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01769

Sigma-Aldrich

Folic acid

Synonym(s):

Acidum folicum, PteGlu, Pteroyl-L-glutamic acid, Vitamin M

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About This Item

Empirical Formula (Hill Notation):
C19H19N7O6
CAS Number:
59-30-3
Molecular Weight:
441.40
Beilstein/REAXYS Number:
100781
EC Number:
200-419-0
MDL number:
MFCD00079305
UNSPSC Code:
12352209
eCl@ss:
34058014
PubChem Substance ID:
329747356

biological source

synthetic

agency

USP/NF

assay

96.0-102.0% anhydrous basis

form

powder

color

yellow

mp

250 °C

solubility

cold water: very slightly soluble 0.0016 mg/ml at 25 degrees C
boiling water: soluble 1%
1-butanol: partially soluble
acetone: insoluble
benzene: insoluble
chloroform: insoluble
diethyl ether: insoluble
dilute HCl: soluble (Hot)
ethanol: partially soluble
methanol: slightly soluble
sulfuric acid: soluble

storage temp.

2-8°C

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 was injected in control and manifest diabetic pregnant rats for studying whether folic acid supplementation can moderate diabetes and glucose-induced dysmorphogenesis in rat embryos.[1] It can also be used in the synthesis of N10-trifluoroacetylpteroic acid.[2]

Biochem/physiol Actions

Folic acid also referred to as folate, vitamin M or vitamin Bc is a form of water-soluble vitamin B9. Folic acid therapy can reduce elevated plasma levels of arginine and asymmetric dimethylarginine (ADMA) in hyperhomocysteinaemic subjects.[3] Folic acid used as a food supplement in early pregnancy can diminish the risk of neural tube defects.[4]

Preparation Note

Folic acid dissolves in hot dil HCl, H2SO4 and about 1% boiling water. It is slightly soluble in methanol and shows very slight solubility in cold water (0.0016 mg/ml at 25°C). Additionally, the product appreciably dissolves in ethanol and butanol and has relative solubility in acetic acid, phenol, pyridine, solutions of alkali hydroxides and carbonates. It is insoluble in acetone, benzene, ether and chloroform.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBR2469V
BCBQ2830V
BCBM5494V
BCBP9129V
BCBP0398V

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Kirsten B Holven et al.
The British journal of nutrition, 89(3), 359-363 (2003-03-12)
Asymmetric dimethylarginine (ADMA), an endogenous inhibitor of NO synthase, has been suggested to be a novel risk factor for endothelial dysfunction. It has previously been reported that hyperhomocysteinaemia may be associated with impaired endothelium-dependent vasodilation and reduced plasma level of
Parri Wentzel et al.
Diabetes, 54(2), 546-553 (2005-01-29)
Maternal administration of folic acid diminishes the risk of neural tube defects (NTDs) in offspring, but whether folic acid exerts a similar effect in diabetic pregnancy is unknown. The aim was to investigate whether maldevelopment in rat embryos caused by
Ruben M Sandoval et al.
American journal of physiology. Cell physiology, 287(2), C517-C526 (2004-04-23)
Intravital two-photon microscopy was used to follow the uptake and trafficking of fluorescent conjugates of folic acid in the rat kidney. Intravenously administered folate-linked dye molecules quickly filled the plasma volume but not cellular components of the blood. Glomerular filtration
A Milunsky et al.
JAMA, 262(20), 2847-2852 (1989-11-24)
We examined the relation of multivitamin intake in general, and folic acid in particular, to the risk of neural tube defects in a cohort of 23,491 women undergoing maternal serum alpha-fetoprotein screening or amniocentesis around 16 weeks of gestation. Complete
Tihomir Tomasić et al.
Bioorganic & medicinal chemistry letters, 19(1), 153-157 (2008-11-19)
Mur ligases catalyze the biosynthesis of the UDP-MurNAc-pentapeptide precursor of peptidoglycan, an essential polymer of bacterial cell-wall. They constitute attractive targets for the development of novel antibacterial agents. Here we report on the synthesis of a series of 2,4-diaminoquinazolines, quinazoline-2,4(1H,3H)-diones
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