Apigeninidin

Apigeninidin (chloride)
Names

Other names 3-desoxy- pelargonidin 5,7-dihydroxy-2-(4-hydroxyphenyl)benzopyrilium chloride
Identifiers
CAS Number	1151-98-0^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL590784^Y
ChemSpider	140151^Y
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^Y Key: GYQDOAKHUGURPD-UHFFFAOYSA-N^Y
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).
Y verify (what is ^YN ?)
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

↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

3-deoxyanthocyanidins

O-methylated anthocyanidins

Anthocyanins
(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)-beta-D-glucosyl)oxybenzoyl)-beta-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

Misc.

Metalloanthocyanins (Commelinin
Cyanosalvianin
Protocyanin
Protodelphin)
Pyranoanthocyanins
Copigmentation
Anthocyanone A (degradation product of oenin)
Malvone (oxidation product of malvin)

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