CN113736558A - Oil composition containing litsea cubeba kernel oil and preparation method and application thereof - Google Patents
Oil composition containing litsea cubeba kernel oil and preparation method and application thereof Download PDFInfo
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- CN113736558A CN113736558A CN202110836451.9A CN202110836451A CN113736558A CN 113736558 A CN113736558 A CN 113736558A CN 202110836451 A CN202110836451 A CN 202110836451A CN 113736558 A CN113736558 A CN 113736558A
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- litsea cubeba
- kernel oil
- cubeba kernel
- grease
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- 240000002262 Litsea cubeba Species 0.000 title claims abstract description 80
- 235000012854 Litsea cubeba Nutrition 0.000 title claims abstract description 80
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000003921 oil Substances 0.000 claims abstract description 141
- 235000019198 oils Nutrition 0.000 claims abstract description 140
- 239000004519 grease Substances 0.000 claims abstract description 48
- 150000002148 esters Chemical class 0.000 claims abstract description 43
- 230000008018 melting Effects 0.000 claims abstract description 37
- 238000002844 melting Methods 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 34
- 108090000790 Enzymes Proteins 0.000 claims abstract description 29
- 102000004190 Enzymes Human genes 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 19
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000002156 mixing Methods 0.000 claims abstract description 14
- 235000019482 Palm oil Nutrition 0.000 claims abstract description 11
- 230000004048 modification Effects 0.000 claims abstract description 11
- 238000012986 modification Methods 0.000 claims abstract description 11
- 239000002540 palm oil Substances 0.000 claims abstract description 11
- 239000008160 cosmetics carrier oil Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000013329 compounding Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims description 41
- 238000003756 stirring Methods 0.000 claims description 21
- 238000005194 fractionation Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 108010048733 Lipozyme Proteins 0.000 claims description 11
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 108090001060 Lipase Proteins 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- 102000004882 Lipase Human genes 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 claims description 2
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- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 23
- 238000007254 oxidation reaction Methods 0.000 abstract description 23
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract description 18
- 229960001295 tocopherol Drugs 0.000 abstract description 18
- 229930003799 tocopherol Natural products 0.000 abstract description 18
- 235000010384 tocopherol Nutrition 0.000 abstract description 18
- 239000011732 tocopherol Substances 0.000 abstract description 18
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 abstract description 18
- 230000036760 body temperature Effects 0.000 abstract description 13
- 230000007760 free radical scavenging Effects 0.000 abstract description 6
- 238000007670 refining Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 19
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 17
- 230000006698 induction Effects 0.000 description 15
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- 239000005639 Lauric acid Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229940116364 hard fat Drugs 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002292 Radical scavenging effect Effects 0.000 description 3
- 235000011869 dried fruits Nutrition 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 235000019441 ethanol Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
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- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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Images
Classifications
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- 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
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead
-
- 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
- C11B3/006—Refining fats or fatty oils by extraction
-
- 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
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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Abstract
The invention discloses a grease composition containing litsea cubeba kernel oil, a preparation method and application thereof. The method comprises the following steps: separating and extracting the litsea cubeba kernel oil to obtain litsea cubeba kernel oil stearin and litsea cubeba kernel oil soft ester; compounding Litsea cubeba kernel oil stearin and Litsea cubeba kernel oil soft ester to obtain grease A; mixing 10-15 parts of grease A and 85-90 parts of palm oil by weight, adding an enzyme catalyst into the mixture, setting the reaction temperature, performing ester exchange modification, and removing the enzyme preparation after the modification is finished. The melting point of the grease composition prepared by the invention is suitable for body temperature, the hydrophobicity is reduced, the skin feeling is enhanced, the refractive index is reduced, the viscosity spreadability is enhanced, the loss of tocopherol content is small, the oxidation stability is reserved, and the free radical scavenging capacity is enhanced; the oil and fat composition can be used as cosmetic base oil without refining and deacidifying.
