(1R,2S,5R)-(-)-Menthol - Standard for GC, ≥99.5%(GC) , CAS No.2216-51-5

CAS: 2216-51-5 Cat. No.: M107058 Molecular Weight: 156.27 Beilstein Registry Number: 1902293 EC Number: 218-690-9
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GRADE & PURITY Standard for GC ? GC reference standard — characterized compound for calibrating GC methods. Use to build calibration curves and verify GC quantitation. ≥99.5%(GC)
Synonyms
CCRIS 375 | l-Menthol (TN) | (-)-Menthyl alcohol | (1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol | DTXSID1022180 | Levomentholum [INN-Latin] | CHEBI:15409 | Racementol [INN-Spanish] | SR-05000001936 | (1R,2S,5R)-5-methyl-2-propan-2-
Storage
Room temperature
Shipped In
Normal
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Size
Status
Price
Qty
1g
M107058-1g
10
$28.90
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Why this grade

Standard for GC, ≥99.5%(GC) Standard for GC for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Room temperature Ships Normal Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 24 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Specifications

Synonyms
CCRIS 375 | l-Menthol (TN) | (-)-Menthyl alcohol | (1R-(1-alpha, 2-beta, 5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol | DTXSID1022180 | Levomentholum [INN-Latin] | CHEBI:15409 | Racementol [INN-Spanish] | SR-05000001936 | (1R, 2S, 5R)-5-methyl-2-propan-2-
Specifications & Purity
Standard for GC, ≥99.5%(GC)
Storage
Room temperature
Shipped In
Normal
Grade
Standard for GC
Purity
≥99.5%(GC)
Names and Identifiers
Canonical SmilesCC1CCC(C(C1)O)C(C)C
IUPAC Name(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
InChIKeyNOOLISFMXDJSKH-KXUCPTDWSA-N
INCHI1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
Isomeric SMILES C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
WGK Germany 2
RTECS OT0700000
Molecular Weight 156.27
Beilstein 1902293
Reaxy-Rn 1902288
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1902288&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree Nodes Not available
Direct ParentMenthane monoterpenoids
Alternative Parents Monocyclic monoterpenoids  Cyclohexanols  Cyclic alcohols and derivatives  Hydrocarbon derivatives  
Molecular FrameworkAliphatic homomonocyclic compounds
Substituents P-menthane monoterpenoid - Monocyclic monoterpenoid - Cyclohexanol - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
External Descriptors Menthane monoterpenoids
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
TRPV3 Tchem Transient receptor potential cation channel subfamily V member 3 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT2A1 UDP-glucuronosyltransferase 2A1 (59 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OR5K1 Tdark Olfactory receptor 5K1 (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TAS2R7 Tchem Taste receptor type 2 member 7 (31 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Monographella nivalis var. nivalis (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

