Lipid blend

Abstract

The present invention relates to a blend comprising fatty acids and / or lipids such as sphingolipids, wherein the blend comprises C in an amount between approximately 0.5 and 30 wt%. 22 -C 38 The present invention also relates to compositions containing aliphatic alcohols and lipid blends. The present invention further provides a method for producing the lipid blend on a large scale, wherein rice bran wax (RBW) is used as a source of fatty acids.

Description

[Technical Field]

[0001] The present invention relates to a lipid blend containing fatty acids and / or ceramides, and a method for producing the same. [Background technology]

[0002] Sphingolipids are an important class of polar lipids, primarily found on the surface of eukaryotic cells. Their structural features lie in a sphingoid base backbone and an N-acyl group derived from fatty acids. Sphingolipids may be further divided into distinct classes such as ceramides and sphingoglycolipids.

[0003] Sphingolipids are involved in various biological processes and play important structural and functional roles such as cell-cell recognition, communication, and intercellular adhesion. In particular, sphingoglycolipids (e.g., gangliosides) are found in the brain and play a role in neurological diseases, while ceramides are the main components of the stratum corneum lipid layer and play a major role in the moisture retention properties of the epidermis and the barrier function of the skin.

[0004] Therefore, sphingolipids have great potential as therapeutic agents and cosmetics.

[0005] Human skin contains over 1000 different ceramide types. Ceramides are N-acylated sphingoid bases, which lack an additional head group at the 1-position of the sphingoid base skeleton, where the N-acyl group of ceramide is typically derived from a fatty acid. The high diversity of ceramides stems from their molecular structure, which may consist of various combinations of sphingoid base and acyl group moieties. The diversity and complexity of ceramide molecules present a challenge to their low-cost industrial production, which typically involves synthesizing each component of ceramide molecules through a single procedure, each procedure generally comprising multiple steps.

[0006] Large-scale production of sphingoid bases has already progressed, and the sphingoid bases may be used as building units for synthesizing ceramides (WO2009150022, WO2013023878, WO2017033463, WO201923897).

[0007] Sphingoid bases, such as phytosphingosine, its derivatives and its ceramides, are currently commercially available (e.g., Skinmimics® of Evonik). However, the majority of commercially available ceramides contain an acyl group portion of palmitic acid or stearic acid (C 16 or C 18 acyl group), while naturally occurring ceramides typically contain a long acyl group portion.

[0008] Ceramides containing a long acyl group portion (i.e., ≥ C 20 acyl group) and long fatty acids (i.e., ≥ C 20 ) are not widely commercialized, but there is a great demand for their applications in cosmetics and therapeutics. In fact, according to reports, skin rich in blends containing ceramides with a long acyl group portion (i.e., ≥ C 20 acyl group) and / or long-chain fatty acids (i.e., ≥ C 20 ) has an improved barrier function, as described, for example, in Smeden et al., J. Invest. Dermatol [Journal of Investigative Dermatology] 2014, 134:1238-1245.

[0009] Natural sources of fatty acids are vegetable oils and waxes. Fatty acids can be produced by biotechnology, but biotechnological production is still limited to medium-chain length fatty acids such as C 16 -C 18 fatty acids.

[0010] Plant waxes, especially rice bran wax (RBW), have a unique composition of very long-chain esters and, therefore, long-chain fatty acids (e.g., C 22 -C 38It may also be used as a source of fatty acids. Recently, plant waxes (especially carnauba wax) have been fractionally distilled to obtain more than 60 wt% C 26 -C 33 Very long-chain fatty acids containing fatty acids (≧C 24 Industrially applicable techniques for obtaining the fatty acids have already been described (WO2022124600). However, the referenced document does not describe a method for synthesizing ceramide using the resulting fatty acids.

[0011] The production of ceramides from sphingoid bases may be carried out chemically or enzymatically.

[0012] Chemical or enzymatic methods for producing ceramides are typically based on the N-acylation of sphingoid bases, which may include the use of acylating agents such as acyl chloride (WO0172701A1), activators such as 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (Skolova et al., Biochim Biophys Acta Biomembr. [Biochemical and Biophysical Journal - Biomembrane Division] 2017, 1859, 824-834, WO0172701A1), or enzymes such as lipases (WO1994026919A1, US2011077302A1). Alternatively, acid esters have already been used for the N-acylation of phytosphingosine and dihydrosphingosine (EP2757090A1, EP2796444A1).

[0013] However, currently, ceramides containing very long-chain fatty acids or long-chain acyl groups are not commercially available, and their industrial-scale production is a challenge. [Brief explanation of the drawing]

[0014] [Figure 1] This is a schematic diagram of a method for producing lipid blends. [Overview of the Initiative]

[0015] In a first aspect, the present invention relates to a method for producing a lipid blend from defatted and saponified rice bran wax (dsRBW), wherein the dsRBW comprises 50 wt% aliphatic alcohols, and the blend is -A lipid having formula (1) in an amount of approximately 70-99.5 wt%, [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, R 2 -OH and / or -NHR 3 Selected from, here, R 3 This is the part having equation (2), [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6This is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen. -Contains approximately 0.5-30 wt% aliphatic alcohols, Here, The method described above includes the step of reducing the aliphatic alcohol content of the dsRBW or its derivative to approximately 0.5 to 30 wt%.

[0016] In a second aspect, the present invention relates to a lipid blend comprising a lipid having formula (1), [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, R 2 -OH and / or -NHR 3 Selected from, here, R 3 This is the part having equation (2), [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6 is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen. Here, the lipid blend contains approximately 0.5-30 wt% C 22 -C 38 Contains aliphatic alcohols.

[0017] In a third aspect, the present invention relates to a cosmetic or therapeutic composition, which comprises the lipid blend of the second aspect.

[0018] In a fourth aspect, the present invention relates to the use of lipid blends or compositions containing them for maintaining physiologically normal skin barrier function in an individual or for improving impaired skin barrier function. [Modes for carrying out the invention]

[0019] The present invention relates to a blend comprising lipids such as fatty acids and / or sphingolipids, wherein the majority of the lipids are long-chain fatty acids, for example C 22 and C 24 The blend represents or contains fatty acids (behenic acid and tetracosanoic acid, respectively). In one preferred embodiment, the blend contains at least 50 wt% lipids, which are long-chain fatty acids, such as C15. 22 and C 24 Represents or contains fatty acids. According to the present invention, the lipid blend contains C between approximately 0.5 and 30 wt%. 22 -C 38 It also contains aliphatic alcohols.

[0020] The present invention further provides a method for producing the lipid blend on a large scale, wherein rice bran wax (RBW) is used as a source of fatty acids.

[0021] Unless otherwise specified, terms and definitions described herein should be understood to apply to all aspects and embodiments of the present invention.

[0022] The term "one / type (a)" is grammatically singular, but it can also mean the plural form of a desired compound, for example. For example, a person skilled in the art will understand that the expression "lipid having formula (1)" can refer not only to providing a single lipid having formula (1), but also to providing multiple lipids having formula (1).

[0023] The terms “about,” “around,” or “approximately” are interchangeable and, as understood by those skilled in the art, mean values ​​or ranges close to these terms and include a deviation of up to 10 percent from the following value or range.

[0024] The term "at least" refers to an unlimited range of values ​​starting from the indicated value, or, in the case of a wt% range, a range from the indicated value up to 100 wt%.

[0025] The terms “blend,” “composition,” “mixture,” or “mix” refer to a combination of different elements (e.g., molecules), where the component elements are all different, and in some embodiments, the component elements may be the same, while in other embodiments, the difference between them may be one or more structural features.

[0026] The terms "derivative" and "derivate" are interchangeable and refer to compounds synthesized by chemically replacing one or a set of atoms from a structurally similar compound. For example, esters are derivatives of carboxylic acids.

[0027] As used herein, the term “group” means several (two or more) identical or structurally different entities that exist simultaneously in the same location, such as one or more molecules in a composition.

[0028] The term "cosmetic" refers to the improvement of appearance, particularly the appearance of keratinous tissue (i.e., human skin and hair).

[0029] The term "therapeutic" refers to the cure of a disease or pathological condition.

[0030] As used herein, the term “treat” means, in different embodiments, to cosmetically resolve a deterioration in the appearance of keratin tissue or to therapeutically resolve a pathological condition or disease, with the aim of improving or stabilizing the patient’s outcomes, addressing potential needs, or preventing the progression of a pathological condition or disease by maintaining a normal / healthy state. “Treatening” and “treatment” have grammatically corresponding meanings. Treatment includes both cosmetic and therapeutic treatments, preferably performed topically.

[0031] The term "local treatment / therapy" refers to treatments / therapy applied to the surface of the body (e.g., skin).

[0032] Throughout this specification, "wt%" refers to the amount of the nominated substance contained in 100g of the nominated composition, for example, at least about 50 wt% of C 22 and C 24 Blends containing fatty acids typically contain at least 50g of C per 100g. 22 and C 24 This means it contains fatty acids.

[0033] In a formula representing a part or group (for example, an alkyl group having formula (2)), the symbol [ka] This refers to a bonding site with another group or atom.

[0034] As used herein, the various functional groups or substituents represented are understood to have a bonding site at the functional group or atom where the bond line (-) is located. For example, -OR 7 In this case, the bonding site is understood to be an oxygen atom. When groups without bonding lines are listed, the bonding site is indicated by the usual and general meaning of the listed group.

[0035] Those skilled in the art will understand that when referring to positions C-1, C-2, C-3, C-4, C-5, etc., in this specification, the corresponding carbon atoms of a lysosphingolipid having formula (5), a lipid having formula (6), or a moiety having formula (2) are always being referred to. Positions C-1, C-2, C-3, C-4, and C-5 may also be called positions 1-, 2-, 3-, 4-, and 5-, respectively.

[0036] Those skilled in the art will understand that in formulas representing specific compounds, such as formulas (2), (5), or (6), unless the chemical formula explicitly states which carbon atoms have a specific stereochemical configuration, the formula is intended to cover compounds in which such stereocenters have an R or S configuration, or in which the double bond has a cis or trans configuration.

[0037] As used herein, the term “hydrocarbyl group (alkyl)” refers to an acyclic linear or branched hydrocarbyl group having 1 to 50 carbon atoms, which may be saturated, or contain one or more double and / or triple bonds (thus forming, for example, an alkenyl or alkynyl group), and / or be substituted or unsubstituted, as further described herein. Typically, the term hydrocarbyl group refers to a linear acyclic hydrocarbyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted.

[0038] As used herein, the term “aryl group” refers to a cyclic aromatic hydrocarbyl group having 5 to 14 cyclic carbon atoms, which may be monocyclic or polycyclic, contain fused rings, preferably 1 to 3 fused or unfused rings, and contain one or more heteroatoms, and / or be substituted or unsubstituted, as further described herein. Examples of “aryl groups” include, but are not limited to, phenyl, naphthyl, anthryl, phenanthryl, pyrrolyl, imidazolyl, thienyl, furyl, oxazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, and benzofuryl groups, each of which may be substituted or unsubstituted. Typically, the term “aryl group” refers to a substituted or unsubstituted phenyl group.

[0039] As used herein, the term “acyl group” refers to a group derived by removing one or more hydroxyls from an oxoacid, preferably a carboxylic acid. The acyl groups according to the present invention are typically saturated or unsaturated C2-C2 groups. 34 It is an acyl group, which may be substituted or unsubstituted.

[0040] As used herein, the term “substitution” refers to the substitution of a group under consideration with a group that typically alters the general chemical properties of the group under consideration. Substituents can be used to alter molecular properties such as molecular stability, molecular solubility, or the molecular’s ​​ability to form crystals. Those skilled in the art will recognize that other suitable substituents having similar size and charge properties may be used as substitutes in a given case.

[0041] Regarding the terms "alkyl group," "aryl group," and "acyl group," the term substitution refers to the group being considered as follows: hydroxyl group (which may exist in the form of a tautomeristic ketone group when bonded to an unsaturated carbon atom), oxo, C1-C6-alkoxy group (i.e., C1-C6-alkyl-oxy group), C2-C6-alkenyloxy group, carboxyl group, oxo, C1-C6-alkoxycarbonyl group, C1-C6-alkylcarbonyl group, formyl group, aryl group, aryloxy Carbonyl group, aryloxy group, arylamino group, arylcarbonyl group, heteroaryl group, heteroarylamino group, heteroaryloxycarbonyl group, heteroaryloxy group, heteroarylcarbonyl group, amino group, mono- and di-(C1-C6-alkyl)amino group, aminoformyl group, mono- and di-(C1-C6-alkyl)aminocarbonyl group, amino-C1-C6-alkyl-aminocarbonyl group, mono- and di-(C1-C6-alkyl) (L) Amino-C1-C6-alkyl-aminocarbonyl group, C1-C6-alkylcarbonylamino group, cyano group, guanidino group, ureido group, C1-C6-alkyl-sulfonyl-amino group, aryl-sulfonyl-amino group, heteroaryl-sulfonyl-amino group, C1-C6-alkanoyloxy group, C1-C6-alkyl-sulfonyl group, C1-C6-alkyl-sulfinyl group, C1-C6-alkylsulfonyloxy group, nitro group, C1-C6-al This refers to substitution with one or more groups selected from a kylthio group and a halogen, preferably 1 to 3 times, where any alkyl group, alkoxy group, etc. representing the substituent can be substituted with a hydroxyl group, a C1-C6-alkoxy group, a C2-C6-alkenyloxy group, a carboxyl group, a C1-C6-alkylcarbonylamino group, a halogen, a C1-C6-alkylthio group, a C1-C6-alkyl-sulfonyl-amino group, or a guanidino group.

