532-43-4

Basic information

• Product Name: Thiamine nitrate
• Synonyms: mnitrate;nitrate(salt);thiaminenitrate(salt);Thiaminenitratel;Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-,nitrate(salt);vitaminb(sub1)nitrate;Thiamin Mononitrate;Thiaminenitrate,98%
• CAS NO: 532-43-4
• Molecular Formula: C₁₂H₁₇N₄OS*NO₃
• Molecular Weight: 327.36
• EINECS: 208-537-4
• Product Categories: Biochemistry;Vitamins;Vitamins and derivatives
• Mol File: 532-43-4.mol

Chemical Properties

• Melting Point: 196-200°C
• Appearance: white crystal powder
• Storage Temp.: 2-8°C
• Solubility: Sparingly soluble in water, freely soluble in boiling water, slightly soluble in alcohol and in methanol.
• PKA: 4.8(at 25℃)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9295
• BRN: 3857790
• CAS DataBase Reference: Thiamine nitrate(CAS DataBase Reference)
• NIST Chemistry Reference: Thiamine nitrate(532-43-4)
• EPA Substance Registry System: Thiamine nitrate(532-43-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 1
• RTECS: XI7400000
• TSCA: Yes
• Hazardous Substances Data: 532-43-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Thiamine nitrate is used as a certified pharmaceutical secondary standard for quality control in pharmaceutical laboratories and manufacturing. It provides a convenient and cost-effective alternative to the preparation of in-house working standards.
Used in Food Industry:
Thiamine nitrate is used as a dietary supplement in various food products, such as crackers, egg substitutes, and enriched flour. It is also preferred for the preparation of multivitamins and as a fortification agent in dry blends and dry products, including wheat flour.
Used in Antioxidant Applications:
Thiamine nitrate exhibits antioxidant properties, inhibiting lipid peroxidation in rat liver microsomes and free radical oxidation of oleic acid in vitro at concentrations ranging from 1 to 100 μM.
Used in Neuroprotection:
Thiamine nitrate has neuroprotective effects, as it reverses predator stress-induced suppression of hippocampal neurogenesis and decreases the latency of step-down from a platform, indicating anxiolytic-like activity in mice.
Used in Reducing Neurodegeneration:
Thiamine nitrate (8.5 mg/100 g food) has been shown to reduce neurodegeneration and increase survival in Slc19a3-/mice, a model of thiamine metabolism dysfunction syndrome-2 (THMD-2).

References

[1] Food and Agriculture Organization of the United Nations, Food Fortification: Technology and Quality Control: Report of an FAO technical meeting Rome, 1995 [2] Ronald R. Eitenmiller, W. O. Landen Jr and Lin Ye, Vitamin Analysis for the Health and Food Sciences, Second Edition, 2008 [3] Thomas J. Macek, Beate A. Feller and Edward J. Hanus, Pharmaceutical studies with thiamine mononitrate, Journal of Pharmaceutical Sciences, 1950, vol. 39, 365-369

Safety Profile

Poison by intravenous and intraperitoneal routes. A powerful oxidizer. When heated to decomposition it emits very toxic fums of SOx, and NOx. See also NITRATES.

InChI:InChI=1/C12H17N4OS.NO3/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;2-1(3)4/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);/q+1;-1

Synthetic route

thiamine sulfate → vitamin B1 mononitrate (532-43-4)

Conditions	Yield
With ammonium hydroxide; nitric acid at 10℃; for 3.5h; pH=7 - 8; Temperature; pH-value;	94.56%

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione (299-35-4) → vitamin B1 mononitrate (532-43-4)

Conditions	Yield
With dihydrogen peroxide; nitric acid

Thiamine hydrochloride (67-03-8) → vitamin B1 mononitrate (532-43-4)

Conditions	Yield
With sodium hydroxide; silver nitrate In water

Aneurin (70-16-6) → vitamin B1 mononitrate (532-43-4)

Conditions	Yield
With dihydrogen peroxide; nitric acid In water at 20℃; pH=3.5;

thiamine sulfate (2380-61-2) → vitamin B1 mononitrate (532-43-4)

Conditions	Yield
With ammonium nitrate; ammonium hydroxide for 0.25h; pH=7.3; Reagent/catalyst; pH-value;	47.92 g

vitamin B1 mononitrate (532-43-4) + CYTIDINE (65-46-3) → 2-methyl-8-ribosylcytosichrome

Conditions	Yield
In methanol for 3h; Heating;	40%

vitamin B1 mononitrate (532-43-4) → <5,12,19,26,33,40-hexaamino-3,10,17,24,31,38-hexamethyl<1.6>(1,5)pyrimidiniophane> hexanitrate

