Folic Acid

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Folic Acid (Wikipedia)
Folic acid
Skeletal formula
Ball-and-stick model
Space-filling model
Folic acid as an orange powder
Names
IUPAC name
(2S)-2-[[4-[(2-Amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Other names
N-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid; pteroyl-L-glutamic acid; Vitamin B9; Vitamin Bc; Vitamin M; Folacin
Identifiers
59-30-3 YesY
ChEBI CHEBI:27470 YesY
ChEMBL ChEMBL1622 YesY
ChemSpider 5815 YesY
DrugBank DB00158 YesY
4563
Jmol 3D image Interactive graph
KEGG C00504 N
PubChem 6037
RTECS number LP5425000
UNII 935E97BOY8 YesY
Properties
C19H19N7O6
Molar mass 441.40 g·mol−1
Appearance yellow-orange crystalline powder
Melting point 250 °C (482 °F; 523 K) (decomposition)
1.6 mg/L (25 °C)
log P -2.5
Acidity (pKa) 1st: 4.65, 2nd: 6.75, 3rd: 9.00
Pharmacology
B03BB01 (WHO)
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Folic acid or folate is a B vitamin. It is also referred to as vitamin M,vitamin B9,vitamin Bc (or folacin), pteroyl-L-glutamic acid, and pteroyl-L-glutamate.

Food supplement manufacturers often use the term folate for something different from "pure" folic acid: in chemistry, folate refers to the deprotonated ion, and folic acid to the neutral molecule—which both coexist in water. The International Union of Pure and Applied Chemistry and the International Union of Biochemistry and Molecular Biology state that folate and folic acid are the preferred synonyms for pteroylglutamate and pteroylglutamic acid, respectively.

Folate indicates a collection of "folates" that is not chemically well-characterized, including other members of the family of pteroylglutamates, or mixtures of them, having various levels of reduction of the pteridine ring, one-carbon substitutions and different numbers of glutamate residues.

Folic acid is synthetically produced, and used in fortified foods and supplements on the theory that it is converted into folate. However, folic acid is a synthetic oxidized form, not significantly found in fresh natural foods. To be used it must be converted to tetrahydrofolate (tetrahydrofolic acid) by dihydrofolate reductase (DHFR). Increasing evidence suggests that this process may be slow in humans.

Vitamin B9 is essential for numerous bodily functions. Humans cannot synthesize folates de novo; therefore, folic acid has to be supplied through the diet to meet their daily requirements. The human body needs folate to synthesize DNA, repair DNA, and methylate DNA as well as to act as a cofactor in certain biological reactions. It is especially important in aiding rapid cell division and growth, such as in infancy and pregnancy. Children and adults both require folate to produce healthy red blood cells and prevent anemia.

Folate and folic acid derive their names from the Latin word folium, which means "leaf". Folates occur naturally in many foods and, among plants, are especially plentiful in dark green leafy vegetables.

A lack of dietary folates can lead to folate deficiency. A complete lack of dietary folate takes months before deficiency develops as normal individuals have about 500–20,000 micrograms ( µg) of folate in body stores. This deficiency can result in many health problems, the most notable one being neural tube defects in developing embryos—a relatively rare birth defect affecting 300,000 (0.2%) births globally each year and 3,000 pregnancies in the United States each year. Common symptoms of folate deficiency include diarrhea, macrocytic anemia with weakness or shortness of breath, nerve damage with weakness and limb numbness (peripheral neuropathy), pregnancy complications, mental confusion, forgetfulness or other cognitive deficits, mental depression, sore or swollen tongue, peptic or mouth ulcers, headaches, heart palpitations, irritability, and behavioral disorders. Low levels of folate can also lead to homocysteine accumulation. Low levels of folate have been associated with specific cancers. However, it is not clear whether consuming recommended (or higher) amounts of folic acid—from foods or in supplements—can lower cancer risk in some people.

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