Water-rich yellow peel oil composition, preparation method and uses

Abstract

This article provides a water-wheat peel oil composition suitable for animal consumption, particularly human consumption, and a method for producing such a composition. The composition is edible and non-bitter, and possesses certain properties that make it suitable for use in and / or in a variety of food and beverage products. Methods for analyzing water-wheat peel oil are also provided.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to U.S. Provisional Application No. 63 / 004,787, filed April 3, 2020, the entire disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] This disclosure generally relates to pongamia compositions, and more specifically, to edible and non-bitter pongamia oil, methods of producing the oil, and methods of using the oil in food and beverage products. Background Technology

[0004] Growing concerns about population growth, climate change, and the viability of existing agricultural practices in the coming decades have led to a surge in research and development of alternative food sources to ensure future global food security. Sources based on renewable plants have spurred significant interest in environmentally friendly and sustainable approaches to alleviate pressures on global food supplies.

[0005] Millettia pinnata, also known as Pongamia pinnata or Pongamia glabra, or more commonly as water wampee or karanja, is a common tree throughout Asia and could provide a major source of future plant-based foods. The water wampee tree uses a fraction of the land required for soybean plants to produce the same amount of legumes. It can grow in degraded soils and allows for avoiding the deforestation problems associated with soybeans. Each acre of water wampee also produces significantly more protein and vegetable oil compared to soybeans. Water wampee oil, extracted from water wampee oilseeds, provides a potentially renewable source of oil for use in foods comparable to legumes. However, water wampee oilseeds also contain other components known in the art to have unpleasant tastes and odors, including quercetin and quercetin dione. It is desirable to use oils with minimal amounts of quercetin and quercetin dione as viable food sources.

[0006] Currently, the widespread use of water-wax peel-derived foods is hindered by the lack of methods for preparing water-wax peel compositions with low levels of quercetin and quercetin diketone while maintaining the inherently high nutrient content (protein, carbohydrates, etc.) of the oilseeds. Existing methods for removing these undesirable components from water-wax peel seed cake and oil are inadequate and often require harsh, destructive conditions that reduce and degrade nutrients to a degree that severely impacts the nutritional value of water-wax peel. The lack of methods for producing water-wax peel compositions with a critical balance of preserving nutrient content and sufficiently low levels of anti-nutrients makes the blending of water-wax peel-derived oils on a sufficiently large scale economically unfeasible.

[0007] Therefore, what is desired in the art is a commercially viable method for obtaining edible compositions from water flavone oilseeds that maintains optimal nutritional balance while minimizing components such as water flavonein and water flavone dione. Summary of the Invention

[0008] In some respects, this article provides an edible and non-bitter water citrus oil composition. This water citrus oil composition can be used as a useful ingredient in a variety of food and beverage products and addresses a large unmet industrial demand for emerging plant-based products.

[0009] In some aspects, a method for producing a water-wheat peel oil composition using solid-liquid separation is provided. In some embodiments, the method includes: combining crude water-wheat peel oil with a nonpolar solvent to produce a crude mixture; eluting the crude mixture with the nonpolar solvent through silica gel to separate at least a portion of the furan flavonoids present in the crude mixture from the water-wheat peel oil, and to produce a purified mixture comprising water-wheat peel oil and a nonpolar solvent; and removing at least a portion of the nonpolar solvent from the purified mixture to produce the water-wheat peel oil composition. In some variations, the nonpolar solvent includes alkanes.

[0010] Crude water flavone oil contains water flavonein and water flavone dione, and in the above method, at least a portion of the water flavonein and water flavone dione are adsorbed onto silica gel. The adsorbed components can be separated. In some embodiments, the method further includes eluting the silica gel with a polar solvent to separate water flavonein and water flavone dione. In some embodiments, a stepwise gradient elution of silica gel is used with a polar solvent in an increased proportion in a non-polar solvent to separate water flavonein and water flavone dione separately. In some variations, the polar solvent includes alkyl esters of alkanonic acids.

[0011] In one aspect, a water-wampee oil composition produced according to any of the methods described herein is provided. In other aspects, an edible and non-bitter water-wampee oil composition is provided.

[0012] In other respects, the use of the water-wheat peel oil composition in food or beverage products is provided. In some variations, the water-wheat peel oil composition can be used as or incorporated into salad oil; frying oil; sautéing oil; vinaigrette; sauces; dressings; vegan meat mimetics; beverages; or as a fat in the blending of margarine and other solid fat applications.

[0013] In other aspects, analytical methods are provided to measure the content of quercetin and quercetin dione that may be present in a sample of *Cephalotaxus fortunei* oil. In some embodiments, the method includes: combining *Cephalotaxus fortunei* oil with an extraction solvent to provide an extraction mixture; sonicating the extraction mixture; separating the sonicated mixture into an extracted *Cephalotaxus fortunei* composition and an extract comprising quercetin or quercetin dione or both; and measuring the concentration of quercetin or quercetin dione or both present in the extract. In some variations, the extraction solvent includes an alkyl ketone. In some embodiments, the measurement step involves determining the concentration of quercetin and / or quercetin dione by high-performance liquid chromatography (e.g., using HPLC-DAD) with a UV detector.

[0014] In one aspect, this document provides a water flavoured fruit oil composition comprising: a combination of water flavourin and water flavoured fruit dione at a concentration of less than or equal to about 1000 ppm, as determined by HPLC-DAD analysis of an acetone extract obtained from the water flavoured fruit oil composition; less than or equal to about 1% unsaponifiable matter by weight; a peroxide value of less than or equal to about 5 meq / kg; a p-anisidine value of less than or equal to about 10; and a residual solvent of less than or equal to about 25 ppm. In some embodiments, the water flavoured fruit oil composition comprises water flavourin at a concentration of less than or equal to about 150 ppm, as determined by HPLC-DAD analysis of an acetone extract obtained from the water flavoured fruit oil composition; water flavoured fruit dione at a concentration of less than or equal to about 150 ppm, as determined by HPLC-DAD analysis of an acetone extract obtained from the water flavoured fruit oil composition; less than or equal to about 1% unsaponifiable matter by weight; a peroxide value of less than or equal to about 5 meq / kg; a p-anisidine value of less than or equal to about 5; and a residual solvent of less than or equal to about 25 ppm.

[0015] In another aspect, this document provides a method for producing a water-loving hibiscus oil composition, comprising: combining crude water-loving hibiscus oil with a non-polar solvent to produce a crude mixture, wherein the non-polar solvent comprises an alkane, and wherein the crude water-loving hibiscus oil comprises water-loving hibiscus oil and furan flavonoids; eluting the crude mixture with the non-polar solvent via silica gel to separate at least a portion of the furan flavonoids from the water-loving hibiscus oil, and producing a purified mixture comprising water-loving hibiscus oil and the non-polar solvent; and removing at least a portion of the non-polar solvent from the purified mixture to produce a water-loving hibiscus oil composition, wherein the composition has a combination of water-loving hibiscus linolenic acid and water-loving hibiscus dione at a concentration of less than or equal to about 1000 ppm as determined by HPLC-DAD analysis of an acetone extract obtained from the water-loving hibiscus oil composition; less than or equal to about 1% by weight of unsaponifiable matter; a peroxide value of less than or equal to about 5 meq / kg; and a p-anisidine value of less than or equal to about 10.

[0016] In other aspects, this document provides food or beverage products comprising a water flavour oil composition obtainable by the methods described herein. In some embodiments, the water flavour oil composition is a pale yellow as determined by the Lovibond color-AOCS scale; the composition comprises a combination of water flavourin and water flavouredione in amounts less than or equal to about 200 ppm as determined by HPLC-DAD analysis of an acetone extract obtained from the water flavour oil composition, and the composition has a neutral flavor. In other embodiments, the water flavour oil composition is a yellow as determined by the Lovibond color-AOCS scale; the composition comprises water flavourin and water flavouredione in amounts less than or equal to about 150 ppm as determined by HPLC-DAD analysis of an acetone extract obtained from the water flavour oil composition, and the composition has one or more sensory properties selected from the group consisting of: nutty ness, buttery ness, grassy ness, smoothness, and sweetness, and any combination thereof. Attached Figure Description

[0017] This application can be understood by referring to the following description in conjunction with the accompanying drawings.

[0018] Figure 1 An exemplary analytical method for determining the concentration of quercetin and / or quercetin dione in a sample of quercetin oil is described.

[0019] Figure 2 An exemplary method is described for purifying a crude water wampee oil mixture to produce an edible and non-bitter water wampee oil composition.

[0020] Figure 3A and 3B The crude water-based yellow peel oil determined by HPLC was compared. Figure 3A The furan flavonoids present in the exemplary purified water yellow peel oil composition ( Figure 3B Furan flavonoids that are not present in ( ). Detailed Implementation

[0021] The following description sets forth exemplary methods, parameters, etc. However, it should be understood that this description is not intended to be a limitation on the scope of this disclosure, but is provided as a description of exemplary embodiments.

[0022] In some aspects, this document provides water frangipani oil compositions and methods for producing such compositions. In some variations, the water frangipani oil compositions pass human taste tests. In some variations, the water frangipani oil compositions are edible and non-bitter. Methods for producing edible water frangipani oil are provided to remove or reduce the amount of present furan flavonoids, including removing or reducing the amount of quercetin and / or quercetin dione, which are generally considered inedible and potentially harmful to humans. Additionally, the provided water frangipani oil compositions possess various properties that make such compositions suitable for food and beverage products. For example, in some variations, the water frangipani oil compositions have low insoluble impurities, low soap content, high smoke point, low monoglycerides and diglycerides, low glycerol, fewer unidentified fatty acids, low total sterols, and a light color (including, for example, low chlorophyll content).

[0023] Watery yellow skin oil composition

[0024] In some embodiments, the water-wheat peel oil composition provided herein is edible, non-bitter, and has an generally acceptable sensory profile in humans (e.g., regarding taste and odor).

[0025] Unsaponifiables

[0026] Unsaponifiables present in the *Phellodendron amurense* composition typically include compounds other than fatty acids. For example, unsaponifiables may include furan flavonols, chlorophyll, tocopherols, and sterols. In some embodiments, the *Phellodendron amurense* oil compositions provided herein (including those produced according to the methods herein) have a lower unsaponifiable content compared to crude *Phellodendron amurense* oil from which the composition is obtained. In some embodiments, the *Phellodendron amurense* oil compositions provided herein (including those produced according to the methods herein) have a low unsaponifiable content. In some variations, the *Phellodendron amurense* oil compositions provided herein (including those produced according to the methods herein) have less than or equal to 5%, less than or equal to 4%, less than or equal to 3%, less than or equal to 2%, or less than or equal to 1% unsaponifiables by weight in the oil. In some variations, the *Phellodendron amurense* oil compositions provided herein (including those produced according to the methods herein) have less than 50%, at least 55%, at least 60%, at least 70%, at least 80%, or at least 90% unsaponifiables by weight compared to crude *Phellodendron amurense* oil from which the composition is obtained. The unsaponifiable content can be measured or determined using any suitable method known in the art. In some variations, the unsaponifiable content is determined by AOCS Ca6a-40.

[0027] As described above, furan flavonols are a type of unsaponifiable matter. Furan flavonoids are a class of compounds commonly found in the oilseeds of *Cinnamomum camphora*, and include anti-nutritional compounds such as quercetin and quercetin dione. In some embodiments, a *Cinnamomum camphora* oil composition is provided having a low, negligible, or undetectable content of furan flavonoids. In some variations, the *Cinnamomum camphora* oil composition has less than or equal to about 1000 ppm, less than or equal to about 750 ppm, less than or equal to about 500 ppm, less than or equal to about 300 ppm, less than or equal to about 250 ppm, or less than or equal to about 200 ppm of furan flavonoids. In some variants, the water-based yellow peel oil composition contains less than or equal to 500 ppm, less than or equal to 450 ppm, less than or equal to 400 ppm, less than or equal to 350 ppm, less than or equal to 300 ppm, less than or equal to 250 ppm, less than or equal to 200 ppm, less than or equal to 150 ppm, less than or equal to 100 ppm, less than or equal to 50 ppm, less than or equal to 40 ppm, less than or equal to 30 ppm, less than or equal to 20 ppm, or less than or equal to 10 ppm of furan flavonoids.

