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Determination of Chlorogenic Acid in Coffee Products
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Introduction OH,Chlorogenic acid is a natural product O OH. occurring in a large number of different 1 O HO O,plants or parts of the plant for example 5 3. in green coffee beans Chemically it is HO O HO OH,the ester of caffeic acid and quinic OH O. acid 3 O caffeoylquinic acid 3 CQA,Other isomers are crypto chlorogenic OH O. acid 4 CQA and neo chlorogenic n Chlorogenic acid Cynarine. acid 5 CQA Additionally there are 3 O caffeoylquinic acid 3 CQA 1 5 dicaffeoylquinic acid. other isomers called iso chlorogenic Figure 1 Formula of chlorogenic acid as an example for the mono caffeic acid esters and cynarine as. acids with two caffeic acid moieties an example for the dicaffeic acid esters of quinic acid other isomers can be draw according to the. such as 3 4 dicaffeoylquinic acid numbers and chemical names given in the text. 3 5 dicaffeoylquinic acid and,1 5 dicaffeoylquinic acid cynarine.
Figure 1 Chlorogenic acids are the Experimental Columns. ingredient of coffee considered to 1 Agilent ZORBAX Eclipse Plus. cause problems for coffee drinkers Equipment 4 6 150 mm 5 m p n 959993 902. with a sensitive stomach On the other Agilent 1260 Infinity LC System. hand as a polyphenol compound it is 2 Agilent Poroshell 120. a highly potent antioxidant with some Agilent 1260 Infinity Binary Pump EC C18 3 0 150 mm 2 7 m. attributed positive health effects1 To G1312B with external degasser p n 693975 302. control the content of chlorogenic acid G1322A, in coffee different roasting procedures 3 Agilent Poroshell 120. are applied More chlorogenic acid is Agilent 1260 Infinity Standard EC C18 3 0 50 mm 2 7 m. degraded at a slow roasting process at p n 699975 302. Autosampler G1329B with, lower temperature 20 minutes at 200 C Sample Thermostat G1330B. compared to a faster roasting procedure Chemicals, at higher temperature 3 5 minutes at All chemicals were purchased from. 400 600 C Regular coffee contains Agilent 1260 Infinity Thermostatted. Column Compartment G1316A Sigma Aldrich Germany Acetonitrile. about 3 5 g chlorogenic acid per 100 g2 was purchased from Merck Germany. Fresh ultrapure water was obtained from, The measurement of chlorogenic acid in Agilent 1260 Infinity Diode Array a Milli Q Integral system equipped with. roasted coffee is standardized in the DIN Detector G4212B with 10 mm LC Pak Polisher and a 0 22 m membrane. regulations3 In addition to chlorogenic flow cell G4212 60008 point of use cartridge Millipak Coffee. acid other important compounds inherent,was purchased from a local super market.
in coffee have to be controlled like,caffeine4 5 16 O methyl cafestol6 7 and Software. contaminants such as mycotoxins8 9 Agilent OpenLAB CDS ChemStation Standards. Edition for LC LC MS Systems Rev Chlorogenic acid stock solution. C 01 04 100 mg L,Dilution series for calibration 1 2. 20 0 10 0 5 0 2 5 1 25 0 625,0 3125 312 5 g L and 0 15625. 156 25 g L mg L,Sample preparation HPLC method, A 2 g amount of the roasted coffee Parameter Value. sample was extracted with 150 mL,Solvents A water 1 phosphoric acid.
methanol water 50 50 v v in a Soxhlet B acetonitrile. extractor After four to five extraction,Flow rate 1 0 mL min with Column 1. cycles the solution was allowed to,0 43 mL min with Column 2. cool down to room temperature The 0 43 0 86 and 1 72 mL min with Column 3. extract was transferred quantitatively,Gradient 0 minutes 10 B. to a 200 mL volumetric flask and 20 minutes 20 B, filled up to the 200 mL level with the 25 minutes 30 B. methanol water mixture After mixing 35 minutes 40 B. the extract was filtered by a syringe filter 40 minutes 40 B. Agilent Captiva Premium Syringe Filter Stop time 40 minutes. Regenerated Cellulose 0 45 m 25 mm Post time 10 minutes. p n 5190 5111 and the filtrate was used This gradient was used for Column 1 at a flow rate of 1 mL min For the other. directly for injection columns the gradient and flow rate were adjusted accordingly. Injection volume 10 L with Column 1,4 3 L with Columns 2 and and 1 4 L with Column 3.
