Apigeninidin

Apigeninidin (chloride)

Names
Other names 3-desoxy- pelargonidin 5,7-dihydroxy-2-(4-hydroxyphenyl)benzopyrilium chloride
Identifiers
CAS Number	1151-98-0
ChEMBL	ChEMBL590784
ChemSpider	140151
Jmol 3D model	Interactive image
PubChem	441647
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 Key: GYQDOAKHUGURPD-UHFFFAOYSA-N
SMILES [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

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. 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.
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.
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.