[0028] In some embodiments, the water flavone oil composition has less than or equal to 150 ppm of water flavone and / or water flavone dione. In some of the foregoing variations, the concentrations of water flavone and water flavone dione are determined by the solvent extraction analysis method described herein.

[0029] In some embodiments, the contents of chlorophyll and chlorophyll dione in the *Cephalotaxus fortunei* oil composition are determined by HPLC analysis of the alkyl ketone extract obtained from the *Cephalotaxus fortunei* oil composition. In other embodiments, the contents of chlorophyll and chlorophyll dione in the *Cephalotaxus fortunei* oil composition are determined by HPLC analysis of the alkyl ketone extract obtained from the *Cephalotaxus fortunei* oil composition according to the analytical methods described herein. In some embodiments, the alkyl ketone is acetone. In some embodiments, the HPLC analysis of the alkyl ketone extract further includes mass spectrometry or ultraviolet detection. In some other embodiments, the contents of chlorophyll and chlorophyll dione in the *Cephalotaxus fortunei* oil composition are determined by HPLC-DAD analysis of the acetone extract obtained from the *Cephalotaxus fortunei* oil composition according to the analytical methods described herein.

[0030] In some variations, the water-based quercetin composition has 500 ppm, 400 ppm, 300 ppm, 250 ppm, 200 ppm, 150 ppm, 140 ppm, 130 ppm, 120 ppm, 110 ppm, 100 ppm, 90 ppm, 80 ppm, 70 ppm, 60 ppm, 50 ppm, 40 ppm, 30 ppm, 20 ppm, or 10 ppm.

[0031] In some variations, the water-rich yellow peel oil composition has water-rich yellow peel diketone at 500 ppm or less, 400 ppm or less, 300 ppm or less, 250 ppm or less, 200 ppm or less, 150 ppm or less, 140 ppm or less, 130 ppm or less, 120 ppm or less, 110 ppm or less, 100 ppm or less, 90 ppm or less, 80 ppm or less, 70 ppm or less, 60 ppm or less, 50 ppm or less, 40 ppm or less, 30 ppm or less, 20 ppm or less, or 10 ppm.

[0032] In other variations, the water flavone oil compositions can be characterized by the concentrations of water flavonein and water flavone dione in their combination. For example, in some variations, the water flavone oil compositions have combinations of water flavonein and water flavone dione of less than or equal to about 1000 ppm, less than or equal to about 750 ppm, less than or equal to about 500 ppm, less than or equal to about 300 ppm, less than or equal to about 250 ppm, or less than or equal to about 200 ppm. In certain variations, the water flavone oil composition contains less than or equal to 200 ppm, less than or equal to 150 ppm, less than or equal to 140 ppm, less than or equal to 130 ppm, less than or equal to 120 ppm, less than or equal to 110 ppm, less than or equal to 100 ppm, less than or equal to 90 ppm, less than or equal to 80 ppm, less than or equal to 70 ppm, less than or equal to 60 ppm, less than or equal to 50 ppm, less than or equal to 40 ppm, less than or equal to 30 ppm, less than or equal to 20 ppm, or less than or equal to 10 ppm of water flavone and water flavone dione.

[0033] In other variations, the water flavoured tangerine oil composition has a ratio of water flavoured tangerine to water flavoured tangerine greater than or equal to about 1. In other variations, the water flavoured tangerine oil composition has a ratio of water flavoured tangerine to water flavoured tangerine less than or equal to about 1.

[0034] In one variant, based on the solvent extraction analysis method described herein, the water flavone oil composition has undetectable amounts of water flavonein and / or water flavone dione.

[0035] In other variations, the water flavoured tangerine oil composition produced according to the methods described herein (e.g., obtained from crude water flavoured tangerine oil) has an amount of less than 100 times, less than 500 times, or less than 1000 times that of the crude water flavoured tangerine oil from which the composition is obtained. In some embodiments, the water flavoured tangerine oil composition produced according to the methods described herein (e.g., obtained from crude water flavoured tangerine oil) has an amount of less than 100 times, less than 150 times, or less than 200 times that of the crude water flavoured tangerine oil from which the composition is obtained.

[0036] fatty acid

[0037] In some embodiments, the water-rich ...

[0038] In some embodiments, the amount of total fatty acids identified in the water croton composition is at least 90%; or between 80% and 99%, or between 85% and 95%.

[0039] The *Phellodendron amurense* oil compositions contain various combinations of monounsaturated, polyunsaturated, and / or saturated fatty acids. In some variants, the *Phellodendron amurense* compositions have a higher content of monounsaturated fatty acids than polyunsaturated fatty acids. In some variants, the *Phellodendron amurense* compositions have a higher content of saturated fatty acids than polyunsaturated fatty acids. In some variants, the *Phellodendron amurense* compositions have a higher content of monounsaturated fatty acids than saturated fatty acids.

[0040] In some embodiments, the water-wheat peel oil composition has a low or even lower trans fatty acid content compared to the crude water-wheat peel oil from which the water-wheat peel oil composition is obtained (e.g., according to the method described herein). In some variations, the amount of trans fatty acids in the water-wheat peel composition is less than or equal to 5%, less than or equal to 1%, less than or equal to 0.5%, or less than or equal to 0.25%.

[0041] In some embodiments, the methods provided herein do not alter the healthy fatty acid profile unless in a positive manner (e.g., by increasing the oleic acid content on a percentage weight basis). This generally contrasts with other methods known in the art that can fundamentally alter the fatty acid profile in an unfavorable manner (e.g., lower yields, fewer healthy or functionally balanced fatty acids). In some embodiments, the water citrus oil composition comprises ω6 fatty acids or ω9 fatty acids, or any combination thereof. In some embodiments, the water citrus oil composition comprises ω3 fatty acids, ω6 fatty acids, ω7 fatty acids, or ω9 fatty acids, or any combination thereof. In some variations, the amount of ω9 fatty acids is greater than that of ω6 fatty acids. In some variations, the combined amounts of ω6 and ω9 fatty acids are greater than the combined amounts of ω3 and ω7 fatty acids. In some variations, the combined amounts of ω6 and ω9 fatty acids are at least 50% or at least 60%; or between 15% and 80%, or between 20% and 75%. In some variants, the amounts of ω3 fatty acids and / or ω7 fatty acids are less than 5%, less than 4%, less than 3%, less than 2%, or less than 1%.

[0042] In some embodiments, the water-yellow peel oil composition includes myristic acid, palmitic acid, palmitoleic acid, heptadecanic acid, heptadecanenoic acid, stearic acid, isoleic acid, oleic acid, linoleic acid, arachidic acid, squalene, eicosadienoic acid, behenic acid, erucic acid, or ceramide, or any isomer thereof, or any combination thereof.

[0043] In some variations, the water citrus oil composition includes oleic acid. In one variation, the amount of oleic acid in the water citrus oil composition is at least 40%, or at least 50%; or between 30% and 70%, between 30% and 60%, or between 45% and 55%.

[0044] In some variations, the water celery oil composition includes linoleic acid or an isomer thereof. In one variation, the amount of linoleic acid or an isomer thereof in the water celery oil composition is at least 15%; or between 10% and 20%. In some variations, the water celery oil composition includes linolenic acid or an isomer thereof. In some variations, the linolenic acid is α-linolenic acid. In one variation, the amount of α-linolenic acid in the water celery oil composition is between 1% and 5%.

[0045] In some variations, the water citrus oil composition includes palmitic acid. In one variation, the amount of palmitic acid in the water citrus oil composition is at least 5%; or between 5% and 10%.

[0046] In some variations, the water citrus oil composition includes stearic acid. In one variation, the amount of stearic acid in the water citrus oil composition is at least 5%; or between 5% and 10%.

[0047] In some variations, the water safflower oil composition includes behenic acid. In one variation, the amount of behenic acid in the water safflower oil composition is between 1% and 10%, or between 1% and 5%.

[0048] In some variations, the water-based wampee oil composition includes arachidic acid, squalinoic acid, or ligninic acid, or any combination thereof. In one variation, the amount of arachidic acid, squalinoic acid, or ligninic acid in the water-based wampee oil composition is independently between 1% and 5%.

[0049] In some variations, the water-wheat safflower oil composition includes erucic acid. In one variation, the amount of erucic acid is at least 0.06%.

[0050] Any suitable method or technique known in the art can be used to measure the fatty acid content in the compositions described herein. For example, in some variations, the test method used is AOAC 996.06.

[0051] Tocopherol

[0052] In some embodiments, the water croton oil composition includes tocopherol. In some variations, the tocopherol is α-tocopherol, β-tocopherol, δ-tocopherol, γ-tocopherol, or any combination thereof. In some embodiments, the water croton oil composition has a total tocopherol content of at least 250 ppm, at least 300 ppm, at least 350 ppm, at least 400 ppm, or at least 450 ppm; or between 200 ppm and 500 ppm.

[0053] In some variants, the α-tocopherol content is the highest among the four tocopherols mentioned above. In some variants, the combined α-tocopherol and γ-tocopherol contents are greater than the combined β-tocopherol and δ-tocopherol contents.

[0054] In one embodiment, the water-based yellow peel oil composition has an α-tocopherol content of at least 200 ppm, at least 250 ppm, or at least 300 ppm; or between 200 ppm and 500 ppm, between 200 ppm and 400 ppm, between 200 ppm and 350 ppm, or between 200 ppm and 300 ppm.

[0055] In another embodiment, the water-based yellow peel oil composition has a γ-tocopherol content of at least 100 ppm or at least 150 ppm; or between 100 and 200 ppm.

[0056] Any suitable method or technique known in the art can be used to measure the tocopherol content in the compositions described herein. For example, in some variations, the test method used is AOAC 971.30 using HPLC.

[0057] Sterols

[0058] In some embodiments, the water hyacinth peel oil composition includes sterols. In some variations, the water hyacinth peel oil composition described herein has a lower amount of sterols compared to crude water hyacinth peel oil from which the water hyacinth peel oil composition is obtained (e.g., according to the method described herein).

[0059] In some variations, the sterol is 24-methylene-cholesterol, β-sitosterol, brassosterol, sterol, cholesterol, sterol, Δ-5,23-stigmasterdienol, Δ-5,24-stigmasterdienol, δ-5-acidosterol, δ-7-acidosterol, δ-7-vestigmasterol, δ-7-stigmasterenol, sitosterol, or stigmasterol, or any combination thereof. In some embodiments, the water safflower oil composition has a total sterol content of less than or equal to 2500 ppm, less than or equal to 2000 ppm, less than or equal to 1500 ppm, less than or equal to 1000 ppm, less than or equal to up to 750 ppm, less than or equal to 500 ppm, or less than or equal to 100 ppm.

[0060] In some variants, the *Phellodendron chinense* oil composition further comprises β-sitosterol. In some of the aforementioned variants, the *Phellodendron chinense* oil composition further comprises brassosterol, stigmasterol, or δ-5-acidosterol, or any combination thereof. In other of the aforementioned variants, the *Phellodendron chinense* oil composition further comprises sterol, Δ-5,24-stigmasterdienol, or sitosterol, or any combination thereof.

[0061] Any suitable method or technique known in the art can be used to measure the sterol content in the compositions described herein. For example, in some variations, the test method used is COI / T.20 / Doc No.10.

[0062] Residual solvent

[0063] The methods described herein for producing the *Phellodendron amurense* oil composition may result in the presence of residual solvents in the composition. A low level of residual solvents in such compositions is desirable because their presence can affect the sensory profile of the composition. In some variations, the *Phellodendron amurense* oil composition produced by the methods herein may be processed to remove or desolventize the composition to achieve the residual solvent levels described herein.

[0064] In some embodiments, the water hyacinth oil composition includes a residual solvent. In some variations, the residual solvent includes a nonpolar solvent used in the purification methods described herein. In some variations, the alkane is a C1-20 alkane or a C-10 alkane. In some variations, the alkane is straight-chain. In other variations, the alkane is branched. In other variations, a mixture of alkanes may be used. In one variation, the nonpolar solvent includes hexane. In still other embodiments, the water hyacinth oil composition includes a residual solvent, wherein the residual solvent includes hexane. In yet another embodiment, the water hyacinth oil composition includes a residual solvent, wherein the residual solvent is hexane.