7 results found

Lot NumberCertificate TypeDateItem
G2209200Certificate of AnalysisJan 20, 2026 M107058
K2512592Certificate of AnalysisNov 19, 2025 M107058
G2515369Certificate of AnalysisJul 29, 2025 M107058
D2514401Certificate of AnalysisMay 06, 2025 M107058
G2408310Certificate of AnalysisAug 21, 2024 M107058
K1524056Certificate of AnalysisMay 10, 2023 M107058
F2126129Certificate of AnalysisJun 29, 2021 M107058
Chemical and Physical Properties
Refractive Index1.46
Specific Rotation[α]-50 ° (C=10, EtOH)
Flash Point(°F)213.8 °F
Flash Point(°C)93℃
Boil Point(°C)212°C
Melt Point(°C)41-43°C
Molecular Weight156.260 g/mol
XLogP33.000
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass156.151 Da
Monoisotopic Mass156.151 Da
Topological Polar Surface Area20.200 Ų
Heavy Atom Count11
Formal Charge0
Complexity120.000
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Documents & Articles
Citations of This Product
References
1. Ang Li, Song Xue, Yu Xu, Sihui Ding, Di Wen, Qi Zhang.  (2022)  A feasibility study on the use of hydrophobic eutectic solvents as pseudo-stationary phases in capillary electrophoresis for chiral separations.  ANALYTICA CHIMICA ACTA,      [PMID:36628761] [10.1016/j.aca.2022.340693]
2. Liyu Liu, Zaiyong Zhang, Yinxiang Cheng, Yihua Jiang, Liye Lu, Jian-Rong Wang, Xuefeng Mei.  (2022)  Stabilizing L-Menthol by Cocrystallization: Supramolecular Cavities Succeeded in Retaining the Volatile Flavor.  CRYSTAL GROWTH & DESIGN,      [PMID:] [10.1021/acs.cgd.2c00919]
3. Li Yang, Shuang Wang, Zhongshui Xie, Rongrong Xing, Runqin Wang, Xuan Chen, Shuang Hu.  (2022)  Deep eutectic solvent - loaded Fe3O4@MIL-101(Cr) with core–shell structure for the magnetic solid phase extraction of non-steroidal anti-inflammatory drugs in environmental water samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2022.108150]
4. Xinjiao Cui, Donghao Ye, Jiankun Wei, Xiaodi Du, Pengzhao Wang, Junsheng Li.  (2022)  Controlled Thermal Release of L-Menthol with Cellulose-Acetate-Fiber-Shelled Metal-Organic Framework.  MOLECULES,  27  (18): (6013).  [PMID:36144758] [10.3390/molecules27186013]
5. Li Liu, Wenna Wu, Xiaoli Chen, Jingcheng Hao, Xingcen Liu, Shuli Dong, Shoutao Cao, Binbin Yao, Hongxiao Yu.  (2022)  Responsive emulsion gels of glycyrrhizic acid and alanine for cigarette capsules.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2022.129878]
6. Taotao Fan, Zongcheng Yan, Chanyuan Yang, Shunguo Qiu, Xiong Peng, Jianwei Zhang, Lihua Hu, Li Chen.  (2021)  Preparation of menthol-based hydrophobic deep eutectic solvents for the extraction of triphenylmethane dyes: quantitative properties and extraction mechanism.  ANALYST,  146  (6): (1996-2008).  [PMID:33507168] [10.1039/D0AN01864C]
7. Xiao-Hong Fan, Li-Tao Wang, Yuan-Hang Chang, Juan-Yan An, Ya-Wei Zhu, Qing Yang, Dong Meng, Yu-jie Fu.  (2020)  Application of green and recyclable menthol-based hydrophobic deep eutectic solvents aqueous for the extraction of main taxanes from Taxus chinensis needles.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2020.114970]
8. Long Ye, Yichao Lv, Yuanjiang Zhao, Zhuxian Zhou, Youqing Shen, Liming Jiang.  (2020)  Encapsulation of fragrances in micron-size silk fibroin carriers via coaxial electrohydrodynamic techniques.  MATERIALS CHEMISTRY AND PHYSICS,      [PMID:] [10.1016/j.matchemphys.2020.124167]
9. Ziman Hu, Songnan Li, Shaokang Wang, Bin Zhang, Qiang Huang.  (2020)  Encapsulation of menthol into cyclodextrin metal-organic frameworks: Preparation, structure characterization and evaluation of complexing capacity.  FOOD CHEMISTRY,      [PMID:32822901] [10.1016/j.foodchem.2020.127839]
10. Xiao-Hong Fan, Yuan-Hang Chang, Li-Tao Wang, Ya-Wei Zhu, Ming-Zhu Dong, Mu-Jie Lv, Juan-Yan An, Qing Yang, Jiao Jiao, Dong Meng, Yu-Jie Fu.  (2020)  A simple and efficient sample preparation for taxanes in Taxus chinensis needles with natural menthol-based aqueous deep eutectic solvent.  JOURNAL OF SEPARATION SCIENCE,  43  (7): (1339-1347).  [PMID:32017401] [10.1002/jssc.201900754]
11. Changcheng Wu.  (2015)  Synthesis and Characterization of a Series of Cholesterol-Based Liquid Crystalline Dimers with a Chiral (-)- Menthyl Terminal Group.  MOLECULAR CRYSTALS AND LIQUID CRYSTALS,      [PMID:] [10.1080/15421406.2014.953759]
