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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
Form:
powder
Solubility:
0.1 M phosphate pH 7.0: soluble-5 mg/mL, clear to slightly hazy, light yellow to brownish-yellow
Biological source:
synthetic
Color:
faintly yellow to light brown
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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

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_c

No data available

ppe

Eyeshields, Gloves, type N95 (US)

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

hcodes

H252,H317

Hazard Classifications

Self-heat. 2 - Skin Sens. 1

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

flash_point_f

No data available

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Certificates of Analysis (COA)

Lot/Batch Number
0000496153
0000496153
0000483083
0000483083
0000426528

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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
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
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)
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