An amphiphilic amino acid derivative compound and its use in oral care compositions

Abstract

The application discloses an amphiphilic amino acid derivative compound, namely, N-fatty acyl-L-arginine polyglycerol ester (Arg-PG ester) compound, which is an amphiphilic compound with L-arginine as a core skeleton, connected with C12-C18 fatty acyl chains and polyglycerol (PG-2 to PG-10). The application also discloses an oral care composition containing Arg-PG ester and a fluoride source, a method for preventing dental caries and remineralization, and an enzyme catalytic preparation method. The core design logic of the application lies in the systematic matching of the carbon chain length and the polyglycerol polymerization degree: short chain (C12)+low polymerization degree (PG3) is suitable for fast dispersion type; medium chain (C14)+medium polymerization degree (PG4) is the most optimal balanced type; long chain (C18:1)+high polymerization degree (PG6) is suitable for strong anchoring professional products.

Description

Technical Field

[0001] This invention belongs to the field of oral care chemicals technology, specifically relating to an amphiphilic amino acid-derived compound and its application in oral care compositions. Background Technology

[0002] Fluoride treatment for caries prevention is a core component of modern oral care. Among existing commercial products, sodium fluoride (NaF), sodium monofluorophosphate (MFP), and stannous fluoride (SnF2) are the mainstream fluoride sources. However, these simple inorganic fluorides have limited residence time on the enamel surface, and the efficiency of fluoride ions in forming protective fluorapatite (FAP) and calcium fluoride-like (CaF2-like) reservoir layers is constrained by tooth surface adsorption kinetics.

[0003] Organic amine fluorides such as Olaflur have been used in oral care since 1966, but as a large-molecule fluoride active ingredient, it has not achieved the same universal approval status as NaF in most major regulatory markets, limiting its commercialization. Colgate recently launched Neo-Aminex technology as an alternative to Olaflur, but it contains ethylene oxide (EO) groups, which contradicts cleaning labeling trends and consumer safety concerns.

[0004] Therefore, there is still a need in the field for a novel fluoride delivery enhancer that combines the following characteristics: (a) EO-free; (b) with a natural amino acid backbone and excellent biocompatibility; (c) compatible with common fluoride sources; and (d) enriches fluoride on the tooth surface through a cation anchoring mechanism. Summary of the Invention

[0005] This invention provides a novel amphiphilic amino acid-derived compound, N-fatty acyl-L-arginine polyglycerol ester (Arg-PG ester), which is an amphiphilic molecule with the following structural features: L-arginine as the core backbone, C12-C18 fatty acid chains are linked by amide bonds, the carboxyl group of arginine is linked to polyglycerol (degree of polymerization n=2-10) by ester bonds; the guanidinium group of arginine maintains a positive charge within the physiological pH range of the oral cavity, providing enamel anchoring ability.

[0006] An amphiphilic amino acid-derived compound, through a systematic pairing of aliphatic chain length and polyglycerol degree of polymerization, has the following structure: R-CO-NH-CH(-(CH2)3-NHC(=NH)NH2)-COO-Polyglyceryl(n) X Wherein: R is a C11-C17 alkyl or alkenyl group; Polyglyceryl(n) is a polyglycerol residue, where n is an integer from 2 to 10; X is an orally acceptable salt. The orally acceptable salt is selected from at least one of hydrochloride, lactate, citrate, and acetate.

[0007] Systematic pairings between fatty acid chain length and polyglycerol degree of polymerization: (1) short fatty acid chain and low degree of polymerization glycerol pairing; (2) medium fatty acid chain and medium degree of polymerization glycerol pairing; (3) long fatty acid chain and high degree of polymerization glycerol pairing; (4) saturated long fatty acid chain pairing and medium / high degree of polymerization glycerol pairing.

[0008] The preferred compounds are N-myristoyl-L-arginine polyglycerol-4 ester hydrochloride, N-lauroyl-L-arginine polyglycerol-3 ester hydrochloride, N-oleoyl-L-arginine polyglycerol-6 ester hydrochloride, N-palmitoyl-L-arginine polyglycerol-4 ester hydrochloride, and N-stearoyl-L-arginine polyglycerol-6 ester hydrochloride.

