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Levomefolic acid

Active form of folic acid CAS# 31690-09-2

Levomefolic acid

2D Structure

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Levomefolic acid

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Chemical Properties of Levomefolic acid

Cas No. 31690-09-2 SDF Download SDF
PubChem ID 444412 Appearance Powder
Formula C20H25N7O6 M.Wt 459.46
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 5-MTHF
Solubility H2O : 5 mg/mL (10.88 mM; Need ultrasonic)
DMSO : < 1 mg/mL (insoluble or slightly soluble)
Chemical Name (2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
SMILES CN1C(CNC2=C1C(=O)N=C(N2)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
Standard InChIKey ZNOVTXRBGFNYRX-STQMWFEESA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Levomefolic acid

DescriptionLevomefolic acid (5-MTHF) is the natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. IC50 value: Target: Folate analog Levomefolic acid has been proposed for treatment of cardiovascular disease and advanced cancers such as breast and colorectal cancers. Levomefolic acid (5-MTHF) has the prominent antioxidant activity. A high dose of 5-MTHF or folic acid does not influence Natural killer (NK) cell function in vitro.

References:
[1]. Hirsch S, Miranda D, Mu?oz E, et al. Natural killer cell cytotoxicity is not regulated by folic acid in vitro. Nutrition. 2013 Jan 9. pii: S0899-9007(12)00404-2. [2]. Liu Y, Green TJ, Wong P, Kitts DD. Microencapsulation of L-5-methyltetrahydrofolic Acid with ascorbate improves stability in baked bread products. J Agric Food Chem. 2013 Jan 9;61(1):247-54. [3]. Merola N, Alonso FJ, Ros G, Castón MJ. Antioxidant activity comparison between [6S]-5-methyltetrahydrofolic acid calcium salt and the related racemate form. Food Chem. 2013 Jan 15;136(2):984-8. [4]. Liu Y, Tomiuk S, Rozoy E, et al. Thermal oxidation studies on reduced folate, L-5-methyltetrahydrofolic acid (L-5-MTHF) and strategies for stabilization using food matrices. J Food Sci. 2012 Feb;77(2):C236-43. [5]. Bashir M Rezka, Guido R.M.M Haenena, Wim J.F van der Vijgha, et al. Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore. 2003,555(3):601-605. [6]. Levomefolic acid

Levomefolic acid Dilution Calculator

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Levomefolic acid Molarity Calculator

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Preparing Stock Solutions of Levomefolic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1765 mL 10.8823 mL 21.7647 mL 43.5294 mL 54.4117 mL
5 mM 0.4353 mL 2.1765 mL 4.3529 mL 8.7059 mL 10.8823 mL
10 mM 0.2176 mL 1.0882 mL 2.1765 mL 4.3529 mL 5.4412 mL
50 mM 0.0435 mL 0.2176 mL 0.4353 mL 0.8706 mL 1.0882 mL
100 mM 0.0218 mL 0.1088 mL 0.2176 mL 0.4353 mL 0.5441 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Levomefolic acid

Levomefolic acid (5-MTHF) is the natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. Levomefolic acid has been proposed for treatment of cardiovascular disease and advanced cancers such as breast and colorectal cancers. Levomefolic acid (5-MTHF) has the prominent antioxidant activity. A high dose of 5-MTHF or folic acid does not influence Natural killer (NK) cell function in vitro.

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References on Levomefolic acid

Feeding steam-pelleted rapeseed affects expression of genes involved in hepatic lipid metabolism and fatty acid composition of chicken meat.[Pubmed:28371860]

Poult Sci. 2017 Aug 1;96(8):2965-2974.

