Apiin

Apiin
Names
	IUPAC name 7-[(2S,3R,4S,5S,6R)-3-[(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)chromen-4-one
	Other names Apioside; Apigenin-7-apioglucoside; Apigenin-7-O-apioglucoside
Identifiers
CAS Number	26544-34-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15932 ;
ChEMBL	ChEMBL1535342 ;
ChemSpider	4444321 ;
ECHA InfoCard	100.043.421
EC Number	247-780-0;
KEGG	C04858;
PubChem CID	5280746;
UNII	6QU3EZE37U ;
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 Key: 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;
Properties
Chemical formula	C26H28O14
Molar mass	564.496 g·mol−1
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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

References

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.
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.
page 245 "Methods in plant biochemistry" volume 2: "Carbohydrates", ISBN 0080984207
page 136 "Advances in Carbohydrate Chemistry and Biochemistry", Volume 31, ISBN 0080562906

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[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] 245 "Methods in plant biochemistry" volume 2: "Carbohydrates", ISBN 0080984207

[4] 136 "Advances in Carbohydrate Chemistry and Biochemistry", Volume 31, ISBN 0080562906

Apiin

See also

References