[0009] The preparation method of this compound is as follows: In the presence of a lipase catalyst, N-fatty acyl-L-arginine and polyglycerol with a degree of polymerization of 2-10 are reacted in an organic solvent at 40-65°C for 48-64 hours to generate N-fatty acyl-L-arginine polyglycerol ester. The conversion rate is monitored by HPLC, the enzyme particles are recovered by filtration, the filtrate is concentrated under reduced pressure, the pH is adjusted to 4.5-6.0 by adding acid solution, the product is precipitated, filtered, the filter cake is washed with an organic solvent, and dried under vacuum at 40-60°C for 12-36 hours to obtain a powder, which is the compound.

[0010] The lipase catalyst is an immobilized lipase; the organic solvent is at least one of tert-amyl alcohol and acetone; and the acid is one of hydrochloric acid, lactic acid, citric acid, and acetic acid.

[0011] The immobilized lipase was immobilized Candida antarcticis lipase B (Novozym 435).

[0012] This amphiphilic amino acid-derived compound can be used in oral care compositions. An oral care composition comprises the following components: (1) an N-fatty acyl-L-arginine polyglycerol compound in an amount of 0.02%-0.50%; (2) a fluoride source providing 500-1500 ppm of free fluoride ions; and (3) an oral-acceptable carrier.

[0013] The N-fatty acyl-L-arginine polyglycerol ester compound content is preferably 0.05%-0.30%; the fluoride source is selected from at least one of NaF, SnF2, and sodium monofluorophosphate; the carrier in the oral care composition does not contain ethylene oxide derivatives; the composition does not contain sodium lauryl sulfate; the composition contains cocamidopropyl betaine; and the composition contains potassium nitrate.

[0014] The oral care composition is available in the form of toothpaste, dental gel, mouthwash, and professional care coating.

[0015] This compound was designed to match the carbon chain length with the degree of polymerization of polyglycerol.

[0016] One of the core design logics of this invention lies in the systematic matching between the length of the fatty acid chain (hydrophobic tail) and the degree of polymerization of polyglycerol (hydrophilic head group) to achieve optimal amphiphilic balance and oral application performance.

[0017] (1) Short chain (C12, lauroyl) + low degree of polymerization (PG3): C12 chain is long and has moderate hydrophobicity. Combined with PG3, it provides a moderate hydrophilic head group. The overall HLB is moderate and it dissolves quickly in water. It is suitable for low viscosity formulations such as mouthwash and oral spray that require rapid dispersion. (2) Medium chain (C14, myristoyl) + medium degree of polymerization (PG4): The C14 chain length performs best in terms of amphiphilic balance - the hydrophobic anchoring ability is strong enough, while not impairing water dispersibility. When combined with PG4, it achieves HLB balance and is suitable for most toothpaste and dental gel formulations, making it the optimal implementation scheme. (3) Long chain (C18:1, oleoyl, containing unsaturated double bonds) + high degree of polymerization (PG6): C18:1 long chain is highly hydrophobic and requires a larger hydrophilic head group to balance it. Combined with PG6, it provides sufficient hydrophilic groups to form a stable O / W emulsion or micelle, which is suitable for professional care products that require strong anchoring and high emulsion stability. (4) Saturated long chains (C16, C18) can be flexibly combined with PG4-PG8 depending on the specific application scenario, all of which are within the protection scope of this invention.

[0018] Therefore, the preferred compound (reflecting the matching logic between carbon chain length and polyglycerol degree of polymerization) is: First choice: N-Myristoyl-L-arginine polyglycerol-4 ester hydrochloride (C14-Arg-PG4 HCl) - medium chain + medium degree of polymerization, balanced type, most versatile; Second preferred option: N-lauroyl-L-arginine polyglycerol-3 ester hydrochloride (C12-Arg-PG3 HCl) – short chain + low degree of polymerization, fast dispersible, suitable for low viscosity formulations; Third preferred option: N-oleoyl-L-arginine polyglycerol-6 ester hydrochloride (C18:1-Arg-PG6 HCl) - long chain (unsaturated) + high degree of polymerization, strong anchoring, suitable for professional care products; Other preferred options: N-palmitoyl-L-arginine polyglycerol-4 ester hydrochloride (C16-Arg-PG4 HCl) and N-stearoyl-L-arginine polyglycerol-6 ester hydrochloride (C18-Arg-PG6 HCl).

[0019] The above combination logic has been verified by QCM-D adsorption kinetics experiments and KOH-F synergistic assays: C12-Arg-PG3 disperses 40% faster in mouthwash than C14-Arg-PG4; C14-Arg-PG4 has the best KOH-F enhancement effect in toothpaste formulation (+31%); C18:1-Arg-PG6 has the best emulsion stability in professional gels (no stratification after 30 days).

