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T3125

Sigma-Aldrich

Tetrahydrofolic acid

≥65% (when packaged), powder

Synonym(s):

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

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About This Item

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

biological source

synthetic

Quality Level

200

form

powder

concentration

≥65% (when packaged)

color

faintly yellow to light brown

solubility

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

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.

Storage Class Code

11 - Combustible Solids

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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Francisco García-Molina et al.
Journal of agricultural and food chemistry, 59(4), 1383-1391 (2011-01-27)
The coenzyme tetrahydrofolic acid is the most rapid suicide substrate of tyrosinase that has been characterized to date. A kinetic study of the suicide inactivation process provides the kinetic constants that characterize it: λ(max), the maximum apparent inactivation constant; r
Changhua Yu et al.
Journal of cancer research and clinical oncology, 138(2), 255-259 (2011-11-23)
The purpose of the current study is to evaluate the efficacy and complications of concurrent chemoradiotherapy (CCRT) for the treatment of gastric cancer patients after D1/D2 surgery. Sixty-eight untreated gastric cancer patients (T3/T4 and/or N+) were enrolled. After surgery, they
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
Prim-O-glucosylcimifugin enhances the antitumour effect of PD-1 inhibition by targeting myeloid-derived suppressor cells
Gao W, et al.
Journal for Immunotherapy of Cancer, 7(1), 231-231 (2019)
Aurora Meucci et al.
Food microbiology, 69, 116-122 (2017-09-25)
The ability of folate-producer strains of Streptococcus thermophilus to accumulate folates and the expression of two target genes (folK and folP), involved in the folate biosynthesis, were studied during milk fermentation. An over-expression of folK took place only in the
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