[0042] For the term "alkyl group", the term "substituted" preferably refers to the group under consideration being substituted one or more times, preferably 1 to 3 times, with one or more groups selected from hydroxy groups, alkoxy groups, acyloxy groups, amide groups, thiols, thioethers or phosphorus-containing functional groups.

[0043] As used herein, the term "glycosyl moiety" is defined to include a moiety derived from a monosaccharide or an oligosaccharide (more than one monosaccharide unit), where the anomeric carbon of the monosaccharide or the anomeric carbon of the reducing end of the oligosaccharide is bonded to another chemical entity via a glycosidic bond, and unless otherwise stated, the bond may be an α or β glycosidic bond. A glycosyl moiety having more than one monosaccharide unit can represent a linear or branched structure.

[0044] The monosaccharide unit can be any sugar having 5 to 9 carbon atoms, including aldoses (e.g., D-glucose, D-galactose, D-mannose, D-ribose, D-arabinose, L-arabinose, D-xylose, etc.), ketoses (e.g., D-fructose, D-sorbose, D-tagatose, etc.), deoxysugars (e.g., L-rhamnose, L-fucose, etc.), deoxy-amino sugars (e.g., N-acetylglucosamine, N-acetylmannosamine, N-acetylgalactosamine, etc.), uronic acids, ketoaldonic acids (e.g., sialic acid). The monosaccharide unit can form different cyclic structures such as pyranose (6-member) cyclic structures or furanose (5-member) cyclic structures.

[0045] The glycosyl moiety according to the present invention may be represented in the form of Galβ1-4Glc1-, where the dash (-) represents the binding site of the glycosyl moiety, and here, the glycosyl moiety can be linked via an α or β glycosidic bond, preferably a β glycosidic bond.

[0046] As used herein, the term "aliphatic alcohol" refers to an acyclic aliphatic primary alcohol, preferably C 38 ​22 -C 38 This refers to acyclic aliphatic primary alcohols. Aliphatic alcohols may be straight-chain or branched, and saturated or unsaturated.

[0047] In the context of this invention, the term "lipid" refers to hydrophobic or amphiphilic molecules such as fatty acids, sphingolipids, sphingoglycolipids, and phospholipids.

[0048] The lipids according to the present invention are typically represented by lipids having formula (1), [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, R 2 -OH and / or -NHR 3 Selected from, here, R 3 This is the part having equation (2), [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] is R 5 When R is hydrogen, it may be a double bond or a single bond, or R 5 is -OR 7 in which case it is a single bond, R 6 is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen.

[0049] In some embodiments, R of the lipid having the formula (1) 2 is -OH. Therefore, in some embodiments, the lipid having the formula (1) is a fatty acid having the formula (3),

Chemical formula

[0050] In some embodiments, R of the lipid having the formula (1) 2 is -NHR 3 where R 3 is a moiety having the formula (2). Therefore, in some embodiments, the lipid having the formula (1) is a lipid having the formula (6),

Chemical formula

Chemical formula

[0051] In some embodiments, for the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6), R 4 is a saturated unsubstituted C 13 -C 17 alkyl group, R 5 is -OH, R 6 is hydrogen, and the bond

Chemical formula

[0052] In some embodiments, for the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6), R 4 is a saturated unsubstituted C 13 -C 17 alkyl group, R 5 and R 6It is hydrogen and bonded [ka] It is a single bond.

[0053] In some examples, the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6) are R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 and R 6 It is hydrogen and bonded [ka] It is a double bond.

[0054] In some preferred embodiments, W is hydrogen in the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6). Therefore, in some preferred embodiments, the lipid having formula (1) is the lipid having formula (6), where the lipid having formula (6) is ceramide.

[0055] In some examples, the lipid having formula (6) is a ceramide selected from the group consisting of CER[NP], CER[NDS], CER[NS], or CER[NH].

[0056] In some embodiments, the present invention is C8-C 34 Non-hydroxy fatty acids (N), preferably C 14 -C 30 This paper describes a method for producing a blend containing ceramides with an acyl group moiety of a non-hydroxy fatty acid (N).

[0057] In some embodiments, the present invention is C8-C 34 Non-hydroxy fatty acids (N) and C8-C 34 A method for producing a blend containing a ceramide having an acyl group moiety of a non-hydroxy fatty acid (N) is described.

[0058] In some embodiments, the present invention is C 14 -C 30 Non-hydroxy fatty acids (N) and C 14 -C 30 A method for producing a blend containing a ceramide having an acyl group moiety of a non-hydroxy fatty acid (N) is described.

[0059] In some embodiments, the present invention describes a method for producing a blend containing CER[N(8-34:0)P(18)].

[0060] In some embodiments, the present invention describes a method for producing a blend containing CER[N(14-30:0)P(18)].

[0061] In some embodiments, the present invention describes a method for producing a blend containing CER[N(8-34:0)DS(18)].

[0062] In some embodiments, the present invention describes a method for producing a blend containing CER[N(14-30:0)DS(18)].

[0063] In some embodiments, the present invention describes a method for producing a blend containing CER[N(8-34:0)S(18)].

[0064] In some embodiments, the present invention describes a method for producing a blend containing CER[N(14-30:0)S(18)].

[0065] In some embodiments, the present invention describes a method for producing a blend containing CER[N(8-34:0)H(18)].

[0066] In some embodiments, the present invention describes a method for producing a blend containing CER[N(14-30:0)H(18)].

[0067] In some embodiments, the present invention describes a method for producing a blend comprising CER[N(8-34:0)P(18)] and CER[N(8-34:0)DS(18)].

[0068] In some embodiments, the present invention describes a method for producing a blend comprising CER[N(14-30:0)P(18)] and CER[N(14-30:0)DS(18)].

[0069] In some embodiments, the present invention is C8-C 34 This document describes a method for producing a blend containing non-hydroxy fatty acids and CER[N(8-34:0)P(18)].

[0070] In some embodiments, the present invention is C 14 -C 30 This paper describes a method for producing a blend containing non-hydroxy fatty acids and CER[N(14-30:0)P(18)].

[0071] In some embodiments, the present invention is C8-C 34 A method for producing a blend containing non-hydroxy fatty acids and CER[N(8-34:0)DS(18)] is described.

[0072] In some embodiments, the present invention is C 14 -C 30 A method for producing a blend containing non-hydroxy fatty acids CER[N(14-30:0)P(18)] and CER[N(14-30:0)DS(18)] is described.

[0073] In the context of this invention, ceramide refers to naturally occurring ceramides, their analogues, or derivatives. Preferred ceramides are those naturally occurring in humans. Naturally occurring human-type ceramides (CERs) include, but are not limited to, CER[NS], CER[AS], CER[EOS], CER[NH], CER[AH], or CER[EOH], CER[NP], CER[AP], or CER[EOP], CER[NDS], CER[ADS], or CER[EODS]. Here, the letters in parentheses refer to an abbreviation developed by Motta et al., Biochim Biophys Acta. [Biochemical and Biophysical Journal], 1993, 1182:147-151, and extended by Rabionet et al., Biochim Biophys Acta [Biochemical and Biophysical Journal], 2014, 1841:422-434 and Masukawa et al., Journal of Lipid Research [Journal of Lipid Research], 2008, 49, 1466-1476. The letters N, A, and EO represent non-hydroxy fatty acids (N), α-hydroxy fatty acids (A), and ω-linoleoyloxy fatty acids (EO), respectively, where the number of fatty acid carbons and the number of unsaturated carbons can be expressed in parentheses after the letters N, A, E, and O. The letters S, H, P, and DS represent ortho-erythro-sphingosine (S), 6-hydroxy-D-erythro-sphingosine (H), D-ribo-phytosphingosine (P), and D-erythro-dihydrosphingosine (DS), respectively, where the number of sphingosine carbons can be expressed in parentheses after the letters S, H, P, and DS. Ceramides CER[NDS], CER[ADS], or CER[EODS] may also be called CER[NG], CER[AG], or CER[EOG], respectively, where the letter G represents the INCI name for D-erythro-dihydrosphingosine.

[0074] In some examples, W is the glycosyl moiety for the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6). Therefore, in some examples, the lipid having formula (1) is the lipid having formula (6), where the lipid having formula (6) is a sphingoglycolipid.

[0075] In some preferred embodiments, W is a glycosyl moiety selected from the group consisting of Glc1-, Gal1-, and Galβ1-4Glc1-.

[0076] In some embodiments, the present invention is C8-C 34 This paper describes a method for producing a blend containing a sphingoglycolipid having an acyl group moiety of a non-hydroxy fatty acid [N(8-34:0)].

[0077] In some examples, for lipids having formula (6), W is Glc1-.

[0078] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of GlcCER[N(8-34:0)P(18)], GlcCER[N(8-34:0)DS(18)], GlcCER[N(8-34:0)S(18)], or GlcCER[N(8-34:0)H(18)].

[0079] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of GlcCER[N(14-30:0)P(18)], GlcCER[N(14-30:0)DS(18)], GlcCER[N(14-30:0)S(18)], or GlcCER[N(14-30:0)H(18)].

[0080] In some examples, for lipids having formula (6), W is Gal1-.

[0081] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of GalCER[N(8-34:0)P(18)], GalCER[N(8-34:0)DS(18)], GalCER[N(8-34:0)S(18)], or GalCER[N(8-34:0)H(18)].

[0082] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of GalCER[N(14-30:0)P(18)], GalCER[N(14-30:0)DS(18)], GalCER[N(14-30:0)S(18)], or GalCER[N(14-30:0)H(18)].

[0083] In some examples, for lipids having formula (6), W is Galβ1-4Glc1-.

[0084] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of LacCER[N(8-34:0)P(18)], LacCER[N(8-34:0)DS(18)], LacCER[N(8-34:0)S(18)], or LacCER[N(8-34:0)H(18)].

[0085] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of LacCER[N(14-30:0)P(18)], LacCER[N(14-30:0)DS(18)], LacCER[N(14-30:0)S(18)], or LacCER[N(14-30:0)H(18)].

[0086] In some embodiments, the present invention is C8-C 34 Non-hydroxy fatty acids (N) and C8-C 34 A method for producing a blend containing a sphingoglycolipid having an acyl group moiety of a non-hydroxy fatty acid (N) is described.

[0087] In some embodiments, the present invention is C14 -C 30 Non-hydroxy fatty acids (N) and C 14 -C 30 A method for producing a blend containing a sphingoglycolipid having an acyl group moiety of a non-hydroxy fatty acid (N) is described.

[0088] As used herein, the term "lysosphingolipid" refers to a sphingolipid lacking an amide-bonded fatty acid at the C-2 position of its sphingoid base backbone. Suitable lysosphingolipids as used in the context of the present invention are sphingoid bases, glycosylated sphingoid bases and their analogues, and are preferably represented by lysosphingolipids having formula (5). [ka] Here, W is either H or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6 This is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen.

[0089] In some examples, for lysosphingolipids having formula (5), R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 is -OH, and R 6 It is hydrogen and bonded [ka] It is a single bond.

[0090] In some examples, for lysosphingolipids having formula (5), R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 and R 6 It is hydrogen and bonded [ka] It is a single bond.

[0091] In some examples, for lysosphingolipids having formula (5), R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 and R 6 It is hydrogen and bonded [ka] It is a double bond.

[0092] In some examples, W is H in the lysosphingolipid having formula (5). Therefore, in some examples, the lysosphingolipid having formula (5) is a sphingoid base.

[0093] In some examples, the lysosphingolipid having formula (5) is a sphingoid base selected from the group consisting of D-erythro-sphingosine [S(18)], 6-hydroxy-D-erythro-sphingosine [H(18)], D-ribo-phytosphingosine [P(18)], and D-erythro-dihydrosphingosine [DS(18)].

[0094] In some preferred embodiments, the lysosphingolipid having formula (5) is D-ribo-phytosphingosine [P(18)].

[0095] In some preferred embodiments, the lysosphingolipid having formula (5) is D-erythro-dihydrosphingosine [DS(18)].

[0096] In some examples, the lysosphingolipid having formula (5) is a mixture of D-ribo-phytosphingosine [P(18)] and D-erythro-dihydrosphingosine [DS(18)].

[0097] In some examples, W is the glycosyl moiety of the lysosphingolipid having formula (5). Therefore, in some examples, the lysosphingolipid having formula (5) is a glycosylated sphingoid base.

[0098] In some preferred embodiments, W is a glycosyl moiety selected from the group consisting of Glc1-, Gal1-, and Galβ1-4Glc1-.

[0099] In some examples, W is Glc1-. Therefore, in some examples, the lysosphingolipid having formula (5) is a glycosylated sphingoid base selected from the group consisting of Glc[P(18)], Glc[DS(18)], Glc[S(18)], or Glc[H(18)].

[0100] In some examples, W is Gal1-. Therefore, in some examples, the lysosphingolipid having formula (5) is a glycosylated sphingoid base selected from the group consisting of Gal[P(18)], Gal[DS(18)], Gal[S(18)], or Gal[H(18)].