Description
Technical Field
The invention belongs to the field of light industrial oil, and particularly relates to an oil composition containing litsea cubeba kernel oil, a preparation method and application thereof.
Background
The oil and fat can form a hydrophobic film on the surface of the skin, can prevent the invasion of external harmful substances and resist the invasion of various factors from the nature to a certain extent while endowing the skin with softness, lubrication and glossiness, so that the skin is smooth, soft and elastic and is kept in a good healthy state. The application of the plastic grease in the cosmetics is wider, the plastic grease can improve the spreadability of the cosmetics, and the skin feel of the skin care product is determined to a great extent. Meanwhile, the ointment has great influence on the appearance, viscosity, product stability, efficacy, irritation and the like of the ointment. Under the influence of the tendency of people to return to nature and chose green, the application of natural oil in cosmetics gradually becomes a hot point, palm oil has the advantages of high yield, low price, high thermal stability, oxidation stability and the like, and is the most common plastic fat raw material oil in the industrial field, but the crystallization of the palm oil is slow, the lubricating property of the oil is reduced, and the skin feel is poor. With the improvement of the oil modification technology, the modified vegetable oil has good compatibility due to good physical and chemical properties, and gradually replaces mineral oil and natural vegetable oil.
However, common vegetable oil has the problems of crystallization, strong hydrophobicity, waxy feeling during the use of cosmetics, poor skin feeling and higher refractive index, which leads to low transparency of cosmetic emulsion, and the traditional method is realized by increasing the refractive index of a water phase. For example, some lower alcohols: propylene glycol, glycerin, 1, 3-butylene glycol, and the like have refractive indices of substantially 1 or more. Therefore, propylene glycol, glycerin, 1, 3-butylene glycol, etc. can be used to adjust the refractive index of the water phase, so that the refractive indexes of the oil phase and the water phase are consistent, thereby obtaining a transparent emulsified body, but this will result in an increase in the cost of auxiliary materials.
Disclosure of Invention
Aiming at the defects of high price of mineral oil and poor skin feel of vegetable oil at present, the invention mainly aims to provide a preparation method of a litsea cubeba kernel oil-containing oil composition. The oil composition is prepared by uniformly mixing palm olein (with the melting point of 24 ℃) and litsea cubeba kernel oil extract and utilizing an enzymatic catalysis transesterification reaction.
The invention also aims to provide the oil composition containing the litsea cubeba kernel oil prepared by the method.
The invention further aims to provide application of the litsea cubeba kernel oil-containing oil composition. The oil and fat composition can be used as cosmetic base oil.
The purpose of the invention is realized by the following technical scheme:
a preparation method of a grease composition containing litsea cubeba kernel oil comprises the following steps:
(1) separating and extracting the litsea cubeba kernel oil to obtain litsea cubeba kernel oil stearin and litsea cubeba kernel oil soft ester;
(2) compounding Litsea cubeba kernel oil stearin and Litsea cubeba kernel oil soft ester to obtain grease A;
(3) mixing 10-15 parts of grease A and 85-90 parts of palm oil by weight, wherein the total weight of litsea cubeba kernel oil and palm oil is 100 parts by weight; adding an enzyme catalyst into the mixture, setting the reaction temperature, performing ester exchange modification, and removing an enzyme preparation after the modification is finished to obtain the litsea cubeba kernel oil-containing oil composition.
The litsea cubeba kernel oil in the step (1) is oil which is extracted from litsea cubeba dry fruits by an organic solvent or by physical squeezing and has the solid fat content of 30-40 percent at 10 ℃.
The fractionation in the step (1) is solvent fractionation or physical fractionation, and the solid fat content of the Litsea cubeba kernel oil stearin at 10 ℃ is 50-55%, and the solid fat content of the Litsea cubeba kernel oil soft ester at 10 ℃ is 20-30%.
