P-Coumaric acid glucoside

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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

Chemical compound

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

## References

[edit]

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

## External links

[edit]

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

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* t
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Types of hydroxycinnamic acids

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|

* Ferulic acid glucoside
* p-Coumaric acid glucoside
* 1-Sinapoyl-D-glucose

Tartaric acid esters|

* Caftaric acid
* Chicoric acid (dicaffeoyltartaric acid)
* Coutaric acid
* Fertaric acid
* Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid|

* Caffeoylmalic acid
* Ethyl caffeate
* Methyl caffeate
* Caffeic acid phenethyl ester (CAPE)
* Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)|

* Echinacoside
* Calceolarioside A, B, C, F
* Chiritoside A, B, C
* Cistanoside A, B, C, D, E, F, G, H
* Conandroside
* Myconoside
* Pauoifloside
* Plantainoside A
* Plantamajoside
* Tubuloside B
* Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)

Oligomeric forms|

| Dimers|

* Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-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′-O-4″-Triferulic acid

Tetramers|

* Tetraferulic acids

Conjugates with
coenzyme A (CoA)|

* Caffeoyl-CoA
* Cinnamoyl-CoA
* Coumaroyl-CoA

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