Riboflavin
Identifiers
CAS number	[83-88-5]
PubChem	1072
MeSH	Riboflavin
Properties
Molecular formula	C17H20N4O6
Molar mass	376.36 g/mol
Melting point	290 °C (dec.) Image File history File links No higher resolution available. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Riboflavin (E101), also known as vitamin B₂, is an easily absorbed micronutrient with a key role in maintaining health in animals. It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B₂ is required for a wide variety of cellular processes. Like the other B vitamins, it plays a key role in energy metabolism, and is required for the metabolism of fats, ketone bodies, carbohydrates, and proteins. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... For the mathematical constant see: E (mathematical constant). ... Micronutrients for plants: There are about eight nutrients essential to plant growth and health that are only present in very small quantities. ... A cofactor is any substance that needs to be present in addition to an enzyme to catalyze a certain reaction. ... For other uses, see FAD (disambiguation). ... Flavin mononucleotide or FMN is derived from riboflavin (vitamin B2) and functions as cofactor of various oxidoreductases. ... Flavoproteins are proteins that contain a nucleic acid derivative of riboflavin: the Flavin-Adenine Dinucleotide or FAD. This proteins acts as dehydrogenation catalysts in biological reactions inside the mitochondria. ... Vitamin B is a complex of several vitamins. ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... Fats is the plural for fat, a generic term for a class of lipids in biochemistry. ... Ketone bodies are three chemicals that are produced as by-products when fatty acids are broken down for energy. ... Lactose is a disaccharide found in milk. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ...

Milk, cheese, leafy green vegetables, liver, kidneys, legumes such as mature soybeans,^[1] yeast, almonds and rock lobsters^{[citation needed]} are good sources of vitamin B₂, but exposure to light destroys riboflavin. A glass of cows milk. ... Cheese is a solid food made from the milk of cows, goats, sheep, and other mammals. ... Chinese cabbage Swiss chard Leaf vegetables, also called greens or leafy greens, are plant leaves eaten as a vegetable, sometimes accompanied by tender petioles and shoots. ... The liver is the largest internal organ in the human body, and is an organ present in vertebrates and some other animals. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... Soy redirects here. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic micro organisms classified in the kingdom Fungi, with about 1,500 species described;[1] they dominate fungal diversity in the oceans. ... For other uses, see Almond (disambiguation). ... Rock Lobster is The B-52s first single, released in 1978 and in a longer version placed on the bands self-titled debut album, The B-52s, one year later. ...

Toxicity

Riboflavin is not toxic when taken orally, as its low solubility keeps it from being absorbed in dangerous amounts from the gut ^[2]. Although toxic doses can be administered by injection^[2], any excess at nutritionally relevant doses is excreted in the urine^[3], imparting a bright yellow color when in large quantities.

