Apigeninidin

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]

Apigeninidin (chloride)
Names
Other names
3-desoxy- pelargonidin
5,7-dihydroxy-2-(4-hydroxyphenyl)benzopyrilium chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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
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

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.
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