hemomin
Vitamin B12
CAS: 68-19-9
Molecular Formula: C63H88CoN14O14P
hemomin - Names and Identifiers
| Name | Vitamin B12 |
| Synonyms | VB12 hemomin hepagon hepavis macrabin hepcovite lldfactor hepacon-b12 Vitamin B12 Cyanocobalamin lactobacilluslactisdornerfactor cyano-5,6-dimethylbenzimidazole-cobalamin 5,6-dimethyl-1-(3-o-phosphono-alpha-d-ribofuranosyl)-1h-benzimidazolmonoes |
| CAS | 68-19-9 |
| EINECS | 200-680-0 |
| InChI | InChI=1/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;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,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);;/q;;+2/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1/rC63H89CoN14O14P/c1-30-20-40-41(21-31(30)2)77(29-73-40)58-53(87)54(42(27-79)90-58)92-93(88,89)91-32(3)26-72-50(86)18-19-60(8)38(22-47(69)83)57-63(11)62(10,25-49(71)85)37(14-17-46(68)82)52(78(63)64-28-65)34(5)56-61(9,24-48(70)84)35(12-15-44(66)80)39(74-56)23-43-59(6,7)36(13-16-45(67)81)51(75-43)33(4)55(60)76-57/h20-21,23,29,32,35-38,42,53-54,57-58,79,87H,12-19,22,24-27H2,1-11H3,(H2,66,80)(H2,67,81)(H2,68,82)(H2,69,83)(H2,70,84)(H2,71,85)(H,72,86)(H,88,89)/q+1/p-1/b39-23+,51-33-,52-34-/t32?,35-,36-,37-,38+,42-,53-,54-,57-,58+,60-,61+,62+,63+/m1/s1 |
| InChIKey | RMRCNWBMXRMIRW-WZHZPDAFSA-L |
hemomin - Physico-chemical Properties
| Molecular Formula | C63H88CoN14O14P |
| Molar Mass | 1355.37 |
| Melting Point | >300°C |
| Boling Point | >300 °C |
| Specific Rotation(α) | 23656 -59 ± 9° (dil aq soln) |
| Flash Point | 9℃ |
| Water Solubility | Soluble |
| Solubility | Slightly soluble in water or ethanol, insoluble in chloroform or ether. |
| Appearance | Deep red crystal or crystalline powder |
| Color | Red to dark red |
| Exposure Limit | NIOSH: IDLH 25 mg/m3 |
| Merck | 14,10014 |
| BRN | 4122889 |
| pKa | pKa 3.28±0.04(H2O,D2O t=23±0.5 Iunspeci?ed) (Uncertain) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic. Keep cold and dry. |
| Sensitive | Hygroscopic |
| MDL | MFCD00151092 |
| Physical and Chemical Properties | Melting point> 300°C water-Soluble Soluble |
| Use | Mainly used for the treatment of megaloblastic anemia, malnutrition, hemorrhagic anemia, neuralgia and disorders |
hemomin - Risk and Safety
| Safety Description | S24/25 - Avoid contact with skin and eyes. |
| Toxicity | LD50 intravenous in mouse: 2gm/kg |
hemomin - Upstream Downstream Industry
| Downstream Products | Mecobalamin |
hemomin - Reference
| Reference Show more | 1. Han long, Ruan Guoxiang, Ma GeSI, et al. Chemical mutagenesis and antibiotic resistance screening of vitamin B12 producing bacteria [J]. Fine and specialty chemicals, 2019, 27(01):40-43. 2. Chen Yinbin, Wang Yufang, Hou Zhifang et al. Effects of Rg1 combined with B vitamins on NO release and Rg1 brain volume in mice with acute myocardial ischemia [J]. Specialty Research 2016(1):5-8. 3. Chen, Yin Bin, et al. "Effect of B- complex vitamins on the absolute activity and bio-availability of ginseng Re after oral administration." Journal of ginsen research 41.2 (2017): 209-214.https:// doi.org/10.1016/j. Jgr.3/006 2016 4. Li, Qingsi, et al. "Hemocompatible hemoadsorbent for effective removal of protein-bound toxin in serum." Journal of colloid and interface science 555 (2019): 145-156.https://doi.org/10.1016/j.jcis.2019.07.045 5. Xu, L., W. X. Cai, and B. J. Xu. "A systematic assesment on vitamins (B2, B12) and GABA profiles in fermented soy products marketed in China ." Journal of Food Processing and Preservation 41.5 (2017): e13126. 6. Zheng, Peihe, et al. "Influence of B- complex vitamins on the pharmacokinetics of ginsenosides Rg1, Rb1, and Ro after oral administration." Journal of medicinal food 20.11 (2017): 1127-1132.https://doi.org/10.1089/jmf.2017.3922 7. [IF=6.06] Yin Bin Chen et al."Effect of B- complex vitamins on the antifatigue activity and bioavailability of ginsenoside Re after oral administration."J Ginseng Res. 2017 Apr;41:209 8. [IF=2.786] Peihe Zheng et al."Influence of B- Complex Vitamins on the Pharmacokinetics of Ginsenosides Rg1, Rb1, and Ro After Oral Administration."J Med Food. 2017 Nov;20(11):1127-1132 9. [IF=2.19] L. Xu et al."A Systematic Assesment on Vitamins (B2, B12) and GABA Profiles in Fermented Soy Products Marketed in China."J Food Process Pres. 2017 Oct;41(5):e13126 |
hemomin - Nature
Open Data Verified Data
deep red crystal or crystalline powder. No bromine, tasteless. No melting at 300 ℃. The color darkened at 210-220 °c. Hygroscopic, in the air can absorb 12% of water, the water-containing crystals in the air stability. Soluble in water and alcohol, insoluble in acetone, chloroform and ether. Its water-soluble neutral, pH 4.5~5 when the most stable. In alkaline or strong acidic solution can be slowly hydrolyzed.