Industrial synthesis

Various biotechnological processes have been developed for industrial scale riboflavin biosynthesis using different microorganisms, including filamentous fungi such as Ashbya gossypii, Candida famata and Candida flaveri as well as the bacteria Corynebacterium ammoniagenes and Bacillus subtilis^[4]. The latter organism has been genetically modified to both increase the bacteria's production of riboflavin and to introduce an antibiotic (ampicillin) resistance marker, and is now successfully employed at a commercial scale to produce riboflavin for feed and food fortification purposes. The chemical company BASF has installed a plant in South Korea, which is specialized on riboflavin production using Ashbya gossypii. The concentrations of riboflavin in their modified strain are so high, that the mycelium has a reddish / brownish color and accumulates riboflavin crystals in the vacuoles, which will eventually burst the mycelium. This article is about the fungi known as molds. ... Binomial name Ashbya gossypii (S.F. Ashby & W. Nowell) Guillierm, 1928 Synonyms Eremothecium gossypii (S.F. Ashby & W. Nowell) Kurtzman, 1995 Nematospora gossypii // Ashbya gossypii is a filamentous fungus or mold which was originally isolated from cotton as a pathogen of stigmatomycosis by Ashby and Novell in 1926. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Binomial name Bacillus subtilis (Ehrenberg 1835) Cohn 1872 Gram-stained Bacillus subtilis Sporulating Bacillus subtilis Bacillus subtilis is a Gram-positive, catalase-positive bacterium commonly found in soil. ... Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. ... This article is about the German chemical company. ... A factory (previously manufactory) or manufacturing plant is a large industrial building where workers manufacture goods or products. ... Binomial name Ashbya gossypii (S.F. Ashby & W. Nowell) Guillierm, 1928 Synonyms Eremothecium gossypii (S.F. Ashby & W. Nowell) Kurtzman, 1995 Nematospora gossypii // Ashbya gossypii is a filamentous fungus or mold which was originally isolated from cotton as a pathogen of stigmatomycosis by Ashby and Novell in 1926. ... In biology, Strain can be used two ways. ... Mycelium is the vegetative part of a fungus, consisting of a mass of branching, thread-like hyphae. ... Vacuoles are large membrane-bound compartments within some eukaryotic cells where they serve a variety of different functions: capturing food materials or unwanted structural debris surrounding the cell, sequestering materials that might be toxic to the cell, maintaining fluid balance (called turgor) within the cell, exporting unwanted substances from the...

Riboflavin in food

Riboflavin is yellow or yellow-orange in color and in addition to being used as a food coloring it is also used to fortify some foods. It is used in baby foods, breakfast cereals, pastas, sauces, processed cheese, fruit drinks, vitamin-enriched milk products, some energy drinks, and is widely used in vitamin supplements. Food coloring spreading on a thin water film. ... Baby food is any food that is made specifically for infants, roughly between the ages of six months to two years. ... This article does not cite any references or sources. ... Percentages are relative to US recommendations for adults. ... For other uses, see Sauce (disambiguation). ... American process cheese Processed cheese, process cheese, or prepared cheese is a food product made from regular cheese and sometimes other unfermented dairy ingredients, plus emulsifiers, extra salt, food colorings and/or whey. ... // Generally energy drinks include methylxanthines (including caffeine), B vitamins, and herbs. ... A multivitamin is any preparation containing more than a single vitamin. ...

Large quantities of riboflavin are often included in multi-vitamins; often, the dose is far more than a normal human can use in a day. The excess is excreted in the urine, causing the urine to be colored bright yellow within a few hours of ingestion of the vitamin.

It is difficult to incorporate riboflavin into many liquid products because it has poor solubility in water. Hence the requirement for riboflavin-5'-phosphate (E101a), a more expensive but more soluble form of riboflavin. Riboflavin-5-phosphate is a coenzyme for a number of oxidative enzymes including NADH dehydrogenase. ... For the mathematical constant see: E (mathematical constant). ...

Nutrition

Riboflavin deficiency

Further information: Ariboflavinosis

Riboflavin is continuously excreted in the urine of healthy individuals^[1], making deficiency relatively common when dietary intake is insufficient. However, riboflavin deficiency is always accompanied by deficiency of other vitamins^[1]. Riboflavin deficiency is seen in association with: protein and energy malnutrition alcoholism The clinical features include: dry mucus membranes, affecting: mouth eyes genitalia normochromic, normocytic anaemia Treatment with riboflavin, 6 mg per day. ...

A deficiency of riboflavin can be primary - poor vitamin sources in one's daily diet - or secondary, which may be a result of conditions that affect absorption in the intestine, the body not being able to use the vitamin, or an increase in the excretion of the vitamin from the body.

In humans, signs and symptoms of riboflavin deficiency (ariboflavinosis) include cracked and red lips, inflammation of the lining of mouth and tongue, mouth ulcers, cracks at the corners of the mouth (angular cheilitis), and a sore throat. A deficiency may also cause dry and scaling skin, fluid in the mucous membranes, and iron-deficiency anemia. The eyes may also become bloodshot, itchy, watery and sensitive to bright light. Riboflavin deficiency is seen in association with: protein and energy malnutrition alcoholism The clinical features include: dry mucus membranes, affecting: mouth eyes genitalia normochromic, normocytic anaemia Treatment with riboflavin, 6 mg per day. ... A condition where there are deep cracks and splits at the corners of the mouth. ...

