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H8017

Sigma-Aldrich

Hydroxocobalamin acetate

vitamin B12 analog

Synonym(s):

Vitamin B12a acetate

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About This Item

Empirical Formula (Hill Notation):
C64H91CoN13O16P
CAS Number:
22465-48-1
Molecular Weight:
1388.39
EC Number:
245-019-7
MDL number:
MFCD00082532
UNSPSC Code:
12352205
eCl@ss:
34058004
PubChem Substance ID:
329815248
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

Assay

≥95% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

red to brown

storage temp.

2-8°C

SMILES string

CC(CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)[C@H]2N=C1C(C)=C3N=C(C=C4N=C(C(C)=C5[C@@H](CCC(N)=O)[C@](C)(CC(N)=O)[C@@]2(C)N5[Co]OC(C)=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.C2H4O2.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(3)4;/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);1H3,(H,3,4);/q;;+2/p-3/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1

InChI key

QHSPIHUMLGFPKX-WYVZQNDMSA-K

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General description

Hydroxocobalamin is an analog of vitamin B12 with OH as an alkyl group. Vitamin B12 cobalamin refers to a group of chemically-related cobalt containing molecules.

Biochem/physiol Actions

Vitamin B12 cobalamin is involved in DNA synthesis and fatty acid synthesis. It also plays a vital role as a coenzyme in the conversion of mitochondrial methylmalonyl co-enzyme A to succinyl co-enzyme A. Vitamin B12 cobalamin is also involved in neurotransmitter synthesis and erythropoiesis. It also functions in the synthesis and maintenance of myelin sheath. Hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

Hazard Classifications

Carc. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Photodegradation of cobalamins in aqueous solutions and in human blood
Juzeniene A and Nizauskaite Z
Journal of Photochemistry and Photobiology. B, Biology, 122(21), 7-14 (2013)
The effect of vitamin B12 deprivation on the enzymes of fatty acid synthesis
Frenkel E P, et al.
The Journal of Biological Chemistry, 248(21), 7540-7546 (1973)
Iron, vitamin B12 and folate
Moll R and Davis B
Medicine, 45(4), 198-203 (2017)
Hydroxocobalamin association during cell culture results in pink therapeutic proteins
MAbs, 5(6), 974-981 (2013)
Mamoru Yamanishi et al.
Trends in biochemical sciences, 30(6), 304-308 (2005-06-14)
Many organic cofactors are both rare and reactive. They are usually in low abundance, which poses problems for efficient collision-based targeting to dependent enzymes, whereas their reactivity is problematic for side reactions. Sequestration and escorted delivery presents one solution to
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