Effect of the Thiazole Moiety of Thiamine Hydrochloride and Selected Model Compounds on Cyanocobalamin Stability

Doerge, Robert F.; Ravin, Louis J.; Caldwell, Henry C.

doi:10.1002/jps.2600540719

Cited by 8 publications

(4 citation statements)

References 11 publications

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“…The result suggested that the presence of other watersoluble vitamins, such as thiamin affects the stability of cyanocobalamin [3,23]. An explanation for this is that thiamin degrades during storage producing a thiazole moiety [24]. It is the breakdown product of the thiazole moiety, particularly cysteine hydrochloride, that is responsible for the degradation of cyanocobalamin [24].…”

Section: Cyanocobalamin In Dietary Supplementsmentioning

confidence: 99%

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The efficiency of ultrasonic-assisted extraction of cyanocobalamin is greater than heat extraction

Chandra-Hioe

Arcot

2020

Heliyon

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Cyanocobalamin, like other water-soluble vitamins, is susceptible to degradation due to exposure to heat, UV, oxygen and pH. Built on our previous finding, this study aimed to assess the extraction efficiency of cyanocobalamin from dietary supplements. Particularly, cyanocobalamin extraction in a 100 C water bath was compared with ultrasonic-assisted extraction, with and without the addition of 1 mg/L sorbitol, xylitol and erythritol. Ground defatted samples of supplement tablets were initially treated for 15 min, centrifuged and filtered before quantitative HPLC analysis. Addition of sorbitol and xylitol significantly minimised the thermal degradation during extraction in a 100 C water bath, as shown in measured cyanocobalamin (~145 μg/tablet) that was higher than the control (100 μg/tablet, p < 0.05). Despite the addition of sugar alcohols, mean cyanocobalamin in ultrasonic extracted samples (~170 μg/tablet) was not significantly different from those without (p > 0.05). Overall, mean cyanocobalamin in sonicated samples was higher than heat-extracted counterparts, suggesting that extraction in a 100 C water bath was likely to cause thermal degradation. It was possible that ultrasonic-assisted extraction had no effect on cyanocobalamin stability and would lead to a higher extraction efficiency. Therefore, 15 min extraction in an ultrasonic bath can be suggested to be adequate to release cyanocobalamin before its quantitative determination.

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Section: Cyanocobalamin In Dietary Supplementsmentioning

confidence: 99%

“…An explanation for this is that thiamin degrades during storage producing a thiazole moiety [24]. It is the breakdown product of the thiazole moiety, particularly cysteine hydrochloride, that is responsible for the degradation of cyanocobalamin [24].…”

Section: Cyanocobalamin In Dietary Supplementsmentioning

confidence: 99%

The efficiency of ultrasonic-assisted extraction of cyanocobalamin is greater than heat extraction

Chandra-Hioe

Arcot

2020

Heliyon

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“…B 12 undergoes photolysis to B 12b in aqueous solution which is degraded to irreversible oxidation products (6)(7)(8)(9)(10)(11). Similar reactions occur on the chemical degradation of B 12 and B 12b in the presence of ascorbic acid (AH 2 ) (12)(13)(14) and may be expressed as follows: The effect of thiamine (15,16), nicotinamide (17,18), and riboflavin (19)(20)(21)(22) on the photolysis of B 12 and B 12b has been investigated. Several studies have been conducted on the incompatibility and interaction of B 12 and AH 2 that lead to the loss of B 12 in aqueous solution (12,13,(23)(24)(25)(26)(27).…”

Section: Introductionmentioning

confidence: 99%

Effect of Ascorbic Acid on the Degradation of Cyanocobalamin and Hydroxocobalamin in Aqueous Solution: A Kinetic Study

et al. 2014

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Abstract. The degradation kinetics of 5×10−5 M cyanocobalamin (B 12 ) and hydroxocobalamin (B 12b ) in the presence of ascorbic acid (AH 2 ) was studied in the pH range of 1. , respectively, indicating a greater effect of AH 2 on B 12b compared to that of B 12 . The k obs -pH profiles for both B 12 and B 12b show the highest rates of degradation around pH 5. The degradation of B 12 and B 12b by AH 2 is affected by the catalytic effect of phosphate ions on the oxidation of AH 2 in the pH range 6.0-8.0.

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“…They found the extent of CNCbl degradation related to thiamine degradation [189,190]. Doerge et al identified the thiol-containing thiamine degradation product, cysteine, as responsible for CNCbl degradation [191]. This destabilization effect is enhanced by the presence of high thiamine concentrations and the presence of pyridoxine or nicotinamide [150,177,192].…”

Section: Vitamin B 12 -Thiaminementioning

confidence: 99%

Vitamin B12 in Foods, Food Supplements, and Medicines—A Review of Its Role and Properties with a Focus on Its Stability

et al. 2022

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Vitamin B12, also known as the anti-pernicious anemia factor, is an essential micronutrient totally dependent on dietary sources that is commonly integrated with food supplements. Four vitamin B12 forms—cyanocobalamin, hydroxocobalamin, 5′-deoxyadenosylcobalamin, and methylcobalamin—are currently used for supplementation and, here, we provide an overview of their biochemical role, bioavailability, and efficacy in different dosage forms. Since the effective quantity of vitamin B12 depends on the stability of the different forms, we further provide a review of their main reactivity and stability under exposure to various environmental factors (e.g., temperature, pH, light) and the presence of some typical interacting compounds (oxidants, reductants, and other water-soluble vitamins). Further, we explore how the manufacturing process and storage affect B12 stability in foods, food supplements, and medicines and provide a summary of the data published to date on the content-related quality of vitamin B12 products on the market. We also provide an overview of the approaches toward their stabilization, including minimization of the destabilizing factors, addition of proper stabilizers, or application of some (innovative) technological processes that could be implemented and contribute to the production of high-quality vitamin B12 products.

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Effect of the Thiazole Moiety of Thiamine Hydrochloride and Selected Model Compounds on Cyanocobalamin Stability

Cited by 8 publications

References 11 publications

The efficiency of ultrasonic-assisted extraction of cyanocobalamin is greater than heat extraction

The efficiency of ultrasonic-assisted extraction of cyanocobalamin is greater than heat extraction

Effect of Ascorbic Acid on the Degradation of Cyanocobalamin and Hydroxocobalamin in Aqueous Solution: A Kinetic Study

Vitamin B12 in Foods, Food Supplements, and Medicines—A Review of Its Role and Properties with a Focus on Its Stability

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