[0065] In some variations, the water hyacinth oil composition has a residual solvent content of less than or equal to about 100 ppm, less than or equal to about 75 ppm, less than or equal to about 50 ppm, or less than or equal to about 25 ppm. In some embodiments, the residual solvent includes hexane. In some variations, the water hyacinth oil composition has a residual hexane content of less than or equal to about 100 ppm, less than or equal to about 75 ppm, less than or equal to about 50 ppm, or less than or equal to about 25 ppm. Any suitable method or technique known in the art can be used to measure the residual solvent content in the compositions herein. In some variations, the residual solvent is determined by AOCS Cg 4-94.

[0066] Peroxide value and p-anisidine value

[0067] In some variations, the water-wheat saffron oil composition can be further characterized by the levels of oxidation products present in the oil. When exposed to oxygen and / or heat, fats and oils can undergo oxidation reactions, resulting in an undesirable rancid odor. As detailed above, the methods disclosed herein for producing water-wheat saffron oil compositions provide a means of removing or reducing the amount of furan flavonoids and other unsaponifiable matter present. Existing methods for removing these components typically utilize harsh conditions, such as highly corrosive agents and extreme temperatures (e.g., reflux).

[0068] In contrast, the method presented herein employs milder temperature and solvent conditions to treat crude water croton oil to remove furan flavonoids and other unsaponifiables. As a result, the water croton oil compositions obtained herein exhibit low furan flavonoid content, low unsaponifiables content, and minimal oxidation.

[0069] The degree of oxidation can be characterized by the presence and concentration of primary oxidation products that may form during initial oxidation and secondary oxidation products that may form during the decomposition of primary oxidation products with broader oxidation. The degree of primary oxidation can be assessed by measuring the peroxide value (in milliequivalents / kg), an indicator used to quantify the amount of hydroperoxides present in the oil. The degree of secondary oxidation can be assessed by measuring the p-anisidine value. Together, the peroxide value and the p-anisidine value provide a complete representation of oxidation in the oil.

[0070] In some variations, the water hyacinth oil composition has a peroxide value of less than or equal to about 5 meq / kg, less than or equal to about 4 meq / kg, less than or equal to about 3 meq / kg, less than or equal to about 2 meq / kg, or less than or equal to about 1 meq / kg. In some variations, the water hyacinth oil composition has a peroxide value of less than or equal to about 5 meq / kg. Any suitable method or technique known in the art can be used to measure the peroxide value in the compositions herein. In some variations, the peroxide value is determined by AOCS test method AOCS Cd 8-53.

[0071] In other variations, the water hyacinth oil composition has a p-anisidine value of less than or equal to about 15, less than or equal to about 12, less than or equal to about 10, less than or equal to about 7, less than or equal to about 5, less than or equal to about 4, less than or equal to about 3, or less than or equal to about 2. In some variations, the water hyacinth oil composition has a p-anisidine value of less than or equal to about 10. In some other variations, the water hyacinth oil composition has a p-anisidine value of less than or equal to about 5. Any suitable method or technique known in the art can be used to measure the p-anisidine value in the compositions herein. In some variations, the p-anisidine value is determined by the AOCS test method AOCS Cd 18-90.

[0072] Thermal and physical properties

[0073] The aquamarine oil compositions provided herein can be further characterized by their thermal and physical properties. The range of applications and uses for different fats and oils is largely determined by the thermal and physical properties of the fat or oil under specific temperature conditions for that particular application. The thermal and physical properties of fats and oils are, in turn, greatly influenced by their fatty acid profile. As stated above, the method provided herein for producing aquamarine oil compositions with reduced concentrations of aquamarine, aquamarine diketone, and other unsaponifiables contrasts with other methods in the art, which can adversely affect the fatty acid content and profile of the resulting oil in an unfavorable manner (e.g., lower yield, fewer healthy or functionally balanced fatty acids).

[0074] The thermal and physical properties of the water-based yellow peel oil compositions presented herein reflect a non-destructive method for removing furan flavonoids and other unsaponifiables used to obtain the compositions.

[0075] In some variations, the water-wheat peel oil compositions of this disclosure can be characterized by their physical state at a given temperature, or their temperature-dependent behavior, such as melting profiles. In some variations, the water-wheat peel oil compositions are liquid at temperatures greater than or equal to about 10°C. In some variations, the water-wheat peel oil compositions are liquid at room temperature. In other variations, the water-wheat peel oil compositions are semi-solid at temperatures of about 0-10°C. In some variations, the melting profiles are determined by differential scanning calorimetry (DSC).

[0076] In other embodiments, the water-loving yellow skin oil compositions of this disclosure can be characterized by their solid-fat content at a given temperature. For example, in some embodiments, the compositions have a solid-fat content between about 1% and about 10% at temperatures of about 0°C, about 2°C, about 5°C, or about 10°C. In some variations, the compositions have a solid-fat content between about 1% and about 10% at a temperature of about 5°C. Any suitable method or technique known in the art can be used to measure the solid-fat content in the compositions herein. In some variations, the solid-fat content is determined by the AOCS test method AOCS-Cd16b-93.

[0077] In other embodiments, the water-based wampee oil composition can be characterized by its dropping point. The dropping point is the upper limit temperature at which a fat or oil can maintain a semi-solid structure. Above the dropping point, the fat or oil transforms into a liquid state. In some embodiments, the water-based wampee oil composition has a dropping point less than or equal to about 20°C, less than or equal to about 15°C, or less than or equal to about 10°C. In some embodiments, the water-based wampee oil composition has a dropping point less than or equal to about 10°C. Any suitable method or technique known in the art can be used to measure the dropping point of the compositions herein. In some variations, the dropping point is determined by AOCS test method AOCS Cc 18-80.

[0078] In some embodiments, the water-based wampee oil composition can be characterized by its flash point. Flash point is the lowest temperature at which the vapor of a substance can be ignited in the presence of an ignition source. In some embodiments, the water-based wampee oil composition has a flash point of at least about 200°C, at least about 220°C, or at least about 240°C. Any suitable method or technique known in the art can be used to measure the flash point of the compositions described herein. In some variations, the flash point is determined by AOCS test method AOCS Cc 9b-55.

[0079] In some embodiments, the water-wheat peel oil composition can be characterized by its smoke point. The smoke point of an oil is the temperature at which the oil begins to produce continuously visible smoke under defined conditions. Oils with higher smoke points can have enhanced utility in food-related applications, such as frying or stir-frying, deep-frying, or baking, where high temperatures are common. In still other embodiments, the water-wheat peel oil composition has a smoke point of at least about 180°C, at least about 190°C, at least about 195°C, at least about 200°C, or at least about 210°C. In still other embodiments, the water-wheat peel oil composition has a higher smoke point than the crude water-wheat peel oil from which it is obtained. Any suitable method or technique known in the art can be used to measure the smoke point in the compositions herein. In some variations, the smoke point is determined by AOCS test method AOCS Cc 9a-48.

[0080] In other variations, the water-wheat peel oil compositions provided herein can be characterized by their viscosity. The viscosity of a liquid (such as oil) is a measure of its resistance to flow and / or deformation. In some embodiments, as determined at about 25°C, the water-wheat peel oil compositions have a viscosity of at least about 30 centipoise, at least about 40 centipoise, or at least about 50 centipoise. In other embodiments, as determined at about 25°C, the water-wheat peel oil compositions have a viscosity less than or equal to 600 centipoise, less than or equal to 500 centipoise, less than or equal to 250 centipoise, less than or equal to 100 centipoise, less than or equal to 90 centipoise, less than or equal to 80 centipoise, less than or equal to about 70 centipoise, or less than or equal to about 60 centipoise. In some embodiments, at about 25°C, the water-wheat peel oil compositions have a viscosity between about 30 centipoise and about 600 centipoise. In still other embodiments, as measured at the same temperature, the water-wheat peel oil compositions have a lower viscosity than the crude water-wheat peel oil from which they are obtained.

[0081] Other features

[0082] In some embodiments, the water-wheat safflower oil composition has one or more of the following properties, selected from:

[0083] (i) Free fatty acid content less than or equal to about 1%;

[0084] (ii) Less than or equal to about 0.1% of insoluble impurities;

[0085] (iii) Phosphorus less than or equal to about 25 ppm;

[0086] (iv) Chlorophyll less than or equal to about 0.1 ppm;

[0087] (v) Residual solvent less than or equal to about 25 ppm;

[0088] (vi) Moisture content less than or equal to about 1%;

[0089] (vii) Glycerin less than or equal to about 1%;

[0090] (viii) Less than or equal to about 1% monoglycerides;

[0091] (ix) Diglycerides less than or equal to about 5%; and

[0092] (x) At least about 90% of triglycerides.

[0093] In some embodiments, the free fatty acid content is determined using the AOCS test method AOCS Ca 5a-40. In some embodiments, the insoluble impurity content is determined using the AOCS test method AOCS Ca 3a-46. In some embodiments, the phosphorus content is determined using AOCS Ca 20-99, mod. In some embodiments, the chlorophyll content is determined using AOCS Ch 4-91. In some embodiments, the moisture content is determined using AOCS Ca 2b-38. In some embodiments, the glycerol content is determined using AOCS Cd 11c-93. In some embodiments, the monoglyceride content is determined using AOCS Cd 11c-93. In some embodiments, the diglyceride content is determined using AOCS Cd 11c-93. In some embodiments, the triglyceride content is determined using AOCS Cd 11c-93.

[0094] In some embodiments, the water-wheat peel oil composition has a lower unsaponifiables content compared to the crude water-wheat peel oil from which the composition is obtained (e.g., according to the method described herein).

[0095] In addition to their composition and content, the water-based yellow bark oil compositions disclosed herein can also be described according to their physical properties, including but not limited to color and / or turbidity.

[0096] In some embodiments, the water wampee oil composition provided herein (e.g., produced according to the methods described herein) has a lighter color compared to the crude water wampee oil from which the composition is obtained. In some variations, the final color of the water wampee oil composition is lighter than the initial color of the crude water wampee oil. In one variation, the crude water wampee oil is red and / or brown (e.g., including red, brown, reddish-brown, or brownish-red); and the water wampee oil composition obtained therefrom (e.g., according to the methods described herein) is yellow and / or white (e.g., including yellow, light yellow, white, or off-white). In some variations, its color is determined using the Lovibond color-AOCS scale. In some embodiments, the color is determined using the Lovibond color-AOCS scale with a 1-inch or 5.25-inch cell path. Therefore, in one variant, crude water citrus oil has a Lovibond color of 1.5R, 70Y according to the Lovibond color-AOCS scale using a 5.25-inch cell path (AOCS method Cc 13b-45); and the resulting water citrus oil composition (e.g., according to the method described herein) has a Lovibond color of 0.5R, 18Y.

[0097] In some variations, the water jasmine oil composition has a Lovibond color, wherein the Y-value is less than 25, as determined by using the Lovibond color-AOCS scale with a 1-inch cell path (AOCS method Cc 13b-45). In some variations where the Y-value is less than 25, the water jasmine oil composition is light yellow, as determined by using the Lovibond color-AOCS scale with a 1-inch cell path (AOCS method Cc 13b-45). In other embodiments, it has a Lovibond color, wherein the Y-value is greater than or equal to 25, as determined by using the Lovibond color-AOCS scale with a 1-inch cell path (AOCS method Cc 13b-45). In some other variations where the Y-value is greater than or equal to 25, the water jasmine oil composition is yellow, as determined by using the Lovibond color-AOCS scale with a 1-inch cell path (AOCS method Cc 13b-45).

[0098] In addition to the color of the water croton oil compositions, their haziness or turbidity can be characterized by methods known in the art. Among other variations, the water croton oil compositions provided in this disclosure have reduced turbidity compared to crude water croton oil from which the compositions are obtained.

[0099] The above characteristics can be measured or determined using any suitable method known in the art.

[0100] Sensory characteristics overview

[0101] As detailed above, the water-based wampee oil composition of this disclosure (in which the content of furan flavonoids and other unsaponifiables has been reduced) is edible, non-bitter, and has an generally acceptable sensory profile in humans (e.g., regarding taste and odor).

