B vitamins

B vitamins are a class of water-soluble vitamins that play important roles in cell metabolism and synthesis
of red blood cells.[1] They are a chemically diverse class of compounds, but are associated in diet, often
occurring together in the same foods.[1] Dietary supplements containing all eight are referred to as a
vitamin B complex. Individual B vitamins are referred to by B-number or by chemical name, such as B1
for thiamine, B2 for riboflavin, and B3 for niacin,[1] while some are more commonly recognized by name
than by number, such as pantothenic acid (B5 ), biotin (B7 ), and folate (B9 ).

Each B vitamin is either a cofactor (generally a coenzyme) for key metabolic processes or is a precursor
needed to make one.[1]

List of B vitamins
List of B vitamins
Vitamin Name Description

Vitamin
Thiamine A coenzyme in the catabolism of sugars and amino acids.
B1

Vitamin A precursor of coenzymes called FAD and FMN, which are needed for flavoprotein
Riboflavin
B2 enzyme reactions, including activation of other vitamins

Niacin (nicotinic
acid)
Vitamin A precursor of coenzymes called NAD and NADP, which are needed in many
Niacinamide
B3 metabolic processes.
Nicotinamide
riboside

Vitamin Pantothenic
A precursor of coenzyme A and therefore needed to metabolize many molecules.
B5 acid

Pyridoxine
Vitamin
Pyridoxal A coenzyme in many enzymatic reactions in metabolism.
B6
Pyridoxamine

Vitamin A coenzyme for carboxylase enzymes, needed for synthesis of fatty acids and in
Biotin
B7 gluconeogenesis.

Vitamin A precursor needed to make, repair, and methylate DNA; a cofactor in various
B9 Folate reactions; especially important in aiding rapid cell division and growth, such as in
infancy and pregnancy.
Commonly cyanocobalamin or methylcobalamin in vitamin supplements. A
Vitamin coenzyme involved in the metabolism of all animal cells, especially affecting DNA
B12 Cobalamins
synthesis and regulation, but also fatty acid metabolism and amino acid
metabolism.
Note: Other substances once thought to be vitamins were given B-numbers, but were disqualified once
discovered to be either manufactured by the body or not essential for life. See #Related compounds for
numbers 4, 8, 10, 11, and others.

Sources
B vitamins are found in abundance in meat, eggs, and dairy products.[1] Processed carbohydrates such as
sugar and white flour tend to have lower B vitamin than their unprocessed counterparts. For this reason, it is
common in many countries (including the United States) that the B vitamins thiamine, riboflavin, niacin,
and folic acid are added back to white flour after processing. This is referred to as "enriched flour" on food
labels. B vitamins are particularly concentrated in meat such as turkey, tuna and liver.[2]

Sources for B vitamins also include spinach, legumes (pulses or beans), whole grains, asparagus, potatoes,
bananas, chili peppers, breakfast cereals.[1] The B12 vitamin is not abundantly available from plant
products[3] (although it has been found in moderate abundance in fermented vegetable products, certain
seaweeds, and in certain mushrooms, with the bioavailability of the vitamin in these cases remaining
uncertain),[4] making B12 deficiency a legitimate concern for those maintaining a vegan diet. Manufacturers
of plant-based foods will sometimes report B12 content, leading to confusion about what sources yield B12 .
The confusion arises because the standard US Pharmacopeia (USP) method for measuring the B12 content
does not measure the B12 directly. Instead, it measures a bacterial response to the food. Chemical variants of
the B12 vitamin found in plant sources are active for bacteria, but cannot be used by the human body. This
same phenomenon can cause significant over-reporting of B12 content in other types of foods as well.[5]

A common way to increase vitamin B intake is by using dietary supplements. B vitamins are commonly
added to energy drinks, many of which have been marketed with large amounts of B vitamins.[6]

Because they are soluble in water, excess B vitamins are generally readily excreted, although individual
absorption, use and metabolism may vary.[6] The elderly and athletes may need to supplement their intake
of B12 and other B vitamins due to problems in absorption and increased needs for energy production. In
cases of severe deficiency, B vitamins, especially B12 , may also be delivered by injection to reverse
deficiencies.[7] Both type 1 and type 2 diabetics may also be advised to supplement thiamine based on high
prevalence of low plasma thiamine concentration and increased thiamine clearance associated with
diabetes.[8] Also, folate deficiency in early embryo development has been linked to neural tube defects.
Thus, women planning to become pregnant are usually encouraged to increase daily dietary folate intake or
take a supplement.[9]