Last Update：2024-01-02 23:10:35
hemomin - Preparation Method
Open Data Verified Data
by Streptomyces griseus fermentation, fermentation broth by acidification, adsorption, elution, purification, conversion with 1% cyanide, and then by solvent and water repeated extraction, concentration, chromatography, obtained by crystallization.
Last Update：2022-01-01 10:10:40
hemomin - Use
Open Data Verified Data
used as a feed Nutrition Fortifier. Anti-anemia, pernicious anemia, nutritional anemia, parasitic anemia are effective.
Last Update：2022-01-01 10:10:41
hemomin - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | vitamin B12, referred to as VB12, also known as cobalamin, one of the B vitamins, it is a kind of complex organic compounds containing cobalt, and the trivalent cobalt is located in the center of the flat surface of the porphyrin like. It is the largest and most complex vitamin molecule that has been found, and it is the only vitamin containing metal ions. Its crystal is red, so it is also called red vitamin. The plant does not contain VB12, and VB12 cannot be produced. Liver is the best source of VB12, followed by milk, meat, eggs, fish and so on. VB12 is an essential coenzyme in the synthesis of ribonucleic acid and deoxyribonucleic acid. Deficiency of VB12 in vivo can cause pathological changes of peripheral nerve and central encephalopathy. The prototype of a family of natural cobalt coordination compounds, known as corrinoids. Analogs of vitamin B12 differ only in the beta ligand of cobalt and are called cobalamin. Almost completely synthesized by bacteria. Dietary sources include fish, meat, liver, and dairy products; There is little or no cobalamin in plants. Methylcobalamin and cobalamin, as cofactors of enzymes, are converted into their biologically active forms by the body. Severe deficiency can lead to megaloblastic anemia and/or nerve damage. The discovery of vitamin B12 should first be attributed to the research work in the treatment of a pernicious anemia disease named after the British physician Addison. The pernicious anemia was an incurable disease at that time, and it was discovered by Minot and Murray in 1926that the disease could be cured by the ingestion of large amounts of liver, for which they received the Nobel Prize in Physiology and Medicine in 1934. This pernicious anemia was successfully treated with liver concentrates following the discovery of Minot and Murray. In 1948, the United States Riches, the United Kingdom Smith and Parker and others were isolated from the liver concentrate of a Red Crystal, named vitamin B12. In the same year, R. West of Columbia University in the United States proved that pernicious anemia can be effectively treated by vitamin B12 injection. Subsequently, in 1955, D. Hodgkin et al. determined the crystal structure of vitamin B12 using X-ray analysis. He also received the 1964 Nobel Prize in Chemistry. In 1972, Woodward successfully completed the total synthesis of vitamin B12. Figure 1 sources of vitamin B12 |
| Character | This product is deep red crystal or crystalline powder, odorless, tasteless, and has strong hygroscopicity. Slightly soluble in water or ethanol, insoluble in chloroform or ether. Heat resistance, but in the case of oxidation or reduction of substances (such as vitamin C or hydrogen peroxide, etc.), heavy metal salts and strong acids, strong bases, can be ineffective. |
| Chemical Structure | vitamin B12 is an isooctahedral compound containing cobalt ions, whose central structure is composed of four pyrroles. Linked to the composition of the planar ring (corrin ring). The molecule of vitamin B12 consists essentially of 3 parts: a ring of 4 N atoms chelated with a central cobalt ion; 5, 6-dimethylbenzimidazole (5, 6-dimethlbenzimidazole, DMBI) as the low (Alpha) ligand of the vitamin B12 molecule, DMBI is linked to aminopropanol via a phosphate group via a N-7 atom and a cobalt ion, aminopropanol is covalently linked to the propionic acid side chain on pyrrole D; Adenosine (adenosyl group) or methyl (methyl group) and cobalt ions are linked to form the upper (β) ligand of the vitamin B12 molecule. Different types of vitamin B12 are formed by different ligands above the axis of the ring. Hydroxyl (-OH) linked to cobalt ions in the ring of the azoline to form hydroxycobalamin, similarly, deoxyadenosine (5 '-deoxyadenosyl), methyl (-CH3), cyano (-CN) groups are linked to cobalt ions to produce adenosylcobalamin, methylcobalamin and cyanocobalamin, respectively. In nature, the final forms of vitamin B12 biosynthesized by microorganisms are adenosylcobalamin (coenzyme B12), methylcobalamin and hydroxocobalamin. However, since their properties are not very stable, sodium cyanide is artificially added during the industrial purification process to convert the natural form of vitamin B12 into the more stable cyanocobalamin. Figure 2 shows the structure of vitamin B12 |