[0102] In other variations, the water hyacinth peel oil composition of this disclosure can be characterized by the presence or absence of one or more sensory properties, including but not limited to water hyacinth peel flavor / aroma, nutty, buttery, grassy, ​​smooth, sweet, oily, astringent, spicy, bitter, and sour. In some variations, the water hyacinth peel oil composition has one or more sensory properties selected from the group consisting of water hyacinth peel flavor / aroma, nutty, buttery, grassy, ​​smooth, sweet, oily, astringent, sharp, bitter, and sour, and any combination thereof.

[0103] In some variations, the water citrus peel oil composition can be characterized by the presence of one or more sensory features selected from the group consisting of water citrus peel flavor / aroma, nutty flavor, buttery flavor, grassy flavor, smoothness, sweetness, and oily flavor.

[0104] In other variations, the water-yellow peel oil composition can be characterized by the absence of one or more sensory features selected from the group consisting of astringent, spicy, bitter and sour tastes.

[0105] In other variations, the water-wheat peel oil composition can be characterized by the mildness of its sensory properties. For example, in some variations, the water-wheat peel oil composition can be characterized as having no bitterness, a neutral flavor, blandness, a pure flavor, or no aftertaste, or any combination thereof.

[0106] In one aspect, this article provides a water-based yellow peel oil composition having:

[0107] (i) A combination of chlorophyll and chlorophyll dione in amounts less than or equal to about 1000 ppm, for example, as determined by HPLC-DAD analysis of an acetone extract obtained from a chlorophyll oil composition;

[0108] (ii) Less than or equal to about 1% by weight of unsaponifiable matter, for example, as determined by AOCS Ca6a-40;

[0109] (ii) Peroxide value less than or equal to about 5 meq / kg, for example, as determined by AOCS Cd 8-53;

[0110] (iv) p-anisidine values ​​less than or equal to about 10, for example, as determined by AOCS Cd 18-90;

[0111] (v) Residual solvent less than or equal to about 25 ppm, for example, as determined by AOCS Cg 4-94;

[0112] (vi) The total fatty acids contain at least 40% oleic acid, for example, as determined by AOAC 996.06;

[0113] (vii) Light yellow or yellow, for example, as determined by the Lovibond color-AOCS scale;

[0114] (viii) Neutral flavor, or one or more sensory attributes selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof; or

[0115] Or any combination of (i)-(viii).

[0116] In some embodiments of this aspect, the water-based yellow peel oil composition has

[0117] The combination of hydroflavin and hydroflavin dione, less than or equal to about 1000 ppm, was determined by HPLC-DAD analysis of the acetone extract obtained from the hydroflavin oil composition;

[0118] Less than or equal to about 1% by weight of unsaponifiables, for example, as determined by AOCS Ca 6a-40;

[0119] Peroxide value less than or equal to about 5 meq / kg, for example, as determined by AOCS Cd 8-53;

[0120] p-Anethole amine values ​​less than or equal to about 10, for example, as determined by AOCS Cd 18-90; and

[0121] Residual solvent less than or equal to about 25 ppm, for example, as determined by AOCS Cg 4-94.

[0122] In other embodiments of this aspect, the water-rich yellow skin oil composition has

[0123] The combination of hydroflavin and hydroflavin dione, less than or equal to about 1000 ppm, for example, as determined by HPLC-DAD analysis of the acetone extract obtained from the hydroflavin oil composition;

[0124] Less than or equal to about 1% by weight of unsaponifiables, for example, as determined by AOCS Ca 6a-40;

[0125] Peroxide value less than or equal to about 5 meq / kg, for example, as determined by AOCS Cd 8-53;

[0126] p-Anethole amine values ​​less than or equal to about 10, for example, as determined by AOCS Cd 18-90; and

[0127] The total fatty acids contain at least 40% oleic acid, for example, as determined by AOAC 996.06.

[0128] In other embodiments, the water-based yellow peel oil composition has

[0129] (i) A combination of chlorophyll and chlorophyll dione in amounts less than or equal to about 1000 ppm, for example, as determined by HPLC-DAD analysis of an acetone extract obtained from a chlorophyll oil composition;

[0130] (ii) Less than or equal to about 1% by weight of unsaponifiable matter, for example, as determined by AOCS Ca6a-40;

[0131] (ii) Peroxide value less than or equal to about 5 meq / kg, for example, as determined by AOCS Cd 8-53;

[0132] (iv) p-anisidine values ​​less than or equal to about 10, for example, as determined by AOCS Cd 18-90;

[0133] (v) Residual solvent less than or equal to about 25 ppm, for example, as determined by AOCS Cg 4-94;

[0134] (vi) The total fatty acids contain at least 40% oleic acid, for example, as determined by AOAC 996.06;

[0135] (vii) Pale yellow or yellow, for example, as determined by the Lovibond color-AOCS scale; and

[0136] (viii) Neutral flavor, or one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth and sweet, and any combination thereof.

[0137] In some embodiments, the aquamarine oil composition has a pale yellow color and a neutral flavor as determined by the Lovibond color-AOCS scale. In other embodiments, the aquamarine oil composition has a yellow color as determined by the Lovibond color-AOCS scale and one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof. In some embodiments that can be combined with any of the foregoing embodiments, the aquamarine oil composition is a pale yellow color as determined by the Lovibond color-AOCS scale, and the composition has a combination of quercetin and quercetin diketone in a concentration of less than or equal to about 200 ppm as determined by HPLC-DAD analysis of an acetone extract obtained from the aquamarine oil composition.

[0138] In other embodiments, the water-wheat peel oil composition:

[0139] (i) It is a liquid at room temperature;

[0140] (ii) Having a viscosity between about 30 centipoise and 600 centipoise, for example, as determined at 25°C;

[0141] (iii) Having a solid fat content between about 1% and about 10% at a temperature of about 5°C, for example, as determined by AOCS-Cd 16b-93;

[0142] (iv) Has a smoke point of at least about 195°C, for example, as determined by AOCS Cc 9a-48; or

[0143] (v) Has a flash point of at least about 200°C, for example, as determined by AOCS Cc 9b-55;

[0144] Or any combination of (i)-(v).

[0145] Method for analyzing water-yellow peel oil composition

[0146] The high concentrations of quercetin and quercetin dione present in the oil and seed cake obtained from *Phellodendron amurense* oilseeds generally hinder their use in food due to their unpleasant taste and odor, as well as potential toxicity, leading to a lack of edibility. These compounds render the oil and seed cake inedible and are potentially harmful to humans and animals. Previous attempts to develop edible *Phellodendron amurense* compositions have been unsuccessful, partly because a consistent maximum threshold for acceptable quercetin concentrations and other edible antinutritional compounds has not been established. Furthermore, existing methods for analyzing *Phellodendron amurense* compositions are inaccurate and unreliable, making it a challenging task to assess quercetin concentrations in these compositions, let alone determine the maximum acceptable quercetin concentration. Therefore, more accurate methods are still needed to determine the levels of quercetin and other antinutritional compounds present in *Phellodendron amurense* compositions.

[0147] This disclosure addresses the need by providing a method for analyzing water flavone oil compositions with higher accuracy and precision than existing methods, namely, a method for determining the concentrations of water flavone and other chemical compounds inherent in water flavone oilseeds. Therefore, in some aspects, this document provides a method for analyzing the concentrations of water flavone and / or water flavone dione in water flavone oil using solvent extraction analysis.

[0148] refer to Figure 1 An exemplary method 100 for analyzing a sample of water-soluble yellow peel oil is provided. In step 102, an extraction mixture is provided by combining the sample with an extraction solvent. In some embodiments, the extraction solvent comprises an alkyl ketone. In some variations, the extraction solvent comprises a methyl ketone. In one variation, the extraction solvent comprises acetone.

[0149] Refer again Figure 1 In steps 104 and 106, the extraction mixture is ultrasonically treated and then separated into an extracted water flavone composition (e.g., oil) and an extract containing water flavonein and / or water flavone dione.

[0150] In step 108, the concentrations of hydroflavin and / or hydroflavindione present in the extract are then measured. In some variations, the concentrations of hydroflavin and / or hydroflavindione are determined by high-performance liquid chromatography with a UV detector. In one variation, the UV detector is a diode array detector (i.e., HPLC-DAD).

[0151] In some aspects, analytical methods are provided, including: combining water frangipani oil with an extraction solvent to provide an extraction mixture, wherein the extraction solvent comprises an alkyl ketone, and wherein the water frangipani oil comprises water frangipaniin or water frangipani dione or both; sonicating the extraction mixture to produce an ultrasonically treated mixture; separating the ultrasonically treated mixture into an extracted water frangipani composition and an alkyl ketone extract, wherein the extract comprises water frangipaniin or water frangipani dione or both; and measuring the concentration of water frangipaniin or water frangipani dione or both present in the extract. In one variation, the alkyl ketone is acetone. In some embodiments described above, the measuring step includes determining the concentration of water frangipaniin or water frangipani dione or both by high-performance liquid chromatography with a UV detector. In one variation, the UV detector is a diode array detector.

[0152] In some respects, the analytical methods provided herein for detecting the concentrations of quercetin and quercetin dione are improvements on analytical methods generally known in the art, including, for example, methods involving HPLC with detection by mass spectrometry (MS) and methods typically used for analyzing quercetin meal samples. The analytical methods provided herein allow for the accurate determination of quercetin oil samples by using specific sample preparation and HPLC with UV detection (e.g., HPLC-DAD) instead of HPLC with mass spectrometry detection (e.g., HPLC-MS-MS).

[0153] Method for producing water-yellow peel oil composition

[0154] In some aspects, this article provides methods for obtaining edible water wampee oil from crude water wampee oil derived from the water wampee tree or plant (also known as "Cytisus pinnatus", "Dalbergia arborea", "Derris indica", "Galedupa pungum", "karanj", "Indian water wampee (Millettia pinnata)", "pongam", "water wampee", "hairless water wampee (Pongamia glabra)", "Pterocarpus flavus", "Pongamia pinnata" and "Robinia mitis", "Indian beech (Indianbeech)" and "mempari"). In some variants, crude water wampee oil is obtained from water wampee oilseeds.

[0155] refer to Figure 2An exemplary purification method 200 includes step 202, wherein crude water frangipani oil is combined with a nonpolar solvent to produce a crude mixture. The resulting crude water frangipani oil comprises water frangipani oil and furan flavonoids, such as water frangipaniin and / or water frangipani dione. In step 204, the crude mixture is eluted with silica gel using an additional nonpolar solvent to separate at least a portion of water frangipaniin and water frangipani dione from the water frangipani oil, and to produce a purified mixture comprising water frangipani oil and a nonpolar solvent. In step 206, at least a portion of the nonpolar solvent is removed from the purified mixture to produce an edible and non-bitter water frangipani oil composition.

[0156] solvent

[0157] In some embodiments, the nonpolar solvent used in the purification methods described herein includes alkanes. In some variations, the alkanes are C1-20 or C-10 alkanes. In some variations, the alkanes are straight-chain. In other variations, the alkanes are branched-chain. In still other variations, mixtures of alkanes may be used. In one variation, the nonpolar solvent includes hexane.

[0158] In some variations, crude water-based yellow peel oil is combined with a non-polar solvent in solvent-to-oil ratios between 1:1 and 3:1 (w / v), between 1:1 and 2.5:1 (w / v), or between 1:1 and 2:1 (w / v).

[0159] silicone

[0160] In some variations, the silica gel has (i) an average particle size of 5 μm to 1000 μm (e.g., based on particle diameter); or (ii) an average sieve particle size range between 18 units and 2,500 units; or (iii) in... to The average porosity range between (i) and (iii), or any combination thereof.

[0161] Crude water yellow peel oil

[0162] In some embodiments, crude water frangipani oil includes water frangipani oil, water frangipani extract, water frangipani dione, other furan flavonoids, and other unsaponifiables.

[0163] In some embodiments, the crude water-processed yellow peel oil has at least 500 ppm, at least 10,000, or at least 30,000 ppm; or between 10,000 ppm and 30,000 ppm of unsaponifiable matter.

