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F7876

Sigma-Aldrich

Folic acid

≥97%

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Synonym(s):
PteGlu, Pteroyl-L-glutamic acid, Vitamin M
Empirical Formula (Hill Notation):
C19H19N7O6
CAS Number:
59-30-3
Molecular Weight:
441.40
Beilstein:
100781
EC Number:
200-419-0
MDL number:
MFCD00079305
UNSPSC Code:
12352106
eCl@ss:
34058014
PubChem Substance ID:
57654192
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

Assay

≥97%

form

powder

technique(s)

HPLC: suitable

color

faint orange to dark orange-yellow
faint yellow to dark yellow

mp

>285 °C

storage temp.

room temp

SMILES string

NC(N1)=NC(C2=C1N=CC(CNC3=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C3)=N2)=O

InChI

1S/C19H19N7O6/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/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1

InChI key

OVBPIULPVIDEAO-LBPRGKRZSA-N

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Application

Folic acid has been used:
  • to induce acute kidney injury in mice
  • as a supplement to cultivate MCF-7 breast cancer cells.
  • to construct folate or TNF-related apoptosis-including ligand (TRAIL)-conjugated nanomicelles

Biochem/physiol Actions

Enzyme cofactor essential for the synthesis, methylation, and repair of DNA. Folic acid supplements may reduce colorectal cancer risk.
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).

WGK

WGK 1

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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Surface-enhanced Raman spectroscopy of cell lysates mixed with silver nanoparticles for tumor classification.
Hassoun M, et al.
Beilstein Journal of Nanotechnology, 8, 1183-1183 (2017)
Romain Froquet et al.
Nature protocols, 4(1), 25-30 (2009-01-10)
Dictyostelium amoebae have been used as a host model to measure virulence of a wide range of bacterial pathogens. The simple protocol described here takes advantage of the ability of Dictyostelium to grow and form plaques on a lawn of
Fibroblast Growth Factor 23 Expression is increased in Multiple Organs in Mice with Folic Acid-induced Acute Kidney Injury.
Egli-Spichtig D, et al.
Frontiers in Physiology, 9, 1494-1494 (2018)
Silvia Ferrè et al.
Kidney international, 96(6), 1359-1373 (2019-10-12)
Sepsis is a systemic inflammatory state in response to infection, and concomitant acute kidney injury (AKI) increases mortality significantly. Endoplasmic reticulum stress is activated in many cell types upon microbial infection and modulates inflammation. The role of endoplasmic reticulum signaling
Tor A Strand et al.
Pediatrics, 135(4), e918-e926 (2015-03-25)
Folate and vitamin B-12 are important for growth. Many children in low- and middle-income countries have inadequate intakes of these nutrients. We undertook a randomized, placebo controlled double-blind trial in 1000 North Indian children, 6 to 35 months of age
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