| physiological function | 1. Improve the utilization rate of folic acid, synthesis of methionine (synthesized by homocysteine) and choline together with folic acid, synthesis of cyanocobalamin pro-precursor substances such as methyl cobalt amine and coenzyme B12 in the process of producing purine and pyrimidine, it is involved in the methylation process of many important compounds. In vitamin B12 deficiency, the activity of transferring methyl groups from methyltetrahydrofolate decreases, rendering the folate into an unusable form, resulting in folate deficiency. 2. Maintain the metabolism and function of nerve myelin. Lack of vitamin B12, can cause neurological disorders, spinal cord degeneration, and can cause serious mental symptoms. Vitamin B12 deficiency can lead to peripheral neuritis. The early manifestations of vitamin B12 deficiency in children are emotional abnormalities, dull expression, slow response, and eventually lead to anemia. 3. Promote the development and maturation of red blood cells. Methylmalonyl-CoA is converted to succinyl-CoA, which is involved in the tricarboxylic acid cycle, where succinyl-CoA is involved in the synthesis of heme. Vitamin B12 is also involved in deoxynucleic acid (DNA) synthesis, fat, carbohydrate and protein metabolism, increase nucleic acid and protein synthesis. (2016-01-22) |
| uses | a prototype of a family of naturally occurring cobalt coordination compounds is termed cooline-like. Analogs of vitamin B12 differ only in the beta-ligand of cobalt, called cobalamin. Almost completely synthesized by bacteria. Dietary sources include fish, meat, liver, and dairy products; Plants have little or no cobalamin. The body converts it into a biologically active form, namely methylcobalamin and cobalamin, which serve as enzyme cofactors. Severe deficiency may lead to megaloblastic anemia and/or neurological dysfunction. vitamin B12 deficiency can lead to anemia and neurological disorders. Can be used for infant food, the use of 10~30g/kg; In the fortified drink in the use of 2~6g/kg. It is mainly used for the treatment of megaloblastic anemia, malnutrition, hemorrhagic anemia, neuralgia and obstructive diseases as a feed Nutrition Fortifier, it has anti-anemia effect on pernicious anemia, nutritional anemia, parasitic anemia were effective dosage of 15-30mg/t. vitamin B12 is an essential vitamin in the metabolism of human tissues. The average total amount of vitamin B12 in the human body is 2-5mg, of which 50-90% is stored in the liver and released into the blood to form red blood cells when needed by the body. Long-term B12 deficiency can lead to pernicious anemia. B12 and folic acid are important enzymes in the process of nucleic acid synthesis, which are involved in the synthesis of purine, pyrimidine, nucleic acid and methionine, and can transfer methyl groups to promote the synthesis of alkali; at the same time, it can increase the synthesis of sugar geography, so as to eliminate the role of liver fat. Clinical often as the treatment of liver disease drugs. The human body needs about 2 micrograms of vitamin B121 micrograms per day, which can provide 2 micrograms of food to ensure normal needs. Vitamin B12 in the hydroxycobalt can react with cyanide, cobalt cyanide acid, which can eliminate the toxicity of cyanide. Therefore, the sensitivity of vitamin B12 deficiency to cyanide is higher than that of the general population. Vitamin B12 is mainly used for the treatment of pernicious anemia, megaloblastic anemia, anemia and polyneuritis, etc. |
| vitamin B12 deficiency | 1. Reasons for vitamin B12 deficiency (1) too little intake of vitamin B12 cannot be synthesized. Dietary vitamin B12 comes from animal food, milk and dairy products are less, plant food is basically free of vitamin B12. Vegetarians are more prone to vitamin B12 deficiency than non-vegetarians. Vitamin B12 intake is positively correlated with serum vitamin B12 levels. A mother's vitamin B12 deficiency or inadequate intake may be due to low levels of vitamin B12 in the milk of the baby's vitamin B12 deficiency. (2) malabsorption of the elderly prone to vitamin B12 deficiency, about 60% is due to gastrointestinal causes caused by food in the combination of cobalamin malabsorption. Taking more than 12 to 30 μg of synthetic vitamin B12 per day can reduce the risk of