US20030165587A1

US20030165587A1 - Production of 2-furfurylthiol in brassica seed and use of same

Info

Publication number: US20030165587A1
Application number: US10/084,899
Authority: US
Inventors: Eva Binggeli; Klaus Gassenmeier; Jeff Molnar; Peter Schieberle
Original assignee: Givaudan SA
Current assignee: Givaudan SA
Priority date: 2002-02-28
Filing date: 2002-02-28
Publication date: 2003-09-04
Also published as: AU2003248346A1; EP1478225A2; WO2003071863A2; US8329241B2; WO2003071863A3; EP1478225B1; ATE522131T1; US20050053714A1

Abstract

A process for producing 2-furfurylthiol (“FFT”) in Brassica seed includes heating Brassica seed under a temperature and for a time sufficient to produce an elevated amount of FFT in the Brassica seed. The heated seed may be extracted and/or otherwise treated, and may be used to provide a flavorant or odorant to consumables such as foods.

Description

FIELD OF THE INVENTION

This invention relates to the production and use of 2-furfurylthiol (“FFT”), and more particularly, to the production of FFT from natural sources.

DESCRIPTION OF THE RELATED ART

2-furfurylthiol (“FFT”) is a highly-desirable flavorant and odorant compound. Not only does FFT provide desirable aroma and taste characteristics, but also it is effective at extremely low concentrations. In particular, the odor threshold for FFT is 0.01 μg/L of water. Accordingly, FFT may be used in small amounts, thereby making its use highly cost-effective.

In the past, the demand for FFT has been met by making FFT synthetically. However, in many situations, this no longer is an acceptable option. In particular, consumers are increasingly demanding “all natural” consumable products. In many instances, in order for a consumable product to be labeled “all natural”, the product may not include any synthetically-made compounds. Accordingly, there is a growing demand for FFT which is derived from natural sources.

In this regard, it is known that heating sesame seed, coffee, beef, pork, lamb, or chicken under particular conditions results in the formation of FFT. Unfortunately, however, when these materials are heated, they produce relatively low concentrations of FFT. Therefore, they are rather inefficient and uneconomical as sources of natural FFT.

SUMMARY OF THE INVENTION

The invention overcomes the limitations discussed above by the identification of new, efficient, and economical raw materials for the generation of 2-furfurylthiol (“FFT”), a flavorant and odorant compound. These raw materials are the seeds from the genus Brassica within the family Brassicaceae (also known as the Cruciferae family). As discovered by the inventors, these seeds contain a minute, natural amount of FFT. In a surprising and unexpected development, when treated according to the principles of the invention, these seeds produce elevated amounts of FFT. Moreover, upon seed treatment, the FFT is produced in concentrations which are dramatically higher than the concentrations which result from treating previously-known natural sources of FFT. Therefore, the invention provides not only a new natural source of FFT, but also a source which yields FFT far more efficiently and economically.

One aspect of the invention is directed to a process for producing FFT in Brassica seed. The process includes the step of heating Brassica seed under a temperature and for a time sufficient to produce an elevated amount of FFT in the Brassica seed.

The Brassica seed may be any seed type or combination of seed types within the Brassica genus. For example, if desired, the Brassica seed type may be one or more of Brassica alba, Brassica junceau, Brassica napus, Brassica nigra, and Brassica rapa.

If desired, the heating step may include heating the Brassica seed in a surrounding temperature, with the surrounding temperature being within a range of about 120° C. to about 250° C. With regard to time, if desired, the Brassica seed may be heated for a period of time of at least about five minutes. Also, if desired, the Brassica seed may be heated for a period of time within a range of about 5 minutes to about 60 minutes. The heating step results in a significant percent-increase in the concentration of FFT. For example, the percent-increase may be at least 100%, at least 500%, at least 1000%, and at least 10,000%.

The process of producing FFT in Brassica seed may further include the step of treating the Brassica seed after the heating step, thereby forming treated Brassica seed. The treating step may include one or more of grinding, flaking, and expanding. In addition, if grinding is used, the Brassica seed may be ground to an average particle size within a range of about 40 mesh to about 10 mesh. If desired, the seed may be ground to an average particle size of about 20 mesh.

