EP3727036A1 - Method for producing a turmeric-based oil solution for food use - Google Patents
Method for producing a turmeric-based oil solution for food useInfo
- Publication number
- EP3727036A1 EP3727036A1 EP18830313.5A EP18830313A EP3727036A1 EP 3727036 A1 EP3727036 A1 EP 3727036A1 EP 18830313 A EP18830313 A EP 18830313A EP 3727036 A1 EP3727036 A1 EP 3727036A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- turmeric
- high oleic
- oleic sunflower
- sunflower oil
- oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 235000003373 curcuma longa Nutrition 0.000 title claims abstract description 71
- 235000003392 Curcuma domestica Nutrition 0.000 title claims abstract description 69
- 235000013976 turmeric Nutrition 0.000 title claims abstract description 69
- 235000013305 food Nutrition 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 244000008991 Curcuma longa Species 0.000 title 1
- 244000163122 Curcuma domestica Species 0.000 claims abstract description 73
- 239000003921 oil Substances 0.000 claims abstract description 65
- 235000019198 oils Nutrition 0.000 claims abstract description 64
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 62
- 235000019486 Sunflower oil Nutrition 0.000 claims abstract description 56
- 239000002600 sunflower oil Substances 0.000 claims abstract description 56
- 239000000843 powder Substances 0.000 claims abstract description 53
- 230000003647 oxidation Effects 0.000 claims abstract description 43
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000011156 evaluation Methods 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 14
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 10
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005642 Oleic acid Substances 0.000 claims abstract description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 6
- 229930195729 fatty acid Natural products 0.000 claims abstract description 6
- 239000000194 fatty acid Substances 0.000 claims abstract description 6
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000011261 inert gas Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000010681 turmeric oil Substances 0.000 abstract description 42
- 239000000243 solution Substances 0.000 description 58
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 27
- 239000000523 sample Substances 0.000 description 27
- UEPVWRDHSPMIAZ-IZTHOABVSA-N (1e,4z,6e)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one Chemical compound C1=C(O)C(OC)=CC(\C=C\C(\O)=C\C(=O)\C=C\C=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-IZTHOABVSA-N 0.000 description 13
- HJTVQHVGMGKONQ-LUZURFALSA-N Curcumin II Natural products C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=CC(O)=CC=2)=C1 HJTVQHVGMGKONQ-LUZURFALSA-N 0.000 description 13
- JYTVKRNTTALBBZ-UHFFFAOYSA-N bis demethoxycurcumin Natural products C1=CC(O)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=CC(O)=C1 JYTVKRNTTALBBZ-UHFFFAOYSA-N 0.000 description 13
- 235000012754 curcumin Nutrition 0.000 description 13
- 229940109262 curcumin Drugs 0.000 description 13
- 239000004148 curcumin Substances 0.000 description 13
- NMRUIRRIQNAQEB-UHFFFAOYSA-N demethoxycurcumin Natural products OC(=CC(C=CC1=CC(=C(C=C1)O)OC)=O)C=CC1=CC=C(C=C1)O NMRUIRRIQNAQEB-UHFFFAOYSA-N 0.000 description 13
- YXAKCQIIROBKOP-UHFFFAOYSA-N di-p-hydroxycinnamoylmethane Natural products C=1C=C(O)C=CC=1C=CC(=O)C=C(O)C=CC1=CC=C(O)C=C1 YXAKCQIIROBKOP-UHFFFAOYSA-N 0.000 description 13
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 13
- UEPVWRDHSPMIAZ-UHFFFAOYSA-N p-hydroxycinnamoyl feruloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(O)=CC(=O)C=CC=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PREBVFJICNPEKM-YDWXAUTNSA-N bisdemethoxycurcumin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)CC(=O)\C=C\C1=CC=C(O)C=C1 PREBVFJICNPEKM-YDWXAUTNSA-N 0.000 description 12
- 230000003078 antioxidant effect Effects 0.000 description 11
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 229930153442 Curcuminoid Natural products 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000010411 cooking Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000002803 maceration Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 235000020238 sunflower seed Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 235000011194 food seasoning agent Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 238000010152 Bonferroni least significant difference Methods 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000234299 Zingiberaceae Species 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 230000002225 anti-radical effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013528 artificial neural network Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000013367 dietary fats Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- -1 formic acid Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010520 ghee Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 235000006486 human diet Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
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- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- JAOZKJMVYIWLKU-UHFFFAOYSA-N sodium 7-hydroxy-8-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)O)N=NC3=C(C=CC4=CC(=CC(=C43)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] JAOZKJMVYIWLKU-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 235000021404 traditional food Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/008—Refining fats or fatty oils by filtration, e.g. including ultra filtration, dialysis
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
Definitions
- the invention relates to a method for producing a turmeric-based oil solution (so- called“turmeric oleolite”) for food use, in particular a method for producing a turmeric oil solution that is usable for seasoning, cooking and/or frying food products.