low vitamin B12 and high MMA in the elderly. Oral administration of large doses of vitamin B12 can normalize MMA in most vitamin B12 deficient elderly people. (3) internal factor deficiency vitamin B12 needs to be combined with internal factor to be finally absorbed. Patients with pernicious anemia develop autoimmune antibodies to intrinsic factors, which can lead to severe vitamin B12 deficiency. (4) other antiepileptic drugs, metformin, histamine H2 receptor inhibitors and proton pump inhibitors, hereditary cobalt amine transfer protein II deficiency, tropical oral diarrhea, Helicobacter pylori infection, parasitic infection, etc, it can also lead to a deficiency of vitamin B12. Vitamin B12 deficiency and disease (1) anemia vitamin B12 deficiency caused by anemia, with the lack of folic acid, is also megaloblastic anemia. However, vitamin B12 deficiency status was not associated with anemia in both the elderly and those with low intake of animal-derived foods. Vitamin B12 supplementation for people with vitamin B12 deficiency does not affect complete blood counts. (2) hyperhomocysteinemia blood total homocysteine concentration of more than 10 μmol /L can increase the risk of atherosclerosis and venous thrombosis. Vitamin B12 is involved in the methylation metabolism of homocysteine and is an essential cofactor for methionine synthetase, an enzyme that catalyzes the methylation of homocysteine. The concentrations of vitamin B12 and folic acid were related to the concentration of homocysteine in blood. In the Indian vegetarian population, a high Incidence Rate of coronary artery disease is associated with vitamin B12 deficiency. In patients with diabetic retinopathy, vitamin B12 deficiency is associated with high homocysteine, and vitamin B12 deficiency may be an independent risk factor for diabetic retinopathy. But vitamin B12 does not reduce the risk of cardiovascular disease or diabetes. (3) neuropsychiatric diseases vitamin B12 and folic acid play an important role in maintaining the normal function of the central nervous system (CNS). SAM is an important donor of methyl groups in the brain, and the imbalance of methylation is one of the causes of neurological and mental diseases. Hyperhomocysteinemia is also a cause of CNS disorders, associated with Cognitive Disorder. Vitamin B12 or folate deficiency can lead to an increase in homocysteine concentration and interfere with the methylation state. MMA is also toxic to the nervous system. Vitamin B12 and folic acid have protective effects on CNS disorders, mood disorders and dementia in the elderly (including vascular dementia and Alzheimer's dementia), while other studies have shown negative results. Although a large body of literature has shown that B vitamins are associated with homocysteine, cognitive and emotional disorders, and dementia, even if they can reduce homocysteine levels, there is no clear evidence in randomised controlled trials that vitamin B12 and folic acid supplements improve by Cognitive Disorder dementia, nor depressive symptoms. (4) birth and birth defects Folic acid is a protective factor for neural tube defects (NTD), and vitamin B12, which is closely related to folate metabolism, is also an independent risk factor for NTD. Vitamin B12 deficiency is also one of the risk factors of early pregnancy abortion, Recurrent Abortion. In the neonatal period, vitamin B12 deficiency can seriously impair the development and function of the nervous system. Infants often show growth retardation and neurological defects rather than anemia. Once vitamin B12 deficiency occurs in infants, low levels of vitamin B12 will persist for at least one year. Even if vitamin B12 deficiency is corrected early, these children may still exhibit long-term neurological and cognitive impairment, including irritability, anorexia, growth retardation, developmental regression and mental retardation. (5) other vitamin B12 deficiency may increase the chance of some cancers. Vitamin B12 and bone mineral density may be related, but the results of different studies are not consistent. |
