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{{chembox |
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{{chembox |
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| Name = Apiin |
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| Watchedfields = changed |
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| Reference= |
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| verifiedrevid = 457811880 |
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| ImageFile = Apiin.svg |
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| ImageSize = 270px |
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| Name = Apiin |
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| Reference= |
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| ImageName = Apigenin |
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| ImageFile = Apiin.svg |
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| IUPACName = 7-oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one |
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| ImageSize = 270px |
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| OtherNames = Apioside |
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| ImageName = Apigenin |
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| Section1 = {{Chembox Identifiers |
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| IUPACName = 4′,5-Dihydroxy-7-flavone |
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| CASNo = <!-- blanked - oldvalue: 26544-34-3 --> |
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| SystematicName = 7-{oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one |
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| ChEBI = 15932 |
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| OtherNames = Apioside<br>Apigenin-7-apioglucoside<br>Apigenin-7-O-apioglucoside |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 26544-34-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6QU3EZE37U |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15932 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1535342 |
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| PubChem = 5280746 |
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| PubChem = 5280746 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444321 |
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| EC_number = 247-780-0 |
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| KEGG = C04858 |
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| 3DMet = |
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| ChemSpiderID = 4444321 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NTDLXWMIWOECHG-YRCFQSNFSA-N |
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| StdInChIKey = NTDLXWMIWOECHG-YRCFQSNFSA-N |
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| SMILES = O=C\4c5c(O)cc(O2O(CO)(O)(O)2O1OC(O)(CO)1O)cc5O/C(c3ccc(O)cc3)=C/4 |
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| SMILES = O=C\4c5c(O)cc(O2O(CO)(O)(O)2O1OC(O)(CO)1O)cc5O/C(c3ccc(O)cc3)=C/4 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=26 | H=28 | O=14 |
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| Formula = C<sub>26</sub>H<sub>28</sub>O<sub>14</sub> |
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| MeltingPt = |
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| MolarMass = 564.49 g/mol |
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| ExactMass = 564.15 |
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| MeltingPt = °C |
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| Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| 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}} |
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'''Apiin''' is a chemical compound isolated from ]<ref></ref> and ]. The aglycone of apiin is ]. |
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'''Apiin''' is a natural ], a ] of the ] ] found in the winter-hardy plants ]<ref>{{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 }}</ref> and ],<ref>{{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}}</ref> and in ].<ref name="Sayadi-et-al-2021">{{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=] | publisher=] | 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 }}</ref> 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.<ref>{{cite book | page = 245 | chapter = Methods in plant biochemistry | volume = 2 | title = Carbohydrates | date = 2 December 2012 | publisher = Academic Press | isbn = 978-0080984209 }}</ref> The sugar ] possibly play a role in winter hardiness of celery, duckweed and parsley.<ref>{{cite book | page = 136 | title = Advances in Carbohydrate Chemistry and Biochemistry | date = 5 November 1975 | volume = 31 | publisher = Academic Press | isbn = 0080562906 }}</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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== See also == |
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*] |
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== References == |
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{{Reflist}} |
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{{flavone}} |
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{{flavone}} |
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{{Natural-phenol-stub}} |
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{{Aromatic-stub}} |
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