DL-Menthol - Moligand™, analytical standard , Activator of TRPA1;Gating inhibitor of TRPA1;Activator of TRPM8;Activator of TRPV3, CAS No.89-78-1, Activator of TRPA1;Gating inhibitor of TRPA1;Activator of TRPM8;Activator of TRPV3

CAS: 89-78-1 Cat. No.: M105139 Molecular Weight: 156.27 Beilstein Registry Number: 3194263 EC Number: 201-939-0

GRADE & PURITY Analytical standard, Moligand™

Synonyms

AKOS016843634 | DTXCID30805 | HY-75161 | MENTHOL, UNSPECIFIED FORM | DTXSID8029650 | Menthol (USP) | DL-Menthol, analytical standard | Menthol racemate | 5-methyl-2-(propan-2-yl)cyclohexan-1-ol | Fisherman's friend lozenges | MFCD00062979 | BBL009325 | Cy

Storage

Room temperature

Shipped In

Normal

Overview

DL-Menthol triggers cold-sensitive TRPM8 receptors in the skin neurons in vitro. The (-)-Menthol form exists naturally in nature, primarily found in fruit extracts or spearmint extracts. This racemic mixture could theoretically be created by the hydrogenation of the monoterpene pulegone.
A chemical which triggers cold-sensitive TRPM8 receptors in the skin neurons in vitro.

Specifications

Synonyms

AKOS016843634 | DTXCID30805 | HY-75161 | MENTHOL, UNSPECIFIED FORM | DTXSID8029650 | Menthol (USP) | DL-Menthol, analytical standard | Menthol racemate | 5-methyl-2-(propan-2-yl)cyclohexan-1-ol | Fisherman's friend lozenges | MFCD00062979 | BBL009325 | Cy

Specifications & Purity

Moligand™, analytical standard

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard, Moligand™

Action Type

ACTIVATOR, GATING INHIBITOR

Mechanism of action

Activator of TRPA1;Gating inhibitor of TRPA1;Activator of TRPM8;Activator of TRPV3

Names and Identifiers

• Canonical Smiles: CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
• IUPAC Name: 5-methyl-2-propan-2-ylcyclohexan-1-ol
• InChIKey: NOOLISFMXDJSKH-UHFFFAOYSA-N
• INCHI: 1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
• Isomeric SMILES: CC1CCC(C(C1)O)C(C)C
• WGK Germany: 2
• RTECS: OT0350000
• Alternate CAS: 15356-70-4;1490-04-6
• Molecular Weight: 156.27
• Beilstein: 3194263
• Reaxy-Rn: 1902293
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1902293&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Menthane monoterpenoids
• Alternative Parents: Monocyclic monoterpenoids Cyclohexanols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-menthane monoterpenoid - Monocyclic monoterpenoid - Cyclohexanol - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
• Description: This 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: a monoterpenol

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV3 Tchem Transient receptor potential cation channel subfamily V member 3 (1 Activities)

Discover Target: TRPV3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (2 Activities)

Discover Target: TRPM8

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT2B7 Tchem UDP-glucuronosyltransferase 2B7 (787 Activities)

Discover Target: UGT2B7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)

Discover Target: UGT2B15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A1 Tchem UDP-glucuronosyltransferase 1-1 (448 Activities)

Discover Target: UGT1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A6 Tbio UDP-glucuronosyltransferase 1-6 (221 Activities)

Discover Target: UGT1A6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A8 Tbio UDP-glucuronosyltransferase 1-8 (233 Activities)

Discover Target: UGT1A8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)

Discover Target: UGT1A9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A3 Tbio UDP-glucuronosyltransferase 1-3 (217 Activities)

Discover Target: UGT1A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

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Cutibacterium acnes (887 Activities)

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Plasmodium falciparum (966862 Activities)

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Spodoptera littoralis (798 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cavia porcellus (23802 Activities)

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Musca domestica (713 Activities)

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Tetranychus urticae (2600 Activities)

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Rdl GABA receptor subunit (76 Activities)

Discover Target: Rdl

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

Discover Target: Trpm8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Colletotrichum gloeosporioides (560 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Culex pipiens (191 Activities)

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Leptinotarsa decemlineata (1161 Activities)

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Psoroptes ovis (78 Activities)

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Lipaphis erysimi (85 Activities)

