Chemical fact sheet: 3,4-O-dicaffeoylquinic acid

3,4-O-dicaffeoylquinic acid

Basics

Category
Hydroxycinnamic & hydroxybenzoic acid derivatives & other organic acid derivatives
IUPAC-name
(1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
Formula
No formula stored
Exact mass
516.12680 g/mol
Molecular weight
No weights stored
Structure
Chemical structure of 3,4-O-dicaffeoylquinic acid
Figure 1.1: Chemical structure of 3,4-O-dicaffeoylquinic acid

Sources

In summary, the chemical 3,4-O-dicaffeoylquinic acid has been analyzed from following sources:

Achillea millefolium  L.
1st 2nd 3rd
Calendula arvensis  L.
1st
Calendula suffruticosa subsp. lusitanica
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. M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .
  2. M. Faustino, D. Pinto, M. Gonçalves, L. Salgueiro, P. Silveira, and A. Silva, "Calendula L. species polyphenolic profile and in vitro antifungal activity.," Journal of Functional Foods , vol. 45 , pp. 254–267 , DOI: 10.1016/j.jff.2018.04.013 .

Analysis results

Analysis result 1

Detection technique Values Units
UV/Vis 328 nm
[M⁻ H]⁻ 515 m/z
MS²⁻ 135
161
173
179
191
203
255
299
335
353 		m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
HPLC-MS/MS
Organism
Achillea millefolium  L.
wild
dried, powdered
Sample note
The wild yarrrow inflorescences and upper leaves were collected by researchers from 50 plants growing in two different grasslands of about one hectare. The gathered material was mixed and made into a unique sample, dried and powdered (20mesh). A voucher specimen was deposited at the Herbarium fo the Excola Superior Agraria de Braganca (BRESA).
Drying methods
lyophilized
Extraction solvents
methanol
Extraction mass/volume-ratio
16.7 mg/mL
Extraction repeats
2
Extraction time
1 h
Extraction temperature
25 °C
Extract drying method
rotary evaporation
Extract drying temperature
40 °C
Analysis solvents
water
Detection note
515 --> the obtained fragments with their relative intensities in the parentheses: 353 (71), 335 (34), 299 (3), 255 (4), 203 (8), 191 (41), 179 (70), 173 (93), 161 (15) and 135 (32).
References

M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .

Analysis result 2

Detection technique Values Units
UV/Vis 328 nm
[M⁻ H]⁻ 515 m/z
MS²⁻ 135
161
173
179
191
203
255
299
335
353 		m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
HPLC-MS/MS
Organism
Achillea millefolium  L.
wild
dried, powdered
Sample note
The wild yarrrow inflorescences and upper leaves were collected by researchers from 50 plants growing in two different grasslands of about one hectare. The gathered material was mixed and made into a unique sample, dried and powdered (20mesh). A voucher specimen was deposited at the Herbarium fo the Excola Superior Agraria de Braganca (BRESA).
Drying methods
lyophilized
Extraction solvents
water
Extraction mass/volume-ratio
5 mg/mL
Extraction repeats
1
Extraction time
10 min
Extraction temperature
100 °C
Extract drying method
lyophilization, Infusion
Analysis solvents
water
Detection note
515 --> the obtained fragments with their relative intensities in the parentheses: 353 (71), 335 (34), 299 (3), 255 (4), 203 (8), 191 (41), 179 (70), 173 (93), 161 (15) and 135 (32).
References

M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .

Analysis result 3

Detection technique Values Units
UV/Vis 328 nm
[M⁻ H]⁻ 515 m/z
MS²⁻ 135
161
173
179
191
203
255
299
335
353 		m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
HPLC-MS/MS
Organism
Achillea millefolium  L.
wild
dried, powdered
Sample note
The wild yarrrow inflorescences and upper leaves were collected by researchers from 50 plants growing in two different grasslands of about one hectare. The gathered material was mixed and made into a unique sample, dried and powdered (20mesh). A voucher specimen was deposited at the Herbarium fo the Excola Superior Agraria de Braganca (BRESA).
Drying methods
lyophilized
Extraction solvents
water
Extraction mass/volume-ratio
5 mg/mL
Extraction repeats
1
Extraction time
10 min
Extraction temperature
100 °C
Extract drying method
lyophilization, decoction
Analysis solvents
water
Detection note
515 --> the obtained fragments with their relative intensities in the parentheses: 353 (71), 335 (34), 299 (3), 255 (4), 203 (8), 191 (41), 179 (70), 173 (93), 161 (15) and 135 (32).
References

M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .

Analysis result 4

Detection technique Values Units
UV/Vis 244
327 		nm
[M⁻ H]⁻ 515 m/z
MS²⁻ 173
179
255
299
335
353 		m/z
STD
False
TLC
False
UV/Vis detector description
UHPLC-DAD
Mass spectrometer description
ESI, UHPLC-MS, linear ion trap
Organism
Calendula arvensis  L.
dried, powdered
Collection dates
2015-3, 2015-4
Sample note
The samples were identified by Dr. Paolo Silveira. A voucher specimen was deposited in the Herbarium of the Department of Biology University of Aveiro, Portugal.
Drying methods
oven-dried
Drying temperature
60 °C
Extraction solvents
methanol
Extraction mass/volume-ratio
100 mg/mL
Extraction repeats
4
Extraction time
2 d
Extraction temperature
20±5 °C
Extract drying method
vacuum evaporation
Extract drying temperature
40 °C
Analysis solvents
MeOH
Detection note
515 --> the obtained fragments: 353 (100), 299 (15) [M-H-caffeoyl-2H2O]-, 335 (5) [caffeoylquinic acid-H- H2O]-, 255 (4) [M-H-caffeoyl-2H2O-CO2]-, 173 (3)[quinic acid-H-H2O]-, 179 (2)[caffeic acid-H]-
References

M. Faustino, D. Pinto, M. Gonçalves, L. Salgueiro, P. Silveira, and A. Silva, "Calendula L. species polyphenolic profile and in vitro antifungal activity.," Journal of Functional Foods , vol. 45 , pp. 254–267 , DOI: 10.1016/j.jff.2018.04.013 .

Analysis result 5

Detection technique Values Units
UV/Vis 244
327 		nm
[M⁻ H]⁻ 515 m/z
MS²⁻ 173
179
255
299
335
353 		m/z
STD
False
TLC
False
UV/Vis detector description
UHPLC-DAD
Mass spectrometer description
ESI, UHPLC-MS, linear ion trap
Organism
Calendula suffruticosa subsp. lusitanica
dried, powdered
Collection dates
2015-3, 2015-4
Sample note
The samples were identified by Dr. Paolo Silveira. A voucher specimen was deposited in the Herbarium of the Department of Biology University of Aveiro, Portugal.
Drying methods
oven-dried
Drying temperature
60 °C
Extraction solvents
methanol
Extraction mass/volume-ratio
100 mg/mL
Extraction repeats
4
Extraction time
2 d
Extraction temperature
20±5 °C
Extract drying method
vacuum evaporation
Extract drying temperature
40 °C
Analysis solvents
MeOH
References

M. Faustino, D. Pinto, M. Gonçalves, L. Salgueiro, P. Silveira, and A. Silva, "Calendula L. species polyphenolic profile and in vitro antifungal activity.," Journal of Functional Foods , vol. 45 , pp. 254–267 , DOI: 10.1016/j.jff.2018.04.013 .