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D7006

Sigma-Aldrich

Dihydrofolic acid

≥90%

Synonym(s):

7,8-Dihydropteroyl-L-glutamic acid, Dihydropteroyl-L-glutamic acid, FAH2

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About This Item

Empirical Formula (Hill Notation):
C19H21N7O6
CAS Number:
4033-27-6
Molecular Weight:
443.41
Beilstein/REAXYS Number:
69017
MDL number:
MFCD00083619
UNSPSC Code:
12352106
PubChem Substance ID:
24894068
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

assay

≥90%

form

powder

color

light yellow to dark yellow-orange

storage temp.

−20°C

SMILES string

NC1=NC(=O)C2=C(NCC(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1

InChI

1S/C19H21N7O6/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/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

InChI key

OZRNSSUDZOLUSN-LBPRGKRZSA-N

Gene Information

human ... DHFRP1(573971)
mouse ... Dhfr(13361)

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Related Categories

General description

Intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). In bacteria, dihydrofolic acid is generated from 7,8-dihydropteroate by dihydrofolate synthetase.

Application

Dihydrofolic acid has been used in diaphorase-coupled assay for dihydrofolate reductase (DHFR) activity. It has also been used as a component in assay buffer to determine dihydrofolate reductase (DHFR) activity.

Biochem/physiol Actions

Folic acid (FA) and dihydrofolic acid (FAH2) are substrates of dihydrofolate reductase(s) which reduce them to tetrahydrofolate (THF), which in turn supports ‘one carbon′ transfer. Tetrahydrofolates are required for de novo synthesis of purines, thymidylic acid and various amino acids and for post-translational methylation (epigenetics).

Packaging

Sealed ampule.

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Description
Pricing

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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David T Manallack
Journal of molecular modeling, 14(9), 797-805 (2008-05-27)
This study employed surface-based properties for use in the superimposition of three series of molecules. The properties used were derived from semiempirical molecular orbital calculations and can be related to the physics of intermolecular interactions. In each case, the superimposition
James L Bodnar et al.
Ticks and tick-borne diseases, 9(3), 443-449 (2017-12-30)
Although nonpathogenic bacterial endosymbionts have been shown to contribute to their arthropod host's fitness by supplying them with essential vitamins and amino acids, little is known about the nutritional basis for the symbiotic relationship of endosymbionts in ticks. Our lab
Tobias Sahr et al.
The Biochemical journal, 396(1), 157-162 (2006-02-10)
pABA (p-aminobenzoate) is a precursor of folates and, besides esterification to glucose, has no other known metabolic fate in plants. It is synthesized in two steps from chorismate and glutamine, the first step being their conversion into glutamate and ADC
Z Attias et al.
Endocrine-related cancer, 13(2), 571-581 (2006-05-27)
The insulin-like growth factor-I receptor (IGF-IR) has an important role in colorectal cancer development and progression. IGF-IR displays a potent anti-apoptotic activity and is overexpressed in primary tumors and colon cancer-derived cell lines. Folic acid, a member of the vitamin
Anna Gliszczyńska-Swigło et al.
Journal of agricultural and food chemistry, 55(20), 8237-8242 (2007-09-13)
Folic acid (FA) is used, in many countries, in nutritional supplements or for the fortification of cereals and their products. It is also used in vitamin pills. Recently, it was reported that folates may act as antioxidants; therefore, in the
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