Results and Discussion,Needle wash In vial with acetonitrile. For n chlorogenic acid a calibration,Column temperature 25 C. curve was created from 0 156 mg L up,Detection 324 nm. to 20 mg L Figure 2 As a standard,bandwidth 8 nm,the isomer n Chlorogenic acid 3 CQA Ref Off. was used for the calibration Due to Data rate 10 Hz. its similar extinction coefficient with,neo and crypto chlorogenic acid the.
calibration can also be used directly for,these compounds The values for the. Correlation 0 99998,iso chlorogenic acids can be converted. to n chlorogenic acid with an extinction 500 8,relation factor 0 77 published in the. scientific literature10 400,0 5 10 15 20,Amount mg L. Figure 2 Calibration curve for n chlorogenic acid for the concentration range 0 156 20 mg L. The calibration showed excellent linearity mAU A 6 998. The limit of quantification LOQ was 60 20 00 mg L,0 09 mg L signal to noise S N 10.
and the limit of detection LOD at,0 03 mg L S N 3 Under the chosen 40. HPLC conditions n chlorogenic acid, eluted at 7 0 minutes and an overlay of 30 10 00 mg L. the injected concentrations from the,calibration shows good peak shapes for 20. all concentrations and retention time 5 00 mg L,conformance Figure 3 2 50 mg L. To demonstrate the performance a 0,5 6 7 8 9 10 min.
statistical evaluation was done by,multiple injections n 10 of the. n chlorogenic acid concentration level at mAU,10 mg L Table 1A 4. 1 250 mg L,The retention time RSD and area RSD,were at 0 07 and 0 15 respectively 3. For the determination of carryover the,highest concentration used for the. calibration was injected and followed 2 0 625 mg L. by a blank injection In this blank no, carryover from n chlorogenic acid could 312 50 g L.
be detected Figure 4 The concentration,precision and accuracy was measured 156 25 g L. for repeated injection n 10 of 12 mg L,5 6 7 8 9 10 min. n chlorogenic acid The precision, was determined to be 0 12 and Figure 3 Overlay of chlorogenic acid peaks of different concentrations used as calibration levels. concentration accuracy was found to be A Concentrations 1 25 20 mg L B Concentrations 0 1563 1 250 mg L. 98 1 Table 1A,5 10 15 20 25 30 35 min, Figure 4 Determination of carryover of n chlorogenic acid for the maximum concentration used A. Maximum concentration of n chlorogenic acid at 20 mg L B Lowest level of n chlorogneic acid used. for calibration at 156 25 g L LOQ 90 g L as comparison C Blank injection following maximum. n chlorogenic acid concentration injection showing no carryover. The analysis according to the description, in the DIN Norm was done under Table 1A Performance data measured for 10 mg L chlorogenic acid with the Eclipse plus.
4 6 150 mm 5 m column as well as concentration precision and accuracy. conventional HPLC conditions at a, flow rate at 1 mL min with a 4 6 mm Column 4 6 150 mm Eclipse plus C18 5 m. id column To save solvent and costs Chlorogenic acid 10 mg L. the described calibration and statistical,r t min 7 021. evaluation was repeated with a solvent, saver column of the same length but with r t RSD 0 07. a 3 0 mm id at a flow rate of 0 43 mL min area RSD 0 15. Table 1B Retention time was found at Calibration 156 25 g L 20 0 mg L. 6 4 minutes due to the low delay volume Linearity R2 0 99998. configuration of the pump by removing LOD 0 03 mg L. mixer and damper The retention time LOQ 0 09 mg L,and area RSD as well as linearity were in. Carry over from 20 0 mg L n d,the same range as the 4 6 mm id column.
Concentration precision 0 12 at 12 0 mg L, In contrast to the conventional columns Concentration accuracy 98 1 at 12 0 mg L. lower LOQ and LOD were as found with,the solvent saver column at 0 05 mg L. and 0 015 mg L respectively This effect Table 1B Performance data measured for 10 mg L chlorogenic acid with the Poroshell. 3 0 150 mm 2 7 m column as well as concentration precision and accuracy. was due to the higher separation power, of this column with its 2 7 m fused core Column 3 0 150 mm Poroshell EC 120 2 7 m. shell particles and hence higher and Chlorogenic acid 10 mg L. sharper peaks delivering improved S N,r t min 6 425. performance,r t RSD 0 22,area RSD 0 21,Calibration 156 25 g L 20 mg L.