- the invention can be applied industrially in the sector of the production of vegetable oils.
- turmeric identifies the species Curcuma longa L., herbaceous plant belonging to the family of Zingiberaceae and original from south-eastern Asia.
- the turmeric and more exactly the turmeric powder (yellow-orange coloured powder, obtained from the boiled and dried rhizomes of the plant), is used in the cookery as an aromatizing agent (spice).
- the active principles contained in the turmeric powder are named curcuminoids and comprise the following molecules (having a linear diarylheptanoid structure): curcumin, bisdemethoxycurcumin and demethoxycurcumin. Curcuminoids active principles have been studied for their properties, in particular for the antioxidant activity and the antiradical activity, tested experimentally and fully documented in the scientific literature.
- turmeric Antioxygenic activity of turmeric (Curcuma longa) in sunflower oil and ghee. Journal of Food Science and Technology (1997) 34 (1), pp. 67-69), as suitable vehicles for the oral administration of curcuminoids active principles.
- a food oil supplemented with curcuminoids active principles can in fact be used as an alternative to a traditional food oil, both for raw seasoning (for example, for seasoning salads) and for cooking, in particular frying, food products.
- a drawback of the aforesaid oils for food use supplemented with curcuminoids principles consists of the fact that these oils have, already originally, a substantially poor resistance to oxidation (oxidation that is caused by the heat treatments underwent by the oil during the cooking or frying step), which causes a significant deterioration of the fats present in the oil.
- Another drawback consists of the fact that, in the oils for food use supplemented with curcuminoids principles of known type, the titre of the active principles is not determined, with a consequent risk of making the oral intake of the oil scarcely effective for the consumer.
- a further drawback consists of the fact that, in order to make an oil for food use supplemented with curcuminoids principles by using the known methods, it is necessary to extract with organic solvents the active principles from the dried rhizome. This makes producing the oil supplemented with extracted curcuminoids principles substantially costly and laborious, also for the need of disposing suitably of the solvents used for the extraction.
- An object of the invention is to improve the known methods for producing oils for food use containing curcuminoids active principles.
- Another object is to make available a method for producing an oil for food use containing curcuminoids active principles and provided with a suitable resistance to oxidation, a deterioration process that occurs, in particular, during a cooking or frying heat treatment.
- a further object is to make available a method for producing an oil for food use containing curcuminoids active principles, in which the titre in curcuminoids active principles is substantially predetermined and high.
- Still another object is to make available a method for producing an oil for food use containing curcuminoids active principles, which enables the need to extract the curcuminoids active principles by using solvents to be avoided.
- a still further object is to make available an oil for food use containing curcuminoids active principles, in which the titre in curcuminoids active principles is substantially predetermined and high and which is provided with a suitable resistance to oxidation.
- a method for producing a turmeric oil solution as defined in claim 1.
- a turmeric oil solution is provided, as defined in claim 10.
- a method for producing a turmeric oil solution and a corresponding product are made available, which enable the previously mentioned objects to be achieved.
- the method according to the invention enables a turmeric oil solution to be produced that is usable as an oil for food use, which is provided with a suitable resistance to the oxidation during cooking or frying.
- the method according to the invention does not require an extraction step with solvents and enables an end product to be obtained in which the minimum total amount in curcuminoids active principles is at least 500 ppm, this making the turmeric oil solution according to the invention able to carry a predetermined amount of curcuminoids active principles.
- Applicants could verify that by mixing high oleic sunflower oil - i.e. a sunflower seed oil with high oleic acid (Cl 8:1) content - and a turmeric powder containing a predetermined total amount of curcuminoids active principles it is possible to produce a turmeric oil solution (which can also be defined as“turmeric oleolite”) having peculiar properties.
- high oleic sunflower oil i.e. a sunflower seed oil with high oleic acid (Cl 8:1) content - and a turmeric powder containing a predetermined total amount of curcuminoids active principles it is possible to produce a turmeric oil solution (which can also be defined as“turmeric oleolite”) having peculiar properties.
- the turmeric oil solution according to the invention is provided with a resistance to the forced oxidation that is greater than the resistance to the forced oxidation with which a high oleic sunflower oil is provided in the absence of curcuminoids active principles.
