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Delphinidin

Delphinidin (also delphinidine[1][2]) is an anthocyanidin, a primary plant pigment, and also an antioxidant.[3] Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates,[4] and bilberries.[5]

Delphinidin
Names
IUPAC name
3,3′,4′,5,5′,7-Hexahydroxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ4-1-benzopyran-1-ylium
Identifiers
  • 13270-61-6 Y
  • 528-53-0 (chloride) Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28436 N
ChEMBL
  • ChEMBL590878 Y
  • ChEMBL276780 N
ChemSpider
  • 114185 N
ECHA InfoCard 100.007.671
E number E163b (colours)
KEGG
  • C05908 Y
  • 68245
UNII
  • 031A4BN94T Y
  • EM6MD4AEHE (chloride) Y
  • InChI=1S/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H Y
    Key: FFNDMZIBVDSQFI-UHFFFAOYSA-N Y
  • InChI=1/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H
    Key: FFNDMZIBVDSQFI-UHFFFAOYAW
  • C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O.[Cl-]
Properties
C15H11O7+
Molar mass 303.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from blue in basic solution to red in acidic solution.

Glycosides edit

Several glycosides derived from delphinidin are known:

  • Myrtillin (delphinidin-3-O-glucoside) and tulipanin (delphinidin-3-O-rutinoside) can be found in blackcurrant pomace.
  • Violdelphin (delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside) is responsible for the purplish-blue flower color of Aconitum chinense.[6]
  • Nasunin (delphinidin-3-(p-coumaroylrutinoside)-5-glucoside) is responsible for the colour of the eggplant fruit's purple skin.[7]
  • Delphinidin ternatins including Clitoria ternatea ternatins

See also edit

References edit

  1. ^ "Delphinidine".
  2. ^ "Delphinidine".
  3. ^ Afaq, F.; Syed, D. N.; Malik, A.; Hadi, N.; Sarfaraz, S.; Kweon, M.-H.; Khan, N.; Zaid, M. A.; Mukhtar, H. (2007). "Delphinidin, an Anthocyanidin in Pigmented Fruits and Vegetables, Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB-Mediated Oxidative Stress and Apoptosis". Journal of Investigative Dermatology. 127 (1): 222–232. doi:10.1038/sj.jid.5700510. PMID 16902416.
  4. ^ Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines". American Journal of Enology and Viticulture. 9: 1–9.
  5. ^ Lätti AK, Riihinen KR, Kainulainen PS (2008). "Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland". J Agric Food Chem. 56 (1): 190–6. doi:10.1021/jf072857m. PMID 18072741.
  6. ^ CID 3083066 from PubChem
  7. ^ Noda Y, Kneyuki T, Igarashi K, Mori A, Packer L (2000). "Antioxidant activity of nasunin, an anthocyanin in eggplant peels". Toxicology. 148 (2–3): 119–23. doi:10.1016/s0300-483x(00)00202-x. PMID 10962130.{{cite journal}}: CS1 maint: multiple names: authors list (link)

delphinidin, also, delphinidine, anthocyanidin, primary, plant, pigment, also, antioxidant, gives, blue, hues, flowers, genera, viola, delphinium, also, gives, blue, color, grape, variety, cabernet, sauvignon, found, cranberries, concord, grapes, well, pomegra. Delphinidin also delphinidine 1 2 is an anthocyanidin a primary plant pigment and also an antioxidant 3 Delphinidin gives blue hues to flowers in the genera Viola and Delphinium It also gives the blue red color of the grape variety Cabernet Sauvignon and can be found in cranberries and Concord grapes as well as pomegranates 4 and bilberries 5 Delphinidin Names IUPAC name 3 3 4 5 5 7 Hexahydroxyflavylium Systematic IUPAC name 3 5 7 Trihydroxy 2 3 4 5 trihydroxyphenyl 1l4 1 benzopyran 1 ylium Identifiers CAS Number 13270 61 6 Y528 53 0 chloride Y 3D model JSmol Interactive image ChEBI CHEBI 28436 N ChEMBL ChEMBL590878 YChEMBL276780 N ChemSpider 114185 N ECHA InfoCard 100 007 671 E number E163b colours KEGG C05908 Y PubChem CID 68245 UNII 031A4BN94T YEM6MD4AEHE chloride Y InChI InChI 1S C15H10O7 ClH c16 7 3 9 17 8 5 12 20 15 22 13 8 4 7 6 1 10 18 14 21 11 19 2 6 h1 5H H5 16 17 18 19 20 21 1H YKey FFNDMZIBVDSQFI UHFFFAOYSA N YInChI 1 C15H10O7 ClH c16 7 3 9 17 8 5 12 20 15 22 13 8 4 7 6 1 10 18 14 21 11 19 2 6 h1 5H H5 16 17 18 19 20 21 1HKey FFNDMZIBVDSQFI UHFFFAOYAW SMILES C1 C C C C C1O O O C2 C C C3C CC CC3 O 2 O O O Cl Properties Chemical formula C15H11O7 Molar mass 303 24 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Delphinidin like nearly all other anthocyanidins is pH sensitive i e a natural pH indicator and changes from blue in basic solution to red in acidic solution Glycosides editSeveral glycosides derived from delphinidin are known Myrtillin delphinidin 3 O glucoside and tulipanin delphinidin 3 O rutinoside can be found in blackcurrant pomace Violdelphin delphinidin 3 rutinoside 7 O 6 O 4 6 O 4 hydroxybenzoyl b D glucosyl oxybenzoyl b D glucoside is responsible for the purplish blue flower color of Aconitum chinense 6 Nasunin delphinidin 3 p coumaroylrutinoside 5 glucoside is responsible for the colour of the eggplant fruit s purple skin 7 Delphinidin ternatin s including Clitoria ternatea ternatinsSee also editProdelphinidin a type of condensed tanninsReferences edit Delphinidine Delphinidine Afaq F Syed D N Malik A Hadi N Sarfaraz S Kweon M H Khan N Zaid M A Mukhtar H 2007 Delphinidin an Anthocyanidin in Pigmented Fruits and Vegetables Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB Mediated Oxidative Stress and Apoptosis Journal of Investigative Dermatology 127 1 222 232 doi 10 1038 sj jid 5700510 PMID 16902416 Ribereau Gayon J Ribereau Gayon P 1958 The Anthocyans and Leucoanthocyans of Grapes and Wines American Journal of Enology and Viticulture 9 1 9 Latti AK Riihinen KR Kainulainen PS 2008 Analysis of anthocyanin variation in wild populations of bilberry Vaccinium myrtillus L in Finland J Agric Food Chem 56 1 190 6 doi 10 1021 jf072857m PMID 18072741 CID 3083066 from PubChem Noda Y Kneyuki T Igarashi K Mori A Packer L 2000 Antioxidant activity of nasunin an anthocyanin in eggplant peels Toxicology 148 2 3 119 23 doi 10 1016 s0300 483x 00 00202 x PMID 10962130 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Retrieved from https en wikipedia org w index php title Delphinidin amp oldid 1152515695, wikipedia, wiki, book, books, library,

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