[0164] In some embodiments, the crude water flavone oil has at least 500 ppm, at least 10,000, or at least 30,000 ppm; or between 10,000 ppm and 30,000 ppm of furan flavonoids. In some embodiments, the crude water flavone oil has at least 10,000 ppm of water flavonein and / or water flavone dione. In some of the foregoing variations, the concentrations of water flavonein and water flavone dione are determined by the solvent extraction analysis method described herein.

[0165] In some variants, crude water frangipani oil contains at least 500 ppm, at least 10,000, or at least 30,000 ppm; or between 10,000 ppm and 30,000 ppm of water frangipani. In other variants, crude water frangipani oil contains at least 500 ppm, at least 10,000, or at least 30,000 ppm; or between 10,000 ppm and 30,000 ppm of water frangipani dione. In other variants, crude water frangipani oil contains at least 500 ppm, at least 10,000, or at least 30,000 ppm; or a combination of water frangipani and water frangipani dione between 10,000 ppm and 30,000 ppm.

[0166] The crude water hyacinth oil used in the methods described herein can be produced from various methods and techniques known in the art or obtained from any commercially available source. In some variations, crude water hyacinth oil is obtained by mechanical separation of water hyacinth oilseeds. In one variation, crude water hyacinth oil is obtained by cold pressing water hyacinth oilseeds.

[0167] Optionally, the water hyacinth oilseeds can be dehulled to obtain crude water hyacinth oil. Therefore, in some variations, crude water hyacinth oil is obtained by: dehulling the water hyacinth oilseeds to produce dehulled oilseeds; and mechanically separating the dehulled oilseeds to produce crude water hyacinth oil and at least partially deoiled seed cake. In other variations, crude water hyacinth oil is obtained by: heating the water hyacinth oilseeds at a temperature between 25°C and 200°C for a suitable time to provide treated oilseeds; dehulling the treated oilseeds to produce dehulled oilseeds; and mechanically separating the dehulled oilseeds to produce crude water hyacinth oil and at least partially deoiled seed cake.

[0168] Dehulling typically involves passing water-wheat beans through a dehulling machine to loosen the outer shell and the beans, separating the two components. Dehulling and shell separation can be achieved using any suitable technique known in the art. For example, in some variations, dehulling is performed by passing water-wheat beans through an impact dehulling machine and loosening the outer shell from the beans. Other types of dehulling equipment, such as abrasive / brush types, can be used for this purpose. The beans can be separated from the shell by, for example, a gravity table or a suction device.

[0169] The beans are then mechanically pressed (e.g., cold-pressed), typically using a press, to remove free oil and produce a water-based yellow skin meal with reduced fat content (e.g., 10-14% fat). Cold pressing can be performed using any suitable technique known in the art. For example, various devices such as the Farmet FL-200 press can be used for cold pressing. In some variations, pressing may include passing hulled beans through a device to produce a meal with reduced free oil and fat content. Partially defatted, mechanically pressed beans can remove approximately 60-75% of the original water-based yellow skin oil content.

[0170] Food and beverage products

[0171] In some respects, food and beverage products made by incorporating or using the aquamarine oil composition of this article are also provided. This aquamarine oil composition can be used as salad oil; frying oil; stir-frying oil; vinaigrette; sauce; condiment; meat imitation; beverage; or as a fat in the application of margarine and other solid fats.

[0172] The water celery oil compositions provided herein possess numerous advantageous compositional properties, including low concentrations of water celeryin, water celery dione, and unsaponifiable matter, low peroxide value, low p-anisidine value, low residual solvent content, and high oleic acid content, making them suitable for food applications. In addition to these compositional properties, the water celery oil compositions disclosed herein also possess a variety of sensory and functional properties that can be selected for various applications requiring fats and / or oils.

[0173] In some embodiments, this document provides food and beverage products comprising a water-wax peel oil composition, wherein the water-wax peel oil composition has a pale yellow color, for example, as determined by the Lovibond color-AOCS scale; and a neutral flavor. In other embodiments, the water-wax peel oil composition has a yellow color, for example, as determined by the Lovibond color-AOCS scale; and one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof. In some embodiments that can be combined with any of the foregoing embodiments, the water-wax peel oil composition is pale yellow, for example, as determined by the Lovibond color-AOCS scale, and, as determined by HPLC-DAD analysis of an acetone extract obtained from the water-wax peel oil composition, the composition has a combination of less than or equal to about 200 ppm of water-wax peelin and water-wax peel diketone.

[0174] In other embodiments, the food or beverage product includes a water-wampee oil composition, wherein the water-wampee oil composition:

[0175] (i) Having a pale yellow or yellow color as determined by the Lovibond color-AOCS scale; and

[0176] (ii) It has a neutral flavor, or one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth and sweet, and any combination thereof.

[0177] (iii) It is a liquid at room temperature;

[0178] (iv) Having a viscosity between about 30 centipoise and 600 centipoise, as determined at 25°C.

[0179] (v) Having a solid fat content between about 1% and about 10% at a temperature of about 5°C, as determined by AOCS-Cd 16b-93;

[0180] (vi) Has a smoke point of at least about 195°C, as determined by AOCS Cc 9a-48; or

[0181] (vii) Has a flash point of at least about 200°C, as determined by AOCS Cc 9b-55;

[0182] Or any combination of (i)-(vii).

[0183] Food and beverage products may include a variety of other components besides the water-based wampee oil composition described herein. For example, food and beverage products may include, for instance, water, other fats and oils, sweeteners (such as sugar), salt, thickeners (such as pectin and other hydrocolloids), defoamers, natural and artificial flavorings, preservatives, and colorings.

[0184] In one variation, the food product is avocado oil mayonnaise. In another variation, the food product is avocado oil margarine and spread. In yet another variation, the food product is avocado oil salad dressing.

[0185] In another aspect, methods for preparing food and / or beverage products are provided. These methods may include one or more of mixing / blending, pasteurization and / or sterilization, and packaging.

[0186] List of implementation methods

[0187] The embodiments listed below are representative aspects of the present invention.

[0188] 1. An analytical method, comprising:

[0189] A water-rich yellow peel oil is combined with an extraction solvent to provide an extraction mixture, wherein the extraction solvent includes an alkyl ketone, and wherein the water-rich yellow peel oil includes water-rich yellow peelin or water-rich yellow peel dione or both;

[0190] The extract mixture is subjected to ultrasonic treatment to produce an ultrasonically treated mixture;

[0191] The ultrasonically treated mixture is separated into an extracted aqueous quercetin composition and an alkyl ketone extract, wherein the extract comprises aqueous quercetin or aqueous quercetin diketone or both; and

[0192] Measure the concentration of hydroflavin or hydroflavin dione, or both, present in the extract.

[0193] 2. The method according to embodiment 1, wherein the alkyl ketone is acetone.

[0194] 3. The method according to embodiment 1 or 2, wherein the measurement step includes determining the concentration of hydroflavin or hydroflavindione or both by high performance liquid chromatography with a UV detector.

[0195] 4. The method according to embodiment 3, wherein the ultraviolet detector is a diode array detector.

[0196] 5. A method for producing a water-based yellow peel oil composition, comprising:

[0197] Crude water-yellow peel oil is combined with a non-polar solvent to produce a crude mixture, wherein the non-polar solvent includes alkanes, and wherein the crude water-yellow peel oil includes water-yellow peel oil and furan flavonoids.

[0198] The crude mixture was eluted with silica gel using a nonpolar solvent to separate at least a portion of the furan flavonoids from the aqueous yellow peel oil, and to produce a purified mixture comprising the aqueous yellow peel oil and a nonpolar solvent; and

[0199] At least a portion of the nonpolar solvent is removed from the purified mixture to produce a water-based wampee oil composition, wherein the composition is edible and has no bitter taste.

[0200] 6. The method according to embodiment 5, wherein the composition has a lower content of furan flavonoids than crude water-processed yellow peel oil.

[0201] 7. The method according to embodiment 5 or 6, wherein the composition has less than or equal to 150 ppm of furan flavonoids.

[0202] 8. The method according to any one of embodiments 5 to 7, wherein the furan flavonoids include hydroflavin or hydroflavin dione or both.

[0203] 9. The method according to any one of embodiments 5 to 8, wherein the crude water-wampee oil has an initial color and the resulting water-wampee oil composition has a final color, wherein the final color of the water-wampee oil composition is lighter than the initial color of the crude water-wampee oil.

[0204] 10. The method according to embodiment 9, wherein the initial color is red and / or brown, and the final color is yellow.

[0205] 11. The method according to any one of embodiments 5 to 10, wherein the crude water yellow peel oil is water yellow peel oil that has been mechanically separated.

[0206] 12. The method according to any one of embodiments 5 to 10, further comprising:

[0207] Dehulling water-yellow-skinned oilseeds to produce dehulled oilseeds; and

[0208] The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

[0209] 13. The method according to any one of embodiments 5 to 10, further comprising:

[0210] Water-yellow-skinned oilseeds are heated at a temperature between 25°C and 200°C for an appropriate time to provide processed oilseeds;

[0211] The processed oilseeds are dehulled to produce dehulled oilseeds; and

[0212] The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

[0213] 14. The method according to any one of embodiments 5 to 13, wherein the nonpolar solvent includes hexane.

[0214] 15. The method according to any one of embodiments 5 to 14, wherein the concentration of hydroflavin or hydroflavindione or both is determined by the method according to any one of embodiments 1 to 4.

[0215] 16. The method according to any one of embodiments 5 to 15, wherein the crude water-processed yellow peel oil and the nonpolar solvent are combined in a ratio between 1:1 and 3:1 (w / v).

[0216] 17. The method according to any one of embodiments 5 to 16, wherein hydroflavin and hydroflavindione are adsorbed onto silica gel, and the method further comprises:

[0217] Silica gel is eluted with a polar solvent to separate hydroflavin and hydroflavin dione, wherein the polar solvent includes alkyl esters of alkanonic acids.

[0218] 18. The method according to any one of embodiments 5 to 16, wherein hydroflavin and hydroflavindione are adsorbed onto silica gel, and the method further comprises:

[0219] A stepped gradient elution silica gel was used to separate hydroquinone and hydroquinone dione, wherein the polar solvent included alkyl esters of alkanonic acid.

[0220] 19. The method according to embodiment 17 or 18, wherein the polar solvent includes ethyl acetate.

[0221] 20. A water-based yellow peel oil composition produced by the method according to any one of the foregoing embodiments.

[0222] 21. A water-based wampee oil composition containing less than 150 ppm of furan flavonoids, wherein the composition is edible and has no bitter taste.

[0223] 22. The composition according to embodiment 21, wherein the furan flavonoids include hydroflavin or hydroflavin dione or both.

[0224] 23. The composition according to embodiment 22, wherein the composition has less than or equal to 150 ppm of hydroflavin or hydroflavin dione or both.

[0225] 24. The composition according to embodiment 23, wherein the concentration of hydroflavin or hydroflavin dione or both is determined by the method described in any one of embodiments 1 to 4.

[0226] 25. The composition according to any one of the embodiments, wherein the composition is obtained from crude water-processed yellow peel oil, and the composition has a lighter color than that of crude water-processed yellow peel oil.

[0227] 26. The composition according to embodiment 25, wherein the color of the composition is yellow.

[0228] 27. The composition according to any one of embodiments 21 to 26, further comprising a nonpolar solvent, wherein the nonpolar solvent comprises an alkane.

[0229] 28. The composition according to embodiment 27, wherein the nonpolar solvent is present at a concentration of less than 25 ppm.

[0230] 29. The composition according to any one of embodiments 21 to 28, wherein the composition comprises fatty acids.

[0231] 30. The composition according to embodiment 29, wherein the fatty acid is a monounsaturated fatty acid, a polyunsaturated fatty acid, a saturated fatty acid, a trans fatty acid, an ω3 fatty acid, an ω6 fatty acid, an ω7 fatty acid, or an ω9 fatty acid, or any combination thereof.

[0232] 31. The composition according to any one of embodiments 21 to 28, wherein the composition comprises oleic acid, linoleic acid, palmitic acid, stearic acid, benzyl acid, α-linolenic acid, creosotenic acid, arachidic acid, squalene, oleic acid, isoleic acid, palmitoleic acid, eicosapentaenoic acid, linoleic acid, heptadecanic acid, squalene, erucic acid, palmitoleic acid, heptadecanic acid or myristic acid or any isomer thereof or any combination thereof.