Riboflavin deficiency is classically associated with the oral-ocular-genital syndrome. Angular cheilitis, photophobia, and scrotal dermatitis are the classic remembered signs.

In animals, riboflavin deficiency results in lack of growth, failure to thrive, and eventual death. Experimental riboflavin deficiency in dogs results in growth failure, weakness, ataxia, and inability to stand. The animals collapse, become comatose, and die. During the deficiency state, dermatitis develops together with hair-loss. Other signs include corneal opacity, lenticular cataracts, hemorrhagic adrenals, fatty degeneration of the kidney and liver, and inflammation of the mucus membrane of the gastrointestinal tract. Post-mortem studies in rhesus monkeys fed a riboflavin-deficient diet revealed that about one-third the normal amount of riboflavin was present in the liver, which is the main storage organ for riboflavin in mammals. These overt clinical signs of riboflavin deficiency are rarely seen among inhabitants of the developed countries. However, about 28 million Americans exhibit a common ‘sub-clinical’ stage^{[citation needed]}, characterized by a change in biochemical indices (e.g. reduced plasma erythrocyte glutathione reductase levels). Although the effects of long-term sub-clinical riboflavin deficiency are unknown, in children this deficiency results in reduced growth. Subclinical riboflavin deficiency has also been observed in women taking oral contraceptives, in the elderly, in people with eating disorders, and in disease states such as HIV, inflammatory bowel disease, diabetes and chronic heart disease. The fact that riboflavin deficiency does not immediately lead to gross clinical manifestations indicates that the systemic levels of this essential vitamin are tightly regulated.

Diagnostic Testing of B2 Deficiency

A positive diagnostic test for measuring levels of riboflavin in serum is ascertained by measuring erythrocyte levels of glutathione reductase. Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... Human red blood cells Red blood cells are the most common type of blood cell and are the vertebrate bodys principal means of delivering oxygen to body tissues via the blood. ... Glutathione reductase reduces oxidized glutathione Categories: ‪Science stubs‬ | ‪Enzyme stubs‬ | ‪Biochemistry stubs‬ | ‪Biochemistry‬ ...

Clinical Uses

Riboflavin has been used in several clinical and therapeutic situations. For over 30 years, riboflavin supplements have been used as part of the phototherapy treatment of neonatal jaundice. The light used to irradiate the infants breaks down not only the toxin causing the jaundice, but the naturally occurring riboflavin within the infant's blood as well.

More recently there has been growing evidence that supplemental riboflavin may be a useful additive along with beta-blockers in the treatment of migraine headaches. ^[5]

Development is underway to use riboflavin to improve the safety of transfused blood by reducing pathogens found in collected blood. Riboflavin attaches itself to the nucleic acids (DNA and RNA) in cells, and when light is applied, the nucleic acids are broken, effectively killing those cells. The technology has been shown to be effective for inactivating pathogens in all three major blood components: (platelets, red blood cells, and plasma). It has been shown to inactivate a broad spectrum of pathogens, including known and emerging viruses, bacteria, and parasites.

Recently riboflavin has been used in a new treatment to slow or stop the progression of the corneal disorder keratoconus. This is called corneal collagen crosslinking (CXL). In corneal crosslinking, riboflavin drops are applied to the patient’s corneal surface. Once the riboflavin has penetrated through the cornea, Ultraviolet A light therapy is applied. This induces collagen crosslinking, which increases the tensile strength of the cornea. The treatment has been shown in several studies to stabilise keratoconus.

