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Merck

C0884

Coenzyme B12

≥97.0%

Synonym(s):

5′-Deoxyadenosylcobalamine, Adenosyl cobalamine, Cobamamide, DMBC coenzyme

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25 MG

₪397.00

100 MG

₪637.00

250 MG

₪1,271.00

1 G

₪4,360.00

₪397.00

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About This Item

Empirical Formula (Hill Notation):
C72H100CoN18O17P
CAS Number:
13870-90-1
Molecular Weight:
1579.58
UNSPSC Code:
12352205
NACRES:
NA.79
PubChem Substance ID:
24892282
EC Number:
237-627-6
Beilstein/REAXYS Number:
4122932
MDL number:
MFCD00135609

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InChI key

ZIHHMGTYZOSFRC-PMDPKNCCSA-L

InChI

1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;4-,6-,7-,10+;/m11./s1

SMILES string

CC(CNC(=O)CCC1(C)C(CC(N)=O)C2N([Co+]C[C@H]3O[C@@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)C1=C(C)C6=NC(=CC7=NC(=C(C)C8=NC2(C)C(C)(CC(N)=O)C8CCC(N)=O)C(C)(CC(N)=O)C7CCC(N)=O)C(C)(C)C6CCC(N)=O)OP([O-])(=O)O[C@H]9[C@@H](O)[C@H](O[C@@H]9CO)n%10cnc%11cc(C)c(C)cc%10%11

assay

≥97.0%

form

powder and chunks

technique(s)

HPLC: suitable

color

red to very dark red, very dark red-brown

storage temp.

−20°C

Quality Level

100

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Show Differences

1 of 4

This Item
M9756H8017C3607
Coenzyme B12 ≥97.0%

Sigma-Aldrich

C0884

Coenzyme B12

Methylcobalamin vitamin B12 analog

Sigma-Aldrich

M9756

Methylcobalamin

Hydroxocobalamin acetate vitamin B12 analog

Sigma-Aldrich

H8017

Hydroxocobalamin acetate

Cyanocobalamin meets USP testing specifications

Sigma-Aldrich

C3607

Cyanocobalamin

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

-

assay

≥97.0%

assay

≥97%

assay

≥95% (HPLC)

assay

96.0-102.0% dry basis

form

powder and chunks

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

color

red to very dark red, very dark red-brown

color

red to very dark red

color

red to brown

color

dark red

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

General description

Vitamin B12 cobalamin refers to a group of chemically-related cobalt containing molecules.[1] The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms.

Application

Coenzyme B12 has been used as a supplement for culturing plasmid variants in in vivo assay of yvrC-lacZ fusions.[2]

Biochem/physiol Actions

Vitamin B12 cobalamin is involved in DNA synthesis and fatty acid synthesis.[1][3] It also plays a vital role as a coenzyme in the conversion of mitochondrial methylmalonyl co-enzyme A to succinyl co-enzyme A.[1]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5011V
0000175013
0000151495
0000151494
0000151496

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Peter Friedrich et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(50), 16114-16122 (2012-10-20)
Coenzyme B(12) can assist radical enzymes that accomplish the vicinal interchange of a hydrogen atom with a functional group. It has been proposed that the Co-C bond homolysis of coenzyme B(12) to cob(II)alamin and the 5'-deoxyadenosyl radical is aided by hydrogen bonding
J R Roth et al.
Annual review of microbiology, 50, 137-181 (1996-01-01)
This review examines deoxyadenosylcobalamin (Ado-B12) biosynthesis, transport, use, and uneven distribution among living forms. We describe how genetic analysis of enteric bacteria has contributed to these issues. Two pathways for corrin ring formation have been found-an aerobic pathway (in P.
Jiayun Pang et al.
Journal of the American Chemical Society, 134(4), 2367-2377 (2012-01-14)
We present here an energetic and atomistic description of how D-ornithine 4,5-aminomutase (OAM), an adenosylcobalamin (AdoCbl; coenzyme B(12))-dependent isomerase, employs a large-scale protein domain conformational change to orchestrate the homolytic rupture of the Co-C bond. Our results suggest that in
Alla Peselis et al.
Nature structural & molecular biology, 19(11), 1182-1184 (2012-10-16)
Coenzyme B(12) has a key role in various enzymatic reactions and controls expression of bacterial genes through riboswitches. Here we report the crystal structure of the Symbiobacterium thermophilum B(12) riboswitch bound to its ligand adenosylcobalamin. The riboswitch forms a unique
Denis Bucher et al.
Journal of the American Chemical Society, 134(3), 1591-1599 (2012-01-11)
Vitamin B(12) and its biologically active counterparts possess the only examples of carbon-cobalt bonds in living systems. The role of such motifs as radical reservoirs has potential application in future catalytic and electronic nanodevices. To fully understand radical generation in
View All Related Papers

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. What is the pH stability of adenosylcobalamine?

    1 answer

    1. The pH stability of this product in solution has not been determined.

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