Chemical and technical information on CALCIUM L-5-METHYLTETRAHYDROFOLATE (L-5-MTHF-Ca)

Calcium L-5-methyltetrahydrofolate (L-5-MTHF-Ca; CAS No. 151533-22-1) is the calcium salt of L-5- methyltetrahydrofolic acid (L-5-MTHF), which is the predominant naturally occurring folate in foods. Folic acid (pteroyl glutamic acid, sometimes known as Vitamin B9), which is widely used for food fortification and as an ingredient in dietary supplements, is the precursor of L-5-MTHF. L-5-MTHF-Ca is intended for use in dry crystalline or microencapsulated form as an alternative to folic acid in foods, including dietary supplements. L-5-MTHF-Ca is a white to light yellowish, almost odourless, water-soluble crystalline powder. It is obtained by reduction of synthetic folic acid with sodium borohydride, condensation of the resulting tetrahydrofolic acid with formaldehyde, further reduction of the 5,10-MTHF with NaBH4 to L-5-MTHF, and finally crystallization as the calcium salt. Crystalline L-5-MTHF-Ca is stable on storage (48 months at 40 oC and up to 75% RH) after micronizing, and when compounded into vitamin and mineral tablets. It appears to be better suited than folic acid for the vitamin enrichment of foods. L-5-MTHF-Ca in microencapsulated form, preferably with ascorbate as an antioxidant, has also been shown to have long-term stability in a variety of foodstuffs.

Tests with L-5-MTHF-Ca have shown that L-5-MTHF has a similar or slightly higher bioavailability and bioefficacy than folic acid. 2 Description Calcium L-5-methyltetrahydrofolate (L-5-MTHF-Ca; C20H23CaN7O6 ; formula weight 497.5; CAS No. 151533-22-1) is a white to light yellowish, almost odourless crystalline powder. The commercial product contains variable amounts of water of crystallization. L-5-MTHF-Ca is sparingly soluble in water (1.07 g/100 g at 20 oC) and very slightly soluble or insoluble in most organic solvents. It is soluble in alkaline hydroxides. L-5-MTHF-Ca decomposes above 300 oC and has a specific rotation of +45.0o to +50.0o. The pH of an aqueous solution (0.5 g/100 ml) is between 6.5 and 7.5. The full chemical name for L-5-MTHF-Ca is N-{4-[[((6S)-2-amino-3,4,5,6,7,8-hexahydro-5-methyl-4- oxo-6-pteridinyl)methyl]amino]benzoyl}-L-glutamic acid, calcium salt. L-5-MTHF-Ca is also referred to in the literature as:

? L-Methylfolate, calcium;

? L-5-Methyltetrahydrofolic acid, calcium salt [(L-5-MTHF-Ca)];

? (6S)-5-Methyltetrahydrofolic acid, calcium salt [(6S)-5-MTHFCa];

? (6S)-5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid, calcium salt;.

? L-5-Methyl-tetrahydrofolic acid (L-5-MTHF), i.e. the cation is not specified.

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