[0101] In some examples, W is Galβ1-4Glc1-. Therefore, in some examples, the lysosphingolipid having formula (5) is a glycosylated sphingoid base selected from the group consisting of Lac[P(18)], Lac[DS(18)], Lac[S(18)], or Lac[H(18)].

[0102] Lysosphingolipids used in the context of the present invention are preferably obtained by synthetic and / or biotechnical methods such as those described in Sarmientos et al., Eur.J.Biochem. [European Journal of Biochemistry] 1986, 160, 527-535.

[0103] In some examples, lysosphingolipids having formula (5) may be prepared or used in the form of a salt, preferably in the form of a pharmaceutically acceptable salt.

[0104] In some examples, salts of lysosphingolipids having formula (5) can be formed from the acids hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphate, acetic acid, camphor sulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and perchloric acid.

[0105] In some examples, the acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphate, and perchloric acid.

[0106] In some preferred embodiments, the acid is hydrochloric acid.

[0107] The term "one or more C8-C" as used herein 34 A "triazine acylating agent" refers to an activated derivative of a carboxylic acid, where the acidic hydroxyl group of the carboxylic acid is converted into a good leaving group by replacing a hydrogen atom with a 1,3,5-triazinyl group. Suitable triazine acylating agents used in the context of the present invention include, for example, those represented by formula (7), or combinations thereof. [ka] Here, [ka] This represents a conjugated system of bonds, where there are two or three double bonds in the ring. Y is C(OC(=O)R 1 ), or C (=O) are selected, X a N, NR 8 , or N(C(=O)R 1 ) are selected from, X b is N, or NR 8 Selected from, Z is C(=O), or C(OR 8 ) are selected from, And as a prerequisite, Y is C(OC(=O)R 1 If ) then Z is C(OR 8 ) and X a and X b It is N, and there are three double bonds in the ring, or Y is C(OC(=O)R 1 If ), then Z is C (=O) and X a and X b One of them is N, and the other is NR 8 And there are two double bonds in the ring, or If Y is C (=O), then Z is C (OR 8 ) and X a is N(C(=O)R 1 ) and X bIt is N, and there are two double bonds in the ring, where, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, R 8 The group is selected from a methyl group, an ethyl group, 2,2,2-trifluoroethyl, and a substituted or unsubstituted benzyl group, and is preferably a methyl group.

[0108] "X a and X b One of them is N, and the other is NR 8 The expression "is" is X a If is N, then another basis X b NR 8 is, or, X b If is N, then another basis X a NR 8 This refers to the fact that...

[0109] A suitable triazine acylating agent used in the context of the present invention is a single acyl group, for example, C8-C 34 Acyl group, preferably C 14 -C 30 They possess an acyl group. Triazine acylating agents with one acyl group can form several isomeric structures, which arise from the movement of substituents at different positions on the 1,3,5-triazine ring. Depending on conditions such as temperature, solvent, and / or the use of certain reagents, such as a base, these isomeric structures may be separated in pure form or obtained as an isomeric mixture.

[0110] Therefore, in the context of the present invention, the term "combination of triazine acylating agents" refers to a mixture containing triazine isomer structures, which differ only in the position of substituents on the triazine ring and can all function as acylating agents.

[0111] In some examples, the triazine acylating agent having formula (7) is a triazine acylating agent having formula (8), (9), (10), or (11). [ka] Here, R 1 and R 8 This is defined for triazine acylating agents having formula (7).

[0112] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (8), (9), (10), and (11), where each of the triazine acylating agents is present in an amount ranging from about 1% to about 99% in the combination.

[0113] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (8) and (10), where each of the triazines is present in an amount ranging from about 1% to about 99% in the combination.

[0114] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (8) and (10), where the triazine acylating agent having formula (8) is present in an amount of about 5% to about 75% in the combination.

[0115] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (8) and (10), where the triazine acylating agent having formula (9) is present in an amount of about 5% to about 75% in the combination.

[0116] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (9) and (11), where each of the triazines is present in an amount ranging from about 1% to about 99% in the combination.

[0117] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (9) and (11), where the triazine acylating agent having formula (8) is present in an amount of about 5% to about 50% in the combination.

[0118] In some examples, the triazine acylating agent having formula (7) is a combination of triazine acylating agents having formulas (9) and (11), where the triazine acylating agent having formula (10) is present in an amount of about 5% to about 50% in the combination.

[0119] In those examples describing combinations of triazine acyling agents, the amount of triazine acyling agent included in the combination is typically 1 This is determined by 1H NMR spectroscopy.

[0120] In a typical procedure, i. Recognize the characteristic signals of each triazine acylating agent from the combination. ii. Integrate these signals, iii. Calculate the integral ratio and use it for the amounts of different combinations of triazine acylating agents.

[0121] Those skilled in the art will understand that the amount of triazine acyling agent in a combination can be expressed as a molar ratio or mol%, or as a weight ratio or wt%. Those skilled in the art will further understand that, due to interconversion between different isomer structures of triazine acyling agents, the molar ratio or mol%, or weight ratio or wt% of triazine acyling agent in a combination may change over time.

[0122] In some preferred examples, the compound having formula (4) and the triazine acylating agent having formulas (8) to (11) are R 8 This is a methyl group.

[0123] The triazine-based acylating agents according to the present invention may be used or manufactured in different polymorphic forms. The polymorphic forms referred to herein may include crystalline and amorphous forms, as well as solvates and hydrates, which may be further characterized as follows:

[0124] i. The crystal morphology involves molecules with different arrangements and / or conformations within the crystal lattice. ii. Amorphous morphology consists of randomly arranged molecules that do not have a discernible crystal lattice. iii. Solvates are crystalline forms containing a stoichiometric or non-stoichiometric solvent. When the solvent incorporated is water, the solvate is usually called a hydrate.

[0125] The present invention provides a method for producing a lipid blend containing a lipid having formula (1) from defatted and saponified rice bran wax (dsRBW), wherein the dsRBW contains 50 wt% aliphatic alcohol, wherein the method comprises the step of reducing the aliphatic alcohol content of the dsRBW or its derivative to about 0.5 to 30 wt%.

[0126] dsRBW can be obtained by methods known to those skilled in the art, for example, by Vali et al., JAOCS [Journal of the American Oil and Fat Chemists] 2005, 82, 57-64, or by the methods described in Examples 1 and 2 below.

[0127] The step of reducing the aliphatic alcohol content is typically carried out by solvent extraction, which may be performed in continuous mode (e.g., Soxhlet extraction) or intermittently, and using one or more extraction solvents.

[0128] The solvent applied in the context of the present invention may be polar or nonpolar, and in particular, C1-C 10 Alkyl esters (e.g., ethyl acetate or butyl acetate), C1-C 10 Aliphatic nitriles (e.g., acetonitrile), C5-C 10 Hydrocarbons (e.g., n-heptane or cyclohexane) or supercritical fluids (e.g., supercritical CO2) may also be referred to. In some examples, one or more extraction solvents are selected from ethyl acetate, n-heptane, cyclohexane, acetonitrile, or supercritical CO2.

[0129] In some examples, the extraction solvent is ethyl acetate.

[0130] In some examples, the extraction solvent is supercritical CO2.

[0131] In some embodiments, extraction is carried out in continuous mode, where dsRBW or its derivatives are brought into contact with the extraction solvent under reflux temperature in a Soxhlet extractor. The extraction is continued for a time sufficient to extract most of the aliphatic alcohols from dsRBW or its derivatives. Typically, the extraction is continued for about 1 to 6 hours, preferably about 4 to 6 hours. Therefore, in some preferred embodiments, the extraction is continued for about 4, 4.5, 5, 5.5, or 6 hours. The solid residue rich in fatty acid salts or their derivatives is collected and used for further processing (e.g., solvent washing, drying, and / or another synthesis step).

[0132] In some embodiments, extraction is performed in intermittent mode, where dsRBW or its derivative is brought into contact with the extraction solvent at a temperature ranging from room temperature to reflux temperature, and the process is continued for a sufficient time to extract most of the aliphatic alcohols from the dsRBW or its derivative. Typically, the extraction is continued for about 1 to 4 hours, preferably about 1 to 2 hours. Therefore, in some preferred embodiments, the extraction is continued for about 1, 1.5, or 2 hours. The solvent extract containing the aliphatic alcohols is separated from the extraction slurry by filtration or centrifugation. The residue rich in fatty acid salts or their derivatives is collected and used for further processing (e.g., solvent washing, drying, and / or another synthesis step). Multiple extraction cycles may be performed on dsRBW or its derivative as described above.

[0133] The solvent extract obtained after continuous or intermittent extraction is rich in aliphatic alcohols.

[0134] Aliphatic alcohols have potential as therapeutic agents, cosmetics, and functional foods. Therefore, the recovery of aliphatic alcohols after extraction is attracting attention.

[0135] Aliphatic alcohols can be easily recovered from solvent extracts by further processing of the solvent extract.

[0136] Typically, in those examples where ethyl acetate is used as the extraction solvent, O-acetylated derivatives of aliphatic alcohols are formed during extraction. Therefore, in some examples, the solvent extract containing aliphatic alcohols and their O-acetylated derivatives is treated with acid.

[0137] Acid treatment of solvent extracts is typically carried out using inorganic or organic acids, preferably inorganic acids. Acids applicable in the context of the present invention include, but are not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphate, camphor sulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and perchloric acid.

[0138] In some examples, the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, and perchloric acid.

[0139] In some preferred embodiments, the acid is hydrochloric acid.

[0140] In some embodiments, the acid may be used in the form of an aqueous solution.

[0141] It is understood that the amount of acid used in a reaction depends on various factors such as the properties of the reactants (including the properties of the acid) and the reaction conditions used. Therefore, it should be understood that the amount of acid can be optimally and independently selected for each reaction.

[0142] Typically, acid treatment is carried out in a solvent, preferably a polar solvent.

[0143] In some examples, the solvent is methanol.

[0144] Acid treatment is typically carried out at temperatures between approximately 60°C and 65°C.

[0145] Therefore, in some examples, the acid treatment is carried out at a temperature of approximately 60°C, 61°C, 62°C, 63°C, 64°C, or 65°C.

[0146] It is understood that the components of the acid treatment can be combined in any order, and the order in which the reactants are combined can be adjusted as needed.

[0147] For example, an acid may be added to the solvent extract. Alternatively, the solvent extract may be added to a solution of acid.

[0148] Acids, solvent extracts, and any other reagents used during acid treatment may be added to the reaction in solid, liquid, or dissolved form in a solvent, in any amount and manner effective for the expected outcome of the reaction.

[0149] In some examples, aliphatic alcohols are precipitated from the reaction of an acid-treated mixture. Precipitation of the aliphatic alcohol can be achieved, for example, by partially removing the reaction solvent by evaporation (i.e., concentrating the reaction mixture), by adding another solvent to the reaction mixture, by changing the temperature or pressure, by adding another solute, or by a combination thereof.

[0150] In some examples, precipitation of aliphatic alcohols is achieved by cooling the acid-treated reaction mixture to about 0°C to about 30°C, preferably about 10°C to about 25°C. Therefore, in some preferred examples, precipitation of salts is achieved by cooling the reaction mixture to a temperature of about 10°C, 11°C, 12°C, 13°C, 14°C, 15°C, 16°C, 17°C, 18°C, 19°C, 20°C, 21°C, 22°C, 23°C, 24°C, or 25°C.

[0151] Following the above procedure, to process the solvent extract, add 55-65 wt% C 22 -C 36 Obtain an aliphatic alcohol blend containing aliphatic alcohols.

[0152] In some examples, the extraction of dsRBW or its derivatives is carried out by supercritical liquid CO2 (scrCO2) extraction.

[0153] scrCO2 extraction is a known technique for extracting oily, waxy, and fatty substances from rice bran, as described, for example, in Garcia A., et al., JAOCS [Journal of the American Oil and Fat Chemists] 1996, 73, 1127-1131, Moreira et al., The Journal of Supercritical Fluids 2023, 192, 105786, and CN102994215A. However, these references do not describe scrCO2 extraction of saponified blends derived from defatted rice bran wax (dsRBW).

[0154] According to the present invention, dsRBW or its derivatives can be extracted in a supercritical fluid apparatus using anhydrous carbonic acid at high pressure (250-500 bar) in a temperature range of about 40°C to about 120°C. The extraction process typically takes 1-4 hours. The dsRBW or its derivatives, rich in fatty acid salts or their derivatives, are collected and used for further processing (e.g., another synthesis step).

[0155] In some examples, scrCO2 extraction is carried out in the presence of a co-solvent.

[0156] Solvent extraction is typically performed using C 22 -C 38 This causes the aliphatic alcohol content to decrease from approximately 50 wt% to approximately 0.5-30 wt%. Therefore, in some examples, the aliphatic alcohol content may be reduced to approximately 0.5-5 wt%, or to approximately 5-10 wt%, or to approximately 10-20 wt%, or to approximately 20-30 wt%.

[0157] In some examples, the step of reducing the alcohol content is performed on a derivative of dsRBW.

