| Riboflavin | |
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| IUPAC name | 7,8-dimethyl-10- ((2R,3R,4S)- 2,3,4,5-tetrahydroxypentyl) benzo[g]pteridine-2,4 (3H,10H)-dione |
| Identifiers | |
| CAS number | [83-88-5] |
| PubChem | |
| MeSH | |
| Properties | |
| Molecular formula | C17H20N4O6 |
| Molar mass | 376. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 36 g/mol |
| Melting point |
290 °C (dec. 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 |
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Riboflavin (E101), also known as vitamin B2, is an easily absorbed micronutrient with a key role in maintaining health in animals. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union. Micronutrients are Nutrients needed for life in small quantities Health is a state of complete physical mental and social well-being and not merely the absence of disease or infirmity It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. A cofactor is a non-protein Chemical compound that is bound (either tightly or loosely to an Enzyme and is required for Catalysis. In Biochemistry, flavin adenine dinucleotide ( FAD) is a Redox cofactor involved in several important reactions in Metabolism. Flavin mononucleotide (FMN or riboflavin-5′-phosphate, is produced from Riboflavin (vitamin B2 by the enzyme Riboflavin kinase and Flavoproteins are Proteins that contain a Nucleic acid derivative of Riboflavin: the Flavin adenine dinucleotide (FAD or Flavin mononucleotide 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 B vitamins are eight water-soluble Vitamins that play important roles in cell Metabolism. Metabolism is the set of Chemical reactions that occur in living Organisms in order to maintain Life. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water Ketone bodies are three water-soluble compounds that are produced as by-products when Fatty acids are broken down for energy in the Liver and Carbohydrates (from ' Hydrates of Carbon ' or saccharides ( Greek σάκχαρον meaning " Sugar " are the most Proteins are large Organic compounds made of Amino acids arranged in a linear chain and joined together by Peptide bonds between the Carboxyl
Milk, cheese, leafy green vegetables, liver, kidneys, legumes such as mature soybeans,[1] yeast, almonds and rock lobsters are good sources of vitamin B2, but exposure to light destroys riboflavin. Milk is an opaque white liquid produced by the Mammary glands of female Mammals (including Monotremes. Cheese is a Food made from Milk, usually the milk of cows, Buffalo, Goats or sheep, by coagulation. Leaf vegetables, also called potherbs, greens, or leafy greens, are plant leaves eaten as a Vegetable, sometimes accompanied The liver is a vital organ in the human body and is present in Vertebrates and some other animals The kidneys are complicated organs that have numerous biological roles Yeasts are a growth form of eukaryotic Microorganisms classified in the kingdom Fungi, with about 1500 Species currently described The Almond ( Prunus dulcis, syn Prunus amygdalus Batsch Amygdalus communis L This article is about the animal For the B-52's song see Rock Lobster.
Contents |
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]. WikipediaManual_of_Style#National_varieties_of_English --> Molds (or History and Significance Ashbya gossypii is a filamentous Fungus or Mold closely related to yeast but growing exclusively in a filamentous The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Bacillus subtilis Sporejpg|thumb|right|Sporulating Bacillus subtilis ]] Bacillus subtilis is a Gram-positive, Catalase -positive 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. Ampicillin is a beta-lactam Antibiotic that has been used extensively to treat bacterial Infections since 1961 The chemical company BASF has installed a plant in South Korea, which is specialized on riboflavin production using Ashbya gossypii. BASF SE () is a German chemical company and the largest chemical company in the world A factory (previously manufactory) or manufacturing plant is an industrial Building where workers manufacture goods South Korea, officially the Republic of Korea and often referred to as Korea ( Korean: 대한민국 tɛː History and Significance Ashbya gossypii is a filamentous Fungus or Mold closely related to yeast but growing exclusively in a filamentous 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. In biology strain is a low-level Taxonomic rank used in three related ways Mycelium (plural mycelia) is the vegetative part of a Fungus, consisting of a mass of branching thread-like Hyphae The mass of hyphae is sometimes called In general vacuole functions include Removing unwanted structural debris Isolating materials that might be harmful or a threat to the cell Containing
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. A food coloring is any substance that is added to Food or Drink to change its Color. 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. Baby food is any Food, other than breastmilk or infant formula that is given specifically to Infants roughly between the ages of four months A breakfast cereal (often simply called cereal is a packaged food product made from Cereal intended to be consumed as part of a Breakfast. Pasta ( Italian for "dough" is a generic term for Italian variants of Noodles. In Cooking, a sauce is Liquid or sometimes semi- Solid food served on or used in preparing other Foods Sauces are not consumed by themselves Processed cheese, process cheese, prepared cheese, or cheese food is a food product made from regular Cheese and sometimes other unfermented Energy drinks are Soft drinks advertised as providing more Energy than a typical drink A multivitamin is a preparation intended to supplement a human diet with Vitamins Dietary minerals and other nutritional elements
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. Flavin mononucleotide (FMN or riboflavin-5′-phosphate, is produced from Riboflavin (vitamin B2 by the enzyme Riboflavin kinase and E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union.