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Theba pisana (23 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (partly), and alcohol.
• Flash Point(°F): 199.4 °F
• Flash Point(°C): 93 °C
• Boil Point(°C): 216°C
• Melt Point(°C): 32-36°C
• Molecular Weight: 156.260 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.151 Da
• Monoisotopic Mass: 156.151 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 120.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 3
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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2. Jingyu Zhang, Zhihui Zhang, Liping Yao, Mingrong Qian, Zuguang Li, Yulin Han, Shanshan Bai, Mawrong Lee.  (2023)  pH-responsive switchable deep eutectic solvents to mediate pretreatment method for trace analysis of triazole fungicides in peel wastes.  FOOD CHEMISTRY,      [PMID:36682163] [10.1016/j.foodchem.2023.135486]

3. Meichao Liao, Lin Yang, Xiaoyue Yang, Erxu Wang, Bin Lu, Jiye Wang, Li Duan.  (2022)  Vortex-assisted liquid–liquid microextraction based on hydrophobic deep eutectic solvent for the urinary excretion study of Taraxacum mongolicum extract in rats.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2022.108167]

4. Wen-wen Deng, Xue-ping Mei, Zi-jun Cheng, Tian-xiang gan, Xuan Tian, Jiang-nan Hu, Chuan-ru Zang, Bo Sun, Jing Wu, Yin Deng, Reza. A. Ghiladi, George H. Lorimer, Gizem Keceli, Jun Wang.  (2022)  Extraction of weak hydrophobic sulforaphane from broccoli by salting-out assisted hydrophobic deep eutectic solvent extraction.  FOOD CHEMISTRY,      [PMID:36370577] [10.1016/j.foodchem.2022.134817]

5. Heng Lu, Xiaohong Tan, Guobin Huang, Shaoru Wu, Yanmei Zhou, Junying Zhang, Qiaowen Zheng, Tianju Chen, Feiming Li, Zhixiong Cai, Jingbin Zeng, Maosheng Zhang.  (2022)  Green synthesis of highly stable CsPbBr3 perovskite nanocrystals using natural deep eutectic solvents as solvents and surface ligands.  Nanoscale,  14  (46): (17222-17229).  [PMID:36250272] [10.1039/D2NR04173A]

6. Jiaze Yan, Shaomin Ma, Mingrui Feng, Jiqi Zheng, Ming Guo.  (2022)  Hydrophobic deep eutectic solvent-based ultrasonic-assisted liquid-liquid microextraction combined with GC for eugenol, isoeugenol, and methyl isoeugenol determination in aquatic products.  Food Additives and Contaminants Part A-Chemistry Analysis Control Exposure & Risk Assessment,      [PMID:35997563] [10.1080/19440049.2022.2112764]

7. Meichao Liao, Yang Zhao, Xiaoyue Yang, Lin Yang, E-Hu Liu, Bin Lu, Jiye Wang, Xiaopeng Liu, Yanzhong Chang, Li Duan.  (2022)  A greener and sustainable route for medicinal plant analysis: Recycle utilization of hydrophobic deep eutectic solvent.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2022.107372]

8. Tian Quan, Dandan Wang, Lijuan Yang, Shaochi Liu, Yongqin Tao, Junji Wang, Linlin Deng, Xun Kang, Kailian Zhang, Zhining Xia, Die Gao.  (2021)  Effective extraction methods based on hydrophobic deep eutectic solvent coupled with functional molecularly imprinted polymers: Application on quercetagetin extraction from natural medicine and blood.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2021.107076]

9. Jing Li, Yanjun Jiao, Qin Luo, Weixin Hu, Shenwen Fang, Chunling Tang, Qiang Liu.  (2021)  Treatment of oil-based drill cuttings by hydrophobic deep eutectic solvents.  CANADIAN JOURNAL OF CHEMICAL ENGINEERING,  100  (8): (1747-1754).  [PMID:] [10.1002/cjce.24263]

10. Tong Wang, Qing Wang, Qing Guo, Ping Li, Hua Yang.  (2021)  A hydrophobic deep eutectic solvents-based integrated method for efficient and green extraction and recovery of natural products from Rosmarinus officinalis leaves, Ginkgo biloba leaves and Salvia miltiorrhiza roots.  FOOD CHEMISTRY,      [PMID:34144425] [10.1016/j.foodchem.2021.130282]

11. Ge Dandan, Gao Ying, Cao Yunxin, Dai Enrui, Yuan Lin.  (2020)  Preparation of a New Polymeric Deep Eutectic Solvent and Its Application in Vortex-Assisted Liquid-Liquid Microextraction of Parabens in Foods, Cosmetics and Pharmaceutical Products.  JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY,  31  (10): (2120-2128).  [PMID:] [10.21577/0103-5053.20200113]

