Monoolein - Moligand™, ≥50%(HPLC) , Agonist of GPR119, CAS No.111-03-5, Agonist of GPR119

CAS: 111-03-5 Cat. No.: M107453 Molecular Weight: 356.54 Beilstein Registry Number: 1728976 EC Number: 203-827-7

GRADE & PURITY Moligand™, ≥50%(HPLC)

Synonyms

1-Oleylglycerol | alpha-Monoolein | Excel O 95F | Oleoyl glycerol | 1-Monooleoyl-rac-glycerol | CHEBI:75342 | Emery oleic acid ester 2221 | Nikkol MGO | rac-1-Monoolein | Monoolein | mono-olein | 1,2,3-Propanetriol mono((Z)-9-octadecenoate) | 2,3-dihydrox

Storage

Protected from light,Argon charged,Room temperature

Shipped In

Normal

Overview

1-Oleoyl-rac-glycerol is a monoglyceride, obtained from natural oils and fats. It contains two alcohol groups that are reactive. It is soluble in chloroform and hexane. It can be crystallized from hexane.

Specifications

Synonyms

1-Oleylglycerol | alpha-Monoolein | Excel O 95F | Oleoyl glycerol | 1-Monooleoyl-rac-glycerol | CHEBI:75342 | Emery oleic acid ester 2221 | Nikkol MGO | rac-1-Monoolein | Monoolein | mono-olein | 1, 2, 3-Propanetriol mono((Z)-9-octadecenoate) | 2, 3-dihydrox

Specifications & Purity

Moligand™, ≥50%(HPLC)

Biochemical and Physiological Mechanisms

1-Oleoyl-rac-glycerol shows both inhibition and anti-inhibition action on the lipoprotein lipase mediated triglyceride hydrolysis. Monoolein (1-Oleoyl-rac-glycerol) is used in the development of monoolein-based nanoparticulate liquid dispersions as possib

Storage

Protected from light, Argon charged, Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of GPR119

Purity

≥50%(HPLC)

Names and Identifiers

• Canonical Smiles: CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)O
• IUPAC Name: 2,3-dihydroxypropyl (Z)-octadec-9-enoate
• InChIKey: RZRNAYUHWVFMIP-KTKRTIGZSA-N
• INCHI: 1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(CO)O
• WGK Germany: 1
• Molecular Weight: 356.54
• Beilstein: 1728976
• Reaxy-Rn: 1728976
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1728976&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerolipids
      • Subclass Monoradylglycerols
        • Level5 Monoacylglycerols
          • Level6 1-monoacylglycerols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerolipids
• Subclass: Monoradylglycerols
• Intermediate Tree Nodes: Monoacylglycerols
• Direct Parent: 1-monoacylglycerols
• Alternative Parents: Fatty acid esters Secondary alcohols Carboxylic acid esters 1,2-diols Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-acyl-sn-glycerol - Fatty acid ester - Fatty acyl - 1,2-diol - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Primary alcohol - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Alcohol - Organic oxide - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.
• External Descriptors: Monoacylglycerols

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)

GPR119 Tclin Glucose-dependent insulinotropic receptor (1 Activities)

Discover Target: GPR119

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

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

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

PLA2G2A Tchem Phospholipase A2 group IIA (1079 Activities)

Discover Target: PLA2G2A

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture & Light & Air sensitive
• Flash Point(°F): 309.2 °F
• Flash Point(°C): 154 °C
• Melt Point(°C): 35-37°C
• Molecular Weight: 356.500 g/mol
• XLogP3: 6.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 19
• Exact Mass: 356.293 Da
• Monoisotopic Mass: 356.293 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 315.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

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2. Qingqing Xu, Xiaoli Qin, Dongming Lan, Xuan Liu, Bo Yang, Sentai Liao, Weifei Wang, Yonghua Wang.  (2022)  Water-in-oil emulsions enriched with alpha-linolenic acid in diacylglycerol form: Stability, formation mechanism and in vitro digestion analysis.  FOOD CHEMISTRY,      [PMID:35609461] [10.1016/j.foodchem.2022.133201]

3. Fu Fangqin, Li Xin, Zheng Tengyi, Xia Xiao, Du Minqun, Huang Zhengwei, Huang Ying, Pan Xin, Wu Chuanbin.  (2021)  Stability Evaluation of Lyotropic Liquid Crystalline Precursor for the Co-delivery of Chlorhexidine and Silver Nanoparticles.  AAPS PHARMSCITECH,  22  (7): (1-9).  [PMID:34545436] [10.1208/s12249-021-02102-x]

4. Weiwei Wang, Zhuangzhuang Liu, Qimin Song, Xindi Zhang, Shengkai Jiao, Yao Xu, Quanda Xu, Dezun Sheng.  (2021)  Tribological performance of organic molybdenum in the presence of organic friction modifier.  PLoS One,  16  (6): (e0252203).  [PMID:34111128] [10.1371/journal.pone.0252203]

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6. Xiao-Wei Chen, Shang-De Sun, Guo-Long Yang, Chuan-Guo Ma.  (2019)  Engineering phytosterol-based oleogels for potential application as sustainable petrolatum replacement.  RSC Advances,  10  (1): (244-252).  [PMID:35492564] [10.1039/C9RA06950J]