Conditions	Yield
In methanol for 2h; Heating;	34%
In methanol for 2h; Heating;

phosgene (75-44-5) + vitamin B1 mononitrate (532-43-4) → 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-chlorocarbonyloxy-ethyl)-4-methyl-thiazolium; chloride (96793-20-3)

Conditions	Yield
In acetic acid at -10℃;

vitamin B1 mononitrate (532-43-4) + methyl iodide (74-88-4) → N1'-methylthiaminium diiodide

Conditions	Yield
In methanol

Upstream product

• 299-35-4 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione 
• 67-03-8 Thiamine hydrochloride 
• 70-16-6 Aneurin 
• 2380-61-2 thiamine sulfate 

Relevant articles and documents

Thiamin Acetate, C12H17N4OS+.C2H3O2-

In thiamin acetate crystals, the thiamin cation -5-(2-hydroxyethyl)-4-methylthiazolium> adopts the usual F conformation, with torsion angles C5'-C3,5'-N3-C2 and N3-C3,5-C5'-C4' (between the pyridinyl and thiazolium moieties) of 5.6(7) and -83.5(6) deg, respectively.Hydrogen bonds involving the O5γ-H hydroxyl and N4α'-H2 amine groups and the N1' and N3' pyrimidine atoms interconnect the thiamin cations.The acetate anions are hydrogen bonded to the N4α'-H2 group and probably also to the C2-H group of the thiazole ring.

Preparation method of thiamine mononitrate

The invention discloses a preparation method of thiamine mononitrate. The preparation method comprises the steps that thiothiamine is oxidized by hydrogen peroxide to obtain thiamine mononitrate, thenthe thiamine mononitrate is converted into salt by using dilute nitric acid and neutralized by using ammonium hydroxide, and finally, cooling, crystallization, filtration and separation are carried out to obtain a thiamine mononitrate solid. The preparation method of the thiamine mononitrate has the advantages that the viewpoint of salt conversion by the ammonium nitrate is improved, the potential safety hazards caused by the use of a large number of the thiamine mononitrate solid during production are avoided, and the step of the preparation of the ammonium nitrate is reduced; on the premiseof not affecting the product quality and yield, the natural stacking density of thiamine mononitrate crystals is improved; the process steps are simple, the production cost is low, control is easy, the stability is good, the particle size is moderate, the degree of purification is high, and industrial large-scale production is facilitated.

A nitric-acid thiamine new synthesis mode (by machine translation)

The invention discloses a method for nitric acid thiamine new synthesis mode, characterized in that the sulfur on behalf of the thiamine by hydrogen peroxide oxidation of oxidizing liquid, rotation of calcium salt, to obtain calcium sulphate solids separation, then the use of ammonia and in [...], get the nitric acid thiamine, after separation, in the mother liquor contains only ammonium sulfate, through three-effect evaporation to obtain pure ammonium sulfate. The invention disclosed nitric acid thiamine new synthetic way improves the traditional view of converting the ammonium nitrate, calcium transfer salt, not only in the yield and quality has not been affected, but also for later mother liquor and processing has the great advantage of, there is a by-product calcium sulfate generation, there is a pure ammonium sulfate generation, can solve the traditional process the mother liquor in the thiamine nitrate high ammonia nitrogen situation. (by machine translation)

Preparation method for bulk crystal product of thiamine nitrate

The present invention discloses a preparation method for a bulk crystal product of thiamine nitrate. The method comprises: adding solid thiothiamine into acidic distilled water with pH=2-6, adding hydrogen peroxide dropwise thereto based on mass fraction with stirring, carrying out reaction, oxidation and decolorization to obtain a thiamine sulfate solution; adding a solution of 40-60 wt% ammonium nitrate to the obtained solution from the above oxidation reaction, and an additive is added with stirring and mixing; When ammonia liquor is used to adjust pH to 3.9-4.3, adding a thiamine nitrate seed and growning for 0.5-2 h, continuing to adjust pH to 6.80-7.05, followed by lowering a temperature to 5 DEG C at a rate of 0.5 DEG C/min; and filtering, washing, and driying to obtain a thiamine nitrate crystal. The product is a bulk crystal with an aspect ratio of 1:1 to 4:1, a bulk density of 0.80-0.93 g/mL, and an angle of repose of 25 DEC to 38 DEC, and has better fluidity, and crystal properties are significantly improved. The preparation process is simple, and is easy for industrialization.