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{{short description|Red anthocyanidin pigment found in certain flowers and fruits}} |
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| ImageFile=pelargonidin.png |
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| ImageSize=200px |
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| verifiedrevid = 409412023 |
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| IUPACName=2-(4-Hydroxyphenyl)chromenylium-3,5,7-triol |
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| ImageFile=pelargonidin.svg |
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| OtherNames= |
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| ImageSize=200px |
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| IUPACName=3,4′,5,7-Tetrahydroxyflavylium |
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| SystematicName=3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ<sup>4</sup>-benzopyran-4-ylium |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=134-04-3 |
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| CASNo=134-04-3 |
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| PubChem=440832 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1=CC(=CC=C1C2=C(C=C3C (=CC(=CC3=2)O)O)O)O |
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| UNII = DFL6200791 |
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| PubChem=440832 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 25863 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1197905 |
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| SMILES = C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=2)O)O)O)O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 389676 |
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| InChI = 1/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1 |
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| InChIKey = XVFMGWDSJLBXDZ-IKLDFBCSAF |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = XVFMGWDSJLBXDZ-UHFFFAOYSA-O |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C05904 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>11</sub>O<sub>5</sub><sup>+</sup> |
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| Formula = C<sub>15</sub>H<sub>11</sub>O<sub>5</sub><sup>+</sup> |
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| MolarMass = 271.24 g/mol |
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| MolarMass = 271.24 g/mol |
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| ExactMass = 271.060648 |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Pelargonidin''' is an ], a type of plant pigment producing a characteristic orange color used in food and industrial dyes.<ref>{{cite patent |
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| country = US |
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| number = 6,767,999 |
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| status = granted |
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| title = Anthocyantin coloring agent and method for the production thereof from organic matter |
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| pubdate = Nov 01, 2001 |
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| gdate = July 27, 2004 |
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| fdate = Dec 21, 2001 |
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| pridate = Apr 26, 2000 |
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| inventor = Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina |
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| url = http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&u=%2Fnetahtml%2FPTO%2Fsearch-adv.htm&r=1&p=1&f=G&l=50&d=PTXT&S1=pelargonidin.ABTX.&OS=abst/pelargonidin&RS=ABST/pelargonidin |
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}}</ref> |
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== Natural occurrences == |
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'''Pelargonidin''' is an ], or type of plant pigment. Like all anthocyanins, it is an ]. It produces a characteristic orange color, and can be found in red ], and ripe ] and ], as well as ], ], ] and ] and ]s. It is present in large amounts in ].<ref>LZ Lin, JM Harnly, MS Pastor-Corrales, DL Luthria. The polyphenolic profiles of common bean (Phaseolus vulgaris L.). Food Chemistry, 2008.</ref> |
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=== Presence in flowers === |
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Pelargonidin can be found in red ]s (Geraniaceae). It is the predominant pigment causing the red coloration in the spathes of '']'' (Araceae). The orange-coloured flowers of blue pimpernel ('']'', Myrsinaceae) have a higher concentration of pelargonidin pigment. Red and Pink ]s (Rosa) obtain their color from this phytochemical. <ref>{{Cite journal|title=Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)|year=2019|last1=Huihua|first1=Wan|last2=Chao|first2=Yu|last3=Yu|first3=Han|last4=Xuelian|first4=Guo|journal=Frontiers in Plant Science|volume=10|pages=123|doi=10.3389/fpls.2019.00123|pmid=30809238|pmc=6379320|doi-access=free}}</ref> |
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=== Presence in food === |
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==See also== |
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Pelargonidin can be found in berries such as ripe ] and ], as well as ], ], ] but also in ]<ref>{{Cite journal|doi=10.1300/J492v05n03_10|title=Compositional and Functional Properties of Saskatoon Berry and Blueberry|year=2005|last1=Mazza|first1=G.|journal=International Journal of Fruit Science|volume=5|issue=3|pages=101–120|s2cid=85691882|doi-access=free}}</ref> and ]. It is also found in ]s and ]s. Pelargonidin gives red ] their color.<ref name="NishioKitashiba2017">{{cite book|author=Takeshi Nishio|editor=Takeshi Nishio, Hiroyasu Kitashiba|title=The Radish Genome|url=https://books.google.com/books?id=8JQ4DwAAQBAJ&pg=PA70|date=4 October 2017|publisher=Springer|isbn=978-3-319-59253-4|page=4}}</ref> |
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It is present in large amounts in ]s.<ref>{{Cite journal|doi=10.1016/j.foodchem.2007.08.038|title=The polyphenolic profiles of common bean (Phaseolus vulgaris L.)|year=2008|last1=Lin|first1=Long-Ze|last2=Harnly|first2=James M.|last3=Pastor-Corrales|first3=Marcial S.|last4=Luthria|first4=Devanand L.|journal=Food Chemistry|volume=107|pages=399–410|url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=11587&content=PDF|pmc=4276374|pmid=25544796|issue=1}}</ref> |
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== Glycosides == |
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In many plant systems, Pelargonidin can be added to a glucose molecule to form ] (callistephin). This is done by the 3GT, anthocyanin 3-O-glucosyltransferase gene. <ref>{{Cite journal |doi=10.1186/s12934-018-0951-6 |title=Engineering de novo anthocyanin production in Saccharomyces cerevisiae |year= 2018 |last1=Levisson |first1=Mark |last2=Patinios |first2=Constantinios |last3=Hein |first3=Sascha |last4=de Groot |first4=Phillip A. |journal=Microbial Cell Factories |volume=17 |issue=103|page=103 |pmid=29970082 |pmc=6029064 |doi-access=free }}</ref> |
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].]] |
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However this glucosidation reduces its antioxidant activity,<ref>{{Cite journal|doi=10.1016/j.lwt.2021.111581|title=Glycosides changed the stability and antioxidant activity of pelargonidin|year=2021|last1=Li|first1=Wenfeng|last2=Gu|first2=Mengyuan|last3=Gong|first3=Pengling|last4=Wang|first4=Jinxia|journal=Lebensmittel-Wissenschaft & Technologie|volume=147|issue=3|page=111581|s2cid=235531625}}</ref> and changes the wavelength of max light absorbance from 520 nm to 516 nm. <ref>{{cite book |last=Gould|first=Kevin S.|date=2009|title=Anthocyanidins: Biosynthesis, Functions, and Applications|location=New York|publisher=Springer|page=286|isbn=978-0-387-77334-6}}</ref> |
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Acylated pelargonidin glycosides can be found in red-purple flowers of '']''.<ref>{{Cite journal|pmid=8987912|year=1996|last1=Saito|first1=N|last2=Tatsuzawa|first2=F|last3=Yokoi|first3=M|last4=Kasahara|first4=K|last5=Iida|first5=S|last6=Shigihara|first6=A|last7=Honda|first7=T|title=Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea|volume=43|issue=6|pages=1365–70|journal=Phytochemistry|doi=10.1016/s0031-9422(96)00501-8}}</ref> |
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== See also == |
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* ] |
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==External links== |
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== References == |
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{{reflist}} |
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== External links == |
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{{commonscat|Pelargonidin}} |
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{{commonscat|Pelargonidin}} |
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==References== |
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<references/> |
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{{Anthocyanins}} |
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{{Anthocyanins}} |
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{{polyphenol-stub}} |
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