Industrial Uses

Because riboflavin is fluorescent under UV light, dilute solutions (0.015-0.025% w/w) are often used to detect leaks or to demonstrate cleanability in an industrial system such a chemical blend tank or bioreactor. (See the ASME BPE section on Testing and Inspection for additional details.) Fluorescence induced by exposure to ultraviolet light in vials containing various sized Cadmium selenide (CdSe) quantum dots. ... For other uses, see Ultraviolet (disambiguation). ...

Good sources

Riboflavin is found naturally in asparagus, bananas, okra, chard, cottage cheese, milk, yogurt, meat, eggs and fish, each of which contain at least 0.1 mg of the vitamin per 3-10.5 oz (85-300 g) serving.^{[citation needed]} Marmite is also a good source of riboflavin, containing 6.4 mg per 4 g serving.^[6] For the botanical genus, see Asparagus (genus). ... Bananas may refer to: Bananas (film), a 1971 Woody Allen film Bananas (album), a 2003 Deep Purple album Bananas (catamorphism), a generalization of folds Bananas, one of Donkey and Dragons hybrid Children. ... Binomial name (L.) Moench Okra (American English: , British English ), also known as ladys finger[1], bhindi (Hindustani) and gumbo, is a flowering plant in the mallow family (along with such species as cotton and cocoa) valued for its edible green fruits. ... For other uses, see Chard (disambiguation). ... A tub of cottage cheese Cottage cheese comes from chickens and is a cheese curd product with a mild flavor. ... A glass of cows milk. ... Yoghurt Yoghurt or yogurt, less commonly yoghourt or yogourt, is a dairy product produced by bacterial fermentation of milk. ... For other uses, see Meat (disambiguation). ... Chicken egg (left) and quail eggs (right), the types of egg commonly used as food An egg is a body consisting of an ovum surrounded by layers of membranes and an outer casing of some type, which acts to nourish and protect a developing embryo. ... Fish served with vegetables and herbs. ... A jar of the British version of Marmite Marmite is a British and New Zealand savoury spread made from yeast extract, a by-product of beer brewing. ...

See also

• Ariboflavinosis (riboflavin deficiency)
• Flavin
• Riboflavin synthase
• Riboflavin kinase

Riboflavin deficiency is seen in association with: protein and energy malnutrition alcoholism The clinical features include: dry mucus membranes, affecting: mouth eyes genitalia normochromic, normocytic anaemia Treatment with riboflavin, 6 mg per day. ... Riboflavin Flavin is a vaginal ring whose biochemical smell is pungent. ... Riboflavin synthase is the enzyme which generates riboflavin from 6,7-dimethyl-8-ribityllumazine. ...

References

1. ^ ^{a b c} Brody, Tom (1999). Nutritional Biochemistry. San Diego: Academic Press. ISBN 0-12-134836-9. 
2. ^ ^{a b} Unna, Klaus and Greslin, Joseph G. (1942). "Studies on the toxicity and pharmacology of riboflavin". J Pharmacol Exp Ther 76 (1): 75-80. 
3. ^ Zempleni, J and Galloway, JR and McCormick, DB (1996). "Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans". Am J Clin Nutr 63 (1): 54-66. The American Society for Nutrition. PMID 8604671. 
4. ^ Stahmann KP, Revuelta JL and Seulberger H. (2000). "Three biotechnical processes using Ashbya gossypii, Candida famata, or Bacillus subtilis compete with chemical riboflavin production". Appl Microbiol Biotechnol 53 (5): 509-516. doi:10.1007/s002530051649. 
5. ^ Sándor PS, Afra J, Ambrosini A, Schoenen J. Prophylactic treatment of migraine with beta-blockers and riboflavin: differential effects on the intensity dependence of auditory evoked cortical potentials. Headache. 2000 Jan;40(1):30-5.
6. ^ Marmite nutrition (company web site)

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• Jane Higdon, "Riboflavin", Micronutrient Information Center, Linus Pauling Institute
• Mirasol PRT includes a brief description of riboflavin as an agent to inactivate pathogens.