CRYSTAL GROWTH & DESIGN
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2022
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IF 4.01
Liyu Liu,Zaiyong Zhang,Yinxiang Cheng,Yihua Jiang,Liye Lu,Jian-Rong Wang,Xuefeng Mei
L-menthol is one of the most important flavoring additives with abundant plant sources. The distinctive odor, cooling characteristic, and diversified biological activities attribute to its widespread application, especially on confections, oral-care commodities, over-the-counter drugs, and tobacco flavors. However, the manufacturing and storage of L-menthol face challenges due to its high volatility and low melting point. In this work, cocrystallization provides a new strategy to manage the stability problem of this important ingredient. Coformers of dietary sources were chosen based on a supramolecular synthon design, and six cocrystals of L-menthol were synthesized by either a solvent-mediated or solvent-free approach. These new solid forms could significantly increase the melting point and reduce the vapor pressure up to 1/45 of the pure L-menthol. Moreover, cocrystals present a high retention rate under storage conditions. The superior stability can be ascribed to diversified supramolecular cavities assembled by coformers, to which L-menthol molecules are restricted by hydrogen bonds.
研究领域:
食品科学
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材料科学
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化学
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产品关联
DOI
高影响因子
MOLECULES
·
2022
·Vol. 27
·期 18
·6013
·
IF 4.927
Xinjiao Cui,Donghao Ye,Jiankun Wei,Xiaodi Du,Pengzhao Wang,Junsheng Li
Fragrances have been widely used in many customer products to improve the sensory quality and cover flavor defects. The key to the successful application of fragrance is to realize controlled fragrance release, which relies on the use of an appropriate carrier for fragrance. An ideal fragrance carrier helps to achieve the stable storage and controlled release of fragrance. In this work, a novel composite fragrance carrier with MIL-101 (Cr) as the fragrance host and cellulose acetate fiber (CAF) as the protective shell was developed. The encapsulation effect of MIL-101 (Cr) and the protective function of the CAF shell significantly improved the storage stability of L-menthol (LM). Only 5 wt % of LM was lost after 40 days of storage at room temperature. Encapsulated LM could also be effectively released upon heating due to the thermal responsiveness of CAF. In addition, the composite carrier was highly stable with neglectable Cr leaching under different conditions. The results of this work showed that the developed composite carrier could be a promising carrier for the thermally triggered release of fragrance.Keywords:composite materials;stable storage;controlled release;adsorption;L-menthol
研究领域:
材料科学
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化学工程
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产品关联
DOI
PubMed
高影响因子
BIOMATERIALS
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2014
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IF 8.312
Kun Zhang,Hangrong Chen,Faqi Li,Qi Wang,Shuguang Zheng,Huixiong Xu,Ming Ma,Xiaoqing Jia,Yu Chen,Juan Mou,Xia Wang,Jianlin Shi
Aiming at substantially enhanced efficacy and biosafety of clinical HIFU therapy, a natural solid medium, L-menthol (LM), characteristic of mild and controllable “solid-liquid-gas” (SLG) tri-phase transition, was adopted, instead of those conventional explosive liquid–gas (LG) bi-phase transitional media, in constructing a multifunctional theranostic system. Owing to the continuous and controllable characteristics of SLG tri-phase transition, such a novel tri-phase transition-based theranostic system has been demonstrated of the repeatedly enhanced HIFU efficacy ex vivo and in vivo under once intravenous injection and the significantly improved treatment precision, controllability and biosafety when comparing to the traditional bi-phase transition medium, perfluorohexane (PFH), thus promising great application potential in clinical HIFU treatment. Moreover, this theranostic system has been demonstrated a long blood-circulation lifetime and continuous accumulation in tumor in 24 h, which is very beneficial for the enhanced tumor ablation in vivo along with SLG tri-phase transition. More importantly, after loading multiple model drugs and real drug, such a theranostic system presents a HIFU-mediated temperature-responsive drug release property, and depending on the versatile miscibility of LM, co-loadings with hydrophobic and hydrophilic drugs are also achieved, which provides the possibility of synergistic treatment combining HIFU therapy and chemotherapy.