[0158] Therefore, in some embodiments, the method is - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -dsRBW is reacted with C1-C6 alcohols in the presence of an acid to obtain a dsRBW derivative, where the derivative is C8-C 34 Fatty acid esters, preferably C 14 -C 30 A step comprising a fatty acid ester and approximately 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the derivative, approximately 70-99.5 wt% C8-C 34 Fatty acid esters, preferably C 14 -C 30The process includes the step of obtaining a blend containing fatty acid esters and approximately 0.5 to 30 wt% aliphatic alcohols.

[0159] The derivatives of dsRBW according to the present invention are typically obtained by reacting dsRBW with an alcohol in the presence of an acid, thereby C8-C 34 Preferably, C 14 -C 30 A dsRBW derivative is obtained that contains a fatty acid ester and an aliphatic alcohol in an amount between approximately 0.5 and 30 wt%.

[0160] Typically, dsRBW is reacted with an alcohol in the presence of an inorganic or organic acid, preferably an inorganic acid. Acids applicable in the context of the present invention include, but are not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, camphor sulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and perchloric acid.

[0161] In some examples, the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, and perchloric acid.

[0162] In some preferred embodiments, the acid is hydrochloric acid.

[0163] In some embodiments, the acid may be used in the form of an aqueous solution.

[0164] In some embodiments, the acid may be used in the form of an alcoholic solution.

[0165] It is understood that the amount of acid used in a reaction depends on various factors such as the properties of the reactants (including the properties of the acid) and the reaction conditions used. Therefore, it should be understood that the amount of acid can be optimally and independently selected for each reaction.

[0166] The alcohols applicable in the context of the present invention include, but are not limited to, C1-C7 alcohols or mixtures of C1-C7 alcohols.

[0167] In some examples, the alcohol is selected from methanol, ethanol, 1-propanol, isopropanol, 1-butanol, or isobutanol.

[0168] In some preferred embodiments, the alcohol is methanol.

[0169] Typically, dsRBW, alcohol, and acid are reacted at a temperature of about 50°C to about 60°C. Preferably, the reaction is carried out at a temperature of about 60°C to about 65°C. Therefore, in some preferred examples, the reaction is carried out at a temperature of about 60°C, 61°C, 62°C, 63°C, 64°C, or 65°C.

[0170] The reaction of dsRBW with alcohol results in the formation of a dsRBW derivative, where the derivative is C8-C 34 Fatty acid esters, preferably C 14 -C 30 It contains fatty acid esters and approximately 50 wt% aliphatic alcohols.

[0171] In some examples, extraction was performed using dsRBW, thereby obtaining C8-C 34 Fatty acid salt, preferably C 14 -C 30 A blend containing fatty acid salts is obtained, wherein the blend may further contain aliphatic alcohols in an amount between approximately 0.5 and 30 wt%.

[0172] Therefore, in some embodiments, the method is - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30The process includes the step of obtaining a blend containing a fatty acid salt and an aliphatic alcohol in an amount between approximately 0.5 and 30 wt%.

[0173] In some examples, the aliphatic alcohol content of the blend containing fatty acid salts is approximately 0.5–5 wt%.

[0174] In some examples, the aliphatic alcohol content of the blend containing fatty acid salts is approximately 5-10 wt%.

[0175] In some examples, the aliphatic alcohol content of the blend containing fatty acid salts is approximately 10–20 wt%.

[0176] In some examples, the aliphatic alcohol content of the blend containing fatty acid salts is approximately 20-30 wt%.

[0177] In some examples, the blend containing fatty acid salts contained at least 50 wt% C 22 and C 24 It contains fatty acid salts. Preferably, the ratio of the fatty acid salts is about 1:10 to about 10:1.

[0178] In some examples, the blend containing fatty acid salts contained at least 50 wt% C 22 and C 24 It contains fatty acid salts, and the ratio of these fatty acid salts is approximately 1:2.5.

[0179] In some embodiments, the method further comprises the step of treating a blend containing a fatty acid salt with an acid, thereby obtaining a fatty acid having formula (3), [ka] R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 Those that are alkyl groups, Obtain a blend containing aliphatic alcohols in the range of approximately 0.5 to 30 wt%.

[0180] Therefore, in some embodiments, the present invention describes a method for producing a lipid blend containing a lipid having formula (1), the method being - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30 A step to obtain a blend containing fatty acid salts and aliphatic alcohols in an amount between approximately 0.5 and 30 wt%, -The process includes the step of treating a blend containing fatty acid salts with acid to obtain a blend containing approximately 70-99.5 wt% of fatty acids having formula (3) and approximately 0.5-30 wt% of aliphatic alcohols.

[0181] Acid treatment of blends containing fatty acid salts is typically carried out by reacting the blend with an inorganic or organic acid, preferably an inorganic acid. Acids applicable in the context of the present invention include, but are not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphate, camphor sulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and perchloric acid.

[0182] In some examples, the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, and perchloric acid.

[0183] In some preferred embodiments, the acid is hydrochloric acid.

[0184] In some embodiments, the acid may be used in the form of an aqueous solution.

[0185] It is understood that the amount of acid used in a reaction depends on various factors such as the properties of the reactants (including the properties of the acid) and the reaction conditions used. Therefore, it should be understood that the amount of acid can be optimally and independently selected for each reaction.

[0186] Typically, acid treatment is carried out in a solvent, preferably a polar solvent.

[0187] In some examples, the solvent is water.

[0188] Acid treatment is typically carried out at temperatures between approximately 50°C and 60°C.

[0189] Therefore, in some examples, the acid treatment is carried out at a temperature of approximately 50°C, 51°C, 52°C, 53°C, 54°C, 55°C, 56°C, 57°C, 58°C, 59°C, or 60°C.

[0190] It is understood that the components of the acid treatment can be combined in any order, and the order in which the reactants are combined can be adjusted as needed.

[0191] For example, an acid may be added to a solution of a blend containing a fatty acid salt. Alternatively, a blend containing a fatty acid salt may be added to a solution of an acid.

[0192] Acids, blends containing fatty acid salts, and any other reagents used during the acid treatment may be added to the reaction in solid, liquid, or solvent form, and in any amount and manner effective for the expected outcome of the reaction.

[0193] Acid treatment of a blend containing fatty acid salts results in the formation of a blend containing fatty acids having formula (3).

[0194] In some embodiments, a blend containing a fatty acid having formula (3) is precipitated in the reaction of an acid-treated mixture. Precipitation can be achieved, for example, by partially removing the reaction solvent by evaporation (i.e., concentrating the reaction mixture), by adding another solvent to the reaction mixture, by changing the temperature or pressure, by adding another solute, or by a combination thereof.

[0195] In some embodiments, precipitation of the blend containing the fatty acid having formula (3) is achieved by cooling the acid-treated reaction mixture to a temperature of about 0°C to about 30°C, preferably about 10°C to about 25°C. Thus, in some preferred embodiments, precipitation is achieved by cooling the reaction mixture to a temperature of about 10°C, 11°C, 12°C, 13°C, 14°C, 15°C, 16°C, 17°C, 18°C, 19°C, 20°C, 21°C, 22°C, 23°C, 24°C, or 25°C.

[0196] Acid treatment of a blend containing fatty acid salts results in the formation of a blend containing 70–99.5 wt% fatty acids having formula (3) and approximately 0.5–30 wt% aliphatic alcohols.

[0197] In some examples, the aliphatic alcohol content of the blend containing the fatty acid having formula (3) is approximately 0.5 to 5 wt%.

[0198] In some examples, the aliphatic alcohol content of the blend containing the fatty acid having formula (3) is approximately 5-10 wt%.

[0199] In some examples, the aliphatic alcohol content of the blend containing the fatty acid having formula (3) is approximately 10-20 wt%.

[0200] In some examples, the aliphatic alcohol content of the blend containing the fatty acid having formula (3) is approximately 20-30 wt%.

[0201] In some examples, the blend containing the fatty acid having formula (3) contains at least about 50 wt% of the fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and fatty acids having formula (3) 1 C 23 It contains alkyl groups, where the ratio of the fatty acids is approximately 1:10 to approximately 10:1.

[0202] In some examples, the blend containing the fatty acid having formula (3) contains at least about 50 wt% of the fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and fatty acids having formula (3) 1 C 23 It contains alkyl groups. Preferably, the ratio of the fatty acids is about 1:2.5.

[0203] In some examples, the method involves reacting a blend containing a fatty acid having formula (3) with an alcohol in the presence of an acid, thereby producing C8-C 34 Fatty acid esters, preferably C 14 -C 30 The process further includes the step of obtaining a blend containing fatty acid esters.

[0204] Therefore, in some embodiments, the present invention describes a method for producing a lipid blend containing a lipid having formula (1), the method being - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30 A step to obtain a blend containing fatty acid salts and approximately 0.5-30 wt% aliphatic alcohols, - A step of treating a blend containing fatty acid salts with acid to obtain a blend containing approximately 70-99.5 wt% fatty acids having formula (3) and approximately 0.5-30 wt% aliphatic alcohols, -By reacting a blend containing fatty acids having formula (3) with alcohol in the presence of an acid, approximately 70-99.5 wt% C8-C is obtained. 34 Fatty acid esters, preferably C 14 -C 30 The process includes the step of obtaining a blend containing fatty acid esters and approximately 0.5 to 30 wt% aliphatic alcohols.

[0205] Typically, a blend containing a fatty acid having formula (3) is reacted with an alcohol in the presence of an inorganic or organic acid, preferably in the presence of an inorganic acid. Acids applicable in the context of the present invention include, but are not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, camphor sulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and perchloric acid.

[0206] In some examples, the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, and perchloric acid.

[0207] In some preferred embodiments, the acid is hydrochloric acid.

[0208] In some embodiments, the acid may be used in the form of an aqueous solution.

[0209] In some embodiments, the acid may be used in the form of an alcoholic solution.

[0210] It is understood that the amount of acid used in a reaction depends on various factors such as the properties of the reactants (including the properties of the acid) and the reaction conditions used. Therefore, it should be understood that the amount of acid can be optimally and independently selected for each reaction.

[0211] The alcohols applicable in the context of the present invention include, but are not limited to, C1-C7 alcohols or mixtures of C1-C7 alcohols.

[0212] In some examples, the alcohol is selected from methanol, ethanol, 1-propanol, isopropanol, 1-butanol, or isobutanol.

[0213] In some preferred embodiments, the alcohol is methanol.

[0214] A blend containing a fatty acid having formula (3), an alcohol, and an acid are typically reacted at a temperature of about 50°C to about 60°C. Preferably, the reaction is carried out at a temperature of about 60°C to about 65°C. Therefore, in some preferred examples, the reaction is carried out at a temperature of about 60°C, 61°C, 62°C, 63°C, 64°C, or 65°C.

[0215] The reaction of a blend containing a fatty acid having formula (3) with an alcohol results in the formation of a blend containing a fatty acid ester.

[0216] In some examples, a blend containing a fatty acid ester is precipitated from the reaction mixture. Precipitation can be achieved, for example, by partially removing the reaction solvent by evaporation (i.e., concentrating the reaction mixture), by adding another solvent to the reaction mixture, by changing the temperature or pressure, by adding another solute, or by a combination thereof.

[0217] In some examples, precipitation of the fatty acid ester blend is achieved by cooling the acid-treated reaction mixture to a temperature of about 0°C to about 30°C, preferably about 10°C to about 25°C. Therefore, in some preferred examples, precipitation is achieved by cooling the reaction mixture to a temperature of about 10°C, 11°C, 12°C, 13°C, 14°C, 15°C, 16°C, 17°C, 18°C, 19°C, 20°C, 21°C, 22°C, 23°C, 24°C, or 25°C.

[0218] The reaction of alcohol with a blend containing fatty acids having formula (3) is approximately 70-99.5 wt% C8-C 34 Fatty acid esters, preferably C 14 -C 30 This results in the formation of a blend containing fatty acid esters and approximately 0.5–30 wt% aliphatic alcohols.

[0219] In some examples, the aliphatic alcohol content of the blend containing fatty acid esters is approximately 0.5–5 wt%.

[0220] In some examples, the aliphatic alcohol content of the blend containing fatty acid esters is approximately 5-10 wt%.

[0221] In some examples, the aliphatic alcohol content of the blend containing fatty acid esters is approximately 10–20 wt%.

[0222] In some examples, the aliphatic alcohol content of the blend containing fatty acid esters is approximately 20-30 wt%.

[0223] In some examples, the blend containing fatty acid esters contained at least about 50 wt% C 22 and C 24 It contains fatty acid esters, where the ratio of these fatty acid esters is approximately 1:10 to approximately 10:1.

[0224] In some examples, the blend containing fatty acid esters contained at least about 50 wt% C 22 and C 24 It contains fatty acid esters, with the ratio of these fatty acid esters being approximately 1:2.5.

[0225] In some embodiments, the method involves a blend containing a fatty acid having formula (3), and a triazine having formula (4), [ka] Here, R 8 The group is selected from a methyl group, an ethyl group, 2,2,2-trifluoroethyl, and a substituted or unsubstituted benzyl group, preferably a methyl group. The process further includes the step of reacting in the presence of an organic base to obtain a blend containing a triazine acylating agent having formula (7) and about 0.5 to 30 wt% aliphatic alcohol.

