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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443421142 |
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| Watchedfields = changed |
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| verifiedrevid = 444073517 |
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| Name = Betanin |
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| Name = Betanin |
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| ImageFile = Betanin.png |
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| ImageFile = Betanin.svg |
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| ImageClass = skin-invert-image |
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<!-- | ImageSize = 200px --> |
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<!-- | ImageSize = 200px --> |
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| ImageName = |
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| ImageName = |
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| ImageFile2 = Betanin ball-and-stick.png |
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| IUPACName = 4-(2-(2-carboxy-5-(beta-<br />D-glucopyranosyloxy)-<br />2,3-dihydro-6-<br /> hydroxy-1H-indol<br />-1-yl)ethenyl)-<br />2,3-dihydro-(S-(R*,R*))-2,6-pyridinedicarboxylic acid |
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| IUPACName = (2''S'')-1-{2-ethylidene}-5-(β-{{sm|d}}-glucopyranosyloxy)-6-hydroxy-2,3-dihydro-1''H''-indol-1-ium-2-carboxylate |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| InChI1 = 1/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12?,14-,17+,18+,19-,20+,24+/m0/s1 |
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| InChI1 = 1/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12?,14-,17+,18+,19-,20+,24+/m0/s1 |
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| InChIKey1 = CTMLKIKAUFEMLE-BOKBUZBTBZ |
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| InChIKey1 = CTMLKIKAUFEMLE-BOKBUZBTBZ |
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| CASNo_Ref = {{cascite|correct|??}} |
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| SMILES1 = OC(=O)C/1C/C(=C\C(=N\1)C(O)=O)/C=C/N4(Cc3cc(O2O(CO)(O)(O)2O)c(O)cc34)C(O)=O |
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| CASNo = 7659-95-2 |
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| CASNo = 7659-95-2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5YJC992ZP6 |
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| ChemSpiderID=21106496 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10128200 |
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| StdInChI = 1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12?,14-,17+,18+,19-,20+,24+/m0/s1 |
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| PubChem = 12300103 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI = 3080 |
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| StdInChIKey = CTMLKIKAUFEMLE-BOKBUZBTSA-N |
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| KEGG = C08540 |
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| SMILES = OCC1(O) (O)<br />(O)(OC2=C(O) C=C<br />(/( (()=O)<br /> C4)=C/C=C3\C (<br />(O)=O) NC(C(O)=O)<br />=C3 )C4=C2)O1 |
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| ChEMBL = 1172614 |
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| InChI = 1/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14-,17+,18+,19-,20+,24+/m0/s1 |
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| InChIKey = DHHFDKNIEVKVKS-FMOSSLLZBW |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14-,17+,18+,19-,20+,24+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DHHFDKNIEVKVKS-FMOSSLLZSA-N |
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| SMILES = OCC1(O)(O)(O)(OC2=C(O)C=C(/((()=O)C4)=C/C=C3\C((O)=O)NC(C(O)=O)=C3)C4=C2)O1 |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>24</sub>H<sub>27</sub>N<sub>2</sub>O<sub>13</sub> |
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| Formula = C<sub>24</sub>H<sub>26</sub>N<sub>2</sub>O<sub>13</sub> |
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| MolarMass = 551.48 g/mol |
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| MolarMass = 550.47 g/mol |
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| Density = |
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'''Betanin''', or '''beetroot red''', is a red ] ] obtained from ]s; its ], obtained by hydrolyzing the ] molecule, is betanidin. As a ], its ] is E162.<ref name="efsa">{{cite journal|author= EFSA Panel on Food Additives and Nutrient Sources added to Food|title=Scientific Opinion on the re-evaluation of beetroot red (E 162) as a food additive |journal=EFSA Journal |date=9 December 2015 |volume=13 |issue=12 |page=4318 |doi=10.2903/j.efsa.2015.4318 |doi-access=free }}</ref> As a food additive, betanin has no safety concerns.<ref name=efsa/> |
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The color of betanin depends on ]; between pH four and five, it is bright bluish-red, becoming blue-violet as the pH increases. Once the pH reaches alkaline levels, betanin degrades by ], resulting in a yellow-brown color.{{citation needed|date=August 2020}} |
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'''Betanin''', or '''Beetroot Red''', is a red ] ] obtained from ]s; its ], obtained by hydrolyzing away the ] molecule, is betanidin. As a ], its ] is E162. Betanin degrades when subjected to ], heat, and ]; therefore, it is used in frozen products, products with short shelf life, or products sold in dry state.<ref>, The Natural Food Colours Association</ref> Betanin can survive ] when in products with high ] content. Its sensitivity to oxygen is highest in products with high content of water and/or containing metal cations (e.g. ] and ]); ]s like ] and ]s can slow this process down, together with suitable packaging. In dry form betanin is stable in presence of oxygen. |
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Betanin is a ] pigment, together with isobetanin and other betacyanins.<ref name="polturak">{{cite journal |vauthors=Polturak G, Aharoni A |title="La Vie en Rose": Biosynthesis, Sources, and Applications of Betalain Pigments |journal=Molecular Plant |volume=11 |issue=1 |pages=7–22 |date=January 2018 |pmid=29081360 |doi=10.1016/j.molp.2017.10.008 |doi-access=free }}</ref> |
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Betanin is usually obtained from the extract of beet juice; the concentration of betanin in red beet can reach 300-600 mg/kg. Other dietary sources of betanin and other ]s include the ] cactus, Swiss chard, and the leaves of some strains of amaranth. |
