Apiin

Apiin

Names
IUPAC name 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β-D-erythrofuranosyl-(1→2)-β-D-glucopyranosyloxy]flavone
Systematic IUPAC name 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
Other names Apioside Apigenin-7-apioglucoside Apigenin-7-O-apioglucoside
Identifiers
CAS Number	26544-34-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15932^Y
ChEMBL	ChEMBL1535342^N
ChemSpider	4444321^Y
ECHA InfoCard	100.043.421
EC Number	247-780-0
KEGG	C04858
PubChem CID	5280746
UNII	6QU3EZE37U^Y
CompTox Dashboard (EPA)	DTXSID90949393
InChI InChI=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^Y Key: NTDLXWMIWOECHG-YRCFQSNFSA-N^Y
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
Properties
Chemical formula	C26H28O14
Molar mass	564.496 g·mol^−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley[1] and celery,[2] and in banana leaf.[3] 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.[4] The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.[5]

See also

• Apiose

References

1. H. Meyer; A. Bolarinwa; G. Wolfram; J. Linseisen (2006). "Bioavailability of Apigenin from Apiin-Rich Parsley in Humans". Ann Nutr Metab. 50 (3): 167–172. doi:10.1159/000090736. PMID 16407641. S2CID 8223136.
2. S. R. Gupta (1952). "A study of apiin from the parsley seeds and plant". Proceedings of the Indian Academy of Sciences, Section A. 35 (5). doi:10.1007/BF03172503. S2CID 91953908.
3. Sayadi, Khali; Akbarzadeh, Fatemeh; Pourmardan, Vahid; Saravani-Aval, Mehdi; Sayadi, Jalis; Chauhan, Narendra Pal Singh; Sargazi, Ghasem (2021). "Methods of green synthesis of Au NCs with emphasis on their morphology: A mini-review". Heliyon. 7 (6). Cell Press: e07250. Bibcode:2021Heliy...707250S. doi:10.1016/j.heliyon.2021.e07250. ISSN 2405-8440. PMC 8220187. PMID 34189304.
4. "Methods in plant biochemistry". Carbohydrates. Vol. 2. Academic Press. 2 December 2012. p. 245. ISBN 978-0080984209.
5. Advances in Carbohydrate Chemistry and Biochemistry. Vol. 31. Academic Press. 5 November 1975. p. 136. ISBN 0080562906.