- the resistance to the forced oxidation exhibited by the turmeric oil solution according to the invention is greater than the resistance to the forced oxidation that could be expected because of the simultaneous presence of high oleic sunflower oil and curcuminoids active principles. Therefore, the Applicants hypothesised a new and surprisingly unexpected synergic effect due to the presence of curcuminoids active principles in a total amount of at least 500 ppm in a high oleic sunflower oil.
- Figure 1 is a chromatogram relating to the chromatographic elution of a standard solution mixture of curcumin, bisdemethoxycurcumin and demethoxycurcumin;
- Figure 2 is a chromatogram relating to the chromatographic elution of a sample of oil solution according to the invention
- Figure 3 is a graph illustrating the outcomes of an analytical evaluation of the total antioxidant activity of the phenol fraction in samples of oil solution according to the invention and in samples of high oleic sunflower oil;
- Figure 4 is a graph illustrating the outcomes of a further analytical evaluation of the total antioxidant activity of the phenol fraction in samples of oil solution according to the invention and in samples of high oleic sunflower oil.
- curcuminoids “curcuminoids active principles” and“active principles of the turmeric” are considered to be synonyms and are used interchangeably;
- the terms“high oleic sunflower oil” and“sunflower seed oil with high oleic acid content” define a sunflower oil that contains at least 80% of oleic acid on the total of fatty acids.
- the turmeric oil solution according to the invention has been obtained by the Applicants by mixing a high oleic sunflower oil, i.e. a sunflower oil containing at least 80% of oleic acid on the total of fatty acids, and a selected turmeric powder, with a 0.5:10 (w/w) oil / turmeric powder ratio.
- the mixture of oil and turmeric powder is produced by stirring (for example through rocking stirrer and at a speed of 250 oscillations/minute) at a temperature comprised between 40°C and 60°C for at least 24 hours in a closed system saturated with inert gas, in particular nitrogen (for example, a container with a sealing stopper and a headspace saturated with nitrogen).
- the turmeric powder has been selected on the basis of the total content thereof in curcuminoids active principles (curcumin, bisdemethoxycurcumin and demethoxycurcumin).
- curcumin, bisdemethoxycurcumin and demethoxycurcumin curcumin active principles
- a turmeric powder has been used containing from 2.22% to 2.85% in curcuminoids active principles.
- the mixture of oil and turmeric powder thus obtained has been subsequently filtered, obtaining an oil solution that is clear and devoid of suspended material.
- the filtering step can be performed by using known methods and devices and can comprise, for example, a filtration by gravity onto a paper filter.
- the stirring step can be performed in a tank that is of suitable capacity and is equipped internally with a motorized mechanical stirrer (for example, a blade stirrer).
- a motorized mechanical stirrer for example, a blade stirrer
- the tank can be provided with a heating gap or liner, which can be supplied with a suitable heating fluid (for example, water), as well as with one or more thermometric probes for the control of the temperature.
- the tank can be equipped with a sealing lid, with safety valves and with a tube for the bubbling of nitrogen into the mixture being stirred.
- a sealing lid In order to perform the filtering step, it is possible to use, for example, an alluviation filter.
- the finished product (turmeric oil solution) has been subsequently analyzed by the Applicants.
- the total content in curcuminoids and the resistance to the forced oxidation have been determined.
- the latter is measured in hours and is determined through evaluation of the oxidative stability index (OSI) at H0°C.
- OSI oxidative stability index
- a procedure for determining analytically the total content in curcuminoids in a turmeric oil solution according to the invention (Example 1); a procedure for evaluating experimentally the oxidative stability index of a turmeric oil solution according to the invention (Example 2); a procedure of evaluation of raw materials that are usable in the method according to the invention (Example 3); a procedure for the preparation in laboratory of a turmeric oil solution according to the invention (Example 4); outcomes of analyses conducted on prototypes of turmeric oil solution according to the invention (Example 5); outcomes of analytical comparisons between a turmeric oil solution according to the invention and samples of high oleic sunflower oil (Example 6); considerations emerging from the experimental plan prepared and implemented by the Applicants (Example 7).
- the total content in curcuminoids of the turmeric oil solution according to the invention has been determined analytically by RP-HPLC (high performance liquid chromatography in reverse phase).
- the extraction of the curcuminoids active principles is carried out with methanol, according to what is indicated by M. Paramasivam ( M . Paramasivam, R. Poi, H. Banerjee, A. Bandy opadhy ay: High-performance thin layer chromatographic method for quantitative _determination of curcuminoids in Curcuma longa germplasm. Food Chem. 113, 640-644, 2009).
