Name: Hydroxocobalamin
SKU: 13422-51-0

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Basic Information

Molecular Structure:
CAS No.:	13422-51-0
Name:	Hydroxocobalamin

Formula:	C₆₂H₈₉CoN₁₃O₁₅P
Molecular Weight:	1347.44
Synonyms:	Cobinamide,dihydroxide, dihydrogen phosphate (ester), mono(inner salt), 3'-ester with5,6-dimethyl-1-a-D-ribofuranosyl-1H-benzimidazole;AlphaRedisol;Axlon;Ciplamin H;Cobalamin, hydroxo-;Cobalex;Cobalin H;Docclan;Docevita;Droxomin;Ducobee Hy;Hydrocobalamin;Hydrovit;Hydroxy vitamin B12;Hyxobamine;Neo-Betalin 12;Neo-Cytamen;Neo-Rojamin;OH-Duphar;Primabalt RP;Redisol H;Vibeden;Vitadurin;Vitamin B12a;
EINECS:	236-533-2
Melting Point:	200oC (decomposes)
Solubility:	Methanol: 10 mg/mL at 20 °C, clear, dark red
Appearance:	dark red crystal or crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	484.10000
LogP:	6.43870

Synthetic route

: aquocob(III)alamine

: 1310-73-2
sodium hydroxide

: 13422-51-0
hydroxocob(III)alamin

Conditions

Conditions	Yield
In water vitamin B12a reacted with NaOH in H2O;

: 13422-51-0
hydroxocob(III)alamin

: 7789-20-0
water-d2

: 74-86-2
acetylene

: vinylcobalamin-d3

Conditions

Yield

With titanium (III) citrate In water-d2 Schlenk technique; C2H2 was allowed to equilibrate for 4 h under Tris buffer in D2O (pD 9.4) and soln. of Ti(III) citrate in D2O; Co complex wasreacted with Ti(III) citrate (60 equiv.) in Tris buffer in D2O and inje cted; soln. was stirred for 1 h; extd. (phenol/CH2Cl2, 1/1); phenol extracts washed (distd. H2O); dild. with 1-butanol/CH2Cl2 (1/1); extd. (distd. H2O); lyophilized; dissolved in ammonium acetate buffer (pH 4); chromd. (buffer/MeCN, 95/5 to 70/30);

85%

...Expand

: 13422-51-0
hydroxocob(III)alamin

: 7732-18-5
water

: aquocob(III)alamine

Conditions

Conditions	Yield
With acetate or citrate buffer or aq. HClO4 In not given (N2); dissolving hydroxocobalamin in buffer or aq. HClO4;

: 13422-51-0
hydroxocob(III)alamin

: 19255-48-2
9-(2-chloroethyl)adenine

: 59209-78-8
(adenylethyl)cobalamine

Conditions

Yield

With NaBH4 In ethanol; water Soln. of NaBH4 in water was added to a soln. of hydroxocobalamine in water and 9-(2-chloroethyl)adenine in ethanol, mixt. was stirred for 30 min under N2;; excess NaBH4 was quenched with acetone, excess of the ligand was filtered; soln. was desalted on an Amberlite XAD-2 column; product was purified with a SP-Sephadex column, eluent - H2O; eluate was concd., product was pptd. by addn. of acetone;;

: 13422-51-0
hydroxocob(III)alamin

: 19255-49-3
9-(3-chloropropyl)-9H-purin-6-amine

: 34502-77-7
(adenylpropyl)cobalamine

Conditions

Yield

With NaBH4 In ethanol; water Soln. of NaBH4 in water was added to a soln. of hydroxocobalamine in water and 9-(3-chloropropyl)adenine in ethanol, mixt. was stirred for 30 min under N2;; excess NaBH4 was quenched with acetone, excess of the ligand was filtered; soln. was desalted on an Amberlite XAD-2 column; product was purified with a SP-Sephadex column, eluent - H2O; eluate was concd., product was pptd. by addn. of acetone;;

: 13422-51-0
hydroxocob(III)alamin

: 69293-19-2
N9-(4-chlorobutyl)adenine

: 21806-90-6
(adehylbutyl)cobalamine

Conditions

Yield

With NaBH4 In ethanol; water Soln. of NaBH4 in water was added to a soln. of hydroxocobalamine in water and 9-(4-chlorobutyl)adenine in ethanol, mixt. was stirred for 30 min under N2;; excess NaBH4 was quenched with acetone, excess of the ligand was filtered; soln. was desalted on an Amberlite XAD-2 column; product was purified with a SP-Sephadex column, eluent - H2O; eluate was concd., product was pptd. by addn. of acetone;;

: 13422-51-0
hydroxocob(III)alamin

: 53359-09-4
N9-(5-chloropentyl)adenine

: 56226-23-4
(adenylpentyl)cobalamine

Conditions

Yield

With NaBH4 In ethanol; water Soln. of NaBH4 in water was added to a soln. of hydroxocobalamine in water and 9-(5-chloropentyl)adenine in ethanol, mixt. was stirred for 30 min under N2;; excess NaBH4 was quenched with acetone, excess of the ligand was filtered; soln. was desalted on an Amberlite XAD-2 column; product was purified with a SP-Sephadex column, eluent - H2O; eluate was concd., product was pptd. by addn. of acetone;;