This study investigated the dietary effect of steam-pelleted rapeseed (RS) diets with different inclusion levels on the fatty acid composition of chicken meat and the expression of lipid metabolism-related genes in the liver. Experimental diets included 6 different wheat-soybean meal based diets either in nonpelleted or steam-pelleted form supplemented with 80, 160, and 240 g RS/kg feed and one nonpelleted wheat-soybean meal based diet without RS supplementation as the control. These diets were fed to newly hatched broiler chickens (Ross 308) for 34 days. Compared to the control diet, steam-pelleted diets containing 160 or 240 g/kg RS significantly increased the content of omega-3 long chain polyunsaturated fatty acids (n-3 LC-PUFA) in the breast and drumstick, while their meat yields were not affected. Moreover, the mRNA levels of fatty acid desaturase 1 (FADS1) and acyl-coenzyme A oxidase 1 (ACOX1) in their livers increased. Therefore, steam-pelleted diets with 160 or 240 g/kg RS can be used to increase the n-3 LC-PUFA content in chicken meat without compromising meat yield.

A protective role for nitric oxide and salicylic acid for arsenite phytotoxicity in rice (Oryza sativa L.).[Pubmed:28371690]

Plant Physiol Biochem. 2017 Jun;115:163-173.

Nitric oxide (NO) and salicylic acid (SA) are important signaling molecules in plant system. In the present study both NO and SA showed a protective role against arsenite (As(III)) stress in rice plants when supplied exogenously. The application of NO and SA alleviated the negative impact of As(III) on plant growth. Nitric oxide supplementation to As(III) treated plants greatly decreased arsenic (As) accumulation in the roots as well as shoots/roots translocation factor. Arsenite exposure in plants decreased the endogenous levels of NO and SA. Exogenous supplementation of SA not only enhanced endogenous level of SA but also the level of NO through enhanced nitrate reductase (NR) activity, whether As(III) was present or not. Exogenously supplied NO decreased the NR activity and level of endogenous NO. Arsenic accumulation was positively correlated with the expression level of OsLsi1, a transporter responsible for As(III) uptake. The endogenous level of NO and SA were positively correlated to each other either when As(III) was present or not. This close relationship indicates that NO and SA work in harmony to modulate the signaling response in As(III) stressed plants.

OsPAP26 Encodes a Major Purple Acid Phosphatase and Regulates Phosphate Remobilization in Rice.[Pubmed:28371895]

Plant Cell Physiol. 2017 May 1;58(5):885-892.

During phosphate (Pi) starvation or leaf senescence, the accumulation of intracellular and extracellular purple acid phosphatases (PAPs) increases in plants in order to scavenge organic phosphorus (P). In this study, we demonstrated that a PAP-encoding gene in rice, OsPAP26, is constitutively expressed in all tissues. While the abundance of OsPAP26 transcript is not affected by Pi supply, it is up-regulated during leaf senescence. Furthermore, Pi deprivation and leaf senescence greatly increased the abundance of OsPAP26 protein. Overexpression or RNA interference (RNAi) of OsPAP26 in transgenic rice significantly increased or reduced APase activities, respectively, in leaves, roots and growth medium. Compared with wild-type (WT) plants, Pi concentrations of OsPAP26-overexpressing plants increased in the non-senescing leaves and decreased in the senescing leaves. The increased remobilization of Pi from the senescing leaves to non-senescing leaves in the OsPAP26-overexpressing plants resulted in better growth performance when plants were grown in Pi-depleted condition. In contrast, OsPAP26-RNAi plants retained more Pi in the senescing leaves, and were more sensitive to Pi starvation stress. OsPAP26 was found to localize to the apoplast of rice cells. Western blot analysis of protein extracts from callus growth medium confirmed that OsPAP26 is a secreted PAP. OsPAP26-overexpressing plants were capable of converting more ATP into inorganic Pi in the growth medium, which further supported the potential role of OsPAP26 in utilizing organic P in the rhizosphere. In summary, we concluded that OsPAP26 performs dual functions in plants: Pi remobilization from senescing to non-senescing leaves; and organic P utilization.

Description

Levomefolic acid (5-MTHF) is the natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions.

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