Molecular functions
Vitamin Name Structure Molecular function
Thiamine plays a central role in the release of energy from
carbohydrates. It is involved in RNA and DNA production,
as well as nerve function. Its active form is a coenzyme
Vitamin B1 Thiamine called thiamine pyrophosphate (TPP), which takes part in
the conversion of pyruvate to acetyl coenzyme A in
metabolism.[10]

Riboflavin is involved in release of energy in the electron

Vitamin B2 Riboflavin transport chain, the citric acid cycle, as well as the
catabolism of fatty acids (beta oxidation).[11]

Niacin is composed of two structures: nicotinic acid and

nicotinamide. There are two co-enzyme forms of niacin:
nicotinamide adenine dinucleotide (NAD) and nicotinamide
adenine dinucleotide phosphate (NADP). Both play an
important role in energy transfer reactions in the
Vitamin B3 Niacin
metabolism of glucose, fat and alcohol.[12] NAD carries
hydrogens and their electrons during metabolic reactions,
including the pathway from the citric acid cycle to the
electron transport chain. NADP is a coenzyme in lipid and
nucleic acid synthesis.[13]
Pantothenic acid is involved in the oxidation of fatty acids
and carbohydrates. Coenzyme A, which can be
synthesised from pantothenic acid, is involved in the
Vitamin B5 Pantothenic synthesis of amino acids, fatty acids, ketone bodies,
acid
cholesterol,[14] phospholipids, steroid hormones,
neurotransmitters (such as acetylcholine), and
antibodies.[15]

The active form pyridoxal 5'-phosphate (PLP) (depicted)

Pyridoxine,
serves as a cofactor in many enzyme reactions mainly in
Vitamin B6 pyridoxal,
amino acid metabolism including biosynthesis of
pyridoxamine
neurotransmitters.[16]

Biotin plays a key role in the metabolism of lipids, proteins

and carbohydrates. It is a critical co-enzyme of four
carboxylases: acetyl CoA carboxylase, which is involved
in the synthesis of fatty acids from acetate; pyruvate CoA
Vitamin B7 Biotin carboxylase, involved in gluconeogenesis; β-
methylcrotonyl CoA carboxylase, involved in the
metabolism of leucine; and propionyl CoA carboxylase,
which is involved in the metabolism of energy, amino
acids and cholesterol.[17]
Vitamin B9 Folate Folate acts as a co-enzyme in the form of tetrahydrofolate
(THF), which is involved in the transfer of single-carbon
units in the metabolism of nucleic acids and amino acids.
THF is involved in purine and pyrimidine nucleotide
synthesis, so is needed for normal cell division, especially
during pregnancy and infancy, which are times of rapid
 growth. Folate also aids in erythropoiesis, the production
of red blood cells.[18]
Vitamin B12 is involved in the cellular metabolism of
carbohydrates, proteins and lipids. It is essential in the
production of blood cells in bone marrow, and for nerve
Vitamin B12 sheaths and proteins.[19] Vitamin B12 functions as a co-
Cobalamin
enzyme in intermediary metabolism for the methionine
synthase reaction with methylcobalamin, and the
methylmalonyl CoA mutase reaction with
adenosylcobalamin.[20]

Deficiencies
Several named vitamin deficiency diseases may result from the lack of sufficient B vitamins.[1] Deficiencies
of other B vitamins result in symptoms that are not part of a named deficiency disease.
 Vitamin Name Deficiency effects

Thiamine deficiency causes beriberi. Symptoms of this disease of the nervous

system include weight loss, emotional disturbances, Wernicke encephalopathy
(impaired sensory perception), weakness and pain in the limbs, periods of
Vitamin B1 Thiamine irregular heartbeat, and edema (swelling of bodily tissues). Heart failure and
death may occur in advanced cases. Chronic thiamine deficiency can also
cause alcoholic Korsakoff syndrome, an irreversible dementia characterized by
amnesia and compensatory confabulation.