: 13422-51-0
hydroxocob(III)alamin

: 56575-56-5
4-bromo-but-1-ene-2,3-dicarboxylic acid

: Co(C19H6N4(CH3)8(C2H4C(O)NH2)3(CH2C(O)NH2)3(C2H4C(O)NHC2H3(CH3)PO4(C4H4O(CH2OH)(OH)(C7H3N2(CH3)2))))(CH2CH(COOH)2CCH2)

Conditions

Conditions	Yield
With zinc In methanol complex reduced with Zn dust in anaerobic MeOH contg. 10% NH4I in a centrifuge tube, injection of soln. of organic compd.;

: 13422-51-0
hydroxocob(III)alamin

: 56575-59-8
dimethyl β-bromomethylitaconate

: Co(C19H6N4(CH3)8(C2H4C(O)NH2)3(CH2C(O)NH2)3(C2H4C(O)NHC2H3(CH3)PO4(C4H4O(CH2OH)(OH)(C7H3N2(CH3)2))))(CH2CH(COOCH3)2CCH2)

Conditions

Conditions	Yield
With zinc In methanol complex reduced with Zn dust in anaerobic MeOH contg. 10% NH4I in a centrifuge tube, injection of organic compd.;

: 13422-51-0
hydroxocob(III)alamin

: 593-63-5
chloroacetylene

: cis-chlorovinylcobalamin

Conditions

Yield

With NaBH4; Co nitrate In water Schlenk technique; aq. soln. of NaBH4 was added to aq. soln. of hydroxocobalamin, Co nitrate under Ar; ClCCH was distd. at 25°C for 2 h; extd. (phenol/CH2Cl2, 1/1); phenol extracts washed (distd. H2O); dild. with 1-butanol/CH2Cl2 (1/1); extd. (distd. H2O); lyophilized; dissolved in ammonium acetate buffer (pH 4); chromd. (Vydec C18 protein and peptidecolumn; buffer/MeCN, 95/5 to 70/30);

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Chemistry

EINECS: 236-534-8
Empirical Formula: C₆₂H₈₉CoN₁₃O₁₅P
Molecular Weight: 1346.3551
Nominal Mass: 1345 Da
Average Mass: 1346.3551 Da
Monoisotopic Mass: 1345.56707 Da
Storage tempreture: 2-8 °C
Solubility: Methanol: 10 mg/mL at 20 °C, clear, dark red
Structure of Hydroxocobalamin (CAS NO.13422-51-0):

InChI
InChI=1/C62H90N13O14P.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);;1H2/q;+3;/p-3/t31-,34+,35+,36+,37-,41+,52+,53+,56?,57-,59+,60-,61-,62-;;/m0../s1/rC62H90CoN13O15P/c1-29-20-39-40(21-30(29)2)75(28-71-39)57-52(85)53(41(27-77)89-57)91-92(87,88)90-31(3)26-70-49(84)18-19-59(8)37(22-46(67)81)56-62(11)61(10,25-48(69)83)36(14-17-45(66)80)51(74-62)32(4)54-60(9,24-47(68)82)34(12-15-43(64)78)38(72-54)23-42-58(6,7)35(13-16-44(65)79)50(73-42)33(5)55(59)76(56)63-86/h20-21,23,28,31,34-37,41,52-53,56-57,77,85-86H,12-19,22,24-27H2,1-11H3,(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H2,69,83)(H,70,84)(H,87,88)/q+1/p-1/b42-23-,54-32-,55-33-/t31-,34+,35+,36+,37-,41+,52+,53+,56?,57-,59+,60-,61-,62-/m0/s1
Smiles
N1([C@@H]2[C@@]3([C@]([C@H](CCC(N)=O)C(=N3)C(=C3[C@]([C@H](CCC(N)=O)C(=N3)C=C3N=C(C(=C1[C@@]([C@H]2CC(N)=O)(CCC(NC[C@@H](OP(O[C@@H]1[C@H](O[C@@H]([C@@H]1O)n1c2c(cc(C)c(c2)C)nc1)CO)(=O)[O-])C)=O)C)C)[C@H](C3(C)C)CCC(N)=O)(CC(N)=O)C)C)(CC(N)=O)C)C)[Co+]O

Uses

Hydroxocobalamin (CAS NO.13422-51-0) is used in many pharmaceuticals, supplements and as food additive; and it has also been used in the treatment of cyanide poisoning. Hydroxocobalamin Injection USP, are used to rectify the following causes of B12 deficiency.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	> 50mg/kg (50mg/kg)		Drugs in Japan Vol. -, Pg. 867, 1990.

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

Specification

Hydroxocobalamin , its cas register number is 13422-51-0. It also can be called Vitamin B12b ; Ciplamin H ; and AlphaRedisol . It is a basic member of the cobalamin family of compounds, and is not a form normally found in the human body, but is easily converted in the body to usable coenzyme forms of B12. It is a term that refers to a group of compounds called cobalamins that are available in the human body in a variety of mostly interconvertible forms. Hydroxocobalamin (CAS NO.13422-51-0) is the form of B12 produced by many bacteria which are used to produce the vitamin commercially.

13422-51-0

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Chemistry

Uses

Toxicity Data With Reference

Safety Profile

Specification