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8. Tengyi Zheng, Xintian Huang, Jintian Chen, Disang Feng, Liling Mei, Ying Huang, Guilan Quan, Chune Zhu, Vikramjeet Singh, Hao Ran, Xin Pan, Chuan-Yu Wu, Chuanbin Wu.  (2018)  A liquid crystalline precursor incorporating chlorhexidine acetate and silver nanoparticles for root canal disinfection.  Biomaterials Science,  6  (3): (596-603).  [PMID:29406548] [10.1039/C7BM00764G]

9. Han Lidong, Yang Rong, Yuan Shengxiao, Ding Shuang, Wu Ziheng, Wu Zhenghong, Qi Xiaole.  (2018)  Soft multiple emulsions demonstrating reversible freeze-thawing capacity and enhanced skin permeability of diclofenac sodium.  COLLOID AND POLYMER SCIENCE,  296  (3): (471-481).  [PMID:] [10.1007/s00396-018-4265-3]

10. Xuan Liu, Chunjin Huang, Dongming Lan, Weifei Wang, Yonghua Wang.  (2024)  Combining phospholipase A1 with monoacylglycerol lipase for crude vegetable oil degumming through improved oil-water separation.  FOOD CHEMISTRY,      [PMID:39644657] [10.1016/j.foodchem.2024.142366]

11. Siliang Ding, Xiaohan Chen, Bo Ouyang, Bo Yang, Weifei Wang, Yonghua Wang.  (2024)  Exploring Diacylglycerol Oil-Based Oleogels as Effective Stabilizers in Peanut Butter: Performance, Structural Insights, and Sensory Evaluation.  Journal of Oleo Science,      [PMID:38311404] [10.5650/jos.ess23122]

12. Ruirui Li, Wei Zhuang, Yan Gao, Yahan Bai, Keke Zhang, Zhenfu Wang.  (2024)  Interfacial modulation of hierarchically porous UIO-66 for the immobilization of Rhizomucor miehei lipase towards the efficient synthesis of 1,3-dioleic acid glycerol.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39710037] [10.1016/j.ijbiomac.2024.138993]

13. Bowen Yang, Tian Zhao, Shengyang Ji, Yan Liu, Minghao Xu, Baiyi Lu.  (2024)  Molecular dynamics simulations of the interfacial behaviors and photo-oxidation of phytosterol under different emulsion oil content.  FOOD CHEMISTRY,      [PMID:38663239] [10.1016/j.foodchem.2024.139292]

14. Huijing Chen, Shanliang Zhong, Guoxiang Chi, Huiying Li, Kewei Chen, Zhirong Wang, Jianquan Kan.  (2025)  Preparation and functional characteristics of starch-lipid complexes with different oleic acid-rich glycerolipids.  FOOD CHEMISTRY,      [PMID:39986078] [10.1016/j.foodchem.2025.143450]

15. Binke Wang, Xinyu Qi, Ruping Yang, Xu Xu, Shiyao Li, Chunli Zhang, Haitao Yu.  (2025)  Cubosome-based co-delivery of doxorubicin and polydatin for targeted cancer therapy.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168855]

16. Huijing Chen, Qi Zhao, Guoxiang Chi, Kewei Chen, Zhirong Wang, Jianquan Kan.  (2025)  Effects of the oleic acid-rich glycerolipids and thermal-mechanical treatment on the functionality of wheat gluten: Multi-spectroscopy and molecular simulation analysis.  FOOD CHEMISTRY,      [PMID:40279899] [10.1016/j.foodchem.2025.144472]

17. Yongxin Li, Wenni Tian, Fang Tian, Yanrong Zhao, Xuguang Zhang, Jie Xiao.  (2025)  Spatiotemporally programmed co-delivery via double emulsions enables absorption synergy of 5-MTHF-ca and vitamin D3.  FOOD RESEARCH INTERNATIONAL,      [PMID:40597517] [10.1016/j.foodres.2025.116800]

18. Yanru Bao, Jiawei Li, Hanhao Qin, Shuning Yuan, Hao Jiang.  (2025)  Glyceride-modulated starch-based emulsion gels with enhanced structural precision for texture-controlled 3D printed dysphagia foods.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:41482229] [10.1016/j.ijbiomac.2025.149979]

19. Huijing Chen, Qi Zhao, Guoxiang Chi, Zhirong Wang, Jianquan Kan.  (2026)  Multi-spectroscopy and molecular simulation reveal the interaction of oleic glycerolipids modified wheat dough induced by thermomechanical treatment.  FOOD CHEMISTRY,      [PMID:41764825] [10.1016/j.foodchem.2026.148650]

20. Huijing Chen, Guoxiang Chi, Xiaowei Peng, Zhirong Wang, Jianquan Kan.  (2026)  Structural and physicochemical properties of thermo-mechanical combined lipid modified wheat starches and their application in model dough.  FOOD CHEMISTRY,      [PMID:] [10.1016/j.foodchem.2026.148974]