The process for producing FFT from Brassica seed may further include the step of recovering at least some of the FFT which was produced in the Brassica seed as a result of the heating step. If desired, the recovering step may include one or more of extracting, distilling, pressing, centrifuging, and chromatographically separating. If extraction is used, the extracting step may include one or more of steeping, immersion, percolation, and batch extraction. If desired, an inert solvent may be used. By way of example, the inert solvent may include one or more of a vegetable oil, an alcohol, water, an aliphatic hydrocarbon, an oxygenated hydrocarbon, a triglyceride, and supercritical carbon dioxide. If desired, the inert solvent may have a temperature within a range of about 20° C. to about 70° C. In addition, during the extraction step, the treated Brassica seed may be kept in the inert solvent for a period of time within a range of about 10 hours to about 36 hours.

In a further aspect of the invention, the recovering step may include grinding the Brassica seed in an inert solvent, thereby forming ground Brassica seed. The grinding performed in this particular recovering step may be in place of, or in addition to, the step of treating the Brassica seed as described above.

Another aspect of the invention is directed to the product produced by the process. Yet another aspect of the invention is directed to a flavorant or odorant, with the flavorant or odorant including heated Brassica seed having an elevated amount of FFT, the Brassica seed having been heated under a temperature and for a time sufficient to produce the elevated amount of FFT. If desired, the Brassica seed may have a concentration of at least about one milligram FFT per kilogram Brassica seed. In addition, the Brassica seed may have a concentration of at least about 5 milligrams FFT per kilogram seed, or a concentration of at least about 10 milligrams FFT per kilogram seed.

A further aspect of the invention is directed to a flavorant or odorant which includes isolated FFT, wherein the FFT is from Brassica seed. If desired, the Brassica seed may have a concentration of at least about one milligram FFT per kilogram Brassica seed.

Yet another aspect of the invention is directed to a process for enhancing the flavor or odor of a consumable. The process includes the step of combining a consumable and a flavor- or odor-enhancing amount of FFT, with the FFT having been produced in Brassica seed by heating the seed. If desired, the Brassica seed may have a concentration of at least about one milligram FFT per kilogram seed. In yet a further aspect, the invention includes a consumable in combination with a flavor- or odor-enhancing amount of FFT. The FFT is produced in Brassica seed by heating the seed; and, if desired, the seed may have a concentration of at least about one milligram FFT per kilogram seed.

These and other aspects and advantages of the invention will be apparent from the following detailed description, including the examples contained in the detailed description.

DETAILED DESCRIPTION

The invention is directed, in part, to the discovery of a naturally-occurring source of 2-furfurylthiol (“FFT”), namely seeds of the Brassica genus. The invention also includes the discovery that, when heated, seeds within the Brassica genus produce a relatively-high concentration of FFT, thereby providing not only a natural FFT source, but also an economical and efficient FFT source.

The invention encompasses all members of the Brassica genus, with non-limiting examples including Brassica adpressa, Brassica alba, Brassica arvensis, Brassica campestris, Brassica cheiranthos, Brassica elongata, subsp. integrifolia, Brassica eruca, Brassica geniculata, Brassica hirta, Brassica juncea, Brassica kaber, var. pinnatifida, Brassica var. schkuhriana, Brassica napus, Brassica nigra, Brassica oleracea, Brassica orientalis, Brassica rapa, and Brassica tournefortii. The genus- and species-names provided above comply with the International Code of Plant Nomenclature. Any of the seeds within the Brassica genus may be obtained through traditional commercial channels.

In accordance with the principles of the invention, the Brassica seed is heated in order to generate a relatively high amount of FFT. While not intending to be bound by theory, it is believed that one or more FFT-precursors contained within the Brassica seed chemically react upon heating the seed, thereby forming FFT. Such a precursor may be a sulfur-containing precursor, and may be a sulfur-containing amino acid. One such precursor candidate is S-furfurylcysteine.