[0233] 32. The composition according to any one of embodiments 21 to 31, wherein the composition comprises:

[0234] (i) Free fatty acid content less than or equal to 1%;

[0235] (ii) Insoluble impurities less than or equal to 0.1%;

[0236] (iii) Phosphorus less than or equal to 25 ppm;

[0237] (iv) Chlorophyll less than or equal to 0.1 ppm;

[0238] (v) Residual solvent less than or equal to 25 ppm;

[0239] (vi) Moisture content less than or equal to 1%;

[0240] (vii) Glycerin less than or equal to 1%;

[0241] (viii) Less than or equal to 1% monoglycerides;

[0242] (ix) Diglycerides less than or equal to 5%; or

[0243] (x) At least 90% triglycerides,

[0244] Or any combination of (i)-(x).

[0245] 33. The composition according to any one of embodiments 21 to 32, wherein the composition has a lower unsaponifiable matter content compared to the crude water-based yellow skin oil from which the composition is obtained.

[0246] 34. The composition according to any one of embodiments 21 to 33, wherein the composition further comprises tocopherol.

[0247] 35. The composition according to embodiment 34, wherein the tocopherol comprises α-tocopherol, β-tocopherol, δ-tocopherol or γ-tocopherol or any combination thereof.

[0248] 36. The composition according to embodiment 34 or 35, wherein the composition has at least 400 ppm of tocopherol.

[0249] 37. The composition according to any one of embodiments 34 to 36, wherein the composition has at least 200 ppm of α-tocopherol.

[0250] 38. The composition according to any one of embodiments 21 to 37, wherein the composition further comprises sterols.

[0251] 39. The composition according to embodiment 38, wherein the sterols include β-sitosterol, campesterol, cholesterol, sterol, Δ-5,24-stigmasterdienol, δ-5-acidosterol, sitosterol or stigmasterol or any combination thereof.

[0252] 40. The composition according to embodiment 38 or 39, wherein the composition has less than 2500 ppm of sterols.

[0253] 41. The use of the water-based yellow skin oil composition according to any one of embodiments 21 to 40 as a salad oil; frying oil; stir-frying oil; vinaigrette; sauce; condiment; meat imitation, beverage or fat used in blends with margarine and other solid fats; or any combination thereof.

[0254] 42. A food or beverage product comprising the water-based yellow peel oil composition according to any one of embodiments 21 to 40.

[0255] 43. The product according to embodiment 42, wherein the product is salad oil; frying oil; stir-frying oil; vinaigrette; sauce; seasoning; meat imitation, beverage or fat used in blends with margarine and other solid fats.

[0256] 44. A water-based yellow peel oil composition, comprising:

[0257] The combination of 1000 ppm or less of quercetin and quercetin dione was determined by HPLC-DAD analysis of the acetone extract obtained from the quercetin oil composition.

[0258] The unsaponifiable matter, determined by AOCS Ca 6a-40, is less than or equal to about 1% by weight.

[0259] Peroxide value less than or equal to about 5 meq / kg as determined by AOCS Cd 8-53;

[0260] p-anesinamine values ​​less than or equal to about 10, determined by AOCS Cd 18-90; and

[0261] The residual solvent was less than or equal to about 25 ppm, as determined by AOCS Cg 4-94.

[0262] 45. The composition according to embodiment 44, comprising:

[0263] The concentration of 150 ppm or less was determined by HPLC-DAD analysis of the acetone extract obtained from the water flavour extract composition.

[0264] The concentration of water-wax diketone was determined to be less than or equal to about 150 ppm by HPLC-DAD analysis of the acetone extract obtained from the water-wax diketone oil composition.

[0265] The unsaponifiable matter, determined by AOCS Ca 6a-40, is less than or equal to about 1% by weight.

[0266] Peroxide value less than or equal to about 5 meq / kg as determined by AOCS Cd 8-53;

[0267] p-anesinamine values ​​less than or equal to about 5, determined by AOCS Cd 18-90; and

[0268] The residual solvent was less than or equal to about 25 ppm, as determined by AOCS Cg 4-94.

[0269] 46. ​​The composition according to embodiment 44 or 45, wherein the residual solvent comprises a nonpolar solvent.

[0270] 47. The composition according to any one of embodiments 44 to 46, wherein the residual solvent comprises a nonpolar solvent and wherein the nonpolar solvent comprises an alkane.

[0271] 48. The composition according to any one of embodiments 44 to 47, wherein the composition is a liquid at room temperature.

[0272] 49. The composition according to any one of embodiments 44 to 48, wherein the composition has a viscosity between about 30 centipoise and 600 centipoise as determined at 25°C.

[0273] 50. The composition according to any one of embodiments 44 to 49, wherein the composition has a solid fat content between about 1% and about 10% at a temperature of about 5°C, as determined by AOCS-Cd16b-93.

[0274] 51. The composition according to any one of embodiments 44 to 50, wherein the composition has a smoke point of at least about 195°C as determined by AOCS Cc9a-48.

[0275] 52. The composition according to any one of embodiments 44 to 51, wherein the composition has at least 400 ppm of tocopherol as determined by AOAC 971.30 HPLC.

[0276] 53. The composition according to any one of embodiments 44 to 52, wherein the composition has less than 2500 ppm of sterols as determined by COI / T.20 / Doc No.10.

[0277] 54. The composition according to any one of embodiments 44 to 53, wherein the composition comprises oleic acid, linoleic acid, palmitic acid, stearic acid, benzyl acid, α-linolenic acid, creosotenic acid, arachidic acid, squalene, oleic acid, isoleic acid, palmitoleic acid, eicosaadienoic acid, linoleic acid, heptadecanic acid, squalene, erucic acid, palmitoleic acid, heptadecanic acid, or myristic acid or any isomer thereof or any combination thereof, as determined by AOAC 996.06.

[0278] 55. The composition according to embodiment 54, wherein the composition comprises at least 40% oleic acid as determined by AOAC 996.06.

[0279] 56. The composition according to any one of embodiments 44 to 55, wherein the color of the composition is yellow or pale yellow, determined by using a 1-inch cell path on the Lovibond color-AOCS scale, wherein:

[0280] When the composition is yellow, it has a Lovibond color Y-value greater than or equal to 25; and

[0281] When the composition is pale yellow, it has a Lovibond color Y-value of less than 25.

[0282] 57. The composition according to any one of embodiments 44 to 56, wherein the composition has one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof.

[0283] 58. The composition according to any one of embodiments 44 to 57, wherein the composition has a ratio of more than about 1 of hydroflavin to hydroflavin dione.

[0284] 59. The composition according to any one of embodiments 44 to 56, wherein the color of the composition is pale yellow and the composition has a Lovibond color Y-value of less than 25, determined by using a 1-inch cell path on the Lovibond color-AOCS scale.

[0285] 60. The composition according to any one of embodiments 44 to 56 and 59, wherein the composition is pale yellow in color, and wherein the composition comprises less than or equal to about 200 ppm of a combination of hydroflavin and hydroflavin diketone.

[0286] 61. The composition according to any one of embodiments 44 to 56, 59 and 60, wherein the composition has a neutral flavor.

[0287] 62. The composition according to any one of embodiments 44 to 56 and 59 to 61, wherein the composition has a ratio of hydroflavin to hydroflavin dione of less than or equal to 1.

[0288] 63. The composition according to any one of embodiments 44 to 62, wherein the composition comprises:

[0289] (i) Free fatty acid content less than or equal to about 1%, as determined by AOCS Ca 5a-40;

[0290] (ii) Insoluble impurities less than or equal to about 0.1% as determined by AOCS Ca 3a-46;

[0291] (iii) Phosphorus less than or equal to about 25 ppm as determined by AOCS Ca 20-99, mod;

[0292] (iv) Chlorophyll less than or equal to about 0.1 ppm as determined by AOCS Ch 4-91;

[0293] (v) Moisture content less than or equal to about 1%, as determined by AOCS Ca 2b-38;

[0294] (vi) Glycerol less than or equal to about 1% as determined by AOCS Cd 11c-93;

[0295] (vii) Less than or equal to about 2% of monoglycerides as determined by AOCS Cd 11c-93;

[0296] (viii) Diglycerides less than or equal to about 5% as determined by AOCS Cd 11c-93; and

[0297] (ix) Triglycerides of at least about 90% as determined by AOCS Cd 11c-93,

[0298] Any combination of (x) or (i)-(ix).

[0299] 64. An analytical method comprising:

[0300] A water-rich yellow peel oil is combined with an extraction solvent to provide an extraction mixture, wherein the extraction solvent includes an alkyl ketone, and wherein the water-rich yellow peel oil includes water-rich yellow peelin or water-rich yellow peel dione or both;

[0301] The extract mixture is subjected to ultrasonic treatment to produce an ultrasonically treated mixture;

[0302] The ultrasonically treated mixture is separated into an extracted aqueous quercetin composition and an alkyl ketone extract, wherein the extract comprises aqueous quercetin or aqueous quercetin diketone or both; and

[0303] Measure the concentration of hydroflavin or hydroflavin dione, or both, present in the extract.

[0304] 65. The method according to embodiment 64, wherein the alkyl ketone is acetone.

[0305] 66. The method according to embodiment 64 or 65, wherein the measurement step includes determining the concentration of hydroflavin or hydroflavindione or both by high performance liquid chromatography with a UV detector.

[0306] 67. The method according to embodiment 68, wherein the ultraviolet detector is a diode array detector.

[0307] 68. A method for producing a water-based yellow peel oil composition, comprising:

[0308] Crude water-yellow peel oil is combined with a non-polar solvent to produce a crude mixture, wherein the non-polar solvent includes alkanes, and wherein the crude water-yellow peel oil includes water-yellow peel oil and furan flavonoids.

[0309] The crude mixture was eluted with silica gel using a nonpolar solvent to separate at least a portion of the furan flavonoids from the aqueous yellow peel oil, yielding a purified mixture comprising the aqueous yellow peel oil and the nonpolar solvent; and

[0310] At least a portion of the nonpolar solvent is removed from the purified mixture to produce a water-based citrus oil composition, wherein the composition has a combination of citrus flavinin and citrus dione in a concentration of less than or equal to about 1000 ppm as determined by HPLC-DAD analysis of the acetone extract obtained from the water-based citrus oil composition; less than or equal to about 1% by weight of unsaponifiable matter as determined by AOCS Ca 6a-40; a peroxide value of less than or equal to about 5 meq / kg as determined by AOCS Cd 8-53; and a value of less than or equal to about 10 p-anisidine as determined by AOCS Cd 18-90.

[0311] 69. The method according to embodiment 68, wherein the crude water-wampee oil has an initial color and the resulting water-wampee oil composition has a final color, wherein the final color of the water-wampee oil composition is lighter than the initial color of the crude water-wampee oil.

[0312] 70. The method according to embodiment 69, wherein the initial color is red and / or brown, and the final color is yellow or pale yellow.

[0313] 71. The method according to any one of embodiments 68 to 70, wherein the crude water yellow peel oil is water yellow peel oil that has been mechanically separated.

[0314] 72. The method according to any one of embodiments 68 to 71, further comprising:

[0315] Dehulling water-yellow-skinned oilseeds to produce dehulled oilseeds; and

[0316] The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

[0317] 73. The method according to any one of embodiments 68 to 72, further comprising:

[0318] Water-yellow-skinned oilseeds are heated at a temperature between 25°C and 200°C for an appropriate time to provide processed oilseeds;

[0319] The processed oilseeds are dehulled to produce dehulled oilseeds; and

[0320] The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

[0321] 74. The method according to any one of embodiments 68 to 73, wherein the nonpolar solvent includes hexane.

[0322] 75. The method according to any one of embodiments 68 to 74, wherein the concentration of hydroflavin or hydroflavindione or both is determined by the method according to any one of embodiments 21 to 24.

[0323] 76. The method according to any one of embodiments 68 to 75, wherein the crude water-processed yellow peel oil and the nonpolar solvent are combined in a ratio between 1:1 and 3:1 (w / v).

