Adventures in Hop oil Extraction using Pressurized Liquid Extraction
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1 Adventures in Hop oil Extraction using Pressurized Liquid Extraction Jared Harkins, 1 Katy Orr 1 Sierra Nevada Brewing Company 1
2 Study Location Arthur s Pass National Park State Highway 73 2
3 Taramakau Valley (east-extending valley) 3
4 Total PAHs Conc (ng g -1 lichen) Wind roses for east-extending valley Distance from road (km) Predominance of northeast winds means up-valley component to wind direction. Concentrations fairly constant throughout valley. 4
5 Waimakariri Valley (west-extending valley) 5
6 Total PAHs Conc (ng g -1 lichen) Wind roses for west-extending valley Wind direction is predominantly down-valley. Linear decrease in concentration away from the road. Distance from road (km) 6
7 Hawdon Valley (north-extending valley) 7
8 Total PAHs Conc (ng g -1 lichen) Wind roses for north-extending valley Distance from road (km) Wind direction is predominantly downvalley. Significant drop in concentration when transect enters narrow valley. 8
9 Total PAHs Conc (ng g -1 lichen) Percent of hourly winds Percentage of up-valley versus down-valley winds also helps explain PAH concentration trends East-extending valley West-extending valley North-extending valley Upvalley Downvalley Upvalley Downvalley Upvalley Downvalley Distance from road (km) 9
10 Purpose To quantitatively measure the amount of hop oils present before and after torpedoing to determine total extraction efficiency. Obtaining absolute quantification also allows insight into the total extract potential.
11 Extraction Content No technique achieves total extraction. o To achieve absolute quantitation, you cannot assume that your extract is equal to total content. Every extraction technique has bias. o Hops have hundreds of unique compounds which extract at different efficiencies depending on the technique.
12 Internal Calibration Curve: A T /A S C T = conc of target C S = conc of surrogate A T = area of target A S = area of surrogate C T /C S meas' d target conc meas' d surrogateconc x actualsurr conc actualtarget conc This is how cal curves are currently set up in our Agilent software. This is why you provide surrogate conc. Reported concentration has automatically been adjusted for losses that occur during sample prep (if you spiked surrogates before extraction)! 12
13 Surrogate Standards A surrogate is a molecule chosen to mimic the extraction behavior of a target molecule. A known amount of surrogate is injected onto the sample before extraction. The extraction efficiency of that surrogate is indicative of the efficiency of the target compound. Surrogates also correct for loss during workup, cleanup, etc. The perfect surrogate standard is one which has the same extraction characteristics as the target. Isotopically labeled compounds have the same chemical properties as their non-labeled counterparts, yet can be distinguished by mass spectrometry. The perfect surrogate!
14 Imperfect Surrogates Isotopically labeled surrogates are best, however labeling can be difficult depending on the molecule. This leads to standards that can be expensive or impossible to find. The next best option is to choose surrogates based on similar chemical properties
15 Surrogate Choices Monoterpenes Sesquiterpenes Oxidized Monoterpenoids Sesquiterpinoids These 3 surrogates were chosen as representatives for the hop oil compounds of interest. 15
16 Method - Correcting with Surrogates Injection of known amount of surrogate [Amount of Target Recovered] Extraction of surrogate and target [Amount of Surrogate Recovered] [Amount of Surrogate Injected] Correction Factor
17 Method - Accelerated Solvent Extraction 17
18 Method - Simultaneous Distillation Extraction 18
19 Experimental Design Concept: 1. Do extractions on unused hops and determine total oil content by GCMS 2. Do extractions on spent torpedoed hops and determine oil content, again by GCMS 3. Find the difference and celebrate!
20 Final Experimental Conditions ASE 2 extraction phases: Hexane followed by Dichloromethane Pressure: 1600psi Temperature: 50 C Static Time: 5 minutes Volume: ca. 100mL Mass Fresh/Spent: g/1.0658g SDE Extraction Solvent: Dichloromethane Cold Finger: ca. 0 C Nitrogen Flow: ca. 2mL/min Purge Time: 45 minutes Run Time: 45 minutes Mass Fresh/Spent: g/1.3233g 20
21 Results ASE Concentrated Myrcene Caryophellene Linalool Spent Unspent Spent Unspent Spent Unspent Mass % % Extracted Myrcene SDE Concentrated Myrcene Caryophellene Linalool Spent Unspent Spent Unspent Spent Unspent Mass % % Extracted Myrcene
22 Results ASE Concentrated Myrcene Caryophellene Linalool Spent Unspent Spent Unspent Spent Unspent Response Mass of Hops (g) Mass Corrected Percent SDE Concentrated Myrcene Caryophellene Linalool Spent Unspent Spent Unspent Spent Unspent Response Mass of Hops (g) Mass Corrected Percent
23 Acknowledgements Sierra Nevada Brewing Company R&D Lab Jared Harkins Tom Nielson Gil Sanchez Ashlynn Fulton QA Lab Filtration James Conery Chris Lindsey Andrew Duensing Zak Driscoll Oregon State University Rachel Hotchko Chemistry Department at CSU, Chico Randy Miller Lisa Ott David Ball Carol Buckman Blaine Wells 23
24 A Rapid Solvent Extraction Method for Hop Essential Oils Kai C. Lam, Gail B. Nickerson, and Max L. Deinzer J. Agric. Food Chem. 1988, 34, Accelerated Solvent Extraction: A Technique for Sample Preparation Bruce E. Richter,* Brian A. Jones, John L. Ezzell, and Nathan L. Porter Anal. Chem. 1996, 68, Artefact Production in the Likens-Nickerson Apparatus when Used to Extract the Volatile Flavorous Components of Cod Alister S. McGill and Roy Hardy J. Sci. Fd Agric. 1977, 28, Comparative Gas Chromatographic Mass Spectrometric Evaluation of Hop (Humulus lupulus L.) Essential Oils and Extracts Obtained Using Different Sample Preparation Methods Magdalena Ligor & Mantas Stankevičius & Anna Wenda-Piesik & Kęstutis Obelevičius & Ona Ragažinskienė & Žydrūnas Stanius & Audrius Maruška & Bogusław Buszewski Food Anal. Methods DOI /s Literature Detection of Certain Hop Oil Constituents in Brewing Products S. T. LIKENS and G. B. NICKERSON", Oregon Agricultural Experiment Station, Corvallis, Oregon Proceedings of the American Society of Brewing Chemists 5-13 Optimized Likens-Nickerson Methodology for Quantifying Honey Flavors Amina Bouseta and Sonia Collin J. Agric. Food Chem. 1995, 43, Recovery of Less-volatile Chemicals from Pure Fat Using a Simultaneous Steam Distillation-extraction Apparatus Fernando E. Figuerola* and Takayuki Shibamoto Agric. Biol Chem., 47 (12), , 1983 Fermentation Science: Oregon State University (Presentation) Thomas H. Shellhammer, Daniel C. Sharp Simultaneous distillation extraction: from birth to maturity review Alain Chaintreau* Flavour Fragr. J. 2001; 16: Compounds Contributing to the Characteristic Aroma of Malted Barley Andrew D. Bealt and Donald S. Mottram* J. Agric. Food Chem. 1994, 42, Superheated water extraction, steam distillation and Soxhlet extraction of essential oils of Origanum onites Mustafa Z. Ozel & Hilal Kaymaz Anal Bioanal Chem (2004) 379:
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