As used herein, the term “Brassica seed” refers to one or more whole seeds of the Brassica genus.

Typically, the Brassica seed is heated in a fluid, for example, air, with the fluid having a temperature in the range of from about 120° C. to about 250° C. As used herein, the term “fluid” refers to any suitable gas, liquid, gas mixture, liquid mixture, vapor, aerosol, solution, dispersion, suspension, or the like. The fluid temperature may be referred to as the “surrounding temperature”. Typically, the Brassica seed is heated in the particular fluid for a period of time in the range of from about 5 minutes to about 60 minutes. If desired, the temperature and/or time may be adjusted so as to alter the flavor and/or aroma characteristics of the heated seed. Any suitable, commercially-available equipment which allows for the control of temperature and time may be used. Non-limiting examples include commercially-available ovens and rotating drums. The particular heating unit may be a closed system (i.e., air-tight) or an open system. In addition, any conventional heating method may be used to heat the seed. Such methods include, but are not limited to, roasting, baking, frying, and microwaving. The Brassica seed, itself, may be arranged within the heating vessel in any fashion.

The heat-treated Brassica seed may be used as a flavorant or an odorant. As used herein, the term “flavorant” means a substance capable of providing a taste sensation, either alone or in combination with another substance. If desired, the heat-treated seed may be combined with a consumable. As used herein, the term “consumable” broadly includes any product which is capable of being ingested, regardless of whether it provides nutritive value and regardless of form. Non-limiting examples include foods, beverages, health-care products, beauty-care products, and tobacco products.

In many instances, it would be desirable to have an FFT extract of the Brassica seed, instead of the heat-treated seed described immediately above. As used herein, the term “extract” means a concentrated preparation of one or more essential constituents of a botanical substance typically separated by a solvent. Although an extract may be prepared from whole seed, the overall recovery process may include a further seed-treating step. This seed-treating step may involve grinding, flaking, and/or expanding the heat-treated Brassica seed using commercially-available equipment and methods. Typically this treating step is performed after the heating step. In one particular method of producing an extract, Brassica seed is heated for at least about 5 minutes in a surrounding temperature of about 160° C., and then ground or flaked.

If the Brassica seed is ground or flaked, the seed may be ground or flaked either with or without the use of a solvent. Typically, a solvent is used because it dissipates the kinetic energy produced during the grinding or flaking process, thereby usually reducing the loss of various volatile flavor or odor compounds. If a solvent is used, the solvent may be inert. As used herein, the term “inert solvent” refers to any suitable solvent which does not chemically react with FFT. Non-limiting examples include vegetable oils, alcohols, water, aliphatic hydrocarbons, oxygenated hydrocarbons, triglycerides, supercritical carbon dioxide, and combinations thereof.

If the seed is ground, the seed may be ground to an average particle size of from about 40 mesh to about 10 mesh. In one version, the seed is ground to an average particle size of about 20 mesh. If the seed is flaked, the seed may be flaked so that it has an average thickness within a range of from about 0.010 inch to about 0.014 inch. In one version, the flaked seed has an average thickness of about 0.012 inch.

If an inert solvent is used in the grinding or flaking process, then the recovery process will begin during the grinding or flaking process. The recovery step may include one or more of extracting, distilling, pressing, centrifuging, and chromatographically separating, using any suitable commercially-available equipment. If extraction is used, the extracting step may include one or more of steeping, immersion, percolation, and batch extraction.

If steeping is used, ground, flaked, or expanded Brassica seed may be steeped in an inert solvent, for example, a vegetable oil. The inert solvent may have a temperature of from about 20° C. to about 70° C.; and the seed may be steeped for a period of time of from about 10 hours to about 36 hours. The solids may be separated from the solvent by filtration. If vegetable oil is used as the extracting solvent, no further processing is required after filtration. However, if one or more other solvents are used (with the exception of ethanol) such solvents may be removed by evaporation, so that the residue (i.e., product) contains, for example, less than about 25 parts per million of the solvent. If desired, sufficient vegetable oil is added to the residue to maintain a viscosity of less than about 100 centipoise in the final extract. If ethanol is used, and if desired, the ethanol may be removed from the product using any suitable method, (e.g., evaporation), until the residue contains 15% (w/w) ethanol ±2%.