Riboflavin deficiency can cause ariboflavinosis, which may result in cheilosis

(cracks in the lips), high sensitivity to sunlight, angular cheilitis, glossitis
Vitamin B2 Riboflavin (inflammation of the tongue), seborrheic dermatitis or pseudo-syphilis
(particularly affecting the scrotum or labia majora and the mouth), pharyngitis
(sore throat), hyperemia, and edema of the pharyngeal and oral mucosa.
Niacin deficiency, along with a deficiency of tryptophan, causes pellagra.
Symptoms include aggression, dermatitis, insomnia, weakness, mental
Vitamin B3 Niacin
confusion, and diarrhea. In advanced cases, pellagra may lead to dementia and
death (the 3(+1) D's: dermatitis, diarrhea, dementia, and death).

Vitamin B5 Pantothenic Pantothenic acid deficiency can result in acne and paresthesia, although it is
acid uncommon.

Pyridoxine, Vitamin B6 deficiency causes seborrhoeic dermatitis-like eruptions, pink eye

Vitamin B6 pyridoxal,
and neurological symptoms (e.g. epilepsy).
pyridoxamine
Biotin deficiency does not typically cause symptoms in adults, other than
cosmetic issues such as decreased hair and nail growth, but may lead to
Vitamin B7 Biotin impaired growth and neurological disorders in infants. Multiple carboxylase
deficiency, an inborn error of metabolism, can lead to biotin deficiency even
when dietary biotin intake is normal.

Folic acid deficiency results in a macrocytic anemia, and elevated levels of

Folate Folic acid homocysteine. Deficiency in pregnant women can lead to birth defects,
particularly neural tube defects such as spina bifida and anencephaly.

Vitamin B12 deficiency results in a macrocytic anemia, elevated methylmalonic

acid and homocysteine, peripheral neuropathy, sense loss, change in mobility,
memory loss and other cognitive deficits. It is most likely to occur among
Vitamin B12 Cobalamins elderly people, as absorption through the gut declines with age; the
autoimmune disease pernicious anemia is another common cause. It can also
cause symptoms of mania and psychosis. Untreated, it is possible to cause
irreversible damage to the brain and nerve system — In rare extreme cases,
paralysis can result.

Side effects

Because water-soluble B vitamins are eliminated in the urine, taking large doses of certain B vitamins
usually only produces transient side effects (only exception is pyridoxine). General side effects may include
restlessness, nausea and insomnia. These side effects are almost always caused by dietary supplements and
not foodstuffs.
 Tolerable Upper
Vitamin Harmful effects
Intake Level (UL)

No known toxicity from oral intake. There are some reports of

[21] anaphylaxis caused by high-dose thiamin injections into the vein or
Vitamin B1 None muscle. However, the doses were greater than the quantity humans can
physically absorb from oral intake.[21]
No evidence of toxicity based on limited human and animal studies. The
[22] only evidence of adverse effects associated with riboflavin comes from
Vitamin B2 None in vitro studies showing the production of reactive oxygen species (free
radicals) when riboflavin was exposed to intense visible and UV light.[22]
Intake of 3000 mg/day of nicotinamide and 1500 mg/day of nicotinic
acid are associated with nausea, vomiting, and signs and symptoms of
liver toxicity. Other effects may include glucose intolerance, and
(reversible) ocular effects. Additionally, the nicotinic acid form may
cause vasodilatory effects, also known as flushing, including redness of
US UL = 35 mg as a the skin, often accompanied by an itching, tingling, or mild burning
Vitamin B3 sensation, which is also often accompanied by pruritus, headaches, and
dietary supplement[23]
increased intracranial blood flow, and occasionally accompanied by
pain.[23] Medical practitioners prescribe recommended doses up to
2000 mg per day of niacin in either immediate-release or slow-release
formats, to lower plasma triglycerides and low-density lipiprotein
cholesterol.[24]
Vitamin B5 None No toxicity known.

Vitamin B6 US UL = 100 mg/day; See Megavitamin-B6 syndrome for more information.

EU UL = 25 mg/day
Vitamin B7 None No toxicity known.

Masks B12 deficiency, which can lead to permanent neurological

Folate 1 mg/day[25]
damage.[25]
Skin and spinal lesions. Acne-like rash [causality is not conclusively
Vitamin B12 None established[26]
established].[26][27]

Discovery
Vitamin Name Discoverer Date Notes

Umetaro Suzuki 1910 Failed to gain publicity.

