins bearing a polyhistidine tag (his-tag); however, the mechanisms for how this occurs are poorly understood. These were investigated using the
R Pace et al.
Clinical toxicology (Philadelphia, Pa.), 52(7), 647-650 (2014-08-05)
Pre-hospital administration of hydroxocobalamin (B12a) is used for empiric treatment of cyanide poisoning because cyanide poisoning is difficult to identify and requires immediate treatment. B12a interferes with the accuracy of several blood laboratory tests. This study aimed to explore how
Ruma Banerjee
ACS chemical biology, 1(3), 149-159 (2006-12-14)
Many coenzymes are vitamins that are assimilated in mammals into their active form from precursors obtained from the diet. They are often both rare and reactive rendering the likelihood low that the cell uses a collision-based strategy for their delivery
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