Glycerol Trilinoleate - 10mM in DMSO , CAS No.537-40-6

CAS: 537-40-6 Cat. No.: G424596 Molecular Weight: 879.41 Beilstein Registry Number: 2(4)1760 EC Number: 208-666-6

GRADE & PURITY 10mM in DMSO

Synonyms

TG(18:2/18:2/18:2) | TG(18:2n6/18:2n6/18:2n6) | DTXSID60163201 | T72589 | TG(18:2omega6/18:2omega6/18:2omega6) | UNII-V5LJ52OGS7 | 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol | (Z,Z)-9,12-Octadecadienoic acid, 1,2,3-propanetriyl ester | Trilinolein | CHEBI

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

A linoleate triacylglycerol compound.

Specifications

Synonyms

TG(18:2/18:2/18:2) | TG(18:2n6/18:2n6/18:2n6) | DTXSID60163201 | T72589 | TG(18:2omega6/18:2omega6/18:2omega6) | UNII-V5LJ52OGS7 | 1, 2, 3-tri-(9Z, 12Z)-octadecadienoylglycerol | (Z, Z)-9, 12-Octadecadienoic acid, 1, 2, 3-propanetriyl ester | Trilinolein | CHEBI

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Glyceryl trilinoleate is a fatty acid comprised of the glycerol core and three linoleic acid moieties. Glyceryl trilinoleate is a very common fatty acid and is useful in studies concerning the effects of fatty acids on lipid and cholesterol handling in or

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CCCCCC=CCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC
• IUPAC Name: 2,3-bis[[(9Z,12Z)-octadeca-9,12-dienoyl]oxy]propyl (9Z,12Z)-octadeca-9,12-dienoate
• InChIKey: HBOQXIRUPVQLKX-BBWANDEASA-N
• INCHI: 1S/C57H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27-
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)COC(=O)CCCCCCC/C=C\C/C=C\CCCCC
• Molecular Weight: 879.41
• Beilstein: 2(4)1760
• Reaxy-Rn: 1718697
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1718697&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerolipids
      • Subclass Triradylcglycerols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerolipids
• Subclass: Triradylcglycerols
• Intermediate Tree Nodes: Not available
• Direct Parent: Triacylglycerols
• Alternative Parents: Lineolic acids and derivatives Tricarboxylic acids and derivatives Fatty acid esters Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Triacyl-sn-glycerol - Octadecanoid - Tricarboxylic acid or derivatives - Fatty acid ester - Fatty acyl - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
• External Descriptors: Triacylglycerols

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat & Air sensitive.
• Refractive Index: 1.48
• Molecular Weight: 879.400 g/mol
• XLogP3: 20.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 50
• Exact Mass: 878.736 Da
• Monoisotopic Mass: 878.736 Da
• Topological Polar Surface Area: 78.900 Ų
• Heavy Atom Count: 63
• Formal Charge: 0
• Complexity: 1130.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 6
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 6
• Covalently-Bonded Unit Count: 1

References

1. Dongyin Liu, Jingtao Cui, Ruibing Zhou, Chen He, Jun Cao, Chuan Li.  (2023)  Comparison and enrichment of sn-2 palmitoyl triacylglycerols (OPO/OPL) in fish oil for its potential application as human milk fat substitutes.  FOOD RESEARCH INTERNATIONAL,      [PMID:37254410] [10.1016/j.foodres.2023.112836]

2. Jing-Jing Zhang, Yan Gao, Mei-Ling Zhao, Xiao Xu, Bo-Nan Xi, Li-Ke Lin, Jing-Yi Zheng, Bang Chen, Yu Shu, Cong Li, Yehua Shen.  (2023)  Detection of walnut oil adulterated with high-linoleic acid vegetable oils using triacylglycerol pseudotargeted method based on SFC-QTOF-MS.  FOOD CHEMISTRY,      [PMID:36905710] [10.1016/j.foodchem.2023.135837]

3. Xuan Liu, Long Xu, Riming Luo, Dongxiao Sun-Waterhouse, Zhuang Liu, Qingqing Xu, Bo Yang, Dongming Lan, Weifei Wang, Yonghua Wang.  (2022)  Thermal properties, oxidative stability, and frying applicability of highly pure soybean-based diacylglycerol oil.  JOURNAL OF FOOD PROCESSING AND PRESERVATION,  46  (5): (e16528).  [PMID:] [10.1111/jfpp.16528]

4. Chen He, Jun Cao, Yuyan Bao, Zexin Sun, Zhongyuan Liu, Chuan Li.  (2021)  Characterization of lipid profiling in three parts (muscle, head and viscera) of tilapia (Oreochromis niloticus) using lipidomics with UPLC-ESI-Q-TOF-MS.  FOOD CHEMISTRY,      [PMID:33484957] [10.1016/j.foodchem.2021.129057]

5. Xing-Li Pei, Xiao-Ning Liu, Jia-Lin Du, Can Gong, Xu Xu.  (2020)  MALDI-MS imaging of lipids in corn using a flexible ultrasonic spraying device as matrix deposition method.  INTERNATIONAL JOURNAL OF MASS SPECTROMETRY,      [PMID:] [10.1016/j.ijms.2020.116373]

6. Yuting Wang, Huiyu Hu, David Julian McClements, Shaoping Nie, Mingyue Shen, Chang Li, Yousheng Huang, Jie Chen, Maomao Zeng, Mingyong Xie.  (2019)  Effect of fatty acids and triglycerides on the formation of lysine-derived advanced glycation end-products in model systems exposed to frying temperature.  RSC Advances,  9  (27): (15162-15170).  [PMID:35514805] [10.1039/C9RA01410A]

7. Yuting Wang, Huiyu Hu, David Julian McClements, Shaoping Nie, Mingyue Shen, Chang Li, Yousheng Huang, Yadong Zhong, Jie Chen, Maomao Zeng, Mingyong Xie.  (2019)  pH and lipid unsaturation impact the formation of acrylamide and 5-hydroxymethylfurfural in model system at frying temperature.  FOOD RESEARCH INTERNATIONAL,      [PMID:31284992] [10.1016/j.foodres.2019.05.001]

8. Shaoxuan Hu, Gang Li, Bo Lei, Chenxiao Hou, Guantao Shi, Yang Wang, Nai Wang, Jing Liu, Xiang Han, Kanshe Li, Qiuhong Wang, Fuxin Chen.  (2026)  Study in Oxidative Reaction of Polyunsaturated Fatty Acid Esters with Nuclear Magnetic Resonance Spectroscopy.  OZONE-SCIENCE & ENGINEERING,      [PMID:] [10.1080/01919512.2026.2637437]