研究领域:
医学影像学
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肿瘤学
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药剂学
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DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2022
·
IF 6.633
Lin Chen,Li Ge,Qinghui Liang,Zhenbo Zhao,Kedi Yang
The enantioseparation of valsartan enantiomers using chiral eutectic solvents (ESs) as extractants was initially studied. The hydrophobic ESs (LM-DTTA) formed by L-menthol and (+)-Di-p-toluoyl-D-tartaric acid is a suitable chiral medium for the enantioselective extraction of R- and S-valsartan. Four principal parameters affecting chiral extraction, such as phase volume ratio, initial rac -valsartan concentration, extraction temperature, and system pH, were evaluated. The results showed that LM-DTTA has better and higher enantioselectivity levels, and one-step chiral extraction achieved an ee value of S-valsartan up to 91% under the optimized conditions. In addition, this chiral medium can be recycled through simple back-extraction with sodium bicarbonate solution and reused at least five times, giving similar results. This work provides a clear example of enantioseparation of the rac -valsartan via liquid–liquid enantioselective extraction using the LM-DTTA as a novel chiral recognition and separation medium. As a result, the established enantioselective extraction method can efficiently separate the R- and S-enantiomer and promote sustainable development for the production of S-valsartan.
研究领域:
药物化学
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分离科学
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产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2024
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IF 5.7
Jiawei Zhou,Yumin Sang,Zhuang Wang,Jiacheng Feng,Linjiang Zhu,Xiaolong Chen
Enzymatic kinetic resolution is a promising way to produce l-menthol. However, the properties of the reported biocatalysts are still unsatisfactory and far from being ready for industrial application. Herein, a para-nitrobenzylesterase (pnbA) gene from Bacillus subtilis was cloned and expressed to produce l-menthol from d,l-menthyl acetate. The highest enantiomeric excess (ee) value of the product generated by pnbA was only approximately 80%, with a high conversion rate (47.8%) of d,l-menthyl acetate with the help of a cosolvent, indicating high catalytic activity but low enantioselectivity (E = 19.95). To enhance the enantioselectivity and catalytic efficiency of pnbA to d,l-menthyl acetate in an organic solvent-free system, site-directed mutagenesis was performed based on the results of molecular docking. The F314E/F315T mutant showed the best catalytic properties (E = 36.25) for d,l-menthyl acetate, with 92.11% ee and 30.58% conversion of d,l-menthyl acetate. To further improve the properties of pnbA, additional mutants were constructed based on the structure-guided triple-code saturation mutagenesis strategy. Finally, four mutants were screened for the best enantioselectivity (ee > 99%, E > 300) and catalytic efficiency at a high substrate concentration (200 g/L) without a cosolvent. This work provides several generally applicable biocatalysts for the industrial production of l-menthol.
研究领域:
生物化学
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酶工程
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合成生物学
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产品关联
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2023
·Vol. 20
·期 7
·e202300539
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IF 2.9
Yi-Gui Qiu,Zi-Hui Yang,Xue-Bao Sun,Dao-Jun Jin,Yi-Ming Zheng,Jia Li,Wen Gu
To discover novel laccase inhibitors as potential fungicides, twenty-six novel L-menthol hydrazide derivatives were designed and synthesized. In the in vitro antifungal assay, most of the target compounds displayed pronounced antifungal activity against Sclerotinia sclerotiorum , Fusarium graminearum , and Botryosphaeria dothidea . Especially, the EC 50 of compounds 3 b and 3 q against B. dothidea was 0.465 and 0.622 mg/L, which was close to the positive compound fluxapyroxad (EC 50 =0.322 mg/L). Scanning electron microscopy (SEM) analysis showed that compound 3 b could significantly damage the mycelial morphology of B. dothidea. In vivo antifungal experiments on apple fruits showed that 3 b exhibited excellent protective and curative effects. Furthermore, in the in vitro laccase inhibition assay, 3 b showed outstanding inhibitory activity with the IC 50 value of 2.08 μM, which is much stronger than positive control cysteine and PMDD-5Y. These results indicated that this class of L-menthol derivatives could be promising leads for the discovery of laccase-targeting fungicides. Graphical
研究领域:
植物保护学
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药理学
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分子生物学
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DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
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2023
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IF 8.1
Siyi Peng,Jiajia Zhao,Yaru Wang,Fang Chen,Xiaosong Hu,Lingjun Ma,Junfu Ji
L-menthol-containing food products generally show the flavor loss during storage due to their high volatility. The hydrophobicity of L-menthol also causes the inadequate flavor release during rehydration. In this study, the stability of L-menthol was enhanced by microencapsulation and the effect of different powder drying techniques was also investigated. The highest efficiency (76.58–78.66 %) and loading content (18.58–28.35 mg/g) of encapsulations were obtained by using a mass ratio of 2:1(α-LA: GA). Then they were dried by non-thermal spray freeze drying (SFD) technique compared to spray drying (SD) and freeze-drying (FD) process. The SFD particles were shown to be spherical and porous with the highest porosity (86.82 %). α-LA/GA based microparticles with spherical shapes were demonstrated to largely enhance flavor retention during high humidity storage. In addition, the porous structures of SFD powders could cause rapid rehydration in liquid models, and the release behaviors of loaded L-menthol followed the Fickian diffusion. Consequently, the SFD technique shows great potential to produce microparticles by regulating the release behaviors of L-menthol during storage and rehydration.
