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T3125

Sigma-Aldrich

Tetrahydrofolic acid

≥65% (when packaged), powder

Synonyme(s) :

5,6,7,8-Tetrahydropteroyl-L-glutamic acid, THF

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About This Item

Formule empirique (notation de Hill):
C19H23N7O6
Numéro CAS:
135-16-0
Poids moléculaire :
445.43
Numéro Beilstein :
9238187
Numéro CE :
205-181-1
Numéro MDL:
MFCD00135583
Code UNSPSC :
12352204
ID de substance PubChem :
24900106
Nomenclature NACRES :
NA.51

Source biologique

synthetic

Niveau de qualité

200

Forme

powder

Concentration

≥65% (when packaged)

Couleur

faintly yellow to light brown

Solubilité

0.1 M phosphate pH 7.0: soluble-5 mg/mL, clear to slightly hazy, light yellow to brownish-yellow

Température de stockage

−20°C

Chaîne SMILES 

NC1=NC2=C(NC(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1

InChI

1S/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

Clé InChI

MSTNYGQPCMXVAQ-KIYNQFGBSA-N

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Application

Tetrahydrofolic acid has been used to determine the inhibitory effect of tetrahydrofolate on polymorphonuclear myeloid-derived suppressor cells (PMN-MDSCs). A recent use of tetrahydrofolate (THF) is for studying the activation of riboswitches.
Tetrahydrofolic acid may also be used as a standard to generate calibration curve to quantify the folate types produced by Streptococcus thermophilus in milk cultures using high-performance liquid chromatography (HPLC). It is also suitable for use in the enzymatic assay of formate-tetrahydrofolate ligase from M. extorquens (MeFtfL).

Actions biochimiques/physiologiques

Tetrahydrofolic acid is the parent molecule of the folate derivatives that donate one-carbon units to amino acids, nucleic acids, and lipids. Tetrahydrofolate metabolites participate in the synthesis of purine and pyrimidine and in synthesis and conversion of amino acids

Conditionnement

Sealed ampule.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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USP

USP

1286300

10-Formylfolic acid

Folic acid-(glutamic acid-13C5) ≥99 atom % 13C, ≥95% (CP)

Sigma-Aldrich

803049

Folic acid-(glutamic acid-13C5)

Dihydrofolate Reductase human ≥80% (SDS-PAGE), recombinant, expressed in E. coli, ≥1 units/mg protein

Sigma-Aldrich

D6566

Dihydrofolate Reductase human

DHFR from mouse recombinant, expressed in E. coli, ≥95% (SDS-PAGE)

Sigma-Aldrich

SRP6119

DHFR from mouse

Folic acid British Pharmacopoeia (BP) Reference Standard

BP937

Folic acid

Folic acid BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, ≥97%

Sigma-Aldrich

F8758

Folic acid

Susanne H Kirsch et al.
Analytical and bioanalytical chemistry, 404(3), 895-902 (2012-06-26)
Folates act as essential coenzymes in many biological pathways, including the synthesis and methylation of DNA. Low folate concentration in serum and whole blood (WB) is associated with several disease conditions. We describe a stable-isotope-dilution ultra performance liquid chromatography tandem
Rima Obeid et al.
Metabolism: clinical and experimental, 60(5), 673-680 (2010-08-24)
Folate deficiency can cause age-related disease. Folic acid (FA) has been used in studies aiming at disease prevention. Recently, unmetabolized FA in plasma raised public health concerns; but numerous studies used FA for disease prevention. Concentrations of the folate forms
Lili Huang et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(36), 14801-14806 (2011-08-30)
Tetrahydrofolate (THF), a biologically active form of the vitamin folate (B(9)), is an essential cofactor in one-carbon transfer reactions. In bacteria, expression of folate-related genes is controlled by feedback modulation in response to specific binding of THF and related compounds
Tseng-Ting Kao et al.
International journal of food microbiology, 141(1-2), 17-27 (2010-05-21)
Staphylococcus aureus (S. aureus) is one of the most common pathogens that causes infectious and foodborne diseases worldwide. Searching for drug and chemical compounds against this bacterium is still in demand. We found that grape seed extract (GSE), a natural
Joseph R Graber et al.
Applied and environmental microbiology, 71(4), 1883-1889 (2005-04-07)
Treponema primitia, an H2-consuming CO2-reducing homoacetogenic spirochete in termite hindguts, requires an exogenous source of folate for growth. Tetrahydrofolate (THF) acts as a C1 carrier in CO2-reductive acetogenesis, a microbially mediated process important to the carbon and energy requirements of
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