59-43-8 Usage
Originator
Thiamine chloride,Sopharma
Uses
Vitamin B1 is used in method for cultivating tremella strain. Also, it is protein compound liquid comprising collagen and Rhodiola rosea extract or preparing injection to remove skin wrinkle.
Manufacturing Process
2 Methods of preparation of thiamine:1. 3-Ethoxypropionitrile reacted with diethoxymethoxy-ethane and 3-ethoxy-
2-methoxymethylenpropionitrile was obtained.Then to the 3-ethoxy-2-methoxymethylenpropionitrile acetamidine was added
and reaction mixture was stirred to give 4-amino-5-ethoxy-methyl-2-
methylpyrimidine.The 4-amino-5-ethoxy-methyl-2-methylpyrimidine was treated by hydrobromic
acid to afford 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide.The 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide reacted with
5-(2-hydroxyethyl)-4-methylthiazole in the presence of hydrobromic acid and
as the result thiaminbromide was produced. For changing of the thiaminbromide to the thiamincloride the thiaminbromide was treated by AgCl.2. To diethoxymethoxy-ethane malononitrile was added and ethoxymethylenmalononitrile
was obtained. The ethoxymethylen-malononitrile reacted with
acetamidine as a result 4-amino-5-cyano-2-methylpyrimidine was produced,
which was reduced by H2/Raney-Ni to 4-amino-5-aminomethyl-2-
methylpyrimidine.To the 4-amino-5-aminomethyl-2-methylpyrimidine 1-acetoxy-3-chloropentan-
4-one was added in the presence CS2 and NH3, and reaction mixture was
stirred, then to this mixture hydrochloric acid was added and thiamin (base)
was obtained.To thiamin (base) H2O2 and hydrocloricum acid are added, in the result
reaction the thiamine chloride was obtained.
Therapeutic Function
Enzyme cofactor vitamin, Antineuritic
General Description
Thiamine, the preferred name for vitamin B1, holds a prominent place in the history of vitamin discovery because beriberi, the disease resulting from insufficient thiamine intake, was one of the earliest recognized deficiency diseases.
Biological Activity
Some earlier designations for this substance included aneurin, antineuritic factor, antiberiberi factor, and oryzamin. Thiamine is metabolically active as thiamine pyrophosphate (TPP). TPP functions as a coenzyme which participates in decarboxylation of α-keto acids. Dehydrogenation and decarboxylation must precede the formation of “active acetate” in the initial reaction of the TCA cycle (citric acid cycle):
This reaction is a good example of the interrelationship of vitamin B coenzymes. Four vitamin coenzymes are necessary for this one reaction: (1) thiamine (in TPP) for decarboxylation; (2) nicotinic acid in nicotinamide adenine dinucleotide (NAD); (3) riboflavin in flavin adenine dinucleotide (FAD); and (4) pantothenic acid in coenzyme A (CoA) for activation of the acetate fragment.
Clinical Use
Thiamine chloride, as the base or as the hydrochloride salt, is indicatedin the treatment or prophylaxis of known or suspected thiaminedeficiencies. Severe thiamine deficiency is calledberiberi, which is very rare in developed countries. The mostlikely cause of thiamine deficiency in the United States is theresult of chronic alcoholism, which leads to multiple vitamindeficiencies as a result of poor dietary intake. The major organsaffected are the nervous system (dry beriberi), whichmanifests as neurological damage, the cardiovascular system(wet beriberi), which manifests as heart failure and edema, andthe gastrointestinal tract. Thiamine administration reverses thegastrointestinal, cardiovascular, and neurological symptoms;however, if the deficiency has been severe or of prolonged duration, the neurological damage may be permanent.
Safety Profile
Poison by
subcutaneous and intravenous routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits very toxic fumes of
NOx, SOx, and Cl-.
Check Digit Verification of cas no
The CAS Registry Mumber 59-43-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 59-43:
(4*5)+(3*9)+(2*4)+(1*3)=58
58 % 10 = 8
So 59-43-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H17N4OS.ClH/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);1H/q+1;/p-1
59-43-8Relevant articles and documents
A Convenient Synthesis of 1'-Alkyl- and 1'-Benzylthiaminium Salts
Karimian, Khashayar,Mohanazadeh, Farajollah
, p. 1065 - 1067 (1986)
A convenient and efficient method for the quaternization at N-1' of thiamin and 2-(1-hydroxyethyl)-thiamin with various alkyl halides and benzyl bromide is presented.Quaternization of 2-(1-ethoxycarbonyl-1-hydroxyethyl)-thiamin was unsuccessful, resulting in the release of ethyl pyruvate and the formation of quaternized thiamin.The N-1'-derivatized thiaminium salts were found to possess drastically different physical properties as compared to their parent heterocycles.
NOVEL THIAMINE-ORGANIC ACID SALT
-
, (2019/12/15)
The present disclosure relates to novel thiamine-organic acid salt, and the method of making the novel thiamine-organic acid salt.
OXIDATIVE DECOMPOSITION OF 2-(α-HYDROXYBENZYL)THIAMINE UNDER THE ACTION OF A BASE AND SUBSTITUTED QUINONES
Vovk, A. I.,Murav'eva, I. V.
, p. 937 - 940 (2007/10/02)
The reaction of 2-(α-hydroxybenzyl)thiamine and its thiazolium structural analogs with substituted quinones in the presence of acetate buffer in deaerated methanolic solutions at 27 deg C and ionic strength of 0.15 is characterized by first-order kinetics with respect to the thiazolium salt and the acetate and by zero-order kinetics with resoect to quinone.The rate constant of the reaction catalyzed by the basic component of the buffer decreases in the following series of oxidants: 2-methyl-5-isopropyl-p-benzoquinone, trimethyl-p-benzoquinone, tetramethyl-p-benzoquinone.It was supposed that fast reversible formation of a complex between the deprotonated 2-(α-hydroxybenzyl)thiazole and the oxidant precedes electron transfer to the quinone.In the one-electron transfer stage, which determines the overall reaction rate, the 5-hydroxyethyl substituent exerts an adverse effect for steric reasons.