12. Yingjie Zhang, Li Kang, Huajun Huang, Jianping Deng.  (2020)  Optically Active Janus Particles Constructed by Chiral Helical Polymers through Emulsion Polymerization Combined with Solvent Evaporation-Induced Phase Separation.  ACS Applied Materials & Interfaces,      [PMID:31939279] [10.1021/acsami.9b21222]

13. Ge Dandan, Wang Ying, Jiang Qian, Dai Enrui.  (2019)  A Deep Eutectic Solvent as an Extraction Solvent to Separate and Preconcentrate Parabens in Water Samples Using in situ Liquid-Liquid Microextraction.  JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY,  30  (6): (1203-1210).  [PMID:] [10.21577/0103-5053.20190014]

14. Dandan Ge, Yi Zhang, Yixiu Dai, Shumin Yang.  (2017)  Air-assisted dispersive liquid–liquid microextraction based on a new hydrophobic deep eutectic solvent for the preconcentration of benzophenone-type UV filters from aqueous samples.  JOURNAL OF SEPARATION SCIENCE,  41  (7): (1635-1643).  [PMID:29282887] [10.1002/jssc.201701282]

15. Linzhou Zhuang, Beibei Ma, Siyu Chen, Xunan Hou, Shuixia Chen.  (2015)  Fast synthesis of mesoporous silica materials via simple organic compounds templated sol–gel route in the absence of hydrogen bond.  MICROPOROUS AND MESOPOROUS MATERIALS,      [PMID:] [10.1016/j.micromeso.2015.04.007]

16. Jiaze Yan, Chao Jiang, Jiqi Zheng, Ming Guo.  (2025)  Enhanced microdialysis based on hydrophobic deep eutectic solvents for sampling of eugenol in Glyptocidaris crenularis.  ANALYTICA CHIMICA ACTA,      [PMID:40021328] [10.1016/j.aca.2025.343774]

17. Yuxin Liu, Chenjie Ma, Mantang Chen, Jufang Hao, Wei Liu, Jingjing Yu.  (2025)  Hydrophobic deep eutectic solvent-based ferrofluid for the multi-residue analysis of pyrethroid insecticides in agricultural products: Facile pretreatment and MS-friendly detection.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:40773813] [10.1016/j.chroma.2025.466262]

18. Xiaoyan Jiang, Renxiu Huang, Guohua Zhu, Lingqi Shen, Panfei Li, Xuerong Yang, Fangxi Xu, Zuguang Li.  (2025)  Determination of liquid crystal monomers in environmental water by ultrasound-assisted pH-responsive deep eutectic solvent based homogeneous liquid-liquid microextraction.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:40819546] [10.1016/j.chroma.2025.466279]

19. Yan Li, Kun Hu, Chao Huang, Yong Hu, Hongwu Ji, Shucheng Liu, Jing Gao.  (2022)  Improvement of solubility, stability and antioxidant activity of carotenoids using deep eutectic solvent-based microemulsions.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:35679734] [10.1016/j.colsurfb.2022.112591]

20. Zixing Zhang, Yuxin Xu, Yun Hu.  (2025)  Enhancing the water resistance and functional properties of chitosan-based films using a hydrophobic deep eutectic solvent.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40446998] [10.1016/j.ijbiomac.2025.144776]

21. Yan Zhou, Xujing Dong, Xiaoyi Tian, Shuai Wang, Fanqing Meng, Jianguang Qi, Yinglong Wang, Ekemini Ituen.  (2025)  Highly efficient separation of adipic and glutaric acids from aqueous solutions by phosphonate-based deep eutectic solvents: Experimental and molecular insights.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2025.136258]

22. Yalu Liu, Zhenpeng Wang, Yapeng Zhang, Jiutao Hu, Sen Huang, Bin Hao, Xiaobo Huang.  (2025)  Photocurable 3D-Printed Hydrophobic Eutectic Gels for Underwater Wearable Sensors.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2025.139322]

23. Minjie Gao, Congfei Zhu, Yasen Dai, Bingru Wang, Shuhang Ren, Weize Wu.  (2026)  Physicochemical Properties of Ethylene Glycol-Based Deep Eutectic Solvents for CO2 Capture.  JOURNAL OF CHEMICAL AND ENGINEERING DATA,      [PMID:] [10.1021/acs.jced.5c00729]