Apigeninidin
{{chembox
| Watchedfields = changed
| verifiedrevid = 413868299
| Name = Apigeninidin (chloride)
| ImageFile = Apigeninidin.svg
| ImageSize = 250px
| IUPACName =
| OtherNames = 3-desoxy- pelargonidin
5,7-dihydroxy-2-(4-hydroxyphenyl)benzopyrilium chloride
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 140151
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 590784
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GYQDOAKHUGURPD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 1151-98-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CWI2JJB0W1
| PubChem = 441647
| SMILES = [Cl-].Oc1ccc(cc1)c3[o+]c2cc(O)cc(O)c2cc3
}}
|Section2={{Chembox Properties
| Formula = C15H11O4+
| MolarMass = 255.24 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Apigeninidin (Also, apigenidin,{{cite journal|last1=Asahina|first1=Yasuhiko|last2=Inubuse|first2=Mototaro|title=Über die Reduktion der Flavon- und Flavanon-Derivate (III. Mitteilung über die Flavanon-glucoside)|journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series)|volume=61|issue=8|year=1928|pages=1646–1650|issn=0365-9488|doi=10.1002/cber.19280610810}} or Gesneridin) is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in the Patagonian plant Ephedra frustillata{{cite journal|last1=Gurni|first1=Alberto A.|last2=Wagner|first2=Marcelo L.|title=Apigeninidin as a leucoderivative in Ephedra frustillata|journal=Phytochemistry|volume=21|issue=9|year=1982|pages=2428–2429|issn=0031-9422|doi=10.1016/0031-9422(82)85229-1|bibcode=1982PChem..21.2428G }} and in the soybean.{{cite journal|last1=Boveris|first1=AD|last2=Galatro|first2=A|last3=Sambrotta|first3=L|last4=Ricco|first4=R|last5=Gurni|first5=AA|last6=Puntarulo|first6=S|title=Antioxidant capacity of a 3-deoxyanthocyanidin from soybean.|journal=Phytochemistry|date=December 2001|volume=58|issue=7|pages=1097–105|pmid=11730874|doi=10.1016/s0031-9422(01)00378-8|bibcode=2001PChem..58.1097B }} Apigeninidin is one of the principal pigments found in sorghum.{{cite journal|last1=Awika|first1=Joseph M.|last2=Rooney|first2=Lloyd W.|last3=Waniska|first3=Ralph D.|title=Properties of 3-Deoxyanthocyanins from Sorghum|journal=Journal of Agricultural and Food Chemistry|volume=52|issue=14|year=2004|pages=4388–4394|issn=0021-8561|doi=10.1021/jf049653f|pmid=15237941}} Extremely high level of apigeninidin (49 mg/g) has been documented in sorghum leaf sheath.{{cite journal|last1=Geera|first1=Bhimalingeswarappa|last2=Ojwang|first2=Leonnard O.|last3=Awika|first3=Joseph M.|title=New Highly Stable Dimeric 3-Deoxyanthocyanidin Pigments from Sorghum bicolor Leaf Sheath|journal=Journal of Food Science|volume=77|issue=5|year=2012|pages=C566–C572|issn=0022-1147|doi=10.1111/j.1750-3841.2012.02668.x|pmid=22489620}} Like all anthocyanidins it exists in a variety of tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core.{{cite journal|last1=Costantino|first1=Luca|last2=Rastelli|first2=Giulio|last3=Rossi|first3=Maria C.|last4=Albasini|first4=Albano|title=Quantitative measurement of proton dissociation and tautomeric constants of apigeninidin|journal=Journal of the Chemical Society, Perkin Transactions 2|date=1995|issue=2|pages=227|doi=10.1039/P29950000227}}