A Novel Extraction Method for Aroma Isolation from Dark Chocolate Based on the Oiling-Out Effect

Suzuki, Daisuke; Sato, Yuko; Nishiura, Hiromi; Harada, Risa; Kamasaka, Hiroshi; Kuriki, Takashi; Tamura, Hirotoshi

doi:10.1007/s12161-019-01642-0

Cited by 9 publications

(4 citation statements)

References 33 publications

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“…Many hydrophobic pharmaceutical compounds exhibit oiling‐out behavior, [ 6 ] such as active pharmaceutical ingredients (butyl parben, antiandrogen, erythromycin ethylsuccinate, and idebenone), food compounds (vanillin and lauric acid), and some polymer such as polyethylenglycoldimethylether. [ 7–12 ] Recent development of many hydrophobic pharmaceutical compounds including new anticancer and antivirus drugs has led to increasing interest in controlling oiling‐out crystallization. [ 13–17 ]…”

Section: Introductionmentioning

confidence: 99%

Oiling‐Out Crystallization of Beta‐Alanine on Solid Surfaces Controlled by Solvent Exchange

Zhang

Wei

Choi

et al. 2020

Adv Materials Inter

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In this work, the solvent‐exchange crystallization processes of beta‐alanine in mixture of isopropanol and water on solid surfaces are reported. As the antisolvent isopropanol displaces the alanine solution pre‐filled in a microchamber, liquid–liquid phase separation occurs at the mixing front. The alanine‐rich subphase forms surface microdroplets that subsequently crystallize with during the solvent exchange. It is found that the flow rates and solid surfaces have significant influence on the droplet size, growth rate, and crystal size and morphology. At fast flow rates, the droplets solidify rapidly, forming spherical‐cap structures resembling the shape of droplets, in contrast to crystal microdomains or thin films formed at slow flow rates. On a highly hydrophilic surface, the crystals form thin film without droplets formation. It is further demonstrated that by the solvent exchange, the crystals, generated by using a stock solution with a very low concentration of the precursor, can be used as seeds to facilitate crystallization in bulk solution. The results suggest that the solvent exchange has the potential to be an effective approach for controlling oiling‐out crystallization, and to be wider applied in, such as, separation and purification of many food, medical, and therapeutic ingredients.

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Section: Introductionmentioning

confidence: 99%

Oiling‐Out Crystallization of Beta‐Alanine on Solid Surfaces Controlled by Solvent Exchange

Zhang

Wei

Choi

et al. 2020

Adv Materials Inter

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“…For that, an effective method for extracting volatile compounds from olive oil is needed. We recently proposed a method for extracting a wide range of volatile compounds from edible oils and fat-enriched food based on the oiling-out effect 10 , 11 . The method, named the oiling-out assisted liquid–liquid extraction (OA-LLE), can be used to isolate the volatile compounds from the oil matrix, which has a strong matrix effect.…”

Section: Introductionmentioning

confidence: 99%

A method for gaining a deeper insight into the aroma profile of olive oil

et al. 2021

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Volatile compounds in food play a crucial role in affecting food quality and consumer preference, but the volatile compounds in olive oil are not fully understood due to the matrix effect of oil. The oiling-out assisted liquid–liquid extraction (OA-LLE), which we previously reported, is an effective method for isolating volatile compounds from edible oils with a strong matrix effect. However, when we apply OA-LLE to extra virgin olive oil (EVOO), the aromatic extracts contain non-volatile compounds such as pigments because of solvent-based extraction. Solvent-assisted flavor evaporation (SAFE) can remove such non-volatiles from extracts, but SAFE is affected by a matrix effect during distillation, resulting in a decrease in performance. By combining the advantages of OA-LLE and SAFE, we propose an effective approach, OA-LLE followed by SAFE (OA-LLE + SAFE), for extracting aroma compounds from EVOO. The “two assists” should help to better understand the native aroma profile of EVOO.