The specific steps of the fractionation in the step (1) are as follows: melting Litsea cubeba kernel oil, adding n-hexane for dissolving, stirring and soaking at 20-25 deg.C in water bath for 60-100min until solid substances are separated out, and stirring at 100-; after stirring and dipping, carrying out suction filtration to separate a solid part and a liquid part; removing the solvent from the liquid part to obtain Litsea cubeba kernel oil soft ester, and removing the solvent from the solid part to obtain Litsea cubeba kernel oil stearin.
In the step (2), the solid fat content of the grease A at 10 ℃ is 40-45%.
In the step (2), the litsea cubeba kernel oil stearin and the litsea cubeba kernel oil soft ester are compounded according to the mass ratio of 6-7:3-4, preferably the mass ratio of 7:3, compounding.
The palm oil in the step (3) is commercial palm liquid oil with the melting point of 24 ℃.
In the step (3), the weight ratio of the grease A to the palm oil is 15: 85.
in the step (3), the enzyme catalyst is a low-temperature enzyme, preferably immobilized lipase Lipozyme TL IM or Lipozyme RM IM, and the addition amount of the enzyme catalyst is 1-5% of the mass of the substrate; the temperature of the ester exchange reaction is 50-80 ℃, and the reaction time is 30-60 min.
In the step (3), the adding amount of the enzyme catalyst is 5% of the mass of the substrate; the temperature of the transesterification reaction was 60 ℃ and the reaction time was 30 min.
Removing the enzyme preparation by filtration after the modification in step (3) is completed.
The oil composition containing litsea cubeba kernel oil prepared by the invention can be used as cosmetic base oil without refining and deacidification.
Compared with the prior art, the invention has the following advantages and beneficial effects:
the litsea cubeba kernel oil rich in lauric acid (C12:0) and lauric acid (C12:1) is used as a raw material, a litsea cubeba kernel oil fractionation substance is obtained through fractionation, the fractionation substance is re-compounded to obtain the oil A, the oil A and palm olein are subjected to enzymatic transesterification modification to obtain the oil composition, and the raw material and the product are not required to be refined and deacidified, so that the preparation method of the oil composition is more environment-friendly and efficient.
Compared with common vegetable oil, the grease composition prepared by the invention has the advantages that the melting point is suitable for body temperature, the hydrophobicity is reduced, the skin feeling is enhanced, the refractive index is reduced, the viscosity spreadability is enhanced, the loss of tocopherol content is small, the oxidation stability is reserved, the free radical scavenging capacity is enhanced, and the grease composition is a good choice for the cosmetic base oil.
The modified grease can reduce the refractive index of the grease from the oil phase, reduce the hydrophobicity of the grease, enhance the spreadability, improve the skin feel of the product, and improve the oxidation stability of the grease without adding an antioxidant.
Drawings
FIG. 1 is the change in the hydrophobic contact angle of the product.
FIG. 2 is the product 1, 1-diphenyl-2-trinitrophenylhydrazine (DPPH) radical clearance data.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto. The raw materials related to the invention can be directly purchased from the market. For process parameters not specifically noted, reference may be made to conventional techniques. The palm olein used in the examples and comparative examples had a melting point of 24 ℃. The immobilized lipases used in the examples are all available from Novitin.
The invention aims to obtain the grease composition by extracting and re-compounding the litsea cubeba kernel oil, and after the composition is mixed with palm liquid oil and subjected to ester exchange, the base oil which has proper solid fat content (moderate hardness) and smooth temperature change can be prepared and can be applied to cosmetics. Compared with the traditional vegetable oil, the spreadability of the cosmetic base oil is increased, the melting point is close to the body temperature, the hydrophobicity is reduced, the refractive index is reduced, the free radical scavenging capacity is enhanced, and the tocopherol content is not lost, so that the oxidation stability is reserved.