- turmeric oil solution is weighed and the extraction is carried out by adding 10 ml of methanol, stirring the mixture of oil solution and methanol through vortex (model ST5, Janke & Kunkel, Germany) for 1 minute, placing the mixture in an ultrasound bath (Branson 2510) for 15 minutes, centrifuging (ALC PK 120 model, ALC, Italy) and repeating the extraction another 2 times in the same mode.
- the collected methanol fractions are gathered and dried with rotating evaporator (Rotavapor, Buchi R-200). The residue is dissolved in methanol, brought up to the appropriate volume to obtain the optimum concentration necessary for chromatography injection and filtered with a 0.45 pm nylon filter (Phenomenex).
- the method for the chromatographic determination is the one, appropriately modified, suggested by R. Li (Rui Li, Cheng Xiang, Min Ye, Hui-Fang Li, Xing Zhang, De-An Guo: Qualitative and quantitative analysis of curcuminoids in herbal medicines derived from Curcuma species, Food Chemistry 126 (2011) 1890-1895).
- the signal is monitored through a photodiode detector, at a 420 nm wavelength.
- the quantification of the curcuminoids active principles is then carried out with the method of the external standard, through the construction of calibration curves obtained by evaluating solutions with known concentration of analytical standards of pure curcumin for analysis (Sigma-Aldrich, Steinheim, Germany), bisdemethoxycurcumin (>98%-HPLC_Sigma- Aldrich, Steinheim, Germany) and demethoxycurcumin (>98%-HPLC Sigma-Aldrich, Steinheim, Germany).
- Figure 1 shows a chromatogram (indicated by the letter A) relating to the chromatographic elution of a standard solution mixture of curcumin (CU), bisdemethoxycurcumin (BDMC) and demethoxycurcumin (DMC).
- the stability against the oxidation, or oxidative stability index (OSI), of a turmeric oil solution according to the invention has been evaluated experimentally by measuring the so-called Osi-Time.
- the oxidative stability is determined by subjecting the oil solution to a forced oxidation, which is induced through heating and bubbling of air in standardized conditions.
- a tool of known type is used, in which the tested oil solution is heated to H0°C in the presence of a continuous flow of air having a speed of 150 ml/min. In this manner the end products of the oxidation step, above all organic acids such as formic acid, are induced first to volatilize and then to solubilize in bidistilled water.
- the resistance to the oxidation is determined by an electrode, which measures the variations in conductivity of the deionized water in which the air flow arrives that contains the volatilized substances.
- the instrument extrapolates, from the initial step of the oxidation to the step in which the oxidation takes on an exponential trend, the datum relating to the induction period, expressed in hours and hundredths of hours and named as Osi-Time ( Jebe , Matlock, Sleeter, 1993: Collaborative study of the Oil Stability Index Analysis. - JAOCS, Vol. 70, 1055-1061).
- the instrument (OSI-8, produced by Omnion Scientific Instruments under licence from Archer Daniels Midland Co.) has 8 housings that are thermostated at H0°C, in each of which a glass sample-holding tube can be inserted that contains 5 ⁇ 0.1 g of oil to be tested. Air is blown into each tube at a flowrate of 150 ml/min. Each tube containing the sample is connected to a polycarbonate tube containing 50 ml of bidistilled water, in which the volatile substances are bubbled that are formed during the oxidation of the lipid matrix of the oil solution and which are conveyed by the air flow. Inside the polycarbonate tube the electrode is contained by means of which it is possible to measure continuously the variation in conductivity of the bidistilled water. Alternatively to the measurement of the Osi-Time, it is possible to use another method that is based on the forced oxidation, which is named as AOM (Active Oxygen Method) and is standardized (AOCS Standard Method Cd-l2-b92).
- AOM Active Oxygen Method
- Example 3 Evaluation of raw materials to be used in the method according to the invention (high oleic sunflower oil; turmeric powder)
- An analytic evaluation has been made of the raw materials to be used in the method according to the invention, i.e. high oleic sunflower oil and turmeric powder.
- turmeric three different typologies of dried powdered turmeric (provided by three different Manufacturers) were evaluated, in which both the content of total curcuminoids and the quantity of each single curcuminoid - bisdemethoxycurcumin (BDMC), demethoxycurcumin (DMC) and curcumin (CET) - were quantified. From the obtained results, it is inferred that BDMC, DMC and CU are present in the evaluated samples, but in very different amounts. In different turmeric powders, above all different BDMC and DMC contents are pointed out, with an always prevalent presence of CU.