The invention is illustrated further by the following working examples.

WORKING EXAMPLES

These examples are provided to help illustrate various aspects of the invention. However, the examples do not limit the scope of the invention. [0028]
All of the seeds used in these working examples were obtained from Forbes Frozen Foods of Cincinnati, Ohio. [0029]
1. Concentration of FFT in Heated Brassica Seed [0030]
Approximately ten grams each of various types of Brassica seed were heated as described in Table 1 below. The concentration of FFT subsequently was determined by using a stable isotope dilution assay, although other procedures may be used, as known to those of ordinary skill. [0031]

The heated Brassica seed was weighed and extracted with dichloromethane (50 ml) containing deuterated FFT ([ ²H₂]-furfurylthiol, at a concentration of 20 μg per 50 mg). The volatile compounds subsequently were isolated by applying the high vacuum transfer technique described by Jung et al. (Lebensm.-Wiss. U Technol. 225:55-60, 1992), the Jung et al. article being incorporated in its entirety into this patent document by reference. The dichloromethane extract was placed into a high vacuum apparatus. The solvent and the volatiles were captured in a cooling trap which was cooled with liquid nitrogen to a temperature of −150° C. The resulting extract was dried over sodium sulfate and concentrated in a vigreux distillation column until enough solvent had been distilled off so as to leave a final volume of 1 mL. Subsequently, the extract was analyzed by gas chromatography/mass spectroscopy. The amount of FFT was calculated from the area m/z 81 for the analyte and m/z 83 for the internal standard.

TABLE I


				Concentration
		Temperature		(milligrams
Type of	Type of	of Fluid in	Duration of	FFT per
Seed	Container	Container	Heat	kilogram seed)

Brassica	10 mL Pyrex	200° C.	10 minutes	40 mg/kg
alba	container with
(Example	a loose-fitting
1a)	cap (i.e., not
	a closed
	system
Brassica	10 mL Pyrex	200° C.	10 minutes	9.2 mg/kg
napus	container with
(Example	a loose-fitting
1b)	cap (i.e., not
	a closed
	system
Brassica	10 mL Pyrex	200° C.	10 minutes	8.2 mg/kg
nigra	container with
(Example	a loose-fitting
1c)	cap (i.e., not
	a closed
	system)

