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Apiin

From Wikipedia, the free encyclopedia
Apiin
Apigenin
Apigenin
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.043.421Edit this at Wikidata
EC Number
  • 247-780-0
KEGG
UNII
  • 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 checkY
    Key: NTDLXWMIWOECHG-YRCFQSNFSA-N checkY
  • 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
C26H28O14
Molar mass564.496 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H319,H335
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Apiin is a naturalflavonoid, adiglycoside of theflavoneapigenin found in the winter-hardy plantsparsley[1] andcelery,[2] and inbanana 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 sugarapiose possibly play a role in winter hardiness of celery, duckweed and parsley.[5]

See also

[edit]

References

[edit]
  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.
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs


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