Eriodictyol

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Eriodictyol
Eriodictyol.png
Eriodictyol 3D BS.png
Names
IUPAC name
(2S)-3′,4′,5,7-Tetrahydroxyflavan-4-one
Systematic IUPAC name
(2S)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Eriodictiol
Identifiers
3D model (JSmol)
92358
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.198 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-016-4
KEGG
PubChem CID
UNII
  • InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2/t13-/m0/s1 X mark.svgN
    Key: SBHXYTNGIZCORC-ZDUSSCGKSA-N X mark.svgN
  • InChI=1/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2/t13-/m0/s1
    Key: SBHXYTNGIZCORC-ZDUSSCGKBZ
  • O=C2c3c(O[C@H](c1ccc(O)c(O)c1)C2)cc(O)cc3O
Properties
C15H12O6
Molar mass 288.255 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa ( Eriodictyon californicum ), a plant native to North America. [1] Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin. [2]

Eriodictyol has garnered scientific attention for its strong antioxidant, anti-inflammatory, and neuroprotective properties. Structurally similar to other flavonoids, such as hesperidin and naringenin, eriodictyol scavenges free radicals and regulates inflammatory responses.

Eriodictyol was also found in the twigs of Millettia duchesnei , [3] in Eupatorium arnottianum , [4] and its glycosides (eriocitrin) in lemons and rose hips (Rosa canina). [5]

Eriodictyol belongs to the flavanone subclass of flavonoids and has a chemical structure defined by the molecular formula C15H12O6, with a molecular weight of 288.25 g/mol. [6]

References

  1. ↑ Kaminski, Patricia; Katz, Richard. "Yerba Santa Eriodictyon californicum". Flower Essence Society. Retrieved 2022-01-20.
  2. ↑ Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ (July 2005). "Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae)". J. Agric. Food Chem. 53 (15): 6061–6. Bibcode:2005JAFC...53.6061L. doi:10.1021/jf0505170. PMID   16028996.
  3. ↑ Ngandeu F, Bezabih M, Ngamga D, et al. (January 2008). "Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei". Phytochemistry. 69 (1): 258–63. Bibcode:2008PChem..69..258N. doi:10.1016/j.phytochem.2007.05.038. PMID   17640692.
  4. ↑ Clavin M, Gorzalczany S, Macho A, et al. (July 2007). "Anti-inflammatory activity of flavonoids from Eupatorium arnottianum". J Ethnopharmacol. 112 (3): 585–9. doi:10.1016/j.jep.2007.04.007. PMID   17570627.
  5. ↑ Hvattum E (2002). "Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode-array detection". Rapid Commun. Mass Spectrom. 16 (7): 655–62. Bibcode:2002RCMS...16..655H. doi:10.1002/rcm.622. PMID   11921243.
  6. ↑ "Eriodictyol". FoodStruct. Retrieved 1 October 2024.
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