2. Concentration of FFT in Unheated Brassica Seed [0033]
The concentration of FFT in unheated Brassica seed was determined using a stable isotope dilution assay, as described in Example 1 above. In further detail, 300 g of [0034] Brassica alba were extracted with dichloromethane containing 1 μg of labeled FFT. The remaining steps were performed as described in Example 1 above. Through this testing procedure, it was determined that the unroasted seed contained less than 1 μg FFT per kg of seed.
3. Roasted [0035] Brassica Alba Seed
125 g of [0036] Brassica alba seed were roasted in a Probat Sample Roaster (PRE 1Z, Probat-Werke von Gimborn Maschinenfabrik GmbH, Germany) at 160° C. for 10 minutes. The resulting seed had a strong peanut-like aroma with chicken, sulfur, earthy, roasty, and popcorn by-notes, as determined by a panel of trained flavorists.
4. Roasted [0037] Brassica Alba Seed
125 g of [0038] Brassica alba seed were roasted in a Probat Sample Roaster (PRE 1Z, Probat-Werke von Gimborn Maschinenfabrik GmbH, Germany) at 200° C. for 10 minutes. The resulting seed had a strong coffee-like aroma, as determined by a panel of trained flavorists.
5. Roasted [0039] Brassica Nigra Seed
125 g of [0040] Brassica nigra seed were roasted in a Probat Sample Roaster (PRE 1Z, Probat-Werke von Gimborn Maschinenfabrik GmbH, Germany) at 200° C. for 20 minutes. The resulting seed had an aroma with very strong roasty and coffee notes, dominated with burnt sulfury, earthy, meaty, and caramel aspects, as determined by a panel of trained flavorists.
6. Roasted [0041] Brassica Junceau Seed
125 g of [0042] Brassica junceau seed were roasted in a Probat Sample Roaster (PRE 1Z, Probat-Werke von Gimborn Maschinenfabrik GmbH, Germany) at 160° C. for 10 minutes. The resulting seed had an aroma with a very strong “oriental kitchen” note, as determined by a panel of trained flavorists.
7. Roasted [0043] Brassica Rapa Seed
125 g of [0044] Brassica rapa seed were roasted in a Probat Sample Roaster (PRE 1Z, Probat-Werke von Gimborn Maschinenfabrik GmbH, Germany) at 160° C. for 10 minutes. The resulting seed had an aroma with very strong roasty and meaty notes, as determined by a panel of trained flavorists.
8. Preparation of Encapsulated Roasted [0045] Brassica Alba Seed Extract
125 g of [0046] Brassica alba seed were roasted at 200° C. for 10 minutes in a Probat Sample Roaster (PRE1Z), and then ground in a coffee grinder (Moulinex Type 53402, Paris, France) to an average particle size of about 40 mesh. The ground seed was subjected to an extraction process by adding 250 g of a vegetable oil (Miglyol 812 from Abitech Corporation of Columbus, Ohio) to the ground seed. The seed was steeped in a Certomat lab shaker (B. Brown Biotech International, Inc. Allentown, Pa.) at 50° C. for 20 hours. The extract was added to an aqueous solution of modified food starch, maltodextrin, and sugar, at total solids of 60%, and mixed with high shear in a Waring commercial blender (Blender 7012 Model 34BL21, Waring Products Division, Dynamics Corporation of America, New Hartford, Conn.) to form an emulsion (<3 μm droplet size). This emulsion was then dried using an Anhydro PRD55 spray dryer (from APV Anhydro of Denmark) at an inlet air temperature of 340° F., an outlet air temperature of 210° F., and an atomizer wheel speed of 35,000 rpm. Powder containing 15% w/w flavor was recovered with a yield of 85%.
9. Encapsulated Roasted [0047] Brassica Alba Seed Extract in an Instant Coffee
An instant coffee was prepared by mixing 1.58 g of Nestle Nescafe instant coffee powder (Nestle, Glendale, Calif.) with 0.02 g of the encapsulated [0048] Brassica alba seed of Example 8. The powder mixture was dissolved in 180 mL of water, with the water having been heated to a temperature of 170° F. The resulting coffee had an aroma and taste which was both pleasing and stronger than that of the coffee without the encapsulated extract, as determined by a panel of trained flavorists.
10. Roasted [0049] Brassica Nigra Seed in a Bouillon

500 g of Brassica nigra seed were roasted in a circulating air oven (Memmet Type U50, Memmet, 854 Schwabach, Germany) at 200° C. for 60 minutes. The roasted seed was ground in a coffee grinder (Moulinex Type 53402, Paris, France) to an average particle size of about 40 mesh. A bouillon base was prepared from the ingredients listed in Table 2 below. The fats were molten and combined. Then the turmeric powder was added and mixed until homogeneous. The remaining ingredients, which had been premixed, were added and mixed until homogenous. The mixture was left at a temperature of approximately 50-70° C. for 24 hours. Then the mixture was passed through a sieve to break any lumps. The bouillon was prepared by dissolving 22 g of bouillon base in 1000 mL of hot water. Then the ground seed was added to the bouillon at a concentration of 50 g of ground seed to 100 kg of the bouillon. The resulting bouillon exhibited a roasty chicken note with a roasted bone aspect, as determined by a panel of trained flavorists.