[0226] Therefore, in some embodiments, the present invention describes a method for producing a blend containing a lipid having formula (1), the method being - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30 A step to obtain a blend containing fatty acid salts and approximately 0.5-30 wt% aliphatic alcohols, - A step of treating a blend containing fatty acid salts with acid to obtain a blend containing approximately 70-99.5 wt% fatty acids having formula (3) and approximately 0.5-30 wt% aliphatic alcohols, -By reacting a blend containing a fatty acid having formula (3) with a triazine having formula (4) in the presence of an organic base, C8-C 34 Triazine-based acylating agent, preferably C 14 -C 30 The process includes the step of obtaining a blend containing a triazine-based acylating agent and approximately 0.5 to 30 wt% aliphatic alcohol.

[0227] Typically, the step of reacting a blend containing a fatty acid having formula (3) with a triazine having formula (4) is carried out in the presence of an organic base.

[0228] In some examples, the organic base is selected from 4-methylmorpholine and 1,4-diazabicyclo[2.2.2]octane, preferably 4-methylmorpholine.

[0229] Typically, the step of reacting a blend containing a fatty acid having formula (3) with a compound having formula (4) is carried out in a non-halogenated solvent.

[0230] The non-halogenated solvent is preferably selected from ketones, alcohols, or aliphatic hydrocarbons. In some examples, the non-halogenated solvent is a ketone selected from acetone, diethyl ketone, methyl isobutyl ketone, or butane-2-one, preferably acetone. In some examples, when the solvent is a ketone, water may be added to the reaction mixture. In some examples, the non-halogenated solvent is an alcohol selected from methanol, ethanol, propanol, isopropanol, butanol, isobutanol, preferably methanol, or a mixture thereof. In some examples, the non-halogenated solvent is an aliphatic hydrocarbon selected from petroleum ether, hexane or a mixture thereof, n-heptane or a mixture thereof, octane or a mixture thereof. In some examples, the non-halogenated solvent is a mixture of two alcohols, where the mixture of two alcohols is preferably selected from methanol and ethanol, methanol and propanol, methanol and isopropanol, methanol and butanol, or a mixture of methanol and isobutanol, preferably a mixture of methanol and ethanol.

[0231] In some examples, the step of reacting a blend containing a fatty acid having formula (3) with a triazine having formula (4) is carried out at a temperature between about 30°C and about 100°C, preferably between about 30°C and about 55°C.

[0232] The step of reacting a blend containing a fatty acid having formula (3) with a triazine having formula (4) is C8-C 34Triazine-based acylating agent, preferably C 14 -C 30 This causes the formation of a blend containing triazine-based acylating agents.

[0233] In some examples, the blend containing the triazine acylating agent is precipitated from the reaction. Precipitation can be achieved, for example, by partially removing the reaction solvent by evaporation (i.e., concentrating the reaction mixture), by adding another solvent to the reaction mixture, by changing the temperature or pressure, by adding another solute, or by a combination thereof.

[0234] In some examples, precipitation is carried out at a temperature between about -20°C and about 25°C, preferably between about -10°C and about 25°C, and more preferably between about 5°C and about 25°C.

[0235] The reaction between a blend of fatty acids having formula (3) and a triazine having formula (4) is C8-C 34 Triazine-based acylating agent, preferably C 14 -C 30 This causes the formation of a blend containing a triazine-based acylating agent, the blend further containing about 20-30 wt% aliphatic alcohol.

[0236] In some examples, the aliphatic alcohol content of the blend containing the triazine acylating agent is approximately 0.5–5 wt%.

[0237] In some examples, the aliphatic alcohol content of the blend containing the triazine acylating agent is approximately 5-10 wt%.

[0238] In some examples, the aliphatic alcohol content of the blend containing the triazine acylating agent is approximately 10-20 wt%.

[0239] In some examples, the aliphatic alcohol content of the blend containing the triazine acylating agent is approximately 20-30 wt%.

[0240] In the context of the present invention, C8-C 34 The triazine acylating agent may also be represented by a triazine acylating agent having formula (7).

[0241] In some examples, the blend containing the triazine acylating agent contains at least about 50 wt% of the triazine acylating agent having formula (7) (where R 1 C 21 (where R is an alkyl group) and a triazine acylating agent having formula (7) (where R 1 C 23 The content of the alkyl group is such that the ratio of the triazine acylating agents is approximately 1:10 to approximately 10:1.

[0242] In some examples, the blend containing the triazine acylating agent contains at least about 50 wt% of the triazine acylating agent having formula (7) (where R 1 C 21 (where R is an alkyl group) and a triazine acylating agent having formula (7) (where R 1 C 23 It contains an alkyl group, where the ratio of the triazine-based acylating agents is approximately 1:2.5.

[0243] In some examples, the method further includes the step of reacting a blend comprising a lysosphingolipid having formula (5) and a fatty acid ester in the presence of a base to obtain a blend comprising a lipid having formula (6) and 0.5 to 30 wt% aliphatic alcohol.

[0244] Therefore, in some embodiments, the present invention describes a method for producing a blend containing a lipid having formula (6), the method being - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30 A step to obtain a blend containing fatty acid salts and approximately 0.5-30 wt% aliphatic alcohols, - A step of treating a blend containing fatty acid salts with acid to obtain a blend containing approximately 70-99.5 wt% fatty acids having formula (3) and approximately 0.5-30 wt% aliphatic alcohols, -By reacting a blend containing fatty acids having formula (3) with alcohol in the presence of an acid, approximately 70-99.5 wt% C8-C is obtained. 34 Fatty acid esters, preferably C 14 -C 30 The process includes the step of obtaining a blend containing fatty acid esters and approximately 0.5 to 30 wt% aliphatic alcohols. - A lysosphingolipid having formula (5) or a salt thereof, [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR7 If that is the case, it is a single bond, R 6 This is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen. A blend containing fatty acid esters is reacted with a base to obtain a blend containing lipids having formula (6). [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, W,R 4 , R 5 and R 6 This is defined for lysosphingolipids having formula (5).

[0245] Typically, a blend containing a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of a base such as an alkoxide, amine, carbonate, or bicarbonate.

[0246] In some examples, a blend comprising a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of an amine, where the amine is preferably selected from triethylamine, N,N-diisopropylethylamine, and pyridine.

[0247] In some examples, a blend containing a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of a carbonate, where the carbonate is preferably selected from Na2CO3, K2CO3, CaCO3, Li2CO3, and (NH4)2CO3.

[0248] In some examples, a blend containing a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of a bicarbonate, where the bicarbonate is preferably selected from NaHCO3, KHCO3, Ca(HCO3)2, LiHCO3, and NH4HCO3.

[0249] In some preferred embodiments, a blend comprising a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of an alkoxide, where the alkoxide is an alkoxide having formula (12). [ka] Here, R 9 This is a C1-C4 alkyl group, preferably selected from a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and more preferably selected from a methyl group or an ethyl group. X + is, Na + , K + Li + or NH 4+ A cation selected from, preferably Na + That is the case.

[0250] In some more preferred examples, a blend comprising a lysosphingolipid having formula (5) and a fatty acid ester is reacted in the presence of methanol.

[0251] The base may be used in catalytic, equimolar, or excess amounts.

[0252] In some examples, the lysosphingolipid having formula (5) is in free base form, and the base is used in a catalytic amount of about 0.1 to about 0.5 molar equivalents based on the amount of lysosphingolipid.

[0253] In some examples, the lysosphingolipid having formula (5) is in salt form, and the base is used in an amount of about 1.0 to about 1.7 molar equivalents based on the amount of lysosphingolipid.

[0254] In some preferred embodiments, the lysosphingolipid having formula (5) is in salt form, and the base is used in an amount of about 1.2 to 1.3 molar equivalents based on the amount of lysosphingolipid.

[0255] In some examples, a blend containing lysosphingolipids, fatty acid esters, and a base is reacted in a polar solvent, such as methanol, ethanol, propanol, isopropanol, butanol, or isobutanol.

[0256] In some preferred embodiments, the reaction is carried out in methanol.

[0257] In some examples, the reaction is carried out in a mixture of one or more polar solvents, such as methanol and ethanol, methanol and propanol, methanol and isopropanol, methanol and butanol, methanol and isobutanol, or a mixture of water and an aliphatic alcohol. In some examples, the reaction is carried out in acetonitrile.

[0258] In some examples, a blend containing lysosphingolipids, fatty acid esters, and a base is C5-C 10 The reaction is carried out in a hydrocarbon solvent, preferably heptane.

[0259] In some examples, the reaction is carried out without a solvent.

[0260] The lysosphingolipid, fatty acid ester blend, and base are typically reacted at temperatures ranging from about 50°C to about 125°C. Preferably, the reaction is carried out at temperatures ranging from about 60°C to about 65°C. Therefore, in some preferred examples, the reaction is carried out at temperatures of about 60°C, 61°C, 62°C, 63°C, 64°C, or 65°C.

[0261] It is understood that the reaction components may be combined in any order, and the order in which the reactants are combined can be adjusted as needed.

[0262] For example, a base may be added to a solution of a blend containing lysosphingolipids and fatty acid esters. Alternatively, a solvent may be added to a flask containing the blend of lysosphingolipids and fatty acid esters, and then the base may be added.

[0263] Lysosphingolipids, blends containing fatty acid esters, bases, and any other reagents used in the reaction may be added to the reaction in any amount and manner effective for the expected outcome, either as solids or dissolved in a solvent.

[0264] In some examples, the method further includes the step of reacting a blend containing a lysosphingolipid having formula (5) and a triazine acylating agent in the presence of a base to obtain a blend containing a lipid having formula (6) and 0.5 to 30 wt% aliphatic alcohol.

[0265] Therefore, in some embodiments, the present invention describes a method for producing a blend containing a lipid having formula (6), the method being - Provides degreased and saponified rice bran wax (dsRBW), wherein the dsRBW comprises a step of 50 wt% aliphatic alcohol, -By reducing the aliphatic alcohol content of the dsRBW, approximately 70-99.5 wt% C8-C 34 Fatty acid salt, preferably C 14 -C 30A step to obtain a blend containing fatty acid salts and approximately 0.5-30 wt% aliphatic alcohols, - A step of treating a blend containing fatty acid salts with acid to obtain a blend containing approximately 70-99.5 wt% fatty acids having formula (3) and approximately 0.5-30 wt% aliphatic alcohols, -By reacting a blend containing a fatty acid having formula (3) with a triazine having formula (4) in the presence of an organic base, C8-C 34 Triazine-based acylating agent, preferably C 14 -C 30 The process includes the step of obtaining a blend containing a triazine-based acylating agent and approximately 0.5 to 30 wt% aliphatic alcohol. - A lysosphingolipid having formula (5) or a salt thereof, [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6This is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen. By reacting with a blend containing a triazine-based acylating agent, a blend containing a lipid having formula (6) is obtained. [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, W,R 4 , R 5 and R 6 This is defined for lysosphingolipids having formula (5).

[0266] Typically, a blend containing lysosphingolipids and triazine acylating agents is reacted in a polar solvent, such as methanol, ethanol, propanol, isopropanol, butanol, or isobutanol.

[0267] In some preferred embodiments, the reaction is carried out in methanol. In some embodiments, the reaction is carried out in a mixture of one or more polar solvents, such as methanol and ethanol, methanol and propanol, methanol and isopropanol, methanol and butanol, methanol and isobutanol, or methanol and water.

[0268] In some examples, a blend containing lysosphingolipids and triazine acylating agents is reacted in the presence of a base, such as NaOH, KOH, LiOH, Ca(OH)2, triethylamine, N,N-diisopropylethylamine, and pyridine. In some preferred examples, the base is selected from NaOH or KOH.

[0269] The reaction of lysosphingolipids with a blend containing a triazine acylating agent typically takes place at temperatures ranging from about 25°C to about 65°C. Therefore, in some examples, the reaction takes place at temperatures ranging from about 25°C, 26°C, 27°C, 28°C, 29°C, 30°C, 31°C, 32°C, 33°C, 34°C, 35°C, 36°C, 37°C, 38°C, 39°C, 40°C, 41°C, 42°C, 43°C, 44°C, 45°C, 46°C, 47°C, 48°C, 49°C, 50°C, 51°C, 52°C, 53°C, 54°C, 55°C, 56°C, 57°C, 58°C, 59°C, 60°C, 61°C, 62°C, 63°C, 64°C, or 65°C. Preferably, the reaction takes place at temperatures ranging from about 45°C to about 55°C.

[0270] Therefore, in some preferred embodiments, the reaction is carried out at a temperature of 45°C, 46°C, 47°C, 48°C, 49°C, 50°C, 51°C, 52°C, 53°C, 54°C, or 55°C.

[0271] It is understood that the reaction components may be combined in any order, and the order in which the reactants are combined can be adjusted as needed.

[0272] For example, lysosphingolipids may be added to a solution of a blend containing a triazine acylation agent. Alternatively, a blend containing a triazine acylation agent may be added to a solution of lysosphingolipids. Yet another example is adding a solvent to a flask containing a blend of lysosphingolipids and a triazine acylation agent.

[0273] The blend containing lysosphingolipids and triazine acylating agents, as well as any other reagents used during the reaction, may be added to the reaction in solid or solvent form, and in any amount and manner effective for the expected outcome of the reaction.

