An internal standard for the quantification of levomefolate
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Unlabeled Version(s)
21616Levomefolate (calcium salt hydrate)
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Levomefolate-13C-d3

Item No. 29579

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4-((((S)-2-amino-5-(methyl-13C-d3)-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid
CAS Number
1356019-94-7
Synonyms
  • L-Methyl Folate-13C-d3
  • [6S]-5-Methyltetrahydrofolate-13C-d3
  • [6S]-5-MTHF-13C-d3
Molecular Formula
C19[13C]H22D3N7O6
Formula Weight
463.5
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
aqueous base: slightly solubleDMSO: slightly, heated
SMILES
O=C1C2=C(NC[C@H](CNC3=CC=C(C(N[C@H](C(O)=O)CCC(O)=O)=O)C=C3)N2[13C]([2H])([2H])[2H])NC(N)=N1
InChi Code
InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1/i1+1D3
InChi Key
ZNOVTXRBGFNYRX-OWXPWHJLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $636

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    Product Description

    Levomefolate-13C-d3 is intended for use as an internal standard for the quantification of levomefolate (Item No. 21616) by GC- or LC-MS. Levomefolate is the single (S) isomer of 5-methyltetrahydrofolic acid (Item No. 16159) and an endogenous active form of folic acid (Item No. 20515).1 It donates a methyl group to homocysteine in the biosynthesis of methionine.2 Levomefolate (2 mg/kg) prevents decreases in circulating polymorphonucleates induced by methotrexate (Item No. 13960) in an L1210 murine skin lymphocytic leukemia model, and it increases survival in the same model when administered in combination with methotrexate.3 Formulations containing levomefolate have been used as dietary supplements, as well as in oral contraceptives for the prevention of neural tube defects in unintended pregnancies.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, X., Shen, F., Freisheim, J.H., et al. Differential stereospecificities and affinities of folate receptor isoforms for folate compounds and antifolates. Biochem. Pharmacol. 44(9), 1898-1901 (1992).

    2. Ragsdale, S.W. Catalysis of methyl group transfers involving tetrahydrofolate and B12. Vitam. Horm. 79, 293-324 (2008).

    3. Simile, M.M., DeMiglio, M.R., Nufris, A., et al. l-5-formyltetrahydrofolate and l-5-methyltetrahydrofolate rescue in L1210 leukemia treated with high methotrexate doses. Res. Commun. Chem. Pathol. Pharmacol. 81(2), 251-254 (1993).