TABLE 2


Ingredients of Bouillon Base

	Weight (grams)

	Salt (Sodium Chloride)	350.0
	Corn Syrup Solids (Maltodextrin)	408.0
	Lactose Monohydrate	100.0
	Monosodium Glutamate	70.0
	Beef Fat	35.0
	Vegetable Fat	20.0
	Burnt Sugar, Powder	7.0
	Onion Powder	5.5
	Nucleotides	3.0
	Turmeric Powder	1.5

11. Roasted [0051] Brassica Nigra Seed in a Coffee-Flavored Yogurt
500 g of [0052] Brassica nigra seed were roasted in a circulating air oven (Memmet Type 050, Memmet, 854 Schwabach, Germany) at 200° C. for about 20 minutes. The roasted seed then was ground in a coffee grinder (Moulinex Type 53402, Paris, France) to an average particle size of about 40 mesh. The ground seed was added to a coffee flavor at 10% (w/w). The coffee flavor was coffee paste flavor, commercially available under the product code 96504789 from Givaudan, Ueberlandstrasse CH-8600 Duebendorf, Switzerland. The resulting coffee flavor was added to yogurt at a concentration of 0.5% (w/w), and compared with the same yogurt containing the same coffee flavor without the roasted Brassica nigra seed. The yogurt, itself, was a set-type yogurt, commercially available from Swiss Dairy Foods of Ostermundigen, Switzerland, under the product name Tony Jogurt Natur. The yogurt which contained the coffee flavor which had been enhanced with the ground seed exhibited stronger coffee notes and a longer lasting coffee aftertaste relative to the yogurt, which had been flavored with the plain coffee flavor, as determined by a panel of trained flavorists.
12. Roasted [0053] Brassica Nigra Seed in a Cream Soup Base

500 g of Brassica nigra seed were roasted in a circulating air oven (Memmet Type 050, Memmet, 854 Schwabach) at 200° C. for 60 minutes. The roasted seed was ground in a coffee grinder (Moulinex Type 53402, Paris, France) to an average particle size of about 40 mesh. A cream soup base was prepared from the ingredients listed in Table 3. All dry ingredients (except roux) were mixed, and molten fat was well-dispersed in the blend. The mixture was sieved, the roux was added, and this subsequent blend was mixed well. The cream soup was prepared by dissolving 50 g cream soup base in 500 mL of hot water. Then the ground seed was added to the cream soup at a concentration of 50 g of ground seed to 100 kg of cream soup. The resulting cream soup exhibited a roasty chicken note with a roasted bone aspect, as determined by a panel of trained flavorists.

TABLE 3


Ingredients of Cream Soup Base

	Amount
	(grams)

	Roux*	483.35
	Starch, Native	150.00
	Corn Syrup Solids (Maltodextrin)	88.32
	Salt (Sodium Chloride) 0.4 mm	78.65
	Whipping Agent	66.65
	Skim Milk Powder	66.65
	Monosodium Glutamate	33.35
	Yeast Extract	8.35
	Sugar, Extra Fine	8.35
	Vegetable Fat	8.30
	Xanthan Gum	6.65
	Citric Acid, Anhydrous	0.80
	Pepper Granuseal 12273-72	0.13
	Pepper Granuseal 12274-72	0.13
	Bay leaf Granuseal 12332-72	0.13
	Turmeric 87675-DO	0.12
	Nutmeg Granuseal 12331-72	0.07

13. The Eight Main Flavorants Formed by Roasting [0055] Brassica Alba At 200° C. for 10 Minutes

Approximately 5 g of Brassica alba seed were put into a test tube (16 cm×1.5 cm inner diameter) to a height of about 3 cm. The test tube was closed with aluminum foil and heated in an aluminum thermoblock (Fa. Liebisch, Type 2090, Bielefeld, Germany) at 200° C. for 10 minutes. Following this heating step, an extract was prepared using 100 g of roasted Brassica alba seed. This seed was frozen using liquid nitrogen and then was ground. The ground seed was extracted three times for 30 minutes with 100 mL of diethylether. The combined diethylether phases were concentrated on a Vigreux distillation column to a residual volume of 150 mL. The volatile compounds were isolated by distillation in vacuo, as described by Jung et al. See Example 1 for the citation to the Jung et al. article. Then an aroma extract dilution analysis (“AEDA”) was performed to determine the flavor-dilution (“FD”) factor for each of several compounds, according to the AEDA methodology described in the textbok by Peter Schieberle entitled Characterization of Food: Emerging Methods, Gaonkar AG (editor), pp.403-431, 1995. Pages 403-431 of the Schieberle article are expressly incorporated into this patent document by reference. Those flavorants which had an FD factor greater than 128 are shown in Table 4 below. The data shown in the Table indicate that, based on FD-factor, FFT is the most important odorant/flavorant compound extracted from the roasted Brassica alba seed, as determined by AEDA. The odor qualities of the compounds listed in Table 4 were determined by a panel of trained flavorists.