[0274] The reaction of a blend containing a fatty acid ester with a lysosphingolipid having formula (5), or the reaction of a blend containing a triazine acylating agent with a lysosphingolipid having formula (5), produces a blend containing a lipid having formula (6) by causing selective N-acylation of the amino group on the C-2 carbon atom of the lysosphingolipid having formula (5), wherein the blend may further contain aliphatic alcohols in an amount between approximately 0.5 and 30 wt%.

[0275] In some examples, the aliphatic alcohol content of the blend containing the lipid having formula (6) is approximately 0.5 to 5 wt%.

[0276] In some examples, the aliphatic alcohol content of the blend containing lipids having formula (6) is approximately 5-10 wt%.

[0277] In some examples, the aliphatic alcohol content of the blend containing lipids having formula (6) is approximately 10-20 wt%.

[0278] In some examples, the aliphatic alcohol content of the blend containing lipids having formula (6) is approximately 20-30 wt%.

[0279] In some examples, the blend containing the lipid having formula (6) contains at least about 50 wt% of the lipid having formula (6) (where R 1 C 21 Lipids having formula (6) (where R is an alkyl group) and lipids having formula (6) 1 C 23 It contains alkyl groups, where the ratio of the lipids is approximately 1:10 to approximately 10:1.

[0280] In some examples, lipids having formula (6) (where R 1 C 21 Lipids having formula (5) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0281] In some embodiments, the present invention relates to a lipid blend comprising a lipid having formula (1), [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, R 2 -OH and / or -NHR 3 Selected from, here, R 3 This is the part having equation (2), [ka] Here, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6 is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen. Here, The blend may further contain aliphatic alcohols in an amount between approximately 0.5 and 30 wt%.

[0282] In some examples, the R of a lipid having formula (1) 2 It is -OH. Therefore, in some examples, the lipid having formula (1) is the fatty acid having formula (3), [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group.

[0283] In some embodiments, the present invention relates to a blend comprising a fatty acid having formula (3), wherein the blend comprises at least about 50 wt% of the fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and fatty acids having formula (3) 1 C 23 A fatty acid having formula (3) (where R is an alkyl group), wherein R is an alkyl group. 1 C 21 (where R is an alkyl group) and a fatty acid having formula (3) 1 C 23 The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in the range of approximately 0.5 to 30 wt%.

[0284] In some embodiments, the present invention relates to a blend comprising a lipid having formula (3), wherein the blend comprises at least about 50 wt% of a fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and fatty acids having formula (3) 1 C 23A fatty acid having formula (3) (where R is an alkyl group), wherein R is an alkyl group. 1 C 21 (where R is an alkyl group) and a fatty acid having formula (3) 1 C 23 The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in the range of approximately 0.5 to 5 wt%.

[0285] In some embodiments, the present invention relates to a blend comprising a lipid having formula (3), wherein the blend comprises at least about 50 wt% of a fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and fatty acids having formula (3) 1 C 23 A fatty acid having formula (3) (where R is an alkyl group), wherein R is an alkyl group. 1 C 21 (where R is an alkyl group) and a fatty acid having formula (3) 1 C 23 The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in an amount between approximately 20 and 30 wt%.

[0286] In some examples, a fatty acid having formula (3) (where R 1 C 21 (where R is an alkyl group) and a fatty acid having formula (3) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0287] In some examples, the lipid having formula (3) is C8-C 34 It is a non-hydroxy fatty acid. C8-C 34 Non-hydroxy fatty acids may also be called N(8-34:0).

[0288] In some examples, the fatty acid having formula (3) is C 14 -C30 It is a non-hydroxy fatty acid. 14 -C 30 Non-hydroxy fatty acids may also be called N(14-30:0).

[0289] In some examples, the R of a lipid having formula (1) 2 -NHR 3 And here, R 3 This is the part having formula (2). Therefore, in some examples, the lipid having formula (1) is the lipid having formula (6), [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group, W is a hydrogen atom or a glycosyl moiety. R 4 This is hydrogen, an aryl group, or a substituted or unsubstituted C1-C 50 It is an alkyl group, preferably a substituted or unsubstituted C1-C 17 Alkyl alkyl group, more preferably substituted or unsubstituted C 13 -C 17 It is an alkyl group, R 5 is hydrogen or -OR 7 And here, R 7 This is selected from hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C2-C6 acyl group. join [ka] R 5 If it is hydrogen, it may be a double bond or a single bond, or R 5 ga-OR 7 If that is the case, it is a single bond, R 6This is hydrogen, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C1-C6 acyl group, preferably hydrogen.

[0290] In some examples, the part having formula (2) and the lipid having formula (6) are R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 is -OH, and R 6 It is hydrogen and bonded [ka] It is a single bond.

[0291] In some examples, the part having formula (2) and the lipid having formula (6) are R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 and R 6 It is hydrogen and bonded [ka] It is a single bond.

[0292] In some examples, the part having formula (2) and the lipid having formula (6) are R 4 is saturated unsubstituted C 13 -C 17 It is an alkyl group, R 5 and R 6 It is hydrogen and bonded [ka] It is a double bond.

[0293] In some embodiments, the present invention relates to a blend comprising a lipid having formula (6), wherein the blend comprises at least about 50 wt% of the lipid having formula (6) (where R 1 C 21Lipids having formula (6) (where R is an alkyl group) and lipids having formula (6) 1 C 23 It contains an alkyl group, where the lipid of formula (6) (where R 1 C 21 Lipids having formula (6) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in the range of approximately 0.5 to 30 wt%.

[0294] In some embodiments, the present invention relates to a blend comprising a lipid having formula (6), wherein the blend comprises at least about 50 wt% of the lipid having formula (6) (where R 1 C 21 Lipids having formula (6) (where R is an alkyl group) and lipids having formula (6) 1 C 23 It contains an alkyl group, where R is a lipid having formula (6). 1 C 21 Lipids having formula (6) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in the range of approximately 0.5 to 5 wt%.

[0295] In some embodiments, the present invention relates to a blend comprising a lipid having formula (6), wherein the blend comprises at least about 50 wt% of the lipid having formula (6) (where R 1 C 21 Lipids having formula (6) (where R is an alkyl group) and lipids having formula (6) 1 C 23 It contains an alkyl group, where R is a lipid having formula (6). 1 C 21 Lipids having formula (6) (where R is an alkyl group) 1 C 23The ratio of alkyl groups to aliphatic alcohols is approximately 1:10 to 10:1, where the blend may further contain aliphatic alcohols in an amount between approximately 20 and 30 wt%.

[0296] In some examples, lipids having formula (6) (where R 1 C 21 Lipids having formula (6) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0297] In some examples, W is H for the lipid having formula (6). Therefore, in some examples, the lipid having formula (6) is ceramide.

[0298] In some examples, the lipid having formula (6) is a ceramide selected from the group consisting of ceramides or mixtures thereof having formula (13), (14), (15), or (16). [ka] Here, R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 30 It is an alkyl group.

[0299] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (13), wherein the blend comprises at least about 50 wt% of a ceramide having formula (13) (where R 1 C 21 Ceramide having formula (13) (where R is an alkyl group) and formula (13) 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (13). 1 C 21 A ceramide having formula (13) (where R is an alkyl group) 1 C 23The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0300] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (13), wherein the blend comprises at least about 50 wt% of a ceramide having formula (13) (where R 1 C 21 Ceramide having formula (13) (where R is an alkyl group) and formula (13) 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (13). 1 C 21 A ceramide having formula (13) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 5 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0301] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (13), wherein the blend comprises at least about 50 wt% of a ceramide having formula (13) (where R 1 C 21 Ceramide having formula (13) (where R is an alkyl group) and formula (13) 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (13). 1 C 21 A ceramide having formula (13) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to 10:1, where the blend contains approximately 20-30 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0302] In some preferred embodiments, a ceramide having formula (13) (where R 1 C 21 A ceramide having formula (13) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0303] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (14), wherein the blend comprises at least about 50 wt% of a ceramide having formula (14) (where R 1 C 21 Ceramide having formula (14) (where R is an alkyl group) and R is an alkyl group. 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (14). 1 C 21 A ceramide having formula (14) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0304] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (14), wherein the blend comprises at least about 50 wt% of a ceramide having formula (14) (where R 1 C 21 Ceramide having formula (14) (where R is an alkyl group) and R is an alkyl group. 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (14). 1 C 21 A ceramide having formula (14) (where R is an alkyl group) 1 C 23The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 5 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0305] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (14), wherein the blend comprises at least about 50 wt% of a ceramide having formula (14) (where R 1 C 21 Ceramide having formula (14) (where R is an alkyl group) and R is an alkyl group. 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (14). 1 C 21 A ceramide having formula (14) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to 10:1, where the blend contains approximately 20-30 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0306] In some examples, a ceramide having formula (14) (where R 1 C 21 A ceramide having formula (14) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0307] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (15), wherein the blend comprises at least about 50 wt% of a ceramide having formula (15) (where R 1 C 21 Ceramide having formula (15) (where R is an alkyl group) and R 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (15). 1C 21 A ceramide having formula (15) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0308] In some embodiments, the present invention relates to a blend comprising a ceramide having formula (16), wherein the blend comprises at least about 50 wt% of a ceramide having formula (16) (where R 1 C 21 Ceramide having formula (16) (where R is an alkyl group) and R is an alkyl group. 1 C 23 It comprises an alkyl group, where R is a ceramide having formula (16). 1 C 21 A ceramide having formula (16) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0309] In some examples, the R of ceramide having formulas (13) to (16) 1 C7-C 33 It is a non-hydroxyalkyl group. Therefore, in some examples, ceramides having formulas (13), (14), (15), and (16) may be called CER[N(8-34:0)P(18)], CER[N(8-34:0)DS(18)], CER[N(8-34:0)S(18)], and CER[N(8-34:0)H(18)], respectively.

[0310] In some examples, the R of ceramide having formulas (13) to (16) 1 C 13 -C29 It is a non-hydroxyalkyl group. Therefore, in some examples, ceramides having formulas (13), (14), (15), and (16) may be called CER[N(14-30:0)P(18)], CER[N(14-30:0)DS(18)], CER[N(14-30:0)S(18)], and CER[N(14-30:0)H(18)], respectively.

[0311] In some preferred embodiments, the lipid having formula (6) is a glycosyl moiety where W is the glycosyl moiety. Therefore, in some preferred embodiments, the lipid having formula (6) is a sphingoglycolipid.

[0312] In some examples, the lipid having formula (6) is a sphingoglycolipid selected from the group consisting of sphingoglycolipids having formula (17), (18), (19), or (20) or mixtures thereof. [ka] Here, W is a glycosyl moiety selected from the group consisting of Glc1-, Gal1-, and Galβ1-4Glc1-. R 1 C7-C 33 It is an alkyl group, preferably C 13 -C 29 It is an alkyl group.

[0313] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (17), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (17) (where R 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (17). 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) (where R1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0314] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (17), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (17) (where R 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (17). 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) (where R 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 5 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0315] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (17), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (17) (where R 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (17). 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) (where R 1 C 23The ratio of C (which is an alkyl group) is approximately 1:10 to 10:1, where the blend contains approximately 20-30 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0316] In some examples, a sphingoglycolipid having formula (17) (where R 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (17) (where R 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0317] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (18), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (18) (where R 1 C 21 Sphingoglycolipids having formula (18) (where R is an alkyl group) and formula (18) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (18). 1 C 21 Sphingoglycolipid having formula (18) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0318] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (18), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (18) (where R 1 C 21 Sphingoglycolipids having formula (18) (where R is an alkyl group) and formula (18) 1 C 23It comprises an alkyl group, where R is a sphingoglycolipid having formula (18). 1 C 21 Sphingoglycolipid having formula (18) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 5 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0319] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (18), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (18) (where R 1 C 21 Sphingoglycolipids having formula (18) (where R is an alkyl group) and formula (18) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (18). 1 C 21 Sphingoglycolipid having formula (18) (where R is an alkyl group) 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to 10:1, where the blend contains approximately 20-30 wt% C 22 -C 38 It may also contain aliphatic alcohols.

[0320] In some examples, a sphingoglycolipid having formula (18) (where R 1 C 21 Sphingoglycolipid having formula (18) (where R is an alkyl group) 1 C 23 The ratio of alkyl groups to alkyl groups is approximately 1:2.5.

[0321] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (19), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (19) (where R 1 C 21 Sphingoglycolipids having formula (19) (where R is an alkyl group) and formula (19) 1 C 23 It comprises an alkyl group, where R is a sphingoglycolipid having formula (19). 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (19) (where R 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0322] In some embodiments, the present invention relates to a blend comprising a sphingoglycolipid having formula (20), wherein the blend comprises at least about 50 wt% of a sphingoglycolipid having formula (20) (where R 1 C 21 Sphingoglycolipids having formula (20) (where R is an alkyl group) and formula (20) 1 C 23 It contains an alkyl group, where R is a sphingoglycolipid having formula (20). 1 C 21 (where R is an alkyl group) and a sphingoglycolipid having formula (20) (where R 1 C 23 The ratio of C (which is an alkyl group) is approximately 1:10 to approximately 10:1, where the blend contains approximately 0.5 to 30 wt% C. 22 -C 38 It may also contain aliphatic alcohols.