Example 1
1. Preparation of ester exchange modified grease
(1) Drying the litsea cubeba dried fruits in a 105 ℃ oven for 2h, taking out and crushing the litsea cubeba dried fruits by using a crusher, sieving the crushed litsea cubeba dried fruits by using a 100-mesh sieve, weighing 1000g of litsea cubeba powder, adding 3000mL of n-hexane into a 35 ℃ water bath kettle, sealing and stirring the mixture for 20min, centrifuging the mixture to remove residues, and performing rotary evaporation on the residual liquid part to remove an organic solvent to obtain the litsea cubeba kernel oil.
(2) Weighing 300g of litsea cubeba kernel oil sample, melting the litsea cubeba kernel oil sample in a beaker, adding 1500mL of n-hexane to dissolve the oil sample, immersing the beaker in a water bath kettle at 25 ℃ for stirring, stirring and immersing for 60min until solid substances are separated out, stirring at the rotating speed of 200 r/min, and performing suction filtration by using a Buchner funnel to separate out a solid part and a liquid part. The solid part is litsea cubeba kernel oil stearin, the liquid part is subjected to rotary evaporation to recover n-hexane to obtain litsea cubeba kernel oil soft ester, the stearin and the soft ester are both placed in a high-temperature explosion-proof oven, residual solvent is removed, and the final fractionated sample is obtained.
(3) Weighing 70g of Litsea cubeba kernel oil stearin and 30g of Litsea cubeba kernel oil soft ester respectively at a mass ratio of 7:3, and uniformly mixing to obtain oil A; weighing 15g of grease A and 85g of palm liquid oil, heating, melting and uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
2. Characterization of the transesterification modified oils
(1) Solid fat content
Determination of Solid Fat Content (SFC) with reference to AOCS Official Method Cd 16-81, 3mL of oil sample is taken to be placed in a solid fat determination tube, melted for 30min at 60 ℃ to eliminate crystal memory, then transferred to 0 ℃ for 60min, and then transferred to 10, 20, 25, 30, 35 and 40 ℃ for 30min respectively to determine SFC value at each temperature. The flatter the solid fat changes with temperature, the better the spreadability of the fat.
(2) Tocopherol content
Determining the content of the tocopherol component by adopting an Agilent 1260 type high performance liquid chromatograph, wherein the chromatographic conditions are as follows: the fluorescence detector has a detection wavelength of 330nm, mobile phase of chromatographic acetonitrile and chromatographic methanol (9: 1), flow rate of 1mL/min, column temperature of 40 deg.C, sample injection amount of 20 μ L, and detection time of 14 min.
(3) Stability to oxidation
The oxidation stability analysis is carried out by a Rancimat method, the weight of the grease weighed out from the sample is 3.0g, the treatment temperature is 120 ℃, the aeration flow rate is 20L/h, and the oxidation induction time is recorded. The longer the induction time, the better the oxidative stability.
(4) Hydrophobicity
The hydrophobicity of the grease is expressed by the contact angle, and the laboratory test method is as follows: after melting, placing the sample in a mold with the thickness of 6mm for solidification for 24h, then placing 1 drop of deionized water on the surface of the sample, recording the contact angle degree of the water drop and the surface of the sample after 1min, and proving that the surface of the sample is more hydrophobic when the contact angle is larger.
(5) Viscosity of the solution
Performing viscosity test by using Malvern rheometer test, and testing shear rate at 0.1-100s-1。
(6) Refractive index
The refractometer is used for measuring the refractive index of grease, a drop of melted grease is dripped on the grease prism, the upper prism and the lower prism are closed, the reflector is adjusted to enable light to be injected into the prism, the light is observed by the eyepiece, the prism knob is rotated to enable the visual field to be divided into a light part and a dark part, the prism knob is rotated to enable the light and dark boundary to be at the cross point, and reading is carried out on the graduated scale through the magnifying glass.