TABLE 4


Compound	OdorQuality	FD-Factor

2-Furfuryithiol (FFT)	roasty, coffee-like	4096
Methional	potato-like	1024
4-Hydroxy-2,5-dimethyl-3(2H)-furanone	caramel-like	512
3-Methylbutanal	malty	256
2,3-Pentandione	buttery	256
3-Mercapto-2-pentanone	sulfury	256
2-Acetyl-2-thiazoline	popcorn-like	256
3-Hydroxy-4,5-dimethyl-2(5H)-furanone	seasoning-like	256

14. Concentration of FFT in Roasted Brassica Seed Under Different Temperature and Time Conditions [0057]
This example was performed using [0058] Brassica alba seed. For each time and temperature condition shown in Table 5 below, Brassica alba seed was placed in a test tube (16 cm×1.5 cm inner diameter) to a height of 3 cm, and the test tube was closed with aluminum foil. Each test tube contained approximately 5 gms of seed. A thermoblock (Fa. Liebisch, Type 2090, Bielefeld, Germany) was used for heating. The concentration of FFT in the roasted seed was determined using a stable isotope dilution assay, as described in Example 1 above.

TABLE 5

Temperature (° C.) Duration (Min.) FFT Concentration (μg/kg)

160 5 <1

160 10 108

160 20 1706

200 5 514

200 10 3892

200 20 11453

240 5 3550

240 10 19507

240 20 3663
While the present invention has been illustrated by a description of various versions, and while the illustrative versions have been described in considerable detail, it is not the intention of the inventors to restrict or in any way limit the scope of the appended claims to such detail. Additional advantages and modifications will readily appear to those skilled in the art. The invention in its broader aspects is therefore not limited to the specific details, representative apparatus and methods, and illustrative examples shown and described. Accordingly, departures may be made from such details without departing from the spirit or scope of the inventors' general inventive concept.[0059]

Claims

What is claimed is:

1. A process for producing 2-furfurylthiol (“FFT”) in Brassica seed, comprising the step of:

heating Brassica seed, the Brassica seed containing a natural amount of FFT and at least one precursor of FFT, under a temperature and for a time sufficient to produce an elevated amount of FFT.

2. The process of claim 1 wherein the heating step includes heating the Brassica seed in a surrounding temperature, the surrounding temperature being within a range of about 120° C. to about 250° C.

3. The process of claim 2 wherein the Brassica seed is heated for a period of time of at least about 5 minutes.

4. The process of claim 2 wherein the Brassica seed is heated for a period of time within a range of about 5 minutes to about 60 minutes.

5. The process of claim 1 wherein the heating step results in a percent increase in the concentration of FFT of at least 100 percent.

6. The process of claim 1 wherein the heating step results in a percent increase in the concentration of FFT of at least 500 percent.

7. The process of claim 1 wherein the heating step results in a percent increase in the concentration of FFT of at least 1,000 percent.

8. The process of claim 1 wherein the heating step results in a percent increase in the concentration of FFT of at least 10,000 percent.

9. The process of claim 1 further including the step of treating the Brassica seed after the heating step by grinding, flaking, and/or expanding, thereby forming treated Brassica seed containing an elevated amount of FFT.

10. The process of claim 9 wherein the treating step includes grinding the Brassica seed to an average particle size within a range of about 40 mesh to about 10 mesh.

