Apigeninidin

Apigeninidin (chloride)
Names
Other names
3-desoxy- pelargonidin
5,7-dihydroxy-2-(4-hydroxyphenyl)benzopyrilium chloride
Identifiers
CAS Number
  • 1151-98-0 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL590784 checkY
ChemSpider
  • 140151 checkY
PubChem CID
  • 441647
UNII
  • CWI2JJB0W1 checkY
CompTox Dashboard (EPA)
  • DTXSID40921629 Edit this at Wikidata
InChI
  • InChI=1S/C15H10O4.ClH/c16-10-3-1-9(2-4-10)14-6-5-12-13(18)7-11(17)8-15(12)19-14;/h1-8H,(H2-,16,17,18);1H checkY
    Key: GYQDOAKHUGURPD-UHFFFAOYSA-N checkY
  • [Cl-].Oc1ccc(cc1)c3[o+]c2cc(O)cc(O)c2cc3
Properties
Chemical formula
 C15H11O4+
Molar mass 255.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Apigeninidin (Also, apigenidin,[1] or Gesneridin) is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in the Patagonian plant Ephedra frustillata[2] and in the soybean.[3] Apigeninidin is one of the principal pigments found in sorghum.[4] Extremely high level of apigeninidin (49 mg/g) has been documented in sorghum leaf sheath.[5] Like all anthocyanidins it exists in a variety of tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core.[6]

References

  1. ^ Asahina, Yasuhiko; Inubuse, Mototaro (1928). "Über die Reduktion der Flavon- und Flavanon-Derivate (III. Mitteilung über die Flavanon-glucoside)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 61 (8): 1646–1650. doi:10.1002/cber.19280610810. ISSN 0365-9488.
  2. ^ Gurni, Alberto A.; Wagner, Marcelo L. (1982). "Apigeninidin as a leucoderivative in Ephedra frustillata". Phytochemistry. 21 (9): 2428–2429. doi:10.1016/0031-9422(82)85229-1. ISSN 0031-9422.
  3. ^ Boveris, AD; Galatro, A; Sambrotta, L; Ricco, R; Gurni, AA; Puntarulo, S (December 2001). "Antioxidant capacity of a 3-deoxyanthocyanidin from soybean". Phytochemistry. 58 (7): 1097–105. doi:10.1016/s0031-9422(01)00378-8. PMID 11730874.
  4. ^ Awika, Joseph M.; Rooney, Lloyd W.; Waniska, Ralph D. (2004). "Properties of 3-Deoxyanthocyanins from Sorghum". Journal of Agricultural and Food Chemistry. 52 (14): 4388–4394. doi:10.1021/jf049653f. ISSN 0021-8561. PMID 15237941.
  5. ^ Geera, Bhimalingeswarappa; Ojwang, Leonnard O.; Awika, Joseph M. (2012). "New Highly Stable Dimeric 3-Deoxyanthocyanidin Pigments from Sorghum bicolor Leaf Sheath". Journal of Food Science. 77 (5): C566–C572. doi:10.1111/j.1750-3841.2012.02668.x. ISSN 0022-1147. PMID 22489620.
  6. ^ Costantino, Luca; Rastelli, Giulio; Rossi, Maria C.; Albasini, Albano (1995). "Quantitative measurement of proton dissociation and tautomeric constants of apigeninidin". Journal of the Chemical Society, Perkin Transactions 2 (2): 227. doi:10.1039/P29950000227.
  • v
  • t
  • e
Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins3-DeoxyanthocyanidinsO-Methylated anthocyanidinsAnthocyanins
(anthocyaninidin glycosides)
Glucosides:
  • Callistephin (Pelargonidin 3-O-glucoside)
  • Chrysanthemin (Cyanidin 3-O-glucoside)
  • Myrtillin (Delphinidin 3-O-glucoside)
  • Oenin (Malvidin 3-O-glucoside)
  • Peonidin 3-O-glucoside
  • Petunidin 3-O-glucoside
  • Pulchellidin 3-glucoside

Diglucosides:

  • Cyanin (Cyanidin 3,5-O-diglucoside)
  • Delphin (Delphinidin 3,5-O-diglucoside)
  • Malvin (Malvidin 3,5-diglucoside)
  • Pelargonin (Pelargonidin 3,5-O-diglucoside)
  • Peonin (Peonidin 3,5-O-diglucoside)
  • Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

  • Antirrhinin (Cyanidin 3-O-rutinoside)
  • Ideain (Cyanidin 3-O-galactoside)
  • Delphinidin 3-O-rhamnoside
  • Petunidin 3-O-arabinoside
  • Petunidin 3-O-galactoside
  • Petunidin 3-O-rhamnoside
  • Petunidin 3-O-rutinoside
  • Primulin (Malvidin 3-O-galactoside)
  • Pulchellidin 3-rhamnoside
  • Tulipanin (Delphinidin 3-O-rutinoside)
Acylated anthocyanins
Acetylated anthocyanins
  • Cyanidin 3-O-(6-acetyl)glucoside
  • Delphinidin 3-O-(6-acetyl)glucoside
  • Malvidin 3-O-(6-acetyl)glucoside
  • Petunidin 3-O-(6-acetyl)galactoside
  • Petunidin 3-O-(6-acetyl)glucoside
  • Peonidin 3-O-(6-acetyl)glucoside
    • Coumaroylated anthocyanins
    (cis- and trans-)
    • Cyanidin 3-O-(6-p-coumaroyl)glucoside
    • Delphinidin 3-O-(6-p-coumaroyl)glucoside
    • Malvidin 3-O-(6-p-coumaroyl)glucoside
    • Petunidin 3-O-(6-p-coumaroyl)glucoside
    • Peonidin 3-O-(6-p-coumaroyl)glucoside
    Caffeoylated anthocyanins
    • Malvidin 3-O-(6-p-caffeoyl)glucoside
    • Peonidin 3-O-(6-p-caffeoyl)glucoside
    Malonylated anthocyanins
    • Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
    Acylated anthocyanin diglycosides
    • Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
    • Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
    • Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
    • Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside)
    • Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)
    Flavanol-anthocyanin adducts
    • Malvidin glucoside-ethyl-catechin
    • Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    Miscellaneous