(7) Free radical scavenging rate
And (3) testing the free radical clearance, namely adding 4.0mL of 1, 1-diphenyl-2-trinitrophenylhydrazine (DPPH) solution into a 10mL volumetric flask, then adding 4.0mL of solution to be tested, then adding absolute ethyl alcohol to fix the volume to a scale mark, and shaking up. Immediately, the 1cm cuvette was rinsed with the test solution, and then its optical density value (OD1) was measured at a wavelength of 517nm, and then the cuvette was stored at room temperature in the dark for 30min, and then its optical density value (OD2) was measured. The control test was performed by adding 4.0mL of ethanol solution of DPPH alone, and measuring the optical density (OD 3). Similarly, the Optical Density (OD) values of the other samples to be measured were measured by the above-described method. The measurement was repeated 3 times, and the average value was taken as the final result. The measured clearance was compared to the clearance of the vitamin C standard. The radical clearance K (%) (experimental OD 1-experimental OD 2)/blank OD3 × 100% was calculated as follows.
(8) Melting point determination
The melting point is expressed as the sliding melting point temperature, and is measured by the capillary method, with reference to the method of ISO6321, and is measured by a melting point apparatus, and the sliding melting point is an integral part.
The solid fat content of the ester-exchanged oil and fat obtained in the embodiment 1 is remarkably improved at each temperature point, the change trend is more gradual, the spreadability of the oil and fat is improved, meanwhile, the melting point and the body temperature are close to 37 ℃, the viscosity is 128mPa & s, the refractive index is 1.4254, the tocopherol content is 120.65ug/g, the oxidation induction time is 3.38h, the hydrophobicity angle is reduced to 77.5 degrees, and the free radical scavenging rate is 43.1%.
Example 2
The present example is the same as example 1 except for the following technical features: weighing 10g of grease A and 90g of palm olein in the step (3), heating, melting and uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 36 ℃, the viscosity is 132mPa & s, the refractive index is 1.4324, the tocopherol content is 110.37ug/g, the oxidation induction time is 3.10h, the hydrophobicity angle is reduced to 79.3 ℃, and the radical clearance rate is 39.3%.
Example 3
The present example is the same as example 1 except for the following technical features: and (3) weighing 12g of grease A and 88g of palm olein, heating to melt, uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 36 ℃, the viscosity is 129mPa · s, the refractive index is 1.4297, the tocopherol content is 115.50ug/g, the oxidation induction time is 3.18h, the hydrophobicity angle is reduced to 78.2 ℃, and the radical clearance is 40.3%.
Example 4
The present example is the same as example 1 except for the following technical features: and (2) immersing the beaker into a water bath kettle at the temperature of 20 ℃ for stirring, stirring and immersing for 100min until solid substances are separated out, stirring at the rotating speed of 100 revolutions per minute, and performing suction filtration by using a Buchner funnel to separate out a solid part and a liquid part.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 37 ℃, the viscosity is 131mPa & s, the refractive index is 1.4310, the tocopherol content is 113.20ug/g, the oxidation induction time is 3.11h, the hydrophobicity angle is reduced to 79.0 ℃, and the radical clearance is 41.5%.
Example 5
The present example is the same as example 1 except for the following technical features: and (3) weighing 60g of Litsea cubeba kernel oil stearin and 40g of Litsea cubeba kernel oil soft ester respectively in a mass ratio of 6:4, and uniformly mixing to obtain the grease A.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 36 ℃, the viscosity is 121mPa & s, the refractive index is 1.4307, the tocopherol content is 120.50ug/g, the oxidation induction time is 3.23h, the hydrophobicity angle is reduced to 77.7 ℃, and the radical clearance rate is 39.5%.
Example 6
The present example is the same as example 1 except for the following technical features: and (3) adding 5g of immobilized lipase Lipozyme RM IM, stirring for reaction to fully react the oil with the enzyme, and collecting an oil sample which is the enzyme-process ester-exchanged oil after reacting for 30 min.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 37 ℃, the viscosity is 130mPa & s, the refractive index is 1.4299, the tocopherol content is 118.15ug/g, the oxidation induction time is 3.21h, the hydrophobicity angle is reduced to 79.7 ℃, and the radical clearance is 40.6%.
