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MedKoo Cat#: 596555 | Name: Levomefolinic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levomefolinic acid (also known as (6S)-5-methyltetrahydrofolic acid or L-methylfolate) is the biologically active, enantiomerically pure form of folate that directly participates in the folate cycle as a methyl donor in the remethylation of homocysteine to methionine via methionine synthase. It bypasses several enzymatic steps required by folic acid, making it especially relevant in individuals with MTHFR polymorphisms. Bioactivity data shows that levomefolinic acid effectively increases plasma and cerebrospinal fluid levels of methylfolate, with oral doses (e.g., 7.5–15 mg/day) leading to significant CNS folate repletion.

Chemical Structure

Levomefolinic acid
CAS#31690-09-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 596555

Name: Levomefolinic acid

CAS#: 31690-09-2 (free acid)

Chemical Formula: C20H25N7O6

Exact Mass: 459.1866

Molecular Weight: 459.46

Elemental Analysis: C, 52.28; H, 5.48; N, 21.34; O, 20.89

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 650.00 Ready to ship
5g USD 950.00 Ready to ship
10g USD 1,650.00 Ready to ship
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Related CAS #
151533-22-1 (calcium) 1423663-76-6 (sodium) 31690-09-2 (free acid) 419563-18-1 (calcium pentahydrate) 1429498-11-2 (magnesium)
Synonym
Levomefolinic acid; LMSR; Levomefolinic acid; Metafolin; Nutrifolin; Levomefolate; Bodyfolin;
IUPAC/Chemical Name
(4-((((S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid
InChi Key
ZNOVTXRBGFNYRX-STQMWFEESA-N
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
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NC[C@@H]2N(C)C3=C(NC(N)=NC3=O)NC2)C=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
It has demonstrated therapeutic benefit as an adjunct in major depressive disorder, particularly in SSRI-resistant cases, with clinical trials showing improved response rates (e.g., ~30% higher remission in some RCTs). Additionally, it supports DNA synthesis, methylation, and neural development, and exhibits a favorable safety profile without the masking effects of unmetabolized folic acid.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levomefolic acid (5-MTHF) is an orally active, brain-penetrant natural active form of folic acid and is one of the most widely used folic acid food supplements.
In vitro activity:
In addition, FA (folic acid) could ameliorate inflammation and decrease ROS production induced by Hcy. Furthermore, FA pre-treatment suppress palmitate -induced (NF-κB) p65 level in palmitate or Hcy stimulated cells. Reference: Arch Physiol Biochem. 2021 Feb 17:1-8. https://pubmed.ncbi.nlm.nih.gov/33596128/
In vivo activity:
FA (folic acid) significantly reduced the expression levels of nuclear factor-κ-gene binding (NF-κB) p65/Rela and interleukin-6 (IL-6) in rat arterial tissues, as well as the levels of plasma HHcy and serum malondialdehyde (MDA) in hypertension associated with HHcy rats (p < 0.05). Reference: Vascular. 2021 Aug 6:17085381211036549. https://pubmed.ncbi.nlm.nih.gov/34362270/
Solvent mg/mL mM comments
Solubility
DMSO 23.5 51.15
Water 5.0 10.88
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 459.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Bagherieh M, Kheirollahi A, Zamani-Garmsiri F, Emamgholipour S, Meshkani R. Folic acid ameliorates palmitate-induced inflammation through decreasing homocysteine and inhibiting NF-κB pathway in HepG2 cells. Arch Physiol Biochem. 2021 Feb 17:1-8. doi: 10.1080/13813455.2021.1878539. Epub ahead of print. PMID: 33596128. 2. Yang H, Qin D, Xu S, He C, Sun J, Hua J, Peng S. Folic acid promotes proliferation and differentiation of porcine pancreatic stem cells into insulin-secreting cells through canonical Wnt and ERK signaling pathway. J Steroid Biochem Mol Biol. 2021 Jan;205:105772. doi: 10.1016/j.jsbmb.2020.105772. Epub 2020 Oct 19. PMID: 33091596. 3. Zhang L, Li Z, Xing C, Ma X, Xu R. The protective mechanism of folic acid on hyperhomocysteinemia-related arterial injury in spontaneously hypertensive rats: Folic acid against arterial inflammation. Vascular. 2021 Aug 6:17085381211036549. doi: 10.1177/17085381211036549. Epub ahead of print. PMID: 34362270. 4. Budni J, Moretti M, Freitas AE, Neis VB, Ribeiro CM, de Oliveira Balen G, Rieger DK, Leal RB, Rodrigues ALS. Behavioral and neurochemical effects of folic acid in a mouse model of depression induced by TNF-α. Behav Brain Res. 2021 Aug 3;414:113512. doi: 10.1016/j.bbr.2021.113512. Epub ahead of print. PMID: 34358572.
In vitro protocol:
1. Bagherieh M, Kheirollahi A, Zamani-Garmsiri F, Emamgholipour S, Meshkani R. Folic acid ameliorates palmitate-induced inflammation through decreasing homocysteine and inhibiting NF-κB pathway in HepG2 cells. Arch Physiol Biochem. 2021 Feb 17:1-8. doi: 10.1080/13813455.2021.1878539. Epub ahead of print. PMID: 33596128. 2. Yang H, Qin D, Xu S, He C, Sun J, Hua J, Peng S. Folic acid promotes proliferation and differentiation of porcine pancreatic stem cells into insulin-secreting cells through canonical Wnt and ERK signaling pathway. J Steroid Biochem Mol Biol. 2021 Jan;205:105772. doi: 10.1016/j.jsbmb.2020.105772. Epub 2020 Oct 19. PMID: 33091596.
In vivo protocol:
1. Zhang L, Li Z, Xing C, Ma X, Xu R. The protective mechanism of folic acid on hyperhomocysteinemia-related arterial injury in spontaneously hypertensive rats: Folic acid against arterial inflammation. Vascular. 2021 Aug 6:17085381211036549. doi: 10.1177/17085381211036549. Epub ahead of print. PMID: 34362270. 2. Budni J, Moretti M, Freitas AE, Neis VB, Ribeiro CM, de Oliveira Balen G, Rieger DK, Leal RB, Rodrigues ALS. Behavioral and neurochemical effects of folic acid in a mouse model of depression induced by TNF-α. Behav Brain Res. 2021 Aug 3;414:113512. doi: 10.1016/j.bbr.2021.113512. Epub ahead of print. PMID: 34358572.
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