- BDMC single curcuminoid - bisdemethoxycurcumin
- DMC demethoxycurcumin
- CET curcumin
- the powders of turmeric belonging to the Curcuma longa L. species were selected in order to produce the turmeric oil solution according to the invention and in the preparation of prototypes of turmeric oil solution the two typologies of powder corresponding to Sample 2 and Sample 3 of Table 2 have been used, namely the two samples containing the greatest quantity of total curcuminoids.
- the oil solution of turmeric powder has been kept under constant stirring for 48 h, through a DLH model (Velp Scientifica) rod mechanical stirrer at 370-450 rpm. Once completed the stirring step, the turmeric oil solution has been filtered by gravity onto a paper filter.
- oleic sunflower oil upon receipt of the oil and“Osi-Time HOS” indicates the determination carried out on the high oleic sunflower oil on the date on which the prototype of turmeric oil solution has been produced.
- Sample 2 has exhibited an Osi-Time value of 23.15 h and a total curcuminoids content of 923.80 ppm, whilst Sample 3 has exhibited an Osi-Time value of 24.83 h and a total curcuminoids content of 810.62 ppm.
- Example 6 Analytical evaluation of the variation in the total antioxidant activity of the phenol fraction in a turmeric oil solution according to the invention and in samples of high oleic sunflower oil
- the spectrophotometric reading of the absorbance is carried out at regular time intervals, for a total incubation time of 35 minutes.
- the results of the analysis are expressed as percentage of inhibition of the DPPH ⁇ radical.
- the samples are stored in the dark in a cool and dry place until the DPPH ⁇ test is carried out.
- Sample of turmeric oil solution according to the invention made by using a high oleic sunflower oil produced by the Applicant Oleificio Zucchi Spa (sample named as“FS” hereinafter);
- the FS sample (turmeric oil solution according to the invention) shows a significant antioxidant activity (>55%) at all the investigated experimental times (tO, tl and tF) and that such activity is as well significantly greater than that of all the other analyzed samples (p ⁇ 0.000l).
- the FO sample commercially available high oleic sunflower oil
- the FO sample shows a lower antioxidant activity than the FS sample ( ⁇ 20%)
- the FO sample is however provided with an antioxidant activity that is higher than that of the FZ and FE samples.
- the method according to the invention enables a product based on turmeric powder and high oleic sunflower oil (turmeric oil solution) to be obtained that is suitable for human consumption, has a predetermined content (at least 500 ppm) of curcuminoids active principles (curcumin, bisdemethoxycurcumin and demethoxycurcumin) and is provided with a resistance to the forced oxidation that is at least 10% higher than the resistance to the forced oxidation of a high oleic sunflower oil as sampled (i.e. without addition of turmeric powder).
- the aforesaid resistance to the forced oxidation is intended as measured in hours and determined by evaluation of the oxidative stability index (OSI) at 1 l0°C.
- OSI oxidative stability index
- turmeric oil solution according to the invention it is possible to point out a synergic action (between the curcuminoids active principles and the high content in oleic acid of the sunflower oil), which provides the turmeric oil solution with a significant resistance to the oxidation.
- the turmeric oil solution according to the invention is particularly stable against the oxidation and the thermal treatments, being thus suitable not only for the use as a food condiment, but also for cooking and frying foods.
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IT201700147630 | 2017-12-20 | ||
PCT/IB2018/060004 WO2019123135A1 (en) | 2017-12-20 | 2018-12-13 | Method for producing a turmeric-based oil solution for food use |
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CA2388889C (en) * | 1996-04-26 | 2006-06-13 | E.I. Du Pont De Nemours And Company | Soybean oil having high oxidative stability |
US6497908B1 (en) * | 1999-07-19 | 2002-12-24 | Seiri Oshiro | Turmeric-containing cooking oils and fats |
WO2010111070A1 (en) * | 2009-03-26 | 2010-09-30 | Abbott Laboratories | Nutritional composition comprising curcuminoids and methods of manufacture |
CN103960378B (en) * | 2013-01-30 | 2016-10-05 | 丰禾生技股份有限公司 | Edible oil constituent containing curcumin chemical compounds and preparation method thereof |
RU2590804C1 (en) * | 2015-04-14 | 2016-07-10 | Акционерное общество "Нижегородский масло-жировой комбинат" | Composition for frying |
ITMO20150082A1 (en) * | 2015-04-16 | 2016-10-16 | Olitalia S R L | COMPOSITION OF EDIBLE OIL, ESPECIALLY FOR USE IN FRYING AND COOKING FOOD |
KR20160130111A (en) * | 2015-05-01 | 2016-11-10 | 이용화 | Edible-oil containing curcuma longa and manufacturing process thereof |
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