12. Qi Tan, Yiwen Liu, Ruifeng An, Heping Wu, Zhiqiang Tian, Bingliang Gao.  (2024)  DBN-based molecular solvents for highly efficient and reversible CO2 capture.  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2024.114470]
13. Jiawei Zhou, Yumin Sang, Zhuang Wang, Jiacheng Feng, Linjiang Zhu, Xiaolong Chen.  (2024)  Enhancing the Enantioselectivity and Catalytic Efficiency of Esterase from Bacillus subtilis for Kinetic Resolution of l-Menthol through Semirational Design.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:38235660] [10.1021/acs.jafc.3c08321]
14. Bo Yang, Xu Zhang, Liguo Zhang, Jinjin Wu, Wei Wang, Qiaomei Huang, Zhenyuan Wang, Jichuan Zhang, Tongjie Xu, Chengyu Wu, Jiaheng Zhang.  (2024)  Ionic Liquid-Based Grapeseed Oil Emulsion for Enhanced Anti-Wrinkle Treatment.  Pharmaceuticals,  17  (10): (1273).  [PMID:39458914] [10.3390/ph17101273]
15. Jiamin Luo, Heng Lu, Bao-Ying Wen, Qiaowen Zheng, Junying Zhang, Yishan Li, Wenping Hong, Shanshan Zhao, Libo Shun, Feiming Li, Zhixiong Cai, Jin-Ming Lin, Qiang Chen, Maosheng Zhang, Jian-Feng Li.  (2024)  Natural Deep Eutectic Solvents as Absorbing Solution and Preparation Solvent of Perovskite Nanocrystals Simultaneously for CH3I Gas Visual Sensing.  ANALYTICAL CHEMISTRY,      [PMID:39307967] [10.1021/acs.analchem.4c04776]
16. Jue Chen, Hexiang Zhong, Shan Zhu.  (2024)  Study on Cu(II) extraction process optimization and mechanism from acidic leaching solution using the deep eutectic solvent P507/Menthol.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.123968]
17. Zinuo An, Liangbin Hu, Yuyin Fan, Zhenbin Liu, Hongbo Li, Dan Xu, Lu Tian, Jiayi Zhang, Haizhen Mo.  (2025)  Thermally-triggered L-menthol release system based on starch sodium octenyl succinate/Nisin-stabilized high internal phase Pickering Emulsion: Development, characterization and meatball coating application.  Current Research in Food Science,      [PMID:40937070] [10.1016/j.crfs.2025.101187]
18. Zongtao Li, Shaodui Ye, Leshou Zhang, Zhenjuan Duan, Shengchun Yang, Yong Liu, Xiaodong Wen.  (2025)  Highly sensitive and selective sensing of lead (II) ions in Paris polyphylla using fluorescence-enhanced sulfur quantum dots in deep eutectic solvent micelles.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:40896916] [10.1016/j.saa.2025.126868]
19. Yi Chen, Xuan Wang, Hongyang Ma, Shyam Venkateswaran, Benjamin S. Hsiao.  (2025)  Chiral electrospun nanofibrous membranes for selective adsorption of chiral compounds.  POLYMER,      [PMID:] [10.1016/j.polymer.2025.128893]
20. Fuhui Luo, Zhongqiao Zhao, Yong He, Fenfen Zeng, Xia Yang, Fengxiang Zhang, Wei Shi.  (2025)  A novel pH-switchable deep eutectic solvents system regulated by alkaline/acidic electrolytic water: Efficient extraction of polyphenolic compounds and solvent recycling.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.169349]
21. Danni Lin, Sisi Hu, Leyuan Zhou, Xiaojuan Ma, Lihui Chen, Dong Wang, Liulian Huang.  (2025)  Enhancing separation and anti-fouling performance of cellulose acetate ultrafiltration membranes by introducing natural deep eutectic solvent.  Journal of Water Process Engineering,      [PMID:] [10.1016/j.jwpe.2025.109042]
22. Xuejian Zhang, Xiaoke Shi, Hong Xu, Yao Wang, Dikai Zhu, Jianan Liu, Tingting Zhang, Hongqian Shentu, Wei Ding, Jun Lu, Feiyan Tao.  (2026)  Targeted alleviation of local inflammation by a hydroxypropyl-cyclodextrin-encapsulated prodrug of methyl salicylate and menthol though Nrf2/NF-κB pathway.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:41512796] [10.1016/j.intimp.2026.116171]
23. Xiaotong Lyu, Qi Jiang, Kemin Linghu, Yifei Zhou, Mengqian Yu, Chunhui Wei, Liangcai Lin, Qi Zhou, Zhengshu Zhou, Cuiying Zhang.  (2026)  Digital transformation of Jiangxiangxing Baijiu production: integrating flavor compound analysis, machine learning recognition, and genetic algorithm blending of multi-rounds.  FOOD RESEARCH INTERNATIONAL,      [PMID:41794499] [10.1016/j.foodres.2026.118635]
24. Zang Yu, Hou Rui, Wei Bohua, Liu Yuting, Wang Jianjun, Liu Jiao, Xu Liang, Zhang Wei.  (2026)  Cascade-controlled porous composite membranes: pore-supporting synergy enabling high-flux enantioseparation of amino acids and pharmaceuticals.  Science China-Materials,      [PMID:] [10.1007/s40843-025-3936-8]
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