[0323] According to the present invention, all or more examples of a blend containing at least about 50 wt% preferably contain one or more compounds specified in each example that are greater than 50 wt%, for example, about 60 wt% or more, for example, about 65-75 wt%, about 70-80 wt%, about 75-85 wt%, about 80-90 wt%, and about 95-100 wt%.

[0324] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C7-C 33 It is a non-hydroxyalkyl group, and W is Glc1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called GlcCER[N(8-34:0)P(18)], GlcCER[N(8-34:0)DS(18)], GlcCER[N(8-34:0)S(18)], and GlcCER[N(8-34:0)H(18)], respectively.

[0325] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C 13 -C 29 It is a non-hydroxyalkyl group, and W is Glc1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called GlcCER[N(14-30:0)P(18)], GlcCER[N(14-30:0)DS(18)], GlcCER[N(14-30:0)S(18)], and GlcCER[N(14-30:0)H(18)], respectively.

[0326] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C7-C 33It is a non-hydroxyalkyl group, and W is Gal1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called GalCER[N(8-34:0)P(18)], GalCER[N(8-34:0)DS(18)], GalCER[N(8-34:0)S(18)], and GalCER[N(8-34:0)H(18)], respectively.

[0327] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C 13 -C 29 It is a non-hydroxyalkyl group, and W is Gal1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called GalCER[N(14-30:0)P(18)], GalCER[N(14-30:0)DS(18)], GalCER[N(14-30:0)S(18)], and GalCER[N(14-30:0)H(18)], respectively.

[0328] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C7-C 33 It is a non-hydroxyalkyl group, and W is Galβ1-4Glc1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called LacCER[N(8-34:0)P(18)], LacCER[N(8-34:0)DS(18)], LacCER[N(8-34:0)S(18)], and LacCER[N(8-34:0)H(18)], respectively.

[0329] In some examples, for sphingoglycolipids having formulas (17) to (20), R 1 C 13 -C 29It is a non-hydroxyalkyl group, and W is Galβ1-4Glc1-. Therefore, in some preferred examples, the sphingoglycolipids having formulas (17), (18), (19), and (20) may be called LacCER[N(14-30:0)P(18)], LacCER[N(14-30:0)DS(18)], LacCER[N(14-30:0)S(18)], and LacCER[N(14-30:0)H(18)], respectively.

[0330] The aliphatic alcohol content of the blend of the present invention can be determined by techniques known to those skilled in the art, such as HPLC analysis or 1 It can be quantified by 1H NMR spectroscopy.

[0331] In some embodiments, the present invention relates to cosmetic compositions, which include blends according to the present invention. In particular, cosmetic compositions which include blends or combinations thereof of lipids as defined in any one of the above embodiments and claims.

[0332] According to the present invention, the lipid blends according to the present invention are biologically active compounds and can be usefully used in cosmetic compositions, and these cosmetic compositions are - Improves skin tone, - Improves skin radiance, - Improves skin tone, - Reduce premature skin aging, - Smooths out wrinkles, - Improves skin firmness, -Increases the volume of the skin, - Improves skin uniformity, - The aim is to increase moisturizing power.

[0333] The cosmetic applications of the present invention reduce and / or improve signs of skin aging, for example, in the skin, - wrinkles, - To become thinner, - Reduced elasticity, - Sagging, - Fine lines, - Keratin proliferation, -Dry skin, - Skin volume loss, - Wrinkle smoothing, - This includes reducing or improving one or more of the symptoms of hypersensitivity.

[0334] Without being bound by theory, treating mammalian skin, particularly human skin, with the lipids contained in the blend of the present invention is associated with the activation of biological pathways in skin cells, and these biological pathways are - To maintain and / or improve the skin barrier function, - To mitigate the effects of skin exposure to environmental pollutants and unhealthy lifestyles. - Stimulating the regeneration of skin cells, - To promote energy production in the mitochondria of skin cells, - To maintain and improve the adhesion and communication of skin cells, - Related to maintaining a healthy skin microbiome and preventing or recovering from its dysbiosis.

[0335] In one example, the lipid blend described herein can also be beneficially used to improve the beauty of hair.

[0336] The cosmetic composition comprising the lipid blend of the present invention may also contain any other active compounds that can enhance or support any of the beneficial effects mentioned above, such as vitamins, antioxidants, oils, etc.

[0337] Cosmetic compositions may be prepared as liquid, semi-liquid (e.g., emulsion), or solid compositions in accordance with the guidelines of the art.

[0338] Preferably, the cosmetic composition is a topical composition.

[0339] In one embodiment, the present invention relates to a therapeutic composition comprising the lipid blend of the present invention. Preferably, the lipid blend contained in the therapeutic composition according to the present invention is not a therapeutically active compound, but a compound of a cosmetic support agent used in therapeutic treatment (for example, used for cosmetic restoration of the skin after therapeutic treatment).

[0340] example The following examples illustrate non-limiting embodiments of the present invention, and these examples are for illustrative purposes only.

[0341] General methods and materials: Using a Jeol ECZ 500R (500MHz) spectrometer 1 1H NMR and 13 ¹³C NMR was recorded. 1 H and 13 The chemical shift of ¹¹C was given in ppm(δ) relative to the internal standards tetramethylsilane (δ=0.00), CDCl3 (δ=7.26), CD3OD (δ=3.31), and DMSO-d5 (δ=2.50). Thin-layer chromatography (TLC) was performed on silica gel TLC plates (Merck, silica gel, F254), and detection was performed by UV absorption (254 nm) when ammonium molybdate (25 g / L) and cerium ammonium sulfate (10 g / L) were appropriately present in 10% H2SO4 (140°C).

[0342] LC-MS analysis was performed on a SCIEX Triple Quad™ 4500 LC-MS / MS system with an Accucore aQ (150 mm x 4.6 mm, 2.6 μm) column.

[0343] HPLC analysis was performed using a Dionex Ultimate 3000 HPLC system coupled with a Corona Veo charged aerosol detector and an Accucore aQ (150 mm x 4.6 mm, 2.6 μm) column.

[0344] GC analysis was performed using an Agilent 8890 gas chromatograph with a DB-5MS UI (30m x 0.25mm, 0.25μm) column coupled to a flame ionization detector (FID).

[0345] Example 1. Production of defatted rice bran wax (RBW) RBW was suspended in isopropanol (7 volumes) and stirred under reflux until a solution was obtained. The solution was then cooled to room temperature to form a suspension. The suspension was filtered, and the collected solid was washed with isopropanol and vacuum-dried.

[0346] Example 2. Saponification of degreased RBW Defatted RBW was suspended in isopropanol (6 volumes) and potassium hydroxide was added. Complete saponification of RBW was obtained (TLC or 1 The mixture was refluxed until the reaction was monitored by 1H-NMR. The mixture was cooled to approximately 60°C, and acetonitrile (5-6 volumes) was added. The mixture was cooled to room temperature to form a suspension. The suspension was filtered, and the collected solid was washed with acetonitrile and vacuum-dried. Following the above procedure, a blend containing a 1:1 mixture of potassium salts of fatty acids and aliphatic alcohols was obtained.

[0347] Example 3. Reduction of aliphatic alcohols in defatted and saponified RBW. Soxhlet extraction was performed on defatted and saponified RBW (dsRBW) using ethyl acetate (3-5 volumes) as the extraction solvent. Extraction was continued until most of the aliphatic alcohols were removed (approximately 4-6 hours, monitored by TLC). The remaining solid residue, rich in fatty acids, was suspended in ethyl acetate or acetonitrile (3-4 volumes) and stirred at room temperature for approximately 15-30 minutes. The suspension was filtered, and the collected solid was washed with ethyl acetate or acetonitrile and vacuum-dried.

[0348] Following the above procedure, a blend containing 75-95 wt% potassium salts of fatty acids was obtained.

[0349] Example 4. Manufacturing of fatty acid blends The blend obtained in Example 3 was added to a 1:10 mixture of HCl (37% aqueous solution) and water. The resulting suspension was stirred at a temperature of approximately 50°C to 60°C for 1 to 2 hours, then cooled to room temperature and stirred for another 1 to 2 hours. The suspension was filtered, the solid was collected, washed with water (3 to 4 volumes), and dried.

[0350] Following the above procedure, C is between approximately 75-80 wt% 16 -C 30 A blend containing fatty acids was obtained.

[0351] Example 5. LC-MS and HPLC analysis of fatty acid blends The characteristics and content of fatty acids in the blend obtained in Example 4 were determined by LCMS and HPLC analysis.

[0352] The LC-MS eluate distribution consisted of solvent A: 1 L water + 2 mL formic acid + 2 mmol ammonium formate, and solvent B: 1 L MeOH + 1 L acetonitrile + 4 mL formic acid + 4 mmol ammonium formate. A gradient of 80–100% B in A was applied within 50 mins, followed by an isocratic analysis of 80% B in A for 55 mins. The HPLC eluate distribution consisted of solvent A: 1 L water + 2 mL formic acid + 2 mmol ammonium formate, and solvent B: 1 L MeOH + 1 L acetonitrile + 4 mL formic acid + 4 mmol ammonium formate. A gradient of 80–100% B in A was applied within 50 mins, followed by an isocratic analysis of 80% B in A for 55 mins. The fatty acid content of the blend was quantified by peak area analysis using an external standard. The results of the LC-MS and HPLC analyses are summarized in Table 1.

[0353] [Table 1]

[0354] Example 6. Production of fatty acid ester blends from fatty acid blends The fatty acid blend obtained in Example 4 was suspended in methanol (5 vols), and HCl (37% aqueous solution, 0.3-0.6 vols) was added. The reaction mixture was refluxed until the fatty acids were completely converted to the corresponding methyl esters (monitored by TLC). The reaction mixture was cooled to room temperature, and water (5 mL) was added. The resulting suspension was filtered, the solid was collected, washed with a 1:1 mixture of methanol and water (3-4 vols), and vacuum-dried.

[0355] Following the above procedure, C is between approximately 75 and 85 wt% 14 -C 30 A blend containing fatty acid methyl esters was obtained.

[0356] Example 7. GC analysis of a blend of fatty acid methyl esters GC analysis characterized the fatty acid methyl ester blend obtained in Example 6.

[0357] The GC conditions were as follows: The initial oven temperature was 60°C and maintained for 1 minute, then programmed to increase to 180°C at a rate of 40°C / min and held for 5 minutes, and then programmed to increase to 320°C at a rate of 10°C / min and held for 17 minutes. The temperature of the FID detector was 280°C. A constant flow rate of helium gas was supplied at a rate of 2 mL / min.

[0358] The fatty acid methyl ester content of the blend was quantified by peak area analysis using an external standard. The results of the GC analysis are summarized in Table 2.

[0359] [Table 2]

[0360] Example 8. Production of triazine-based acylating agent blends The fatty acid blend obtained in Example 4 was suspended in acetone (8 volumes). 1.1 equivalents of 4-methylmorpholine were added, and the resulting mixture was stirred at 35°C to 40°C for 15 minutes. Then, 1.05 equivalents of 2-chloro-4,6-dimethoxy-1,3,5-triazine were added, and the mixture was stirred at 35°C to 40°C. After 2 hours, the reaction mixture was cooled to room temperature, 12 volumes of water were added, and the resulting suspension was filtered. The collected solid was washed with a 1:1 mixture of acetone and water (5-6 volumes) and vacuum-dried.

[0361] 1 H-NMR(500MHz, CDCl3)δ4.09-3.93(m,11H),2.88-2.80(m,1H),2.56(t,J=7.5Hz,2H) ,2.40(t,J=7.5Hz,1H),1.75-1.47(m,6H),1.41-1.02(m,92H),0.84(t,J=6.9Hz,7H).

[0362] Example 9. General procedure for producing a ceramide blend from a blend of fatty acid methyl esters. One equivalent of a sphingoid base hydrochloride was dissolved in 10 volumes of MeOH, sodium methoxide (25% in MeOH, 1.4 equivalents) was added, and then the fatty acid methyl ester blend obtained in Example 6 (1.1 equivalents) was added.

[0363] The reaction mixture was stirred at 60°C until the starting material was completely converted (monitored by TLC). The reaction mixture was then cooled to room temperature to form a suspension. The suspension was filtered, and the resulting solid was first washed with methanol (10 volumes), then resuspended in methanol and refluxed for approximately 0.5–1 hour. Water was then added to the suspension, and the mixture was first cooled to room temperature and filtered. The collected solid was washed with a 10:1 mixture of methanol and water (twice, 2–3 volumes) and vacuum-dried.

[0364] Example 10. Manufacturing of CER[N(14-30:0)DS(18)] blend D-erythro-dihydrosphingosine hydrochloride (1 equivalent) and a blend of fatty acid methyl esters were reacted under the conditions of Example 9 to obtain non-hydroxy C 16 -C 30 A blend containing ceramide DS(18) with an acyl group was produced.

[0365] The CER[N(14-30:0)DS(18)] blend was characterized by LCMS analysis.

[0366] The LCMS eluate distribution consisted of solvent A: 2 mL formic acid and 2 mM ammonium formate in 1 L of water, and solvent B: 2 mL formic acid and 2 mM ammonium formate in 500 ml of acetonitrile + 500 ml of methanol. A gradient of 80-100% B in A was applied within 10 mins, followed by an isocratic treatment of 100% B in A for 50 mins, and then an isocratic treatment of 80% B in A for 40 mins.