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“…Thus, the Strecker aldehydes 2-and 3-methylbutanal (OAs n • 3 and 4) with their characteristic cocoa and chocolate olfactive notes were found together with other key chocolate aldehydes: 2-methylbut-2-enal (OA n • 12), heptanal (15), oct-2-enal (30), non-2-enal (39), and 2-phenylbut-2-enal (61) [1,27,29,50,51]. The key alcohols heptan-2-ol (OA n • 20), 2-phenylethanol (60), phenol (67), 4-methyphenol (72) [1], butane-2,3-diol (40) [50,52], and guaiacol (58) [29,50] were found to be discriminant together with other alcohols, generally present in cocoa products (Table 1), but for some of them, these have never been described as dark chocolate key aroma compounds: Ethanol (OA n • 5), butan-2-ol (8), 2-methylbut-3-en-2-ol (9), 3-methylbutan-1-ol (16), 3-ethoxypropan-1-ol (23), octan-2-ol (28), 3-ethyl-4-methylpentan-1-ol (37), 1-phenylethanol (54), farnesol (88), and octadecan-1-ol (95). Dark chocolate key esters were also found as discriminative features: Ethyl 2-and 3-methylbutanoate (OA n • 11 and 12), isoamyl acetate (13), pentyl acetate (14), ethyl phenylacetate (52), 2-phenylethyl acetate (55), and ethyl cinnamate (74).…”

Section: Introductionmentioning

confidence: 99%

Key Aroma Compounds of Dark Chocolates Differing in Organoleptic Properties: A GC-O Comparative Study

Deuscher

Gourrat

Repoux³

et al. 2020

Molecules

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Dark chocolate samples were previously classified into four sensory categories. The classification was modelled based on volatile compounds analyzed by direct introduction mass spectrometry of the chocolates' headspace. The purpose of the study was to identify the most discriminant odor-active compounds that should characterize the four sensory categories. To address the problem, a gas chromatography-olfactometry (GC-O) study was conducted by 12 assessors using a comparative detection frequency analysis (cDFA) approach on 12 exemplary samples. A nasal impact frequency (NIF) difference threshold combined with a statistical approach (Khi 2 test on k proportions) revealed 38 discriminative key odorants able to differentiate the samples and to characterize the sensory categories. A heatmap emphasized the 19 most discriminant key odorants, among which heterocyclic molecules (furanones, pyranones, lactones, one pyrrole, and one pyrazine) played a prominent role with secondary alcohols, acids, and esters. The initial sensory classes were retrieved using the discriminant key volatiles in a correspondence analysis (CA) and a hierarchical cluster analysis (HCA). Among the 38 discriminant key odorants, although previously identified in cocoa products, 21 were formally described for the first time as key aroma compounds of dark chocolate. Moreover, 13 key odorants were described for the first time in a cocoa product.Molecules 2020, 25, 1809 2 of 32 Thus, quality attributes of dark chocolate produced from Vietnamese cocoa were recently investigated [2], as well as the influence of the cocoa variety on the fermentation step studied [3][4][5], influence of the cocoa origin on the cocoa flavor examined [6][7][8][9], and the link between the origin and process searched for [10]. The process, starting with fermentation [11][12][13][14][15][16] and followed by drying [17] and roasting [18][19][20][21][22][23] steps, has been the subject of many studies. Specialized reviews and treatises gathered such knowledge [1,[24][25][26].Among these investigations, studies aiming to identify the only aroma-active compounds in dark chocolate (the dark chocolate key aroma compounds) are scarce. Nevertheless, some important gas chromatography-olfactometry (GC-O) studies, completed by GC-MS, allowed identification of the major dark chocolate key aroma compounds. Thus, the influence of conching was examined, with the aim of identifying the key odorant compounds in dark chocolate [27]. Aroma-active compounds in dark and milk chocolate in relation to sensory perception were investigated [28], and recently, key aroma compounds in two commercial dark chocolates with high cocoa contents were characterized [29]. As already cited, the major results are reported in reviews on cocoa and cocoa products [24][25][26] as well as in a specialized treatise dedicated to chocolate [1].Direct injection mass spectrometry (DIMS) methods, such as proton transfer reaction mass spectrometry (PTR-MS), have been used in some studies conducted on dark chocolates. Their obje...

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A Novel Extraction Method for Aroma Isolation from Dark Chocolate Based on the Oiling-Out Effect

Cited by 9 publications

References 33 publications

Oiling‐Out Crystallization of Beta‐Alanine on Solid Surfaces Controlled by Solvent Exchange

Oiling‐Out Crystallization of Beta‐Alanine on Solid Surfaces Controlled by Solvent Exchange

A method for gaining a deeper insight into the aroma profile of olive oil

Key Aroma Compounds of Dark Chocolates Differing in Organoleptic Properties: A GC-O Comparative Study

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