[0324] 77. The method according to any one of embodiments 68 to 76, wherein hydroflavin and hydroflavindione are adsorbed onto silica gel, and the method further comprises:

[0325] Silica gel is eluted with a polar solvent to separate hydroflavin and hydroflavin dione, wherein the polar solvent includes alkyl esters of alkanonic acids.

[0326] 78. The method according to any one of embodiments 68 to 77, wherein hydroflavin and hydroflavindione are adsorbed onto silica gel, and the method further comprises:

[0327] A stepped gradient elution silica gel was used to separate hydroquinone and hydroquinone dione, wherein the polar solvent included alkyl esters of alkanonic acid.

[0328] 79. The method according to embodiment 77 or 78, wherein the polar solvent includes ethyl acetate.

[0329] 80. A water-based yellow peel oil composition produced by the method according to any one of embodiments 68 to 79.

[0330] 81. The use of the water-based yellow skin oil composition according to any one of embodiments 44 to 63 and 80 as a salad oil; frying oil; stir-frying oil; vinaigrette; sauce; condiment; meat imitation; beverage or fat in blends with margarine and other solid fats, or any combination thereof.

[0331] 82. A food or beverage product comprising the water-based yellow peel oil composition according to any one of embodiments 44 to 63 and 80.

[0332] 83. The product according to embodiment 82, wherein the composition is pale yellow; the composition comprises less than or equal to about 200 ppm of aqueous quercetin and aqueous quercetin dione, and the composition has a neutral flavor.

[0333] 84. The product according to embodiment 82, wherein the water-wax rin oil composition is yellow; the composition comprises less than or equal to about 150 ppm water-wax rin and less than or equal to about 150 ppm water-wax rin dione; and the composition has one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth and sweet, and any combination thereof.

[0334] 85. The product according to any one of embodiments 82 to 84, wherein the product is salad oil; frying oil; stir-frying oil; vinaigrette; sauce; seasoning; meat imitation, beverage or fat used in blends with margarine and other solid fats.

[0335] 86. A water-based yellow peel oil composition, comprising:

[0336] (i) A combination of 1000 ppm or less of quercetin and quercetin dione, determined by HPLC-DAD analysis of the acetone extract obtained from the quercetin oil composition;

[0337] (ii) Less than or equal to about 1% by weight of unsaponifiable matter as determined by AOCS Ca 6a-40;

[0338] (ii) Peroxide value less than or equal to about 5 meq / kg as determined by AOCS Cd 8-53;

[0339] (iv) p-anesinamine values ​​less than or equal to about 10, as determined by AOCS Cd 18-90; and

[0340] (v) Residual solvent less than or equal to about 25 ppm as determined by AOCS Cg 4-94;

[0341] (vi) The total fatty acids, as determined by AOAC 996.06, contain at least 40% oleic acid;

[0342] (vii) Pale yellow or yellow color;

[0343] (viii) Neutral flavor, or one or more sensory attributes selected from the group consisting of: nutty, buttery, grassy, ​​smooth and sweet, and any combination thereof;

[0344] (ix) Any combination of (i)-(viii).

[0345] Example

[0346] The subject matter of this disclosure will be better understood by referring to the following embodiments, which are provided as examples of the invention and not as limiting embodiments.

[0347] Example 1

[0348] Production of water-yellow skin oil

[0349] This embodiment demonstrates the production of edible (e.g., non-bitter) water frangipani oil by liquid-solid adsorption chromatography of crude (e.g., bitter) water frangipani oil. Crude water frangipani oil undergoes adsorption purification using silica gel. Water frangipaniin, water frangipani dione, and potentially other anti-nutritional factors and / or bitter compounds are chromatographically removed from the mechanically separated water frangipani oil to obtain a purified oil product.

[0350] Column preparation (wet pack method)

[0351] The chromatographic column used was sintered, 1L in volume, with a spherical reservoir and a top section with an additional approximately 1L capacity. The silica used had a particle size of 40-63μm and Aperture size.

[0352] In a flask, combine 500-550 g of silica (approximately 1 L in volume) with 1000-1100 mL of hexane and swirl to form a silica slurry. Transfer the silica to the flask using a large funnel. Open the stopcock valve at the column outlet just wide enough to allow a flow rate of 1 drop / second. After allowing the silica slurry to reach room temperature, pour it into the column. When the slurry becomes too thick to pour, add additional hexane. Once the column is completely filled, close the stopcock valve at the column outlet, allowing 1-2 cm of solvent to remain above the column head. Add glass wool to the top of the silica slurry bed.

[0353] Preparation of crude mixture

[0354] In two flasks fitted with glass stoppers, approximately 1100 mL (1000–1100 g) of crude water-based yellow peel oil was combined with 500 mL of n-hexane. Initially, two layers were observed to form. The top layer had a milky yellow appearance, indicating that it was an emulsion. The two layers were then mixed to form a homogeneous solution.

[0355] Chromatographic procedures

[0356] Pour 750 mL of the prepared crude mixture into the glass wool at the top of the column bed. Open the stopcock at the column outlet to allow a flow rate of 2 drops / second (approximately 7 mL / min), while covering the top of the column with aluminum foil to minimize evaporation. First, elute and collect the colorless hexane, followed by the yellow fraction. Add the remaining crude mixture and elute and collect the colorless hexane and yellow fraction until the column head is almost empty. Add 1 L of hexane to the column and elute and collect the colorless hexane and yellow fraction. Rinse the inner wall of the spherical reservoir and the glass wool with an equal amount of hexane, then elute and collect. Add another 1 L of hexane to the column and elute and collect. Finally, combine the collected colorless hexane and yellow fractions, which, in addition to those collected during rinsing, were found to contain additional small peaks (but without hydroflavindione or hydroflavinin).

[0357] Elution of polar compounds

[0358] Add 1 L of 100% ethyl acetate to the column at a flow rate of 1 drop / second to wash away all polar compounds bound to silica, including hydroflavin and hydroflavindione. Collect the eluent in a flask. Next, add another 1 L of ethyl acetate to the column and collect the eluent in another flask. Store the fraction at room temperature.

[0359] In other variations, alternative methods for eluting polar compounds can be used. For example, in other experiments, 1 L each of 5%, 10%, 20%, and 30% ethyl acetate in hexane was prepared for stepwise gradient elution. Next, 1 L of 5% ethyl acetate in hexane was added to the column, and the eluent was collected as a yellow fraction and a nearly colorless fraction. Then, 1 L each of 10%, 20%, and 30% ethyl acetate in hexane, followed by 500 mL of 100% ethyl acetate, was added to the column, and the corresponding eluent fractions were collected. After eluting the yellow fraction with hexane, the flow rate was increased. The flow rate was adjusted to allow for rapid dripping (approximately 10 mL / min). Finally, the solvent for each fraction was evaporated.

[0360] Table 1 below compares the chemical composition of crude water citrus oil (“crude oil”) with water citrus oil purified according to the chromatographic procedure described in this embodiment (“purified oil”). The methods used to determine the components measured are described in Table 1, where AOCS refers to the American Oil Chemists' Society, and their test methods are publicly available.

[0361] Table 1. Chemical Composition 1,2

[0362]

[0363]

[0364] 1 The data represents the average of multiple experiments.

[0365] 2 ND: Undetectable

[0366] The following table 2 compares the amounts of fatty acid categories in crude and purified oils. The methods used to determine the components measured are stated in Table 2, where AOAC refers to the Association of Official Analytical Chemists, and the testing methods are publicly available.

[0367] Table 2. Fatty acid categories (total %)

[0368] category crude oil Purified oil Test methods Total identified fatty acids 84.72 92.69 AOAC 996.06 Total monounsaturated fatty acids 46.59 52.09 AOAC 996.06 Total polyunsaturated fatty acids 18.3 18.44 AOAC 996.06 Total saturated fatty acids 19.62 21.93 AOAC 996.06 Total trans fatty acids 0.22 0.24 AOAC 996.06 Total omega-3 fatty acids 2.41 1.99 AOAC 996.06 Total omega-6 fatty acids 15.8 16.37 AOAC 996.06 Total omega-7 fatty acids 0.58 0.65 AOAC 996.06 Total omega-9 fatty acids 46.57 51.12 AOAC 996.06

[0369] Table 3 below shows the amounts of fatty acid composition in crude and purified oils. The methods used to determine the components measured are described in Table 3.

[0370] Table 3. Fatty acid composition (total %) 1

[0371]

[0372]

[0373] 1 The following fatty acids have less than 0.02% of total fatty acids: C4:0, 6:0, 8:0, 10:0, 11:0, 12:0, 14:0, 14:1c9, 15:0, 15:1, 16:2, 16:3, 16:4, 18:3n6, 18:4n3, 20:3n3, 20:3n6, 20:4n6, 20:5n3, 22:2n6, 22:3n3, 22:4n6, 22:5n3, 22:5n6, 22:6n3, 24:1n9.

[0374] Table 4 below shows the tocopherol content in crude and purified oils. The methods used to determine the components measured are described in Table 4.

[0375] Table 4. Tocopherol content (ppm)

[0376] Tocopherol crude oil Purified oil Test method α-Tocopherol 319 294 AOAC 971.30 using HPLC β-Tocopherol 53.3 47.3 AOAC 971.30 using HPLC δ-Tocopherol <46.6 <46.6 AOAC 971.30 using HPLC γ-Tocopherol 173 141 AOAC 971.30 using HPLC Total tocopherol 545 482 AOAC 971.30 using HPLC

[0377] Table 5 below shows the sterol content in crude and purified oils. The methods used to determine the components measured are stated in Table 5, where “COI / T.20 / Doc No.10” is a publicly available test method stated by the International Olive Council.

[0378] Table 5. Sterol Content

[0379]

[0380]

[0381] Table 6 below compares the contents of hydroflavin and hydroflavin dione in crude and purified oils. The contents of hydroflavin and hydroflavin dione were determined according to the scheme described in Example 2 below.

[0382] Table 6. Content of hydroflavin and hydroflavin dione (ppm)

[0383] Watery yellow skin - specific furan flavonoids crude oil Purified oil Watery chlorophyll 11,662 <10 Water-yellow-cortex diketone 2,288 <10

[0384] Table 7 below compares the colors of crude and purified oils. The methods used to determine the color are described in Table 7.

[0385] Table 7. Lovibond Color Description

[0386]

[0387] Example 2

[0388] Characterization of water yellow skin oil

[0389] This embodiment provides a general scheme for characterizing water-yellow peel oil. The methods provided herein are... Figure 1 The scheme described herein is used to characterize the crude oil and purified oil described in Example 1 above.

[0390] A water-flavoir oil sample was combined with acetone to prepare an extraction mixture. The extraction mixture was then sonicated to extract a liquid fraction containing water-flavoirin and / or water-flavoirin dione from the oil. This liquid fraction was injected into an HPLC column equilibrated with 40% acetonitrile for component analysis. The HPLC-DAD settings used are summarized in Table 8 below.

[0391] Table 8. Summary of Basic HPLC-DAD Settings

[0392] type describe chromatographic column Agilent Poroshell C18, 4.6×100mm, 2.6μm Column temperature 35±0.5℃ Mobile phase A HPLC grade water Mobile phase B Acetonitrile Seal wash 90:10 water:acetonitrile Needle flushing Acetonitrile:water ratio 90:10 Needle flushing time 6 seconds (rinse the outlet) Flow rate 0.800 mL / min Injection volume 1.0μL Signal A wavelength 304nm (4nm bandwidth) Signal B wavelength 350nm (4nm bandwidth)

[0393] Once the sample extract was loaded onto a C18 column equilibrated with 40% acetonitrile, the relative concentration of acetonitrile, while maintaining a flow rate of 0.8 mL / min, (i) linearly increased to 90% within 18 minutes, (ii) remained at 90% for 4 minutes, (iii) linearly decreased to 40% within 1 minute, and (iv) remained at 40% for 2 minutes, as summarized in Table 9 below.

[0394] Table 9. Elution Procedure

[0395]

[0396] Hydroquinone was observed to elute at approximately 9.6 min, corresponding to a relative acetonitrile concentration of approximately 67%. Hydroquinone was observed to elute at approximately 14.4 min, corresponding to a relative acetonitrile concentration of approximately 80%. The ppm concentration of each component was determined based on spectral analysis of the eluent fractions corresponding to hydroquinone and hydroquinone.