11. The process of claim 9 further including the step of recovering at least some of the FFT from the treated Brassica seed.

12. The process of claim 11 wherein the recovering step includes one or more of extracting, distilling, pressing, centrifuging, and chromatographically separating.

13. The process of claim 12 wherein the recovering step includes extracting.

14. The process of claim 13 wherein the extracting includes one or more of steeping, immersion, percolation, and batch extraction.

15. The process of claim 13 wherein the extracting includes steeping the treated Brassica seed in an inert solvent.

16. The process of claim 15 wherein the inert solvent includes one or more of a vegetable oil, an alcohol, water, an aliphatic hydrocarbon, an oxygenated hydrocarbon, a triglyceride, and supercritical carbon dioxide.

17. The process of claim 15 wherein the inert solvent includes a vegetable oil.

18. The process of claim 15 wherein the inert solvent has a temperature within a range of about 20° C. to about 70° C.

19. The process of claim 18 wherein the treated Brassica seed is steeped in the inert solvent for a period of time within a range of about 10 hours to about 36 hours.

20. The process of claim 1 further including the step of recovering at least some of the FFT from the heated Brassica seed.

21. The process of claim 20 wherein the recovering step includes one or more of extracting, distilling, pressing, centrifuging, and chromatographically separating.

22. The process of claim 20 wherein the recovering step includes extracting.

23. The process of claim 22 wherein the extracting includes one or more of steeping, immersion, percolation, and batch extraction.

24. The process of claim 22 wherein the extracting includes steeping the Brassica seed in an inert solvent.

25. The process of claim 24 wherein the inert solvent includes one or more of a vegetable oil, an alcohol, water, an aliphatic hydrocarbon, an oxygenated hydrocarbon, a triglyceride, and supercritical carbon dioxide.

26. The process of claim 24 wherein the inert solvent includes a vegetable oil.

27. The process of claim 24 wherein the inert solvent has a temperature within a range of about 20° C. to about 70° C.

28. The process of claim 27 wherein the Brassica seed is steeped in the inert solvent for a period of time within a range of about 10 hours to about 36 hours.

29. The process of claim 1 wherein the Brassica seed is selected from the group consisting of Brassica alba, Brassica juncea, Brassica napus, Brassica nigra, Brassica rapa, and combinations thereof.

30. The product produced by the process of claim 1, 3, 5, 9, or 11.

31. A flavorant or odorant, comprising:

Brassica seed having an amount of 2-furfurylthiol (“FFT”) which is elevated relative to a natural amount of FFT, the Brassica seed having been heated under a temperature and for a time sufficient to produce the elevated amount of FFT.

32. The flavorant or odorant of claim 31 wherein the Brassica seed has a concentration of at least about one milligram FFT per kilogram Brassica seed.

33. The flavorant or odorant of claim 31 wherein the Brassica seed has a concentration of at least about five milligrams FFT per kilogram Brassica seed.

34. The flavorant or odorant of claim 31 wherein the Brassica seed has a concentration of at least about ten milligrams FFT per kilogram Brassica seed.

35. A flavorant or odorant, comprising:

isolated 2-furfurylthiol (“FFT”), wherein the FFT is extracted from Brassica seed.

36. The flavorant or odorant of claim 35 wherein the Brassica seed has a concentration of at least about one milligram FFT per kilogram Brassica seed.

37. A process for enhancing the flavor or odor of a consumable, comprising the step of:

combining a consumable and a flavor- or odor-enhancing amount of 2-furfurylthiol (“FFT”), the FFT having been produced in Brassica seed by heating the Brassica seed.

38. The process of claim 37 wherein the Brassica seed has a concentration of at least about one milligram FFT per kilogram Brassica seed.

39. A consumable in combination with a flavor- or odor-enhancing amount of 2-furfurylthiol (“FFT”), the FFT having been produced in Brassica seed by heating the Brassica seed.

40. The consumable of claim 39 wherein the Brassica seed has a concentration of at least one milligram FFT per kilogram Brassica seed.