| Application | 1. Medical and health care applications are mainly used to treat a variety of VB12 deficiency, such as: can treat megaloblastic anemia, anemia caused by drug poisoning, aplastic anemia and leukopenia; Use with pantothenic acid, can prevent pernicious anemia, contributes to the absorption of Fe2 and the secretion of gastric acid; Is also used in the treatment of arthritis, facial nerve palsy, trigeminal neuralgia, hepatitis, herpes, asthma and other allergies, allergic dermatitis, hives, eczema and bursitis; VB12 can also be used in the treatment of neuroticism, irritability, Sleep Initiation and Maintenance Disorders, memory impairment, depressive disorders. New research shows that VB12 deficiency can also cause mental illness such as depression. VB12 as a therapeutic agent or health care products is very safe, more than RDA thousands of times more than VB12 by intravenous or intramuscular injection found no poisoning phenomenon. 2. The application of VB12 in feed can promote the growth and development of poultry and livestock, especially young birds and animals, and improve the utilization rate of feed protein, which can be used as a feed additive. Treatment of fish eggs or larvae with VB12 aqueous solution can improve the tolerance of fish to toxic substances such as benzene and heavy metals in water by Mortality Rate. Since the European "mad cow disease" incident, the use of vitamins and other chemical structure of the Nutrition Fortifier to replace the "meat and bone meal" has a greater space for development. Most of the VB12 produced in the world is currently used in the feed industry. In other applications in developed countries, VB12 and other substances used in cosmetics; In the food industry, VB12 can be used as ham, sausage, ice cream, fish sauce and other food colorants. In family life, the VB12 solution is adsorbed on activated carbon, zeolite, non-woven fiber or paper, or made into soap, toothpaste, etc.; Can be used in toilets, refrigerators, etc, elimination of sulfide and aldehyde odor; VB12 can also be used for environmental protection in soil and surface water common pollutants-organic halide dehalogenation. |
| content analysis | approximately 30 mg of a sample accurately weighed was transferred into a mL volumetric flask with water and mixed until the volume was set. Another accurate weighing Pharmacopoeia Grade Vitamin B12 reference standard sample, dissolved in water, and then gradually diluted with water to a concentration of about 30 μg/ml standard solution. Water was used as a blank test, and the absorbance of the two solutions in the 1 cm cuvette was measured at the maximum absorption wavelength (about 361NM) with a suitable spectrophotometer. The content (mg) of vitamin B12(C63 H88CoNl4O14P) in the sample was calculated according to the following formula. Vitamin B12 content (mg)= c×au/As Formula C is the concentration of reference standard solution, its unit is μg/ml; au and As are the absorbance of the sample solution and the reference standard solution, respectively. |
| toxicity | GRAS(FDA,§ 182.5945,2000). |
| Use limit | GB 14880-94: infant food, fortified beverage 10-15 μg/kg. FDA,§ 184.1945(2000): limited to (3MP). GB 2760-2002(μg/kg): soft drinks 0.6~1.8; Ready-to-use breakfast cereals 5~10; Jelly 2.0~6.0; Cocoa powder and other flavored nutritional solid beverages, 1~6.6 (the corresponding nutritional milk drinks according to the dilution ratio to reduce the use of). |
| production method | a large amount of vitamin B12 can be synthesized by actinomycetes such as Streptomyces cinerea, the culture broth of such bacteria is industrially used to produce vitamin B12. The total synthesis of vitamin B12 was carried out by R.B. Wood in 1973, which is a very prominent work in organic synthesis. (1) by Streptomyces griseus fermentation preparation, fermentation broth acidification with weak acid acrylic acid cation exchange resin -122 adsorption, followed by elution, purification, conversion with 1% Cyanide, the product was obtained by repeated extraction with solvent and water, lead oxide chromatography and acetone crystallization. (2) using glucose and corn steep liquor as raw materials, the fermentation was carried out by inoculating Propionibacterium hermarii. Cobalt chloride and 5,6-2 methyl benzimidazole were added to the fermentation broth, and the product was obtained by extraction and drying. prepared by fermentation of Streptomyces griseus, the fermentation broth was acidified and then adsorbed with weak acid acrylic cation exchange resin -122, followed by elution, purification, conversion with 1% Cyanide, repeated extraction with solvent and water, concentration, lead oxide chromatography, acetone crystallization to obtain the finished product. Glucose and corn steep liquor were used as raw materials to inoculate Propionibacterium hermarii for fermentation. Cobalt chloride and 5, 6-dimethylbenzimidazole were added to the fermentation broth, and the product was obtained by extraction and drying. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:07
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Downstream Products for hemomin