[0397] The results of characterizing hydroflavin and hydroflavindione in the crude and purified oils of Example 1 above using this method are provided in Table 6 above. Figure 3A and 3B The removal of furan flavonoids and other chemicals from edible oils from the crude and purified oils of Example 1 above was also compared.

[0398] Example 3

[0399] Thermal properties of purified water yellow peel oil

[0400] This embodiment details the evaluation of the thermal and temperature-dependent physical properties of purified water-processed yellow peel oil.

[0401] Purified water-based yellow peel oil was obtained according to the protocol described in Example 1 or 2. Solid fat content (SFC) was measured using nuclear magnetic resonance (NMR) according to AOCS-Cd 16b-93. Furthermore, flash point, dropping point, and smoke point were determined for the same samples according to AOCS Cc 9b-55, AOCS Cc 18-80, and AOCS Cc 9a-48, respectively.

[0402] The melting (heating) and crystallization (cooling) curves of water croton oil were studied using differential scanning calorimetry (DSC).

[0403] Example 4

[0404] Watery yellow skin oil sensory assessment

[0405] This embodiment describes a scheme for evaluating the sensory properties of water-based yellow peel oil compositions that can be obtained according to the methods of Examples 1 and 2.

[0406] The internal tasting of water-based wampee oil involved six individuals. Each participant evaluated each oil sample based on color, turbidity, odor, taste, and overall acceptability. For taste and odor assessments, participants engaged in free choice analysis by blindly tasting each purified water-based wampee oil sample and assigning the attribute they felt best described the flavor of each oil sample. Descriptive language was freely chosen for each sample set.

[0407] Example 5

[0408] Food products

[0409] This embodiment provides various examples of food products that can be produced using the water-wheat peel oil composition obtained according to the scheme described in Example 1 above. Table 10 provides exemplary formulations for water-wheat peel oil mayonnaise. Table 11 provides exemplary formulations for water-wheat peel oil margarine and spreads. Table 12 provides exemplary formulations for water-wheat peel oil salad dressings.

[0410] Table 10. Recipe for Water-Based Egg Yolk Mayonnaise

[0411] Element Wt% Watery yellow skin oil 75 Yolk 6 5% vinegar (w / v) 10 Salt 1.1 sugar 2.5 water 4.5 mustard 1.5 Guar glue 0.4 Potassium sorbate 0.07 Sodium benzoate 0.03

[0412] Table 11. Recipes for Water-Yellow Skin Oil Margarine and Spread

[0413]

[0414] Table 12. Recipe for Water Cheese Peel Oil Salad Dressing

[0415]

[0416]

[0417] As used herein, the term "about" refers to the typical range of error for various values ​​that is readily known to those skilled in the art. The reference herein to "about" a value or parameter includes (and describes) an implementation for that value or parameter itself. For example, "about x" includes and describes "x" itself. In some implementations, the term "about," when used in conjunction with a measurement or for modifying a value, unit, constant, or range of values, refers to a change of + / -2% in said value or parameter.

[0418] The phrase "between two values ​​or parameters" as used herein includes (and describes) implementations that include the two values ​​or parameters themselves. For example, a description of "between x and y" includes a description of "x" and "y" themselves.

Claims

1. A method for producing a water-based yellow peel oil composition, comprising: Crude water-based wampee oil is combined with a non-polar solvent to produce a crude mixture, wherein the non-polar solvent includes n-hexane, and wherein the crude water-based wampee oil includes water-based wampee oil and furan flavonoids. The crude mixture was eluted with silica gel using the aforementioned nonpolar solvent to separate the furan flavonoids from the aqueous wampee oil, and to produce a purified mixture comprising the aqueous wampee oil and the nonpolar solvent; and The nonpolar solvent was removed from the purified mixture to produce a water-based flavone oil fraction containing water-based flavonein and water-based flavone dione. The hydroflavin and hydroflavin dione are further adsorbed onto silica gel, and the method further includes eluting the silica gel with a polar solvent to separate the hydroflavin and hydroflavin dione and produce a hydroflavin oil composition, wherein the polar solvent includes ethyl acetate. The composition thereof has less than or equal to about 150 ppm of quercetin or less than or equal to about 150 ppm of quercetin dione or both, as determined by HPLC-DAD analysis of the acetone extract obtained from the quercetin oil composition; less than or equal to about 1% by weight of unsaponifiable matter; less than or equal to about 5% by weight of trans fatty acids; and less than or equal to about 25 ppm of residual solvent; and the composition thereof is edible and non-bitter; and the about refers to a variation of + / - 2% of the stated values.

2. The method according to claim 1, wherein the crude water-wampee oil has an initial color and the resulting water-wampee oil composition has a final color, wherein the final color of the water-wampee oil composition is lighter than the initial color of the crude water-wampee oil, as determined by the Lovibond color-AOCS scale.

3. The method of claim 2, wherein the initial color, determined by the Lovibond color-AOCS scale, is red and / or brown, and the final color is yellow or pale yellow.

4. The method according to any one of claims 1 to 3, wherein the crude water yellow peel oil is water yellow peel oil that has been mechanically separated.

5. The method according to any one of claims 1 to 3, further comprising: Water yellow-skinned oilseeds are dehulled to produce dehulled oilseeds; and The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

6. The method according to any one of claims 1 to 3, further comprising: Water-yellow-skinned oilseeds are heated at temperatures between 25°C and 200°C to provide processed oilseeds; The processed oilseeds are dehulled to produce dehulled oilseeds; and The dehulled oilseeds are mechanically separated to produce crude water-yellow peel oil and at least partially deoiled seed cake.

7. The method according to any one of claims 1 to 3, wherein the nonpolar solvent is n-hexane.

8. The method according to any one of claims 1 to 3, wherein the concentration of hydroflavin or hydroflavin dione or both is determined by HPLC-DAD analysis of an acetone extract obtained from the hydroflavin oil composition.

9. The method according to any one of claims 1 to 3, wherein the crude water-based yellow peel oil is combined with a nonpolar solvent in a ratio between 1:1 and 3:1 (w / v).

10. The method according to any one of claims 1 to 3, wherein the method further comprises: Silica gel is eluted with a polar solvent to separate hydroflavin and hydroflavin dione, wherein the polar solvent is ethyl acetate.

11. The method of claim 1, wherein the method further comprises: A step-gradient elution silica gel is used to separate hydroquinone and hydroquinone dione and produce a hydroquinone oil composition by increasing the proportion of a polar solvent in a non-polar solvent, wherein the polar solvent includes ethyl acetate.

12. The method according to claim 11, wherein the polar solvent is ethyl acetate.

13. An edible and non-bitter aquatic wampee oil composition produced by the method according to any one of claims 1 to 12, comprising: Less than or equal to about 150 ppm of water-based flavin or less than or equal to about 150 ppm of water-based flavindione or both; Less than or equal to about 1% by weight of unsaponifiables; Less than or equal to about 5% trans fatty acids by weight; and Residual solvent less than or equal to approximately 25 ppm Here, "approximately" refers to a change of + / - 2% in the value.

14. The composition according to claim 13, comprising: A concentration of furan flavonoids less than or equal to approximately 500 ppm.

15. The composition according to any one of claims 13 to 14, wherein the residual solvent comprises a nonpolar solvent.

16. The composition according to any one of claims 13 to 14, wherein the residual solvent comprises a nonpolar solvent and wherein the nonpolar solvent comprises n-hexane.

17. The composition according to any one of claims 13 to 14, wherein the composition is a liquid at room temperature.

18. The composition according to any one of claims 13 to 14, wherein the composition has a viscosity determined at 25°C between about 30 centipoise and 600 centipoise.

19. The composition according to any one of claims 13 to 14, wherein the composition has a solid fat content between about 1% and about 10% at a temperature of about 5°C.

20. The composition according to any one of claims 13 to 14, wherein the composition has a smoke point of at least about 195°C.

21. The composition according to any one of claims 13 to 14, wherein the composition has at least 400 ppm of tocopherol.

22. The composition according to any one of claims 13 to 14, wherein the composition has less than 2500 ppm of sterols.

23. The composition according to any one of claims 13 to 14, wherein the composition comprises oleic acid, linoleic acid, palmitic acid, stearic acid, benzyl acid, α-linolenic acid, creosotenic acid, arachidic acid, squalene, oleic acid, isoleic acid, palmitoleic acid, eicosapentaenoic acid, linoleic acid, heptadecanic acid, squalene, erucic acid, palmitoleic acid, heptadecanoic acid, or myristic acid, or any isomer thereof or any combination thereof.

24. The composition of claim 23, wherein the composition comprises at least 40% oleic acid.

25. The composition according to any one of claims 13 to 14, wherein the color of the composition is a yellow or pale yellow determined using a 1-inch cell path on the Lovibond color-AOCS scale, wherein: When the composition is yellow, it has a Lovibond color Y-value greater than or equal to 25; and When the composition is pale yellow, the composition has a Lovibond color Y-value of less than 25.

26. The composition according to any one of claims 13 to 14, wherein the composition has one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof.

27. The composition according to any one of claims 13 to 14, wherein the composition has a ratio of more than about 1 of hydroflavin to hydroflavin dione.

28. The composition according to any one of claims 13 to 14, wherein the color of the composition is pale yellow and the composition has a Lovibond color Y-value of less than 25, determined by using a 1-inch cell path on the Lovibond color-AOCS scale.

29. The composition according to any one of claims 13 to 14, wherein the color of the composition is a pale yellow as determined by the Lovibond color-AOCS scale, and wherein the composition comprises less than or equal to about 150 ppm of aqueous flavinin or less than or equal to about 150 ppm of aqueous flavindione or both.

30. The composition according to any one of claims 13 to 14, wherein the composition has a neutral flavor.

31. The composition according to any one of claims 13 to 14, wherein the composition has a ratio of less than or equal to 1 for hydroflavin and hydroflavin dione.

32. The composition according to any one of claims 13 to 14, wherein the composition comprises: (i) Free fatty acid content less than or equal to about 1%; (ii) Less than or equal to about 0.1% of insoluble impurities; (iii) Phosphorus less than or equal to about 25 ppm; (iv) Chlorophyll less than or equal to about 0.1 ppm; (v) Moisture content less than or equal to about 1%; (vi) Glycerin less than or equal to about 1%; (vii) Less than or equal to about 2% monoglycerides; (viii) Diglycerides less than or equal to about 5%; and (ix) At least approximately 90% of triglycerides, Any combination of (x) or (i)-(ix).

33. The composition according to any one of claims 13 to 14, wherein the concentrations of hydroflavin and hydroflavin dione are determined by HPLC-DAD analysis of an acetone extract obtained from the hydroflavin oil composition.

34. The use of the water-based yellow skin oil composition according to any one of claims 13 to 33 as a salad oil; frying oil; stir-frying oil; vinaigrette; sauce; condiment; meat imitation, beverage or fat used in blends with margarine and other solid fats; or any combination thereof.

35. A food or beverage product comprising the water-based yellow peel oil composition according to any one of claims 13 to 33.

36. The product of claim 35, wherein the composition is pale yellow as determined by the Lovibond color-AOCS scale; the composition comprises less than or equal to about 150 ppm of hydroflavin or less than or equal to about 150 ppm of hydroflavin dione or both, as determined by HPLC-DAD analysis of an acetone extract obtained from the hydroflavin oil composition, and the composition has a neutral flavor.

37. The product of claim 35, wherein the aqua quercetin oil composition is yellow as determined by the Lovibond color-AOCS scale; the composition comprises less than or equal to about 150 ppm aqua quercetin and less than or equal to about 150 ppm aqua quercetin dione or both, as determined by HPLC-DAD analysis of an acetone extract obtained from the aqua quercetin oil composition; and the composition has one or more sensory properties selected from the group consisting of: nutty, buttery, grassy, ​​smooth, and sweet, and any combination thereof.

38. The product according to any one of claims 35 to 37, wherein the product is salad oil; frying oil; stir-frying oil; vinaigrette; sauce; condiment; meat imitation, beverage, or fat used in blends with margarine and other solid fats.

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