p-Coumaric acid glucoside

p-Coumaric acid glucoside
Names

IUPAC name (2E)-3-[4-(β-D-Glucopyranosyloxy)phenyl]prop-2-enoic acid
Systematic IUPAC name (2E)-3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
Other names p-Coumaric acid 4-O-glucoside
Identifiers
CAS Number	14364-05-7
3D model (JSmol)	Interactive image
ChemSpider	8016010
PubChem CID	9840292
UNII	7ABG62Y8UG^Y
CompTox Dashboard (EPA)	DTXSID101030453
InChI InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-1-8(2-5-9)3-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-3+/t10-,12-,13+,14-,15-/m1/s1 Key: LJFYQZQUAULRDF-FDGSXQGBSA-N InChI=1/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-1-8(2-5-9)3-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-3+/t10-,12-,13+,14-,15-/m1/s1 Key: LJFYQZQUAULRDF-FDGSXQGBBA
SMILES C1=CC(=CC=C1/C=C/C(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
Chemical formula	C₁₅H₁₈O₈
Molar mass	326.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

p-Coumaric acid glucoside is a hydroxycinnamic acid, an organic compound found in commercial breads containing flaxseed.^[1]

References

^ Phenolic glucosides in bread containing flaxseed. C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman, Food Chemistry, Volume 110, Issue 4, 15 October 2008, Pages 997–999, doi:10.1016/j.foodchem.2008.02.088

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-<i>O</i>-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-<i>O</i>-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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This page was last edited on 6 May 2023, at 04:33