Vitamin B1 Thiamine
Casimir Funk 1912

Vitamin B2 D.T Smith and E.G Max Tishler invented methods for
Riboflavin 1926
Hendrick synthesizing it.

Vitamin B3 Niacin Conrad Elvehjem 1937

Vitamin B5 Pantothenic
Roger J. Williams 1933
acid
Pyridoxine
Vitamin B6 Paul Gyorgy 1934
etc.

Research by multiple independent groups in the early 1900s; credits for discovery
Vitamin B7 Biotin include Margaret Averil Boas (1927),[28] Paul Gyorgy (1939, as Vitamin H),[29] and
Dean Burk.[30]

Vitamin B9 Folic acid Lucy Wills 1933

 Five people have been awarded Nobel Prizes for direct and indirect studies of
Vitamin B12 Cobalamins vitamin B12: George Whipple, George Minot and William Murphy (1934), Alexander
R. Todd (1957), and Dorothy Hodgkin (1964).[31]

Related compounds
Many of the following substances have been referred to as vitamins as they were once believed to be
vitamins. They are no longer considered as such, and the numbers that were assigned to them now form the
"gaps" in the true series of B-complex vitamins described above (for example, there is no vitamin B4 ).
Some of them, though not essential to humans, are essential in the diets of other organisms; others have no
known nutritional value and may even be toxic under certain conditions.

Vitamin B4: can refer to the distinct chemicals choline, adenine, or carnitine.[32][33]

Choline is synthesized by the human body, but not sufficiently to maintain good health,
and is now considered an essential dietary nutrient.[34]
Adenine is a nucleobase synthesized by the human body.[35]
Carnitine is an essential dietary nutrient for certain worms, but not for humans.[36]
Vitamin B8: adenosine monophosphate (AMP), also known as adenylic acid.[37] Vitamin B8
may also refer to inositol.[38]
Vitamin B10: para-aminobenzoic acid (pABA or PABA), a chemical component of the folate
molecule produced by plants and bacteria, and found in many foods.[39][40] It is best known
as a UV-blocking sunscreen applied to the skin, and is sometimes taken orally for certain
medical conditions.[39][41]
Vitamin B11: pteroylheptaglutamic acid (PHGA; chick growth factor). Vitamin Bc-conjugate
was also found to be identical to PHGA. Derivative of folate ("pteroylmonoglutamic acid" in
this nomenclature).[42]
Vitamin B13: orotic acid.[43]
Vitamin B14: cell proliferant, anti-anemia, rat growth factor, and antitumor pterin phosphate,
named by Earl R. Norris. Isolated from human urine at 0.33ppm (later in blood), but later
abandoned by him as further evidence did not confirm this. He also claimed this was not
xanthopterin.
Vitamin B15: pangamic acid,[43] also known as pangamate. Promoted in various forms as a
dietary supplement and drug; considered unsafe and subject to seizure by the US Food and
Drug Administration.[44]
Vitamin B16: dimethylglycine (DMG)[45] is synthesized by the human body from choline.
Vitamin B17: pseudoscientific name for the poisonous compound amygdalin, also known as
the equally pseudoscientific name "nitrilosides" despite the fact that it is a single compound.
Amygdalin can be found in various plants, but is most commonly extracted from apricot pits
and other similar fruit kernels. Amygdalin is hydrolyzed by various intestinal enzymes to
form, among other things, hydrogen cyanide, which is toxic to human beings when exposed
to a high enough dosage. Some proponents claim that amygdalin is effective in cancer
treatment and prevention, despite its toxicity and a lack of scientific evidence.[46]
Vitamin B20: L-carnitine.[45]
Vitamin Bf: carnitine.[37]
Vitamin Bm : myo-inositol, also called "mouse antialopaecia factor".[47]
 Vitamin Bp: "antiperosis factor", which prevents perosis, a leg disorder, in chicks; can be
replaced by choline and manganese salts.[36][37][48]
Vitamin BT: carnitine.[49][36]
Vitamin Bv: a type of B6 other than pyridoxine.
Vitamin BW: a type of biotin other than d-biotin.
Vitamin Bx: an alternative name for both pABA (see vitamin B10) and pantothenic
acid.[36][41]

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