研究领域:
食品科学
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材料科学
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化学工程
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产品关联
DOI
PubMed
高影响因子
CARBOHYDRATE POLYMERS
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2025
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IF 12.5
Qian Jiang,Lijia Liu,Xuan Yuan,Huan Li,Yudan Wang,Junqing Li
To address the ecological pollution caused by synthetic antimicrobial agents in conventional food packaging films, we have successfully developed a fully bio-based and sustainable food packaging film that exhibits exceptional antibacterial and antioxidant properties. In this study, we designed and synthesized two novel natural alcohol esters of amino acid (NAEAAs)—L-Trp-Men and L-Trp-Bor—through esterification reactions involving L -tryptophan ( L -Trp) and L -Menthol or Borneol, respectively. A multifunctional composite film system was constructed using natural corn starch (CS) and sodium carboxymethyl cellulose (CMC) as the matrix materials, with NAEAAs serving as the antimicrobial active components and curcumin (Cur) as the antioxidant. Experimental results demonstrated that the CS/CMC/Men2/Cur2 composite film, containing 2 wt% additives, exhibited nearly complete (≈100 %) broad-spectrum antibacterial efficiency against both Escherichia coli and Staphylococcus aureus , alongside a DPPH radical scavenging rate of 45.69 ± 1.39 %. Cytotoxicity tests confirmed the excellent biocompatibility of NAEAAs, which hydrolyze into amino acids and natural alcohols, thereby minimizing environmental contamination. These fully natural material-based films present a novel approach for developing green, pollution-free, and renewable bio-based food packaging materials.
研究领域:
食品科学
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高分子科学
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材料工程
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生物技术
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环境科学
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化学合成
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产品关联
DOI
PubMed
高影响因子
Current Research in Food Science
·
2025
·
IF 7
Zinuo An,Liangbin Hu,Yuyin Fan,Zhenbin Liu,Hongbo Li,Dan Xu,Lu Tian,Jiayi Zhang,Haizhen Mo
Temperature malfunctions that occur frequently during cold chain transportation threaten the shelf life of meat products. This study developed a thermosensitive high-internal-phase Pickering emulsion (HIPE) co-stabilized by starch sodium octenyl succinate (SSOS) and nisin for encapsulating L-menthol, aiming to enhance the shelf-life of pork meatballs under cold-chain interruptions. SSOS-Nisin composite particles (SNCP) exhibited excellent interfacial stabilization via hydrogen bonding, hydrophobic interactions, and electrostatic forces, forming HIPEs with tunable viscosity and freeze-thaw-triggered L-menthol release. Rheological and stability analyses confirmed that the optimum viscosity of 1.89 Pa s was achieved with 10 % SNCP-stabilized HIPEs, which also exhibited excellent colloidal stability. In simulated cold-chain failure scenarios, freeze-thaw cycles induced rapid L-menthol release, achieving complete eradication of foodborne pathogenic microorganisms within 6 h. Applied to pork meatballs, HIPEs loaded with 160 mg/mL L-menthol significantly suppressed microbial growth, delayed lipid oxidation, maintained pH stability and hardness retention under bacterial contamination. These findings demonstrate the potential of thermoresponsive HIPEs as intelligent antimicrobial coatings for meat preservation.
研究领域:
食品科学
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胶体与界面科学
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食品保鲜
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抗菌技术
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材料科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）