[0020] The fluoride delivery enhancement mechanism of Arg-PG ester involves: (1) Arginine guanidine group maintains strong positive charge in the oral pH range and strongly binds to the hydroxyapatite surface of tooth enamel through electrostatic and coordination interactions to achieve tooth surface anchoring; (2) The anchored fatty chain forms a directional monolayer or quasi-micelle structure through hydrophobic interactions, which locally concentrates fluoride ions on the tooth surface; (3) The hydrophilicity of polyglycerol head group ensures good water dispersibility in the formulation; (4) The above-mentioned fluoride enrichment microenvironment on the tooth surface promotes the preferential deposition of CaF2 protective layer.

[0021] The composition of the present invention has the following beneficial effects: when Arg-PG ester is used in combination with NaF, the amount of KOH-soluble fluoride deposited on the enamel surface is significantly increased (at least 20%) compared with the use of an equal amount of NaF alone, while the concentration of free fluoride ions is not less than 90% of that of the NaF-only formulation. Detailed Implementation

[0022] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the scope of the invention.

[0023] Example 1: Preparation of C14-Arg-PG4 HCl Weigh 20.0 g of N-myristoyl-L-arginine and 45.0 g of polyglycerol-4, add 100 mL of tert-amyl alcohol and 4.0 g of Novozym 435, and react at 50 °C for 48 hours. The conversion rate was monitored by HPLC to be greater than or equal to 92%. The enzyme particles were recovered by filtration, the filtrate was concentrated under reduced pressure, and hydrochloric acid solution was added to adjust the pH to 4.5-5.5 to precipitate the product. The product was filtered, washed, and dried under vacuum at 50 °C for 24 hours to obtain a white powder of C14-Arg-PG4 HCl with a yield of 82% and an HPLC purity of 96.5%.

[0024] Example 2: Preparation of C12-Arg-PG3 HCl Weigh 18.5 g of N-lauroyl-L-arginine and 38.0 g of polyglycerol-3, add 100 mL of acetone and 4.0 g of Novozym 435, and react at 48 °C for 52 hours. The conversion rate is greater than or equal to 90%. Post-treatment is the same as in Example 1, yielding a white C12-Arg-PG3 HCl powder with a yield of 80% and an HPLC purity of 95.8%. This compound dissolves in water approximately 40% faster than C14-Arg-PG4, making it particularly suitable for low-viscosity formulations.

[0025] Example 3: Preparation of C18:1-Arg-PG6 HCl 22.0 g of N-oleoyl-L-arginine and 52.0 g of polyglycerol-6 were weighed, 120 mL of tert-amyl alcohol was added, and 5.0 g of Novozym 435 was added. The mixture was reacted at 52 °C for 64 hours, with a conversion rate of ≥87%. Post-treatment was the same as in Example 1, yielding a pale yellow waxy solid of C18:1-Arg-PG6 HCl with a yield of 76% and an HPLC purity of 94.8%. This compound exhibited optimal emulsion stability in a professional gel (no stratification after 30 days).

[0026] Example 4: Preparation of C16-Arg-PG4 HCl N-palmitoyl-L-arginine (21.5 g) and polyglycerol-4 (45.0 g) were weighed, 100 mL of tert-amyl alcohol was added, and Novozym 435 (4.0 g) was added. The mixture was reacted at 55 °C for 60 hours, and the conversion rate was greater than or equal to 88%. The post-treatment was the same as in Example 1, yielding a white powder of C16-Arg-PG4 HCl with a yield of 78% and an HPLC purity of 95.2%.

[0027] Example 5: Preparation of C14-Arg-PG4 lactate C14-Arg-PG4 free base was prepared according to the steps in Example 1. During post-treatment, 0.1 mol / L lactic acid solution was used to adjust the pH to 4.5-5.5, yielding a white powder of C14-Arg-PG4 lactate with a yield of 80% and an HPLC purity of 96.0%. The lactate has a water solubility of approximately 35 mg / mL (superior to the hydrochloride at 22 mg / mL), making it suitable for formulations requiring high concentrations.

[0028] Example 6: Preparation of C14-Arg-PG4 citrate C14-Arg-PG4 free base was prepared according to the steps in Example 1. During post-treatment, 0.05 mol / L citric acid solution was used to adjust the pH to 5.0-6.0, yielding C14-Arg-PG4 citrate as a white powder with a yield of 79% and an HPLC purity of 95.5%. Citrate has a strong pH buffering capacity, which is beneficial for maintaining the pH stability of the formulation.

[0029] Example 7: Preparation of C14-Arg-PG4 acetate C14-Arg-PG4 free base was prepared according to the steps in Example 1. During post-treatment, 0.1 mol / L acetic acid solution was used to adjust the pH to 4.5-5.5, yielding a white powder of C14-Arg-PG4 acetate with a yield of 81% and an HPLC purity of 96.2%. The solubility in acetic acid solution is approximately 40 mg / mL (superior to hydrochloride 22 mg / mL and lactate 35 mg / mL). Furthermore, the acetate ion is a food-grade weak acid ion, offering a mild and non-irritating taste, making it particularly suitable for low-viscosity formulations that emphasize a refreshing taste, such as mouthwash and oral sprays.

[0030] Example 8: Anti-caries toothpaste formulation containing C14-Arg-PG4 HCl Preparation: Mix water and humectant evenly, then add thickener, abrasive, C14-Arg-PG4HCl, NaF, CAPB and flavoring agent in sequence while stirring. Homogenize, adjust pH to 6.8 with NaOH, degas and fill.

[0031] Example 9: Mouthwash Formula Containing C12-Arg-PG3 HCl Preparation: Mix water and glycerin, add C12-Arg-PG3 HCl (fast dissolution, suitable for low viscosity systems), add NaF, CAPB, flavoring agent and preservative, homogenize, adjust pH, filter, and fill. The C12-PG3 combination is particularly suitable for mouthwash and other dosage forms that require rapid dissolution and dispersion.

[0032] Example 10: Specialized gel formulation containing C18:1-Arg-PG6 HCl (strong anchoring type) Preparation: HEC is pre-dissolved in a portion of water to form a gel matrix. Glycerin, C18:1-Arg-PG6HCl, NaF, CAPB, and flavoring agent are added sequentially. The mixture is homogenized, the pH is adjusted, and then it is filled into containers. The C18:1-PG6 combination exhibits excellent emulsification stability and is suitable for professional fluorinated gels.

[0033] Example 11: Low-dose anti-caries toothpaste formulation containing C14-Arg-PG4 HCl The low-dose formulation (0.05%) is suitable for children or sensitive individuals and still provides significant synergistic effects in fluoride delivery.

[0034] Example 12: Anti-sensitivity multi-effect toothpaste formula containing C14-Arg-PG4 HCl Arg-PG ester's arginine guanidino group can help seal dentinal tubules, complementing the nerve desensitization mechanism of potassium nitrate, thus achieving the dual effects of preventing caries and reducing sensitivity.

[0035] Example 13: Determination of KOH-soluble fluoride deposition Acid-etched bovine tooth enamel slices (n=10 / group) were taken and treated with the formulation of three preferred compounds and the NaF control (brushing simulation, 5 days).

[0036] Conclusion: C14-Arg-PG4 showed the best improvement in KOH-F (+31%); C12-Arg-PG3 is suitable for fast dispersion scenarios; and C18:1-Arg-PG6 is suitable for strong anchoring professional products. The three compounds cover different application scenarios.

[0037] Example 14: Evaluation of pH Cyclic Remineralization Effect The White net remineralization model was used, and a 10-day pH cycle test was conducted.

[0038] The remineralization effects of the three selected compound groups were significantly better than those of NaF alone (p<0.01). C14-Arg-PG4 showed the best effect (129%).

[0039] Example 15: SEM-EDX Analysis of Tooth Enamel Surface SEM observation: The density of spherical CaF2 deposits on the glaze surface of the C14-Arg-PG4 group was significantly increased, and the surface film was more continuous and uniform. EDX quantification: The F atom content on the glaze surface of the C14-Arg-PG4 group was 4.5% (NaF control 2.8%), an increase of 61%.

[0040] Example 16: Adsorption kinetics of simulated enamel surfaces in QCM-D The irreversible adsorption capacity of C14-Arg-PG4 on the HAP surface (185 ng / cm2) is on the same order of magnitude as that of Olaflur (198 ng / cm2), and is much higher than that of free L-arginine. C18:1-PG6 forms the most rigid film layer, while C12-PG3 is the best in terms of dispersion rate.

[0041] Example 17: Comparison of the synergistic effect of KOH-F with different Arg-PG ester structures Conclusion: C14-Arg-PG4 HCl is the optimal choice overall. C12-Arg-PG3 is superior in terms of dissolution rate. C18:1-Arg-PG6 is superior in terms of emulsion stability. The three candidate compounds cover different application scenarios, verifying the correctness of the logic of matching carbon chain length with polyglycerol polymerization degree.

[0042] Example 18: Antibacterial Activity Test The minimum inhibitory concentration (MIC) was determined using the microbroth dilution method: The test bacteria (Streptococcus mutans, Streptococcus epidermidis, etc.) were activated and cultured, then diluted to the concentration of the standard bacterial solution, and C14-Arg-PG4 was prepared in gradients at different concentrations. HCl solution was co-cultured with bacterial culture, with a sterile blank control group and a normal bacterial growth control group set up, and cultured anaerobically at constant temperature for 24 h. By observing the turbidity of the bacterial culture and combining it with absorbance quantification, the minimum drug concentration that inhibits bacterial growth was determined, and the half-maximal inhibitory concentration (MIC50) was further calculated.

[0043] Experimental results showed that C14-Arg-PG4·HCl exhibited good inhibitory effects against typical cariogenic bacteria in the oral cavity, *Streptococcus mutans* and *Streptococcus sobrinus*, with a half-maximal inhibitory concentration (MIC50) range of 0.25%–0.30%, effectively inhibiting the proliferation and growth of major cariogenic pathogens. Simultaneously, this compound showed no significant inhibitory effect on normal beneficial commensal bacteria in the oral cavity and did not disrupt the inherent beneficial bacterial community structure. This pathogen-targeting selective antibacterial property can maintain oral microbial homeostasis while inhibiting cariogenic bacteria and reducing the risk of tooth decay, demonstrating superior oral safety and compatibility compared to broad-spectrum antibacterial ingredients.

[0044] Example 19: Formulation stability and free fluorine retention rate test Example 7: The toothpaste formulation, after 6 months of accelerated testing at 40°C, showed a free fluoride retention rate of 95.2% and an Arg-PG ester retention rate of 97.8%. The addition of Arg-PG ester did not affect the chemical stability of the free fluoride in the formulation.

[0045] Example 20: RDA / REA Wear Value Test After adding 0.15% C14-Arg-PG4 HCl, the RDA was 88 (control 85) and the REA was 13 (control 12), with no significant difference (p>0.05), which is well below the FDA upper limit. Arg-PG ester does not increase formulation abrasion.

[0046] Example 21: Cytotoxicity test (ISO 10993-5) At a concentration of 0.3%, C14-Arg-PG4 HCl resulted in a TR146 cell survival rate of 78% and an L929 cell survival rate of 82%, both meeting the ISO 10993-5 negative standard (>70%). The EC50 was approximately 0.85%, significantly higher than the concentration used in the formulation.

[0047] Example 22: Comparison of enzymatic synthesis and chemical synthesis The enzyme-catalyzed method produces products with higher purity, no DCC urea residue, complete preservation of chiral configuration, recyclable catalyst, and conforms to the concept of green chemistry, making it the optimal preparation method of this invention.

[0048] Example 23: Evaluation of the inhibitory effect on the inflammatory cytokine IL-6 The human buccal mucosal epithelial TR146 cell line was used as an in vitro oral mucosal evaluation model. TR146 cells in the logarithmic growth phase were routinely seeded and cultured. After cell adhesion stabilized, ArgiGly-F™ samples with final concentrations of 0.1%, 0.3%, and 1% were added, respectively, and the intervention was continued for 24 h under standard isothermal conditions. After the intervention, cell supernatant was collected, and the secretion level of the inflammatory cytokine interleukin-6 (IL-6) was quantitatively detected using enzyme-linked immunosorbent assay (ELISA). Using a blank control group without medication as a reference, the inhibition rate of each concentration of sample against the IL-6 inflammatory cytokine was calculated, and statistical differences were analyzed.

[0049] ArgiGly-F™ significantly inhibited the secretion of the inflammatory cytokine IL-6 in TR146 cells, and the anti-inflammatory effect showed a clear concentration-dependent increasing trend. The differences between each experimental concentration group and the blank control group were statistically significant (p < 0.05). Specifically, the 0.1% ArgiGly-F™ treatment group showed an IL-6 inhibition rate of 18%, the 0.3% concentration group showed an IL-6 inhibition rate of 30%, and the 1% high concentration group showed the best anti-inflammatory effect, with an IL-6 inhibition rate of up to 45%. These results confirm that ArgiGly-F™ of this invention can effectively downregulate the expression of inflammatory factors in oral mucosa-derived cells, significantly alleviate cellular inflammatory responses, and possess excellent in vitro anti-inflammatory activity. It can effectively improve the oral micro-inflammatory state, providing sufficient experimental evidence for its application in anti-inflammatory, oral mucosal repair, and oral care products related to improving dental and oral inflammatory damage.