[0367] The results of the LCMS analysis are summarized in Table 3.

[0368] [Table 3]

[0369] Example 11. Production of aliphatic alcohol blends The solvent extract containing the aliphatic alcohol and the O-acetylated aliphatic alcohol obtained in Example 3 was concentrated, and MeOH (10 vol) was converted, followed by the addition of HCl (37% aqueous solution, 0.5–1.2 vol). The resulting mixture was stirred under reflux until all O-acetylated aliphatic alcohol derivatives were converted to the corresponding aliphatic alcohols (the reaction was monitored by TLC). The reaction mixture was then cooled to room temperature and stirred for approximately 0.5–1 hour. The resulting suspension was filtered, the solid was collected, washed with MeOH (3–4 vol), and vacuum-dried.

[0370] Following the above procedure, C is between approximately 55 and 65 wt% 22 -C 36A thirteenth blend containing aliphatic alcohols was obtained.

[0371] Example 12. HPLC analysis of aliphatic alcohol blends HPLC analysis characterized the aliphatic alcohol blend obtained in Example 11.

[0372] The HPLC eluate distribution consisted of solvent A: methanol and solvent B: acetonitrile. A gradient of 50–93% A in B was applied within 20 minutes, followed by an isocratic elution of 50% A in B, which was sustained for 45 minutes.

[0373] The aliphatic alcohol content of the blend was quantified using peak area analysis with an external standard. The results of the HPLC analysis are summarized in Table 2.

[0374] [Table 4]

[0375] Example 13. Preparation of fatty acid ester blends from dsRBW Defatted and saponified RBW (dsRBW) containing a 1:1 mixture of potassium salt of a fatty acid and an aliphatic alcohol was suspended in methanol (10 vol). Hydrochloric acid was added to the suspension (37% aqueous solution), and the suspension was stirred under reflux until complete conversion was achieved (monitored by TLC). The reaction mixture was cooled to room temperature, and the resulting suspension was filtered. The resulting solid was washed with methanol (3-4 vol), vacuum-dried, and suspended in ethyl acetate (10 vol). The suspension was refluxed for 1-2 hours, cooled to room temperature, and filtered. The resulting solid was washed with ethyl acetate (3-4 vol) and vacuum-dried.

[0376] Following the above procedure, C is between approximately 60-70 wt% 14 -C 30 A blend containing fatty acid methyl esters was obtained.

[0377] Example 14. scCO2 extraction of defatted and saponified RBW. Degreased and saponified RBW (dsRBW) was extracted at Separex@GSP Lab using anhydrous carbonate under the following processing conditions: a static period of 15 minutes at 60°C and 350 bar, followed by a dynamic period of 150 minutes from 60°C and 350 bar to 80°C and 450 bar.

[0378] Following the above procedure, a blend containing 70-80 wt% potassium salts of fatty acids was obtained.

[0379] If a range is given, it includes the endpoints. Unless otherwise explicitly or otherwise obvious from the context and / or the understanding of those skilled in the art, in different embodiments of the invention, the values ​​expressed as a range may be any specific value within the range, up to one-tenth of the lower limit of the range, unless otherwise specifically stated in the context. Unless otherwise explicitly or otherwise obvious from the context and / or the understanding of those skilled in the art, the values ​​expressed as a range may be any sub-range within a given range, where the endpoints of the sub-range are expressed with the same precision as one-tenth of the lower limit of the range.

[0380] The contents of this disclosure should not be considered to be limited in any way to the embodiments described herein, and those skilled in the art will foresee many possibilities for modification thereof.

[0381] The above embodiments can be combined. The following claims further describe specific embodiments of the present disclosure.

Claims

1. A method for producing a lipid blend from defatted and saponified rice bran wax (dsRBW), wherein the dsRBW contains about 50 wt% aliphatic alcohols. The aforementioned blend is - A lipid having formula (1) in an amount of approximately 70 to 99.5 wt%, 【Chemistry 1】 Here, R １ C ７ -C ３３ It is an alkyl group, preferably C １３ -C ２９ It is an alkyl group, R ２ is -OH and / or -NHR ３ Selected from, here, R ３ This is the part having equation (2), 【Chemistry 2】 Here, W is a hydrogen atom or a glycosyl moiety. R ４ is hydrogen, an aryl group, or a substituted or unsubstituted C １ -C ５０ alkyl group, preferably a substituted or unsubstituted C １ -C １７ alkyl group, more preferably a substituted or unsubstituted C １３ -C １７ alkyl group, R ５ is hydrogen or -OR ７ And here, R ７ C is hydrogen, substituted or unsubstituted. １ -C ６ Alkyl alkyl groups, or substituted or unsubstituted C ２ -C ６ Selected from acyl groups, join 【Transformation 3】 R ５ If is hydrogen, it may be a double bond or a single bond, or R ５ ga- OR ７ If that is the case, it is a single bond, R ６ C is hydrogen, substituted or unsubstituted. １ -C ６ Alkyl alkyl groups, or substituted or unsubstituted C １ -C ６ It is an acyl group, preferably hydrogen, - Contains approximately 0.5 to 30 wt% aliphatic alcohols, Here, The method comprises the step of reducing the aliphatic alcohol content of the dsRBW or its derivative to about 0.5 to 30 wt%.

2. The method according to claim 1, wherein the step of reducing the aliphatic alcohol content is carried out by solvent extraction.

3. The solvent is ethyl acetate, cyclohexane, n-heptane, acetonitrile, or supercritical CO2. ２ The method according to claim 2, wherein the selected member is ethyl acetate, selected from the group consisting of the following.

4. The lipid blend contains at least 50 wt% of R １ C ２１ Lipids having formula (1) which is an alkyl group, and R １ C ２３ The method according to any one of claims 1 to 3, comprising a lipid having formula (1) which is an alkyl group, wherein the ratio of the lipids is about 1:10 to about 10:

1.

5. The step of reducing the aliphatic alcohol content is: - It was held at dsRBW. As a result, approximately 70-99.5 wt% C ８ -C ３４ Fatty acid salt, preferably C １４ -C ３０ A blend containing fatty acid salts and aliphatic alcohols in an amount between approximately 0.5 and 30 wt% is obtained. Or, - This is carried out with a dsRBW derivative, where the derivative is the dsRBW and C １ -C ６ The derivative is obtained by reacting an alcohol in the presence of an acid, and the derivative is C ８ -C ３４ Fatty acid esters, preferably C １４ -C ３０ It contains fatty acid esters and approximately 50 wt% aliphatic alcohols. As a result, approximately 70-99.5 wt% C ８ -C ３４ Fatty acid esters, preferably C １４ -C ３０ The method according to any one of claims 1 to 4, for obtaining a blend comprising a fatty acid ester and about 0.5 to 30 wt% of an aliphatic alcohol.

6. The method further comprises the step of treating a blend containing a fatty acid salt with an acid, thereby obtaining about 70 to 99.5 wt% of a fatty acid having formula (3), 【Chemistry 4】 R １ This is defined as for the lipid having formula (1), The method according to claim 5, for obtaining a blend containing approximately 0.5 to 30 wt% of aliphatic alcohols.

7. The method involves a blend containing the fatty acid having formula (3), -C １ -C ６ By reacting alcohol with an acid, approximately 70-99.5 wt% C is produced. ８ -C ３４ Fatty acid esters, preferably C １４ -C ３０ A step to obtain a blend containing fatty acid esters and approximately 0.5 to 30 wt% aliphatic alcohols, Or, - A triazine having formula (4), 【Transformation 5】 Here, R ８ The group is selected from a methyl group, an ethyl group, 2,2,2-trifluoroethyl, and a substituted or unsubstituted benzyl group, preferably a methyl group. By reacting in the presence of an organic base, C ８ -C ３４ Triazine-based acylating agent, preferably C １４ -C ３０ The method according to claim 6, further comprising the step of obtaining a blend comprising a triazine-based acylating agent and about 0.5 to 30 wt% of an aliphatic alcohol.

8. The method involves a lysosphingolipid having formula (5). 【Transformation 6】 or its salt, W, R ４ , R ５ , R ６ and the combination 【Transformation 7】 This is defined as the part having formula (2), - A step of reacting a blend containing these fatty acid esters in the presence of a base, Or, - By reacting these triazine-based acylating agents with a blend, A lipid having formula (6), 【Transformation 8】 Here, R １ The following is defined for the lipid having formula (1), and W, R ４ , R ５ , R ６ and the combination 【Chemistry 9】 This is defined as the part having formula (2), The method according to any one of claims 5 to 7, further comprising the step of obtaining a blend containing approximately 5 to 30 wt% of an aliphatic alcohol.

9. With respect to the portion having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6), R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ is -OH, and R ６ is hydrogen, and the bond 【Chemistry 10】 The method according to any one of claims 1 to 8, wherein the bond is a single bond.

10. With respect to the portion having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6), R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ and R ６ is hydrogen, and the bond 【Chemistry 11】 The method according to any one of claims 1 to 8, wherein the bond is a single bond.

11. With respect to the portion having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6), at the position, R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ and R ６ is hydrogen, and the bond 【Chemistry 12】 The method according to any one of claims 1 to 8, wherein is a double bond.

12. The method according to any one of claims 1 to 11, wherein W is hydrogen in the portion having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6).

13. The method according to any one of claims 1 to 11, wherein W is a glycosyl moiety selected from the group consisting of Glc1-, Gal1-, and Galβ1-4Glc1-, with respect to the moiety having formula (2), the lysosphingolipid having formula (5), and the lipid having formula (6).

14. A lipid blend comprising a lipid having formula (1), 【Chemistry 13】 Here, R １ C ７ -C ３３ It is an alkyl group, preferably C １３ -C ２９ It is an alkyl group, R ２ is selected from -OH and / or -NHR ３ where R ３ is a moiety having formula (2), 【Chemistry 14】 Here, W is a hydrogen atom or a glycosyl moiety. R ４ is hydrogen, an aryl group, or a substituted or unsubstituted C １ -C ５０ alkyl group, preferably a substituted or unsubstituted C １ -C １７ alkyl group, more preferably a substituted or unsubstituted C １３ -C １７ alkyl group, R ５ is hydrogen or -OR ７ And here, R ７ C is hydrogen, substituted or unsubstituted. １ -C ６ Alkyl alkyl groups, or substituted or unsubstituted C ２ -C ６ Selected from acyl groups, join 【Chemistry 15】 R ５ If is hydrogen, it may be a double bond or a single bond, or R ５ ga- OR ７ If that is the case, it is a single bond, R ６ C is hydrogen, substituted or unsubstituted. １ -C ６ Alkyl alkyl groups, or substituted or unsubstituted C １ -C ６ It is an acyl group, preferably hydrogen, Here, the lipid blend contains approximately 0.5 to 30 wt% C ２２ -C ３８ A lipid blend containing aliphatic alcohols.

15. The blend according to claim 14, wherein the blend comprises about 0.5 to 5 wt% of aliphatic alcohols.

16. The blend according to claim 14, wherein the blend contains about 20-30 wt% of aliphatic alcohols.

17. The blend comprises a lipid having formula (3), 【Chemistry 16】 Here, R １ The blend according to any one of claims 14 to 17, wherein is defined for the lipid having formula (1).

18. The blend comprises a lipid having formula (6), 【Chemistry 17】 Here, R １ The following is defined for the lipid having formula (1): W, R ４ , R ５ , R ６ and the combination [Chemistry 18] The blend according to any one of claims 14 to 17, wherein the portion having formula (2) is defined as follows.

19. The blend comprises a lipid having formula (6), where R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ and R ６ is hydrogen, and the bond 【Chemistry 19】 The blend according to claim 18, wherein the bond is a single bond.

20. The blend comprises a lipid having formula (6), where R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ is -OH, and R ６ is hydrogen, and the bond 【Chemistry 20】 The blend according to claim 18, wherein the bond is a single bond.

21. The blend comprises a lipid having formula (6), where R ４ is saturated unsubstituted C １３ -C １７ It is an alkyl group, R ５ and R ６ is hydrogen, and the bond 【Chemistry 21】 The blend according to claim 18, wherein the bond is a double bond.

22. The blend according to any one of claims 18 to 21, comprising a lipid having formula (6), where W is hydrogen.

23. The blend according to any one of claims 18 to 21, comprising a lipid having formula (6), where W is a glycosyl moiety selected from the group consisting of Glc1-, Gal1-, and Galβ1-4Glc1-.

24. R １ C ２１ Lipids having the alkyl group formula (1), (3), or (6) and R １ C ２３ The blend according to any one of claims 14 to 23, wherein the content of a lipid having formula (1), which is an alkyl group, is at least about 50 wt%.

25. R １ C ２１ Lipids having the alkyl group formula (1), (3), or (6) and R １ C ２３ The blend according to any one of claims 14 to 23, wherein the ratio of the blend to the lipid having formula (1), which is an alkyl group, is about 1:10 to about 10:

1.

26. The blend is the blend according to any one of claims 14 to 25, obtained by the method described in any one of claims 1 to 13.

27. A cosmetic composition comprising a lipid blend according to any one of claims 14 to 26, or a combination thereof.

28. Uses of the lipid blend according to any one of claims 14 to 26 or the cosmetic composition according to claim 27 for maintaining physiologically normal skin barrier function or improving deteriorated skin barrier function in an individual.

Images