Glyceryl monooleate (BioDeep_00000406232)

natural product PANOMIX_OTCML-2023 Chemicals and Drugs

代谢物信息卡片

1-(9Z-octadecenoyl)-rac-glycerol

化学式: C21H40O4 (356.29264400000005)
中文名称: 甘油单油酸酯, 单油酸甘油酯
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 0.58%

Reviewed

Last reviewed on 2024-07-25.

Cite this Page

Glyceryl monooleate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/glyceryl_monooleate (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000406232). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCC/C=C\CCCCCCCC(OCC(O)CO)=O
InChI: 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-

描述信息

1-oleoylglycerol is a 1-monoglyceride where the acyl group is oleoyl. It has a role as a plant metabolite. It is a 1-acylglycerol 18:1 and a monooleoylglycerol. It is functionally related to an oleic acid.

Glyceryl monooleate, also known as monoolein, is a type of monoacylglycerol, which is a class of glycerolipids. Chemically, it is composed of a glycerol molecule esterified with a single fatty acid molecule. The fatty acid in glyceryl monooleate is typically oleic acid, a monounsaturated fatty acid with 18 carbons and one double bond. The double bond in oleic acid is in the cis configuration, which contributes to the fluidity of the molecule.

The chemical structure of glyceryl monooleate features a glycerol backbone with two free hydroxyl groups and one esterified with oleic acid. This structure imparts unique physical and chemical properties to the molecule, including its amphiphilic nature, which means it has both hydrophilic (water-attracting) and hydrophobic (oil-attracting) regions. This amphiphilicity makes glyceryl monooleate an effective emulsifier, helping to stabilize oil-in-water emulsions.

Biologically, glyceryl monooleate plays several important roles. In the food industry, it is used as an emulsifier to improve the texture and stability of food products. It is also used in the pharmaceutical industry as a solubilizing agent for drugs, an excipient in tablet formulations, and a component in liposomes and other drug delivery systems. Its biocompatibility and ability to enhance drug absorption make it particularly useful in the development of oral and topical drug formulations.

Glyceryl monooleate is also involved in lipid metabolism in the body. It is a precursor for the synthesis of other lipids and can be metabolized to produce energy. Additionally, it has been found to have potential health benefits, such as reducing blood cholesterol levels and modulating inflammation.
Monoolein is an endogenous metabolite.
Monoolein is an endogenous metabolite.

同义名列表

7 个代谢物同义名

Glyceryl monooleate; Monoolein; 1-(9Z-octadecenoyl)-rac-glycerol; MG(18:1(9Z)/0:0/0:0)[rac]; MG(18:1/0:0/0:0)[rac]; 1-oleoyl-rac-glycerol; Oleoyl glycerol

数据库引用编号

27 个数据库交叉引用编号

分类词条

甘油酯类

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Alessandro Fracassi, Kira A Podolsky, Sudip Pandey, Cong Xu, Joshua Hutchings, Soenke Seifert, Carlos R Baiz, Sunil K Sinha, Neal K Devaraj. Characterizing the Self-Assembly Properties of Monoolein Lipid Isosteres. The journal of physical chemistry. B. 2023 03; 127(8):1771-1779. doi: 10.1021/acs.jpcb.2c07215. [PMID: 36795462]
Mohamed Dawoud, Mariam Mojally, Randa Abdou, Hany G Attia. Comparative study on the performance of monoolein cubic nanoparticles and trimyristin solid lipid nanoparticles as carriers for docetaxel. Pharmaceutical development and technology. 2023 Mar; 28(3-4):277-287. doi: 10.1080/10837450.2023.2191274. [PMID: 36919494]
Larissa Gabriella Fusco Donadon, Giovanna Cassone Salata, Thalita Pedralino Gonçalves, Lisa de Carvalho Matos, Maria Clara Paiva Evangelista, Nicole Sampaio da Silva, Tereza Silva Martins, João Agostinho Machado-Neto, Luciana Biagini Lopes, Maria Teresa Junqueira Garcia. Monoolein-based nanodispersions for cutaneous co-delivery of methylene blue and metformin: Thermal and structural characterization and effects on the cutaneous barrier, skin penetration and cytotoxicity. International journal of pharmaceutics. 2023 Feb; 633(?):122612. doi: 10.1016/j.ijpharm.2023.122612. [PMID: 36642349]
Ajit Singh, Ajay Vaish, Rahul Shukla. Box-Behnken design optimized silibinin loaded glycerylmonooleate nanoliquid crystal for brain targeting. Chemistry and physics of lipids. 2022 05; 244(?):105193. doi: 10.1016/j.chemphyslip.2022.105193. [PMID: 35278428]
Valentina Notarstefano, Michela Pisani, Massimo Bramucci, Luana Quassinti, Filippo Maggi, Lisa Vaccari, Marco Parlapiano, Elisabetta Giorgini, Paola Astolfi. A vibrational in vitro approach to evaluate the potential of monoolein nanoparticles as isofuranodiene carrier in MDA-MB 231 breast cancer cell line: New insights from Infrared and Raman microspectroscopies. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2022 Mar; 269(?):120735. doi: 10.1016/j.saa.2021.120735. [PMID: 34923374]
Göran Surmeier, Michael Paulus, Eric Schneider, Susanne Dogan, Metin Tolan, Julia Nase. A pressure-jump study on the interaction of osmolytes and crowders with cubic monoolein structures. Soft matter. 2022 Feb; 18(5):990-998. doi: 10.1039/d1sm01425k. [PMID: 35015016]
Jiali Zhai, Sue Lyn Yap, Calum J Drummond, Nhiem Tran. Controlling the pH dependent transition between monoolein Fd3m micellar cubosomes and hexosomes using fatty acetate and fatty acid additive mixtures. Journal of colloid and interface science. 2022 Feb; 607(Pt 1):848-856. doi: 10.1016/j.jcis.2021.08.173. [PMID: 34536939]
Agustín Mangiarotti, Luis A Bagatolli. Impact of macromolecular crowding on the mesomorphic behavior of lipid self-assemblies. Biochimica et biophysica acta. Biomembranes. 2021 12; 1863(12):183728. doi: 10.1016/j.bbamem.2021.183728. [PMID: 34416246]
Nina Královič-Kanjaková, Lukáš Hubčík, Alexander Búcsi, Mária Klacsová, Sophie Combet, José Teixeira, Juan Carlos Martínez, Daniela Uhríková. Calcium mediated DNA binding in non-lamellar structures formed by DOPG/glycerol monooleate. Chemistry and physics of lipids. 2021 09; 239(?):105118. doi: 10.1016/j.chemphyslip.2021.105118. [PMID: 34280362]
N de Lange, J M Kleijn, F A M Leermakers. Self-consistent field modeling of mesomorphic phase changes of monoolein and phospholipids in response to additives. Physical chemistry chemical physics : PCCP. 2021 Jun; 23(25):14093-14108. doi: 10.1039/d1cp00697e. [PMID: 34159985]
Jakub Jagielski, Łucja Przysiecka, Dorota Flak, Magdalena Diak, Zuzanna Pietralik-Molińska, Maciej Kozak, Stefan Jurga, Grzegorz Nowaczyk. Comprehensive and comparative studies on nanocytