59-43-8 Usage
Description
Thiamine chloride, also known as Vitamin B1 chloride, is a water-soluble vitamin and a derivative of thiamine. It plays a crucial role in various biological processes, including energy production and maintaining proper nervous system function.
Uses
Used in Pharmaceutical Industry:
Thiamine chloride is used as a pharmaceutical ingredient for the preparation of injections to remove skin wrinkles. It helps in promoting skin health and reducing the appearance of wrinkles by enhancing collagen production and improving skin elasticity.
Used in Food Industry:
Thiamine chloride is used as a nutrient in the method for cultivating tremella strain, a type of edible mushroom. It helps in enhancing the growth and nutritional value of the tremella, making it a rich source of vitamins and minerals.
Used in Health Supplements:
Thiamine chloride is used as an active ingredient in protein compound liquid formulations, which comprise collagen and Rhodiola rosea extract. It helps in improving overall health and well-being by supporting energy production, muscle growth, and reducing fatigue.
Originator
Thiamine chloride,Sopharma
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
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.