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T3125

Sigma-Aldrich

Tetrahydrofolic acid

≥65% (when packaged), powder

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Synonym(s):
5,6,7,8-Tetrahydropteroyl-L-glutamic acid, THF
Empirical Formula (Hill Notation):
C19H23N7O6
CAS Number:
135-16-0
Molecular Weight:
445.43
Beilstein:
9238187
EC Number:
205-181-1
MDL number:
MFCD00135583
UNSPSC Code:
12352204
PubChem Substance ID:
24900106
NACRES:
NA.51

form

powder

Quality Level

200

concentration

≥65% (when packaged)

color

faintly yellow to light brown

storage temp.

−20°C

SMILES string

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

InChI key

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).

Biochem/physiol Actions

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

Packaging

Sealed ampule.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Ronald R Breaker
Molecular cell, 43(6), 867-879 (2011-09-20)
An expanding number of metabolite-binding riboswitch classes are being discovered in the noncoding portions of bacterial genomes. Findings over the last decade indicate that bacteria commonly use these RNA genetic elements as regulators of metabolic pathways and as mediators of
Tyler D Ames et al.
Chemistry & biology, 17(7), 681-685 (2010-07-28)
Comparative sequence analyses of bacterial genomes are revealing many structured RNA motifs that function as metabolite-binding riboswitches. We have identified an RNA motif frequently positioned in the 5' UTRs of folate transport and biosynthesis genes in Firmicute genomes. Biochemical experiments
Yoko Chiba et al.
The FEBS journal, 279(3), 504-514 (2011-12-07)
Serine hydroxymethyltransferase catalyzes the cleavage of β-hydroxyamino acids into glycine and aldehydes in the absence of tetrahydrofolate. The enzyme accepts various β-hydroxyamino acids as the substrate of this reaction. The reaction rate varies depending on the substituent and stereochemistry at
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