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== Sources == |
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The color of betanin depends on ]; between four and five it is bright bluish-red, becoming blue-violet as the pH increases. Once the pH reaches alkaline levels betanin degrades by ], resulting in a yellow-brown color. |
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Betanin is usually obtained from the extract of beet juice; the concentration of betanin in red beet can reach 300–600 mg/kg. Other dietary sources of betanin and other betalains include the '']'' cactus, ], and the leaves of some strains of ].{{citation needed|date=August 2020}} |
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== Uses == |
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Betanin can be also used for coloring ] and ]s. |
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The most common uses of betanins are in coloring ] and ] ] beverages; other uses are in some sugar ], e.g. ]s, sugar strands, sugar coatings, and fruit or cream fillings. In hot processed candies, it can be used if added at the final part of the processing. Betanin is also used in soups as well as ] and ] products. Betanin has "not been implicated as causing clinical food allergy when used as a coloring agent".<ref name="FoodAllergy">Dean D. Metcalfe, Hugh A. Sampson, Ronald A. Simon: ''Food Allergy: Adverse Reactions to Foods and Food Additives.'' 4th Ed., Blackwell Publishing, 2009, {{ISBN|978-1-4051-5129-0}}, p. 416.</ref> |
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Betanin has also shown to have antimicrobial activity and can be used as a natural antimicrobial agent in ].<ref>{{cite journal |last1=Manohar |first1=Cynthya M. |last2=Kundgar |first2=Saurabh D. |last3=Doble |first3=Mukesh |title=Betanin immobilized LDPE as antimicrobial food wrapper |journal=LWT |date=1 July 2017 |volume=80 |pages=131–135 |doi=10.1016/j.lwt.2016.07.020 }}</ref> |
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The most common uses of betanin are in coloring ] and powdered ] beverages; other uses are in some sugar ], e.g. ]s, ]s, sugar coatings, and fruit or cream fillings. In hot processed candies, it can be used if added at the final part of the processing. Betanin is also used in soups as well as ] and ] products. Betanin has nearly no potential as ]<ref name="FoodAllergy">Dean D. Metcalfe, Hugh A. Sampson, Ronald A. Simon: ''Food Allergy: Adverse Reactions to Foods and Food Additives.'' 4th Ed., Blackwell Publishing, 2009, ISBN 978-1-4051-5129-0, p. 416.</ref>. |
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==Degradation and stability== |
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Betanin absorbs well from the gut and acts as an ]. |
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Betanin degrades when subjected to ], heat, and ]; therefore, it is used in frozen products, products with short shelf life, or products sold in dry state. Betanin can survive ] when in products with high ] content. Its sensitivity to oxygen is highest in products with a high water content and/or containing metal cations (e.g. ] and ]); ]s like ] and ]s can slow this process down, together with suitable packaging. In dry form betanin is stable in the presence of oxygen.<ref>{{Cite journal|last1=Herbach|first1=Kirsten M.|last2=Stintzing|first2=Florian C.|last3=Carle|first3=Reinhold|date=May 2006|title=Betalain Stability and Degradation?Structural and Chromatic Aspects|url=http://dx.doi.org/10.1111/j.1750-3841.2006.00022.x|journal=Journal of Food Science|volume=71|issue=4|pages=R41–R50|doi=10.1111/j.1750-3841.2006.00022.x|issn=0022-1147}}</ref> |
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==Safety== |
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Betanin is a ] pigment, together with ], ], and ]. Other pigments contained in beet are ] and ]s. |
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Use of betanin and other betacyanins as food coloring has a long history in Europe.<ref name=efsa/> |
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A scientific panel for the ] found that acute or chronic toxicity and ] studies were too limited to determine that these food colorants were unsafe.<ref name=efsa/> The panel also concluded that the available toxicological database could not provide data to assign an ] level for beetroot red.<ref name=efsa/> |
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==See also== |
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== See also == |
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* ] |
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* ] |
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==References== |
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== References == |
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{{reflist}} |
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==Further reading== |
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<references/> |
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* {{cite journal |last1=Harmer |first1=R.A. |title=Occurrence, chemistry and application of betanin |journal=Food Chemistry |date=January 1980 |volume=5 |issue=1 |pages=81–90 |doi=10.1016/0308-8146(80)90066-7 }} |
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* {{cite journal |
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| author = R.A. Harmer |
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| year = 1980 |
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| title = Occurrence, chemistry and application of betanin |
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| journal = Food Chemistry |
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| volume = 5 |
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| issue = 1 |
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| pages = 81–90 |
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| pmid = |
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| doi = 10.1016/0308-8146(80)90066-7 |
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| url = |
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}} |
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{{Glycosides}} |
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{{Glycosides}} |
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{{Plant Pigments}} |
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{{Plant Pigments}} |
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