(6S)-Thfa
tetrahydrofolic acid dihydrochloride dihydrate
CAS: 135-16-0
Molecular Formula: C19H23N7O6
(6S)-Thfa - Names and Identifiers
| Name | tetrahydrofolic acid dihydrochloride dihydrate |
| Synonyms | C00101 (6S)-Thfa Tetrahydrofolic acid (6S)-Tetrahydrofolic acid L-5,6,7,8-Tetrahydrofolic acid Tetrahydropteroylglutaamic acid (-)-L-5,6,7,8-Tetrahydrofolic acid tetrahydrofolic acid sealed ampule tetrahydrofolic acid dihydrochloride dihydrate Tetrahydrofolic acid 5,6,7,8-Tetrahydropteroyl-L-glutamic acid Tetrahydrofolic acid,5,6,7,8-Tetrahydropteroyl-L-glutamic acid, THF N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}benzoyl)glutamic acid N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid N-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]carbonyl}-L-glutamic acid |
| CAS | 135-16-0 |
| EINECS | 205-181-1 |
| InChI | InChI=1/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12-/m0/s1 |
(6S)-Thfa - Physico-chemical Properties
| Molecular Formula | C19H23N7O6 |
| Molar Mass | 445.43 |
| Density | 1.4216 (rough estimate) |
| Melting Point | >162°C (dec.) |
| Boling Point | 555.12°C (rough estimate) |
| Solubility | Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | powder |
| Color | off-white to tan |
| BRN | 9238187 |
| pKa | 3.51±0.10(Predicted) |
| Storage Condition | -20°C |
| Stability | We have observed that this material decomposes steadily over time. Use immediately upon receipt. |
| Refractive Index | 1.6800 (estimate) |
(6S)-Thfa - Risk and Safety
| WGK Germany | 3 |
| RTECS | MA0600800 |
| FLUKA BRAND F CODES | 3-8-10 |
(6S)-Thfa - Reference Information
| LogP | -3.685 at 25℃ |
| Introduction | Tetrahydrofolate is a coenzyme in the one-carbon unit transferase system in the body. It is composed of folic acid in the presence of vitamin C and NADH. Under the action of folic acid reductase, dihydrofolate is generated, and then catalyzed by dihydrofolate reductase. Tetrahydrofolate is a carrier of a carbon group, which can transmit a carbon unit, participate in the synthesis of purine and thymine nucleotides, and promote the production of normal blood cells. Therefore, when folic acid deficiency or some drugs inhibit folate reductase, folic acid cannot be converted into tetrahydrofolate, it can affect the development and maturation of blood cells and cause megaloblastic anemia. Folic acid is a one-carbon unit carrier, and tetrahydrofolic acid is another type of one-carbon unit carrier. Folic acid is a water-soluble vitamin B mixture, which is composed of one molecule of pterin, p-aminobenzoic acid and glutamic acid. The tetrahydrofolic acid is obtained by two-step reduction of folic acid, which requires the catalysis of "folate reductase" and "dihydrofolate reductase" respectively. |
| Chemical structure | Tetrahydrofolic acid contains four hydrogen on the 5, 6, 7, 8, and 4 carbon of folic acid, and the one carbon unit it carries is located in N5 or N10, or connect N5 and N10 to form a bridge. The one-carbon unit of tetrahydrofolate as a carrier in the body mainly comes from the carbon skeleton metabolism of different amino acids, such as glycine, serine, histidine, tryptophan, and hydroxyproline. The carbon skeleton metabolism is the source of a carbon unit. However, in terms of quantity, the main source of one carbon unit is the carbon skeleton metabolism of serine. Because serine is catalyzed by "serine transhydroxymethylase", its hydroxymethyl carbon is directly transferred to tetrahydrofolic acid to obtain N5 and N10 methylenetetrahydrofolic acid. |
| Physiological function | Folic acid is further reduced by folate reductase in the intestine to tetrahydrofolate with physiological effects. It is a one-carbon unit transmitter in the biochemical reaction in the body. Folic acid carries a one-carbon unit to form a variety of active forms such as 5-methyltetrahydrofolate and methylenetetrahydrofolate to play a physiological role. 5-Methyltetrahydrofolate is the main form of folic acid in the body. Most of it is transported to the liver, where it is converted into polyglutamic acid derivatives by synthetase and stored. The liver is the main storage site of folic acid, the storage capacity is about 7.5mg ± 2.5mg(Herbert,1962), and there are also reports of 6~14mg(Whitehead,1973) and 11mg(Hoppner,1980). Folic acid in liver accounts for about 50% of the total amount of folic acid in the body. When the polyglutamic folic acid stored in the liver and other tissues is released into the blood, it is hydrolyzed by the binding enzyme into the form of mono-glutamic folic acid and combined with plasma proteins. The liver releases about 0.1mg of folic acid daily into the blood to maintain serum folic acid levels. The folic acid in blood and tissue fluid is mainly 5-methyltetrahydrofolic acid. |
| Preparation | Tetrahydrofolate is a reduced derivative of folic acid, a coenzyme obtained by reducing dihydrofolate by dihydrofolate reductase. |
| biological activity | Tetrahydrofolic acid (L-5,6,7,8-Tetrahydrofolic acid) is a biologically active vitamin B9 folic acid derivative, which is a donor of amino acids, nucleic acids and a carbon atom of lipids. Tetrahydrofolic acid is used as a receptor for free formaldehyde, producing 5, 10-methylenetetrahydrofolate-tetrahydrofolate. |
| Cell Line: | Adh5 -/- DT40 cells Adh5 -/- DT40 cells |
| Concentration: | 0-200 µM 0-200 µM |
| Incubation Time: | 3 days 16 hours |
| Result: | Viability of Adh5 -/- DT40 cells rapidly dropped. Strongly promoted FANCD2 and ser139-H2AX focus formation in Adh5 -/- cells in a dose-dependent manner. Perturbed hematopoiesis, increased ser139-H2AX phosphorylation, and decreased the survival of progenitor cells (HSPCs). |
| Animal Model: | Adh5 -/- mice |
| Dosage: | 62.5 mg/kg |
| Administration: | Intraperitoneal injection; daily |
Last Update：2024-04-10 22:29:15
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