MedKoo Cat#: 597184 | Name: 5-Methyldihydrofolate

Description:

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

5-Methyldihydrofolate is the primary biologically active form of folate used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine. It is also the form found in circulation and transported across membranes into tissues and across the blood-brain barrier. In the cell, L-methylfolate is used in the methylation of homocysteine to form methionine and tetrahydrofolate (THF). THF is the immediate acceptor of one carbon units for the synthesis of thymidine-DNA, purines (RNA and DNA) and methionine. The un-methylated form, folic acid (vitamin B9), is a synthetic form of folate, and must undergo enzymatic reduction by methylenetetrahydrofolate reductase (MTHFR) to become biologically active.

Chemical Structure

5-Methyldihydrofolate
5-Methyldihydrofolate
CAS#59904-24-4

Theoretical Analysis

MedKoo Cat#: 597184

Name: 5-Methyldihydrofolate

CAS#: 59904-24-4

Chemical Formula: C20H23N7O6

Exact Mass: 457.1710

Molecular Weight: 457.44

Elemental Analysis: C, 52.51; H, 5.07; N, 21.43; O, 20.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
5-Methyldihydrofolate;
Synonym
IUPAC/Chemical Name
(4-(((2-amino-5-methyl-4-oxo-1,4,5,8-tetrahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid
InChi Key
VWNDXSYYCICZGD-ZDUSSCGKSA-N
InChi Code
InChI=1S/C20H23N7O6/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/h2-5,9,13,22H,6-8H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t13-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2=CNC(NC(N)=N3)=C(N2C)C3=O)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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 457.44 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
1: Verlinde PH, Oey I, Lemmens L, Deborggraeve WM, Hendrickx ME, Van Loey AM. Influence of reducing carbohydrates on (6S)-5-methyltetrahydrofolic acid degradation during thermal treatments. J Agric Food Chem. 2010 May 26;58(10):6190-9. doi: 10.1021/jf9041134. PubMed PMID: 20423084. 2: Steindal AH, Juzeniene A, Johnsson A, Moan J. Photodegradation of 5-methyltetrahydrofolate: biophysical aspects. Photochem Photobiol. 2006 Nov-Dec;82(6):1651-5. PubMed PMID: 16879038. 3: Lucock MD, Priestnall M, Daskalakis I, Schorah CJ, Wild J, Levene MI. Nonenzymatic degradation and salvage of dietary folate: physicochemical factors likely to influence bioavailability. Biochem Mol Med. 1995 Jun;55(1):43-53. PubMed PMID: 7551825. 4: Matthews RG, Kaufman S. Characterization of the dihydropterin reductase activity of pig liver methylenetetrahydrofolate reductase. J Biol Chem. 1980 Jul 10;255(13):6014-7. PubMed PMID: 6967065. 5: DONALDSON KO, KERESZTESY JC. Naturally occurring forms of folic acid. III. Characterization and properties of 5-methyldihydrofolate, an oxidation product of 5-methyltetrahydrofolate. J Biol Chem. 1962 Dec;237:3815-9. PubMed PMID: 14028582.