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Merck

T3125

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
UNSPSC Code:
12352204
NACRES:
NA.51
PubChem Substance ID:
24900106
EC Number:
205-181-1
Beilstein/REAXYS Number:
9238187
MDL number:
MFCD00135583

Key Documents

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Product Name

Tetrahydrofolic acid, ≥65% (when packaged), powder

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

SMILES string

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

biological source

synthetic

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

Quality Level

200

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Application

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).
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.

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000496153
0000496153
0000483083
0000483083
0000426528

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Avinash C Srivastava et al.
Plant physiology, 155(3), 1237-1251 (2011-01-15)
A recessive Arabidopsis (Arabidopsis thaliana) mutant with short primary roots and root hairs was identified from a forward genetic screen. The disrupted gene in the mutant encoded the plastidial isoform of folylpolyglutamate synthetase (FPGS), previously designated as AtDFB, an enzyme
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
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
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
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