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5-Methyltetrahydrofolic acid

CAT: 0804-HY-113046-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-113046-01Size:50 mg
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Description
5-Methyltetrahydrofolic acid (5-Methyl THF) is the main circulating form of folic acid in the body and is involved in a variety of biochemical reactions. 5-Methyltetrahydrofolic acid regulates cardiovascular function by increasing the production of endothelin-1 (ET-1) in low-density lipoprotein-treated endothelial cells and can be used in the study of cardiovascular diseases[1][2].
CAS Number
134-35-0
Product Name Alternative
5-Methyl THF; 5-MTHF
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease; Cardiovascular Disease
Purity
99.77
Solubility
DMSO : 83.33 mg/mL (ultrasonic)
Smiles
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2N(C)C3=C(NC(N)=NC3=O)NC2)C=C1)=O
Molecular Formula
C20H25N7O6
Molecular Weight
459.46
Precautions
H302, H315, H319, H335
References & Citations
[1]Wright AJ, et al. Comparison of (6 S) -5-methyltetrahydrofolic acid v. folic acid as the reference folate in longer-term human dietary intervention studies assessing the relative bioavailability of natural food folates: comparative changes in folate status following a 16-week placebo-controlled study in healthy adults. Br J Nutr. 2010 Mar;103 (5) :724-9.|[2]Ronco, et al. "5-methyltetrahydrofolic acid stimulates endothelin-1 production in low density lipoprotein-treated human endothelial cells." Nutrition, Metabolism and Cardiovascular Diseases 17.3 (2007) : 188-194.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite
Citation 01
Appl Microbiol Biotechnol. 2024 Dec;108 (1) :1-15.|Aquac Rep. 2025 Apr 15.|bioRxiv. 2025 Nov 20.|J Pharm Biomed Anal. 2025 Oct 3:268:117178.|J Pharm Pharmacol. 2019 Nov;71 (11) :1645-1654.|J Transl Med. 2023 Jun 6;21 (1) :365.|Nucleic Acids Res. 2023 Jan 25;51 (2) :952-965.|Int J Pharm. 2019 Feb 10:556:89-96.

Chemical Information

5-Methyltetrahydrofolic acid

5-methyltetrahydrofolic acid is a methylated derivate of tetrahydrofolate. It is generated by methylenetetrahydrofolate reductase from 5,10-methylenetetrahydrofolate and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferases (also called methionine synthases).

CAS Number134-35-0
PubChem CID135415868
IUPAC Name(2S)-2-[[4-[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Molecular FormulaC20H25N7O6
Molecular Weight459.5
XLogP-0.5
Topological Polar Surface Area198
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count10
Rotatable Bond Count9
Heavy Atom Count33
Formal Charge0
Complexity865
SMILES
CN1C(CNC2=C1C(=O)NC(=N2)N)CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChI
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
InChIKey
ZNOVTXRBGFNYRX-ABLWVSNPSA-N
Chemical Structure
2D Structure
2D structure of 5-Methyltetrahydrofolic acid
CAS: 134-35-0
CID: 135415868
Formula: C20H25N7O6
MW: 459.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight459.5
XLogP3-0.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count10
Rotatable Bond Count9
Exact Mass459.18663154
Monoisotopic Mass459.18663154
Topological Polar Surface Area198 Ų
Heavy Atom Count33
Formal Charge0
Complexity865
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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