p-Coumaric acid glucoside

p-Coumaric acid glucoside
	Skeletal formula of p-coumaric acid glucoside trans 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 ;
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	326.301 g·mol−1
	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]

Biosynthesis

The glucoside is produced by enzymes which add a glucose unit from UDP-glucose to the parent p-coumaric acid. The cis and trans isomers have enzymes specific to each. Thus hydroxycinnamate 4-beta-glucosyltransferase characterised from tomato gives the trans form:^[2]

p-Coumaric acid

+ UDP-glucose

2D representation of the chemical structure of p-Coumaric acid glucoside.

trans glucoside

However, cis-p-coumarate glucosyltransferase in Sphagnum fallax gives the cis equivalent:^[3]

2D representation of the chemical structure of Q27102404.

cis-p-coumaric acid

+ UDP-glucose

UDP

Rightward reaction arrow with minor product(s) to top right

2D representation of the chemical structure of Q27098380.

cis glucoside

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
↑ Fleuriet A, Macheix JJ, Suen R, Ibrahim RK (1980). "Partial purifiction and some properties of a hydroxycinnamoyl glucosyltransferase from tomato fruits". Z. Naturforsch. C: Biosci. 35 (11–12): 967–972. doi:10.1515/znc-1980-11-1217.
↑ Rasmussen S, Rudolph H (1997). "Isolation, purification and characterization of UDP-glucose: cis-p-coumaric acid-β-D-glucosyltransferase from Sphagnum fallax". Phytochemistry. 46 (3): 449–453. doi:10.1016/S0031-9422(97)00337-3.

External links

p-Coumaric acid glucoside at www.phenol-explorer.eu

[1] 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

[2] Fleuriet A, Macheix JJ, Suen R, Ibrahim RK (1980). "Partial purifiction and some properties of a hydroxycinnamoyl glucosyltransferase from tomato fruits". Z. Naturforsch. C: Biosci. 35 (11–12): 967–972. doi:10.1515/znc-1980-11-1217.

[3] Rasmussen S, Rudolph H (1997). "Isolation, purification and characterization of UDP-glucose: cis-p-coumaric acid-β-D-glucosyltransferase from Sphagnum fallax". Phytochemistry. 46 (3): 449–453. doi:10.1016/S0031-9422(97)00337-3.

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