Example 7
The present example is the same as example 1 except for the following technical features: and (3) setting the reaction temperature to be 80 ℃, adding 1g of immobilized lipase Lipozyme TL IM, stirring for reaction, fully reacting oil and enzyme, and collecting an oil sample which is the enzyme method ester exchange oil after reacting for 60 min.
Through detection and calculation by the method in the embodiment 1, the solid fat content of the ester-exchanged grease obtained in the step (3) in the embodiment is remarkably improved at each temperature point, the change trend is relatively smooth, the spreadability of the grease is improved, the melting point and the body temperature are close to 37 ℃, the viscosity is 118mPa & s, the refractive index is 1.4289, the tocopherol content is 109.15ug/g, the oxidation induction time is 3.00h, the hydrophobicity angle is reduced to 78.0 ℃, and the radical clearance rate is 37.5%.
Comparative example 1
This comparative example is the same as example 1 except for the following technical features: and (3) weighing 15g of grease A and 85g of palm olein, heating to melt, and uniformly mixing without performing ester exchange.
Through detection and calculation by the method described in example 1, the product of the comparative example has a steep change trend of solid fat content, substantially no solid fat at 25 ℃, no spreadability, a low melting point of only 25 ℃, a liquid at room temperature, a viscosity of 108mPa · s, a relatively high refractive index of 1.4647, a tocopherol content of 127.65ug/g, an oxidation induction time of 3.48h, a hydrophobic angle of 81.4 degrees, and a radical scavenging rate of 29.0%.
Comparative example 2
This comparative example is the same as example 1 except for the following technical features: weighing 15g of litsea cubeba kernel oil and 85g of palm liquid oil in the step (3), heating, melting and uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
Through detection and calculation by the method described in example 1, the ester-exchanged grease obtained in step (3) of the comparative example has slightly increased solid fat content at various temperature points, lower solid fat at 35 and 40 ℃, slightly poor spreadability, slightly lower melting point than body temperature of 35 ℃, slightly lower viscosity of 109mPa · s, refractive index of 1.4430, tocopherol content of 117.76ug/g, oxidation induction time of 3.20h, reduced hydrophobic angle of 78.0 degrees, and free radical scavenging rate of 39.5%.
Comparative example 3
This comparative example is the same as example 1 except for the following technical features: and (3) weighing 20g of grease A and 80g of palm olein, heating to melt, uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
Through detection and calculation by the method described in example 1, the solid fat content of the ester-exchanged oil obtained in step (3) of the comparative example is obviously increased at each temperature point, but the solid fat at 35 ℃ and 40 ℃ is too high, the spreadability is influenced by too high hardness, the melting point is higher than the body temperature of 40 ℃, the waxy feeling is strong, the viscosity is obviously increased to 137mPa & s, the skin feeling is poor, the refractive index is 1.4422, the tocopherol content is 121.33ug/g, the oxidation induction time is 3.39h, the hydrophobic angle is reduced to 77.1 ℃, and the radical scavenging rate is 41.3%.
Comparative example 4
This comparative example is the same as example 1 except for the following technical features: weighing 15g of litsea cubeba kernel oil fractionated soft ester and 85g of palm olein, heating to melt and uniformly mixing, and then putting into a reactor, wherein the reaction temperature is set to be 60 ℃. When the temperature is constant, 5g of immobilized lipase Lipozyme TL IM is added, stirring is carried out for reaction, oil and enzyme are fully reacted, and an oil sample is collected after the reaction is carried out for 30min and is used as the enzyme method ester exchange oil.
