5-Methyldihydrofolate

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MedKoo CAT#: 597184

CAS#: 59904-24-4

Description: 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

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5-Methyldihydrofolate
CAS# 59904-24-4

Theoretical Analysis

MedKoo Cat#: 597184
Name: 5-Methyldihydrofolate
CAS#: 59904-24-4
Chemical Formula: C20H23N7O6
Exact Mass: 457.17
Molecular Weight: 457.440
Elemental Analysis: C, 52.51; H, 5.07; N, 21.43; O, 20.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.