Chemical fact sheet: (–)-epicatechin

(–)-epicatechin

Basics

Category
Proanthocyanidins
IUPAC-name
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Formula
No formula stored
Exact mass
290.07900 g/mol
Molecular weight
No weights stored
Structure
Chemical structure of (–)-epicatechin
Figure 1.1: Chemical structure of (–)-epicatechin

Sources

In summary, the chemical (–)-epicatechin has been analyzed from following sources:

Aronia melanocarpa 'Galicjanka'
1st 2nd
Vaccinium myrtillus  L.
1st

Note that an analysis result in the database may indicate either presence or lack thereof of a chemical in an analyzed sample.

References

  1. A. Lätti, K. Riihinen, and L. Jaakola, "Phenolic compounds in berries and flowers of a natural hybrid between bilberry and lingonberry (Vaccinium × intermedium Ruthe)," Phytochemistry , vol. 72 , no. 8 , pp. 810–815 , DOI: 10.1016/j.phytochem.2011.02.015 .
  2. A. Primetta, "Phenolic compounds in the berries of the selected Vaccinium species. The potential for authenticity analyses.," PhD thesis, Publications of the University of Eastern Finland. Dissertations in Forestry and Natural Sciences. No 134., 2014 .
  3. A. Primetta, "Personal note," None. Note: The information about the month when the berries were collected in Kuusamo..
  4. J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .

Analysis results

Analysis result 1

Detection technique Values Units
[M⁺ H]⁺ 291 m/z
MS²⁺ 123
139
165
273 		m/z
MS³⁺ 123 m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-diode-array (DAD)
Mass spectrometer description
HPLC-ESI-MS, ion trap, tandem MS
Organism
Vaccinium myrtillus  L.
wild
dried, powdered
Collection dates
2007-8
Sample note
The species is common in Finland. The sample was confirmed by A. Lätti.
Drying methods
freeze-dried
Dried material storage temperature
-25 °C
Dried material storage notes
dark; in a desiccator; as whole; as ground
Extraction solvents
acetonitrile: methanol (85:15, v/v), 8.5 % formic acid
Extraction mass/volume-ratio
27 mg/mL
Extraction repeats
4
Extraction time
25 min
Extraction temperature
20±5 °C
Analysis solvents
ACN; MeOH; formic acid; water
References

A. Lätti, K. Riihinen, and L. Jaakola, "Phenolic compounds in berries and flowers of a natural hybrid between bilberry and lingonberry (Vaccinium × intermedium Ruthe)," Phytochemistry , vol. 72 , no. 8 , pp. 810–815 , DOI: 10.1016/j.phytochem.2011.02.015 .

A. Primetta, "Phenolic compounds in the berries of the selected Vaccinium species. The potential for authenticity analyses.," PhD thesis, Publications of the University of Eastern Finland. Dissertations in Forestry and Natural Sciences. No 134., 2014 .

A. Primetta, "Personal note," None. Note: The information about the month when the berries were collected in Kuusamo..

Analysis result 2

Detection technique Values Units
UV/Vis 280 nm
[M⁻ H]⁻ 289 m/z
STD
True
TLC
False
UV/Vis detector description
UPLC-PDA
Mass spectrometer description
UPLC-PDA-ESI-MS/MS, UPLC-QTOF-MS
Organism
Aronia melanocarpa 'Galicjanka'
cultivated
ground, dried, passed through a strainer (1mm)
Sample note
The fruit samples (about 15kg) were obtained from a horticultural farm in Trzebnica, near Wroclaw, Poland. The raw material was collected at the optimum ripening stage recommended for consumption. The whole fruits were freeze-dried, so that the pressure was reduced to 0.0960 kPa. The temperature in the drying chamber was -60 C, and in the shelves 26C. The dried material was ground with laboratory mill (IKA A.11, Christ) and then passed through a strainer (1mm). The powder (code PDF) was ready for the analyses.
Drying methods
freeze-dried
Drying temperature
26 °C
Extraction solvents
methanol acidified with 2 % formic acid
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
30 min
Analysis solvents
methanol acidified with 2 % formic acid
References

J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .

Analysis result 3

Detection technique Values Units
UV/Vis 280 nm
[M⁻ H]⁻ 289 m/z
STD
True
TLC
False
UV/Vis detector description
UPLC-PDA
Mass spectrometer description
UPLC-PDA-ESI-MS/MS, UPLC-QTOF-MS
Organism
Aronia melanocarpa 'Galicjanka'
cultivated
pressed, dried, passed through a strainer (1mm), ground
Sample note
The fruit samples (about 15kg) were obtained from a horticultural farm in Trzebnica, near Wroclaw, Poland. The raw material was collected at the optimum ripening stage recommended for consumption. The whole, uncrushed fruits were pressed on a hydraulic press (SSRE, Waesaw, Poland). The obtained pomace was freeze-dried using an Alpha 1-4 LSC freeze dryer. The pressure was reduced to 0.960kPa. The temperature in the drying chamber was -60 C, and in the shelves 26C.Then, the material was ground, then passed through a strainer (1mm). After that the powder (code PPUF) was ready for the analyses.
Drying methods
freeze-dried
Drying temperature
26 °C
Extraction solvents
methanol acidified with 2 % formic acid
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
30 min
Analysis solvents
methanol acidified with 2 % formic acid
References

J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .