apiin
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457811880
| Name = Apiin
| Reference=
| ImageFile = Apiin.svg
| ImageSize = 270px
| ImageName = Apigenin
| IUPACName = 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β-D-erythrofuranosyl-(1→2)-β-D-glucopyranosyloxy]flavone
| SystematicName = 7-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
| OtherNames = Apioside
Apigenin-7-apioglucoside
Apigenin-7-O-apioglucoside
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 26544-34-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6QU3EZE37U
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15932
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1535342
| PubChem = 5280746
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EC_number = 247-780-0
| KEGG = C04858
| 3DMet =
| ChemSpiderID = 4444321
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NTDLXWMIWOECHG-YRCFQSNFSA-N
| SMILES = O=C\4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]1OC[C@](O)(CO)[C@H]1O)cc5O/C(c3ccc(O)cc3)=C/4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1
}}
|Section2={{Chembox Properties
| C=26 | H=28 | O=14
| MeltingPt =
}}
| Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley{{cite journal | journal = Ann Nutr Metab | date = 2006 | volume = 50| issue = 3 | pages = 167–172 | title = Bioavailability of Apigenin from Apiin-Rich Parsley in Humans |author1=H. Meyer |author2=A. Bolarinwa |author3=G. Wolfram |author4=J. Linseisen | pmid = 16407641 | doi = 10.1159/000090736| s2cid = 8223136 | url = https://opus.bibliothek.uni-augsburg.de/opus4/frontdoor/index/index/docId/85767 | url-access = subscription }} and celery,{{cite journal|title=A study of apiin from the parsley seeds and plant|journal = Proceedings of the Indian Academy of Sciences, Section A|volume = 35|issue = 5|author=S. R. Gupta|doi=10.1007/BF03172503|year = 1952|s2cid = 91953908}} and in banana leaf.{{cite journal | last1=Sayadi | first1=Khali | last2=Akbarzadeh | first2=Fatemeh | last3=Pourmardan | first3=Vahid | last4=Saravani-Aval | first4=Mehdi | last5=Sayadi | first5=Jalis | last6=Chauhan | first6=Narendra Pal Singh | last7=Sargazi | first7=Ghasem | title=Methods of green synthesis of Au NCs with emphasis on their morphology: A mini-review | journal=Heliyon | publisher=Cell Press | volume=7 | issue=6 | year=2021 | issn=2405-8440 | pmid=34189304| doi=10.1016/j.heliyon.2021.e07250 | pmc=8220187 | page=e07250| doi-access=free | bibcode=2021Heliy...707250S }} The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed.{{cite book | page = 245 | chapter = Methods in plant biochemistry | volume = 2 | title = Carbohydrates | date = 2 December 2012 | publisher = Academic Press | isbn = 978-0080984209 }} The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.{{cite book | page = 136 | title = Advances in Carbohydrate Chemistry and Biochemistry | date = 5 November 1975 | volume = 31 | publisher = Academic Press | isbn = 0080562906 }}