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. Ariboflavinosis is the medical condition caused by deficiency of Riboflavin (vitamin B2 However, riboflavin deficiency is always accompanied by deficiency of other vitamins[1].
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. Ariboflavinosis is the medical condition caused by deficiency of Riboflavin (vitamin B2 Angular cheilitis (also called perlèche cheilosis or angular stomatitis) is an inflammatory lesion at the labial commissure or corner of the mouth and often occurs bilaterally 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 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, 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 Red blood cells are the most common type of Blood cell and the Vertebrate body's principal means of delivering Oxygen to the body tissues via the Blood Glutathione reductase, also known as GSR, is a human Gene. The Protein encoded by this gene is an Enzyme ( which reduces Glutathione
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. Fluorescence is a Luminescence that is mostly found as an Ultraviolet ( UV) light is Electromagnetic radiation with a Wavelength shorter than that of Visible light, but longer than X-rays 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. ASME BPE is the Bioprocess Equipment group of the ASME that provides engineers and quality control professionals a measurable way to specify and purchase equipment )
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. Asparagus officinalis is a flowering plant species in the genus Asparagus from which the Vegetable known as asparagus is obtained For the fruit see Banana. For other meanings see Banana (disambiguation. Okra ( American English:, British English,) also known as lady's finger, bhindi ( Hindustani) and gumbo, is a Chard ( Beta vulgaris var cicla) also known as Swiss Chard, Silverbeet, Perpetual Spinach, Crab Beet and Mangold Cottage cheese is a Cheese Curd product with a mild flavor It is drained but not pressed so some Whey remains Milk is an opaque white liquid produced by the Mammary glands of female Mammals (including Monotremes. Yoghurt, yogurt, yoghourt, youghurt or yogourt (see spelling below is a In modern English usage meat most often refers to Animal tissue used as food mostly Skeletal muscle and associated Fat, but it may also refer An egg is a round or oval body laid by the female of many animals consisting of an Ovum surrounded by layers of Membranes and an outer casing which acts to nourish 1 mg of the vitamin per 3-10. 5 oz (85-300 g) serving.
See also
- Ariboflavinosis (riboflavin deficiency)
- Flavin
- Riboflavin synthase
- Riboflavin kinase
References
- ^ a b c Brody, Tom (1999). Ariboflavinosis is the medical condition caused by deficiency of Riboflavin (vitamin B2 For the town in France see Flavin Aveyron. Flavin (from Latin flavus, "yellow" is the common name for a group of Organic Riboflavin synthase is the enzyme which generates Riboflavin from 67-dimethyl-8-ribityllumazine. In Enzymology, a riboflavin kinase ( is an Enzyme that catalyzes the Chemical reaction ATP + riboflavin \rightleftharpoons Nutritional Biochemistry. San Diego: Academic Press. ISBN 0-12-134836-9.
- ^ 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.
- ^ 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.
- ^ 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:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ 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.
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. Oregon State University ( OSU) is a Coeducational public Research[[ university]] located in Corvallis, Oregon, United
Dictionary
riboflavin
-noun
- (biochemistry) Yellow or orange-yellow water-soluble compound, a member of the vitamin B complex, that acts as a growth-promoting factor in humans and other animals.
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