Through detection and calculation by the method described in example 1, the ester-exchanged grease obtained in step (3) of the comparative example has an increased solid fat content, but the increase is not obvious, the solid fat at 35 ℃ and 40 ℃ is still low, the spreadability is slightly poor, the melting point is lower than the body temperature, only 33 ℃, the viscosity is slightly lower than 111mPa · s, the refractive index is 1.4534, the tocopherol content is 119.47ug/g, the oxidation induction time is 3.05h, the hydrophobic angle is reduced to 79.1 degrees, and the radical clearance is 40.3%.
Comparative example 5
This comparative example is the same as example 1 except for the following technical features: and (3) weighing 100g of palm olein, heating to melt and uniformly mixing without performing ester exchange.
Through detection and calculation by the method described in example 1, the product of the comparative example has a low solid fat content, a melting point of 24 ℃, no spreadability, a viscosity of 87mPa · s, a refractive index of 1.4659 as high as possible, a tocopherol content of 50.85ug/g as low as possible, an oxidation induction time of 1.80h, a maximum hydrophobic angle of 84.9 degrees, and a radical scavenging rate of 24.8%.
Table 1 shows the solid fat content (%) and melting point data at different temperatures for litsea cubeba kernel oil and its fractionated products, examples and comparative examples.
Table 2 shows the tocopherol contents and oxidation induction times of the products of the examples and comparative examples.
Table 3 is the viscosity and refractive index changes of the products of the examples and comparative examples.
TABLE 1
TABLE 2
TABLE 3
And (4) conclusion: the Litsea cubeba kernel oil is rich in medium-short-carbon-chain fatty acids such as lauric acid, myristic acid and lauric acid, and after fractionation, the lauric acid and lauric acid are enriched in stearin. The litsea cubeba kernel oil is subjected to fractionation of hard fat and fractionation of soft ester and then compounded according to a certain proportion to obtain a composition, after the composition is subjected to ester exchange with palm olein, the cosmetic base oil with the melting point of 36-37 ℃ and capable of remarkably improving the spreadability and viscosity of the product can be obtained, and if the ester exchange is not carried out, the indexes of the product such as the melting point, the spreadability and the viscosity cannot meet the requirements of the cosmetic base oil; if the content of the stearin in the composition is too high, the melting point of the ester exchange product is too high, and the skin feeling is poor when the ester exchange product is used as cosmetic base oil; if the amount of the soft ester in the composition is too high, the melting point of the transesterified product is too low, the oxidation stability is lowered, and the viscosity is lowered. In addition, the proper combination of hard fat and soft fat can obtain better fatty acid composition, and the hard fat is rich in more lauric acid, so that the content of hard fat is increased, and the hydrophobicity and the free radical clearance rate of the final transesterification product are also obviously influenced. The increase of the content of the lauric acid is that after ester exchange, the hydrophobic contact angle of a product is reduced, the product is more hydrophilic, the radical clearance rate of a glyceride product after ester exchange is obviously improved, the refractive index of the product is also obviously reduced, the transparency when the product is compounded into emulsion is correspondingly improved, the radical clearance rate of cosmetic base oil can be improved by adding the litsea cubeba kernel oil composition, the hydrophobic contact angle is reduced, and better oxidation stability is obtained, but in order to take care of the spreadability and the melting point of the product, the proper proportion of the stearin and soft ester of the litsea cubeba kernel oil needs to be comprehensively considered, and ester exchange is carried out.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A preparation method of a grease composition containing litsea cubeba kernel oil is characterized by comprising the following steps:
(1) separating and extracting the litsea cubeba kernel oil to obtain litsea cubeba kernel oil stearin and litsea cubeba kernel oil soft ester;
(2) compounding Litsea cubeba kernel oil stearin and Litsea cubeba kernel oil soft ester to obtain grease A;
(3) mixing 10-15 parts of grease A and 85-90 parts of palm oil by weight, wherein the total weight of litsea cubeba kernel oil and palm oil is 100 parts by weight; adding an enzyme catalyst into the mixture, setting the reaction temperature, performing ester exchange modification, and removing an enzyme preparation after the modification is finished to obtain the litsea cubeba kernel oil-containing oil composition.