[0050] The above description is merely a few preferred embodiments of the present invention and is not intended to limit the scope of protection of the present invention. It should be noted that those skilled in the art can make various modifications, equivalent substitutions, or improvements to the above embodiments without departing from the core ideas and technical principles of the present invention. Any such changes and modifications made within the spirit and principles of the present invention should be considered as included within the scope of protection defined by the claims of the present invention.

Claims

1. An amphiphilic amino acid-derived compound, characterized in that, The compound described is a systematic combination of aliphatic chain length and polyglycerol degree of polymerization, and its structural formula is as follows: R-CO-NH-CH(-(CH2)3-NHC(=NH)NH2)-COO-Polyglyceryl(n) X Wherein: R is a C11-C17 alkyl or alkenyl group; Polyglyceryl(n) is a polyglycerol residue, where n is an integer from 2 to 10; X is an orally acceptable salt.

2. The amphiphilic amino acid-derived compound according to claim 1, characterized in that, Oral acceptable salts are selected from at least one of hydrochloride, lactate, citrate and acetate.

3. The amphiphilic amino acid derivative compound according to claim 1, characterized in that, The systematic pairing between the aliphatic chain length and the degree of polyglycerol polymerization is one of the following: (1) Short fatty acid chains and low degree of polymerization glycerol are combined; (2) Combination of medium-fatty acid chain and medium-polymerization degree glycerol; (3) Combination of long fatty acid chains and high degree of polymerization glycerol; (4) Saturated long fatty acid chain combination and medium / high degree of polymerization glycerol combination.

4. The amphiphilic amino acid-derived compound according to claim 3, characterized in that, The compound is one of the following: N-Myristoyl-L-arginine polyglycerol-4 ester hydrochloride, N-Lauroyl-L-arginine polyglycerol-3 ester hydrochloride, N-Oleoyl-L-arginine polyglycerol-6 ester hydrochloride, N-Palmyl-L-arginine polyglycerol-4 ester hydrochloride, and N-Stearyl-L-arginine polyglycerol-6 ester hydrochloride.

5. The amphiphilic amino acid derivative compound according to claim 1, characterized in that, The preparation method of this compound is as follows: In the presence of a lipase catalyst, N-fatty acyl-L-arginine and polyglycerol with a degree of polymerization of 2-10 are reacted in an organic solvent at 40-65°C for 48-64 hours to generate N-fatty acyl-L-arginine polyglycerol ester. The conversion rate is monitored by HPLC, the enzyme particles are recovered by filtration, the filtrate is concentrated under reduced pressure, the pH is adjusted to 4.5-6.0 by adding acid solution, the product is precipitated, filtered, the filter cake is washed with an organic solvent, and dried under vacuum at 40-60°C for 12-36 hours to obtain a powder, which is the compound.

6. The amphiphilic amino acid-derived compound according to claim 5, characterized in that, The lipase catalyst is an immobilized lipase; the organic solvent is at least one of tert-amyl alcohol and acetone; and the acid is one of hydrochloric acid, lactic acid, citric acid, and acetic acid.

7. The amphiphilic amino acid-derived compound according to claim 6, characterized in that, The immobilized lipase is immobilized Candida antarcticis lipase B.

8. A compound derived from an amphiphilic amino acid as described in any one of claims 1-7, characterized in that, It can be applied to oral care compositions; the composition comprises the following components: a. The compound according to claim 1, in a content of 0.02%-0.50%; b. Fluoride source, providing 500-1500 ppm of free fluoride ions; c. Oral-acceptable carriers.

9. The oral care composition according to claim 8, characterized in that, The compound of claim 1 is preferably present in a content of 0.05%-0.30%; the fluoride is selected from at least one of NaF, SnF2, and sodium monofluorophosphate; the orally acceptable carrier is free of ethylene oxide derivatives; the composition is free of sodium lauryl sulfate; the composition contains cocamidopropyl betaine; and the composition contains potassium nitrate.

10. The oral care composition according to claim 9, characterized in that, The oral care composition is available in the form of toothpaste, dental gel, mouthwash, and professional care coating.

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