Linearity R2 0 99999,LOD 0 015 mg L,LOQ 0 05 mg L,Carryover from 20 0 mg L n d. Concentration precision 0 21 at 12 0 mg L,Concentration accuracy 96 0 at 12 0 mg L. The chromatogram of a real sample from mAU 6 958,regularly roasted coffee is shown in. n chlorogenic acid,Figure 5 The peak for n chlorogenic acid 35. elutes at 6 95 minutes Neo chlorogenic n chlorogenic acid 1 19 g 100g. acid eluted a little earlier at 4 35 minutes neo chlorogenic acid 0 54 g 100g. and crypto chlorogenic acid little later at 25 4 358. crypto chlorogenic acid 0 68 g 100g, 7 63 minutes The three iso chlorogenic 7 631 iso chlorogenic acids 0 2 g 100g.
acids eluted between 21 9 and 20,neo chlorogenic acid. crypto chlorogenic acid,24 8 minutes The concentration of. n chlorogenic acid was 1 19 g 100 g 15, coffee The combined content of all iso chlorogenic acids. chlorogenic acids was 2 61 g 100 g,5 21 954 23 236. The same sample was also measured,on Column 2 under identical gradient 0.
conditions but at a flow rate of 5 10 15 20 25 30 min. 0 43 mL min to save about 57 of Figure 5 Determination of chlorogenic acids in regular coffee on column 1 n Chlorogenic acid. solvent The chromatogram showed all 1 19 g 100 g All chlorogenic acids 2 61 g 100 g extraction of 2 g coffee final extraction volume. chlorogenic acid peaks with improved 200 mL dilution of the extract was 1 10. separation of especially the first three,eluting chlorogenic acid isomers. Figure 6 mAU 6 369,n chlorogenic acid,neo chlorogenic acid. crypto chlorogenic acid,20 iso chlorogenic acids,21 588 22 487. 5 10 15 20 25 30 min, Figure 6 Determination of chlorogenic acids in regular coffee on Column 2 at a flow rate of 0 43 mL min. For a further improvement of the A 2 342,productivity the 3 0 150 mm column.
was exchanged with a 3 0 50 mm,column of the same stationary phase The 15. time steps of the gradient were reduced, to one third and the flow rate was kept 1 410 2 706. constant which allowed finishing the 10,separation in one third of the time. 13 minutes improving sample throughput,three times Figure 7A A further 5. improvement of the throughput could 7 814 8 125,be achieved by doubling the flow rate to.
0 86 mL min which reduces the run time 0, to 6 5 minutes Figure 7B A four times 2 4 6 8 10 min. higher flow rate of 1 72 mL min reduces,the run time to 3 25 minutes Figure 7C. 3 964 4 114,1 2 3 4 5 min,mAU C 0 636,2 095 2 167,0 5 1 0 1 5 2 0 2 5 3 0 min. Figure 7 Improved efficiency by means of a shorter column 3 0 50 mm 2 7 m and higher flow. rates A Reduction of column length and gradient step times to one third reduces the elution time of. n chlorogenic acid to 2 342 minutes total run time to 13 minutes and increases sample throughput three. times B Doubling the flow rate to 0 86 mL min reduces the run time to 6 5 minutes and the elution time. of n chlorogenic acid to 1 169 minutes C Four times higher flow rate of 1 72 mL min reduces the run. time to 3 25 minutes and the elution time of n chlorogenic acid to 0 636 minutes. Conclusion References 6 DIN 10779 Coffee and coffee. This Application Note demonstrates the products Determination of. 1 European Food Safety Authority, use of a standard HPLC to determine 16 O methyl cafestol content in. Scientific opinion of the, chlorogenic acids in roasted coffee roasted coffee by HPLC March.
substantiation of health claims related,according to the DIN 10767 The linearity 2011. to coffee including chlorogneic, of the calibration curve is excellent as acids from coffee EFSA Journal 7 Agilent Application Note Publication. well as the RSD values for retention time 9 4 2057 2011 number 5991 2853EN. and area It was shown that comparable, results with even lower LOD and LOQ can 2 www wikipedia org 8 DIN EN 14132 Foodstuff. be achieved by means of solvent a saver Determination of ochratoxin A in. column on the same instrument whereas 3 DIN 10767 Coffee and coffee. barley roasted coffee HPLC method, 57 less solvent is consumed products Determination of. with immunoaffinity column clean up,chlorogenic acids by HPLC 1992.
EN 14132 2009 Sept 2009,4 DIN ISO 20481 Coffee and coffee. 9 Agilent Application Note Publication,products Determination of caffeine. number 5991 2854EN,content by HPLC ISO 20481 2008,Jan 2011 10 K Herrmann Fortschritte der Chemie. organischer Naturstoffe Bd 35,5 Agilent Application Note Publication. Springer Verlag 73 132 1978,number 5991 2851,www agilent com chem.
This information is subject to change without notice. Agilent Technologies Inc 2013 2016,Published in the USA September 1 2016.

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