CAS 3432-99-3

5,10-Methylene-5,6,7,8-tetrahydrofolic acid

Description:

5,10-Methylene-5,6,7,8-tetrahydrofolic acid, commonly referred to as methylenetetrahydrofolate, is a derivative of folate, a B-vitamin essential for various biological processes. This compound plays a crucial role in one-carbon metabolism, particularly in the synthesis of nucleotides and amino acids, which are vital for DNA replication and repair. It is characterized by its tetrahydrofolate structure, which includes a pteridine ring, para-aminobenzoic acid, and a glutamic acid tail. The methylene group at the 5,10 position is significant for its function in transferring one-carbon units. This compound is water-soluble and is typically involved in enzymatic reactions catalyzed by methylene tetrahydrofolate reductase (MTHFR). Deficiencies in this compound can lead to various health issues, including megaloblastic anemia and elevated homocysteine levels, which are associated with cardiovascular diseases. Its role in cellular metabolism and its involvement in the methylation cycle underscore its importance in human health and nutrition.

Formula: C₂₀H₂₃N₇O₆

InChI: InChI=1/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1

InChI key: InChIKey=QYNUQALWYRSVHF-ABLWVSNPSA-N

SMILES: O=C1C=2N3C(CN(C3)C4=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C4)(CNC2NC(N)=N1)[H]

Synonyms:

• (+)-5,10-Methylene-5,6,7,8-tetrahydrofolic acid
• (2s)-2-(4-(3-Amino-1-oxo-5,6,6a,7-tetrahydroimidazo[1,5-f]pteridin-8(1H,4H,9H)-yl)benzamido)pentanedioic acid
• 5,10-Methylene-(6RS)-tetrahydrofolic acid
• 5,10-Methylenetetrafolate
• 5,10-Methylenetetrahydrofolic acid
• <span class="text-smallcaps">L</span>-Glutamic acid, N-[4-(3-amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-
• Anx-510
• Folic acid, tetrahydro-N⁵,N¹⁰-methylene-
• Folitixorin
• Glutamic acid, N-[p-(3-amino-5,6,6a,7-tetrahydro-1-hydroxyimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-, <span class="text-smallcaps">L</span>-
• Imidazo[1,5-f]pteridine, <span class="text-smallcaps">L</span>-glutamic acid deriv.
• L-glutamic acid, N-[4-(3-amino-5,6,6a,7-tetrahydro-1-hydroxyimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-
• N-[4-(3-Amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-<span class="text-smallcaps">L</span>-glutamic acid
• N-[4-(3-amino-1-hydroxy-5,6,6a,7-tetrahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic acid
• N-{4-[(6aR)-3-amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl]benzoyl}-L-glutamic acid
• N⁵,N¹⁰-Methylene-5,6,7,8-tetrahydrofolic acid
• N⁵,N¹⁰-Methylenetetrahydrofolic acid
• N⁵,N¹⁰-Methylenetetrahydropteroylglutamic acid
• Imidazo[1,5-f]pteridine, L-glutamic acid deriv.
• Folic acid, tetrahydro-N5,N10-methylene-
• Glutamic acid, N-[p-(3-amino-5,6,6a,7-tetrahydro-1-hydroxyimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-, L-
• L-Glutamic acid, N-[4-(3-amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-
• N-[4-(3-Amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic acid
• 5,10-METHYLENETETRAHYDROFOLICACID
• N5,N10-Methyl-
• N5,N10-MethylenetetrahydropteroylglutaMic Acid
• Levofolinate Methylene Impurity
• enetetrahydrofolic Acid
• N-[4-[(3-Amino-1,2,5,6,6a,7,8,9-octahydro-1-oxoimidazo[1,5-f]pteridin)-8-yl]benzoyl]-L-glutamic acid
• (Mixture of Diastereomers)
• Folic Acid Impurity 13 Monomer
• Folitixorin (~80%)

5,10-METHYLENETETRAHYDROFOLATE

CAS: 3432-99-3

Formula: C₂₀H₂₃N₇O₆

Purity: 95%

Color and Shape: Solid

Molecular weight: 457.4399

Ref: IN-DA00C95H

(2S)-2-(4-(3-Amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzamido)pentanedioic acid

CAS: 3432-99-3

(2S)-2-(4-(3-Amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzamido)pentanedioic acid

Purity: 95%

Molecular weight: 457.45g/mol

Ref: 54-OR1053159

Calcium Folinate EP Impurity I (Folitixorin) (Mixture of Diastereomers)

CAS: 3432-99-3

Formula: C₂₀H₂₃N₇O₆

Molecular weight: 457.45

Ref: 4Z-C-466006

Folitixorin (~80%)(Mixture of Diastereomers)

CAS: 3432-99-3

Stability Hygroscopic, Moisture Sensitive, Temperature Sensitive
Applications A stable folate lyophilized compound suitable for use in the treatment of cancer and other therapies.
References Park, H., et al.: Science, 268, 1866 (1995), Banerjee, R., et al.: J. Biol. Chem., 282, 14916 (2007), Klar, T., et al.: J. Mol. Biol., 366, 954 (2007),

Formula: C₂₀H₂₃N₇O₆

Color and Shape: Neat

Molecular weight: 457.44

Ref: TR-F680350

Folitixorin-d4 Disodium Salt (>80%) (Mixture of Diastereomers)

Controlled Product

CAS: 133978-76-4, 3432-99-3

Formula: C₂₀H₁₇D₄N₇Na₂O₆

Color and Shape: Neat

Molecular weight: 505.43

Ref: TR-F680352

5,10-Methylene-5,6,7,8-tetrahydrofolic acid - mixture of diastereomers

CAS: 3432-99-3

5,10-Methylene-5,6,7,8-tetrahydrofolic acid is a molecule that is found in cells. It is an essential cofactor for many biological processes. The folate form of 5,10-methylene-5,6,7,8-tetrahydrofolic acid (5MTHF) can be synthesized by the enzyme methylenetetrahydrofolate reductase. This enzyme uses N5,N10-methenyltetrahydrofolate as a substrate and converts it to 5MTHF. The enzyme activity of methylenetetrahydrofolate reductase can be inhibited by methotrexate. In this case 5MTHF will not be produced and the body's supply of folate will decrease. The structural analysis of 5MTHF has been performed using titration calorimetry and x-ray crystallography.

Formula: C₂₀H₂₃N₇O₆

Purity: 80%Min

Color and Shape: Powder

Molecular weight: 457.44 g/mol

Ref: 3D-FM31365

Folitixorin

CAS: 3432-99-3

Folitixorin (ANX-510) is an active folate derivative and coenzyme associated with thymidine synthesis, with potential antitumour activity.

Formula: C₂₀H₂₃N₇O₆

Purity: 95.94%

Color and Shape: Solid

Molecular weight: 457.44

Ref: TM-T21315

Calcium Folinate EP Impurity I

CAS: 3432-99-3

Formula: C₂₀H₂₃N₇O₆

Molecular weight: 457.44

Ref: ST-EA-CP-C509007