Introduction：Basic information about Cocarboxylase CAS 154-87-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cocarboxylase Basic information
| Product Name: | Cocarboxylase |
| Synonyms: | ANEURINEPYROPHOSPHORIC ACID;COCARBOXYLASE;COCARBOXYLASE CHLORIDE;Thiamine, pyrophosphoric acid ester;[2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-5-yl]ethoxy-hydroxy-phosphoryl]oxyphosphonic acid chloride;Thiamine diphosphate chloride;Vitamin B1;Aneurinepyrophosphoric acid, Cocarboxylase, Thiamine pyrophosphate chloride |
| CAS: | 154-87-0 |
| MF: | C12H19ClN4O7P2S |
| MW: | 460.767382 |
| EINECS: | 205-836-1 |
| Product Categories: | API;Biochemistry;Vitamins;Vitamin Ingredients |
| Mol File: | 154-87-0.mol |
|
Cocarboxylase Chemical Properties
| Melting point | 240～241℃ |
| bulk density | 500kg/m3 |
| storage temp. | -20°C |
| solubility | H2O: soluble50mg/mL, clear to very slightly hazy, colorless |
| form | Solid |
| color | White to Off-White |
| PH | 1.0-1.4 (20°C, 100g/L in H2O) |
| Water Solubility | It is soluble in water. |
| BRN | 3875902 |
| Stability: | Hygroscopic |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChI | InChI=1S/C12H18N4O7P2S.ClH/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21);1H |
| InChIKey | YXVCLPJQTZXJLH-UHFFFAOYSA-N |
| SMILES | [Cl-].S1C([H])=[N+](C([H])([H])C2=C([H])N=C(C([H])([H])[H])N=C2N([H])[H])C(C([H])([H])[H])=C1C([H])([H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])O[H] |
| CAS DataBase Reference | 154-87-0(CAS DataBase Reference) |
| EPA Substance Registry System | Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride (154-87-0) |
Safety Information
| Safety Statements | 22-24/25 |
| RIDADR | 1759 |
| WGK Germany | 3 |
| RTECS | XI7552000 |
| F | 3-8-10 |
| TSCA | TSCA listed |
| HazardClass | 8 |
| PackingGroup | III |
| HS Code | 29362200 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Sens. 1 |
| Toxicity | LD50 intramuscular in mouse: > 1gm/kg |
Cocarboxylase Usage And Synthesis
| Originator | Actimide,Tobishi |
| History | Best known as the anti-beriberi factor and called at first simply vitamin B by McCollum, thiamine was shown to be involved in the decarboxylation of pyruvate to acetaldehyde in alcohol fermentation and was named ‘cocarboxylase’ in 1932. Confirmation of its structure as TPP came 5 years later. Its name is meant to signify a vitamin containing sulfur (thios in Greek). |
| Uses | Cocarboxylase can be used in decarboxylation mechanisms in biological systems,and to investigate radical reactions of thiamin pyrophosphate in 2-oxoacid oxidoreductases. |
| Uses | Thiamine Pyrophosphate (Cocarboxylase) is a thiamine (T344185) derivative produced by enzyme thiamine pyrophosphatase. Thiamine pyrophosphate is a cofactor used to catalyze various biochemical reactions. |
| Definition | The active coenzymeform of vitamin B1 which functions in aldehydetransfer reactions. |
| Manufacturing Process | 4.5 kg of aqueous 89% orthophosphoric acid are heated to 135°C, and keptat this temperature for about 3 h while being actively stirred. Then, theheating is discontinued and 3.5 kg of phosphorouspentoxide are added duringa period of 2.5 to 3 h, while being actively stirred. During this period, theinterior temperature rises to 165°-175°C. After completion of the addition ofphosphorouspentoxide, the stirring is continued until all phosphorouspentoxideis dissolved. The phosphoric acid mixture thus produced is subsequentlycooled down to 130°C.
At this temperature 2.0 kg of thiamine chloride hydrochloride (vitamin B1)were added during 2 to 3 h while being well stirred. The stirring is continuedat 130°C until the phosphorylated mixture no longer contains chlorine ions. Aphosphorylated melt is thus obtained. The thus obtained phosphorylation meltis dissolved in 6-8 L of water (with ice) at a temperature below 10°C, whilebeing vigorously stirred. The aqueous solution is stirred into 100 L of 96%alcohol and left standing overnight. The supernatant solvent is decanted fromthe separated syrup; the latter is taken up in 4 L of water. The solution thusobtained is fed, depending upon the volume of phosphoric acid containedtherein, to an exchanger column filled with anion exchanger (weak basic, forinstance Amberlite IRA 45, 20-30 L) (a polystyrene resin with primary,secondary and quaternary amino groups). The solution is caused to seep intothe column from the top thereof and is then washed with water until the runoff at the bottom no longer shows any thiamine reaction. About 25 L of thesolution are obtained, which are concentrated to 6 L at 30°C and 12 Torr. Theconcentrated residue is added to 20 to 30 L of a cationic exchanger (AmberliteIRC 50) in order to separate the thiamine-orthophosphoric acid ester from thethiamine-pyrophosphoric acid ester, and subsequently washed with water untilthe eluate is free of thiamine.
70-80 L of a solution are obtained which are concentrated to 1.5 L in acirculation evaporator at 30°C and 12 Torr. 7.5 L of 96% ethanol are slowlyadded to a concentrate while being stirred. The cocarboxylase-tetrahydrateseparates in the form of fine needles. The yield is 530.0 g with a melting pointof 220°-225°C (dec.).
10.0 g of cocarboxylase-tetrahydrate are dissolved in 25 ml of 5% aqueoushydrochloric acid, and 75 ml acetone are added dropwise while being stirred.The precipitated hydrochloride of the cocarboxylase, melting point 240°C issucked off. The yield is 9.5 g. |
| Therapeutic Function | Coenzyme, Metabolic |
| Biological Functions | Thiamine pyrophosphate, or cocarboxylase, functions as a cofactor in intermediary carbohydrate metabolism. It serves as a coenzyme in the decarboxylation of α-keto acids, that is, α-ketoglutaric acid and pyruvate dehydrogenase; it also acts as a cofactor to the enzyme transketolase in the hexose monophosphate shunt. Deficiency of thiamine in animals results in the accumulation of lactic acid and reduction in oxygen uptake, especially in the brainstem, and depression of transketolase activity, again most strikingly in the brainstem. |
| General Description | Certified pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Thiamine pyrophosphate is a coenzyme of transketolase that catalyzes the cleavage of ribulose-5-phosphate; thereby forming D-glyceraldehyde-3-phosphate. This reaction requires the addition of an acceptor aldehyde such as ribose-5-phosphate, glyceraldehye or glycolaldehyde. |
| Biochem/physiol Actions | Thiamine pyrophosphate (TPP) is a coenzyme of transketolase, that catalyzes the cleavage of ribulose-5-phosphate. This reaction leads to the formation of D-glyceraldehyde-3-phosphate. It requires the addition of an acceptor aldehyde such as ribose-5-phosphate, glyceraldehye or glycolaldehyde. TPP is capable of decarboxylating hydroxypyruvate in the presence of an ′acceptor aldehyde′. |
Cocarboxylase Preparation Products And Raw materials
| Raw materials | Phosphoric acid-->Thiamine hydrochloride |
| Preparation Products | Thiamine chloride |