2. The method for preparing the oil and fat composition containing the litsea cubeba kernel oil according to claim 1, wherein the litsea cubeba kernel oil in the step (1) is the oil and fat which is extracted from dried litsea cubeba fruits by an organic solvent or by physical pressing and has the solid fat content of 30-40% at 10 ℃.
3. The method for preparing the oil and fat composition containing the litsea cubeba kernel oil as claimed in claim 1, wherein the fractionation in the step (1) is solvent fractionation or physical fractionation, and the obtained litsea cubeba kernel oil stearin has a solid fat content of 50-55% at 10 ℃, and litsea cubeba kernel oil soft ester has a solid fat content of 20-30% at 10 ℃.
4. The preparation method of the oil and fat composition containing the litsea cubeba kernel oil according to claim 3, characterized in that the fractionation in the step (1) comprises the following specific steps: melting Litsea cubeba kernel oil, adding n-hexane for dissolving, stirring and soaking at 20-25 deg.C in water bath for 60-100min until solid substances are separated out, and stirring at 100-; after stirring and dipping, carrying out suction filtration to separate a solid part and a liquid part; removing the solvent from the liquid part to obtain Litsea cubeba kernel oil soft ester, and removing the solvent from the solid part to obtain Litsea cubeba kernel oil stearin.
5. The preparation method of the oil composition containing the litsea cubeba kernel oil according to claim 1, characterized in that the solid fat content of the oil A at 10 ℃ in the step (2) is 40-45%;
the litsea cubeba kernel oil stearin and the litsea cubeba kernel oil soft ester in the step (2) are compounded according to the mass ratio of 6-7: 3-4.
6. The method for preparing the litsea cubeba kernel oil-containing fat composition according to claim 1, wherein the palm oil in the step (3) is palm olein with a melting point of 24 ℃;
in the step (3), the weight ratio of the grease A to the palm oil is 15: 85.
7. the method for preparing the oil and fat composition containing the litsea cubeba kernel oil according to claim 1, characterized in that the enzyme catalyst in the step (3) is immobilized lipase TL IM or Lipozyme RM IM, and the adding amount of the enzyme catalyst is 1-5% of the substrate mass; the temperature of the ester exchange reaction is 50-80 ℃, and the reaction time is 30-60 min.
8. The preparation method of the oil and fat composition containing the litsea cubeba kernel oil as claimed in claim 1, wherein the addition amount of the enzyme catalyst in the step (3) is 5% of the mass of the substrate; the temperature of the transesterification reaction was 60 ℃ and the reaction time was 30 min.
9. An oil and fat composition containing Litsea cubeba kernel oil obtained by the method of any one of claims 1 to 8.
10. Use of the litsea cubeba kernel oil-containing fat composition according to claim 9 as a cosmetic base oil.
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| CN109699760A (en) * | 2019-03-13 | 2019-05-03 | 广州市至润油脂食品工业有限公司 | Fat composition and preparation method comprising Ba Sha fish oil and the application in margarine |
| CN109984216A (en) * | 2019-04-03 | 2019-07-09 | 暨南大学 | A method of preparing substitution butter special fat |
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| CN107821642A (en) * | 2017-11-09 | 2018-03-23 | 天津吉好食品有限公司 | Non-hydrogenated oil/fat composition and oil-in-water type whipped cream and preparation method thereof |
| CN109699760A (en) * | 2019-03-13 | 2019-05-03 | 广州市至润油脂食品工业有限公司 | Fat composition and preparation method comprising Ba Sha fish oil and the application in margarine |
| CN109984216A (en) * | 2019-04-03 | 2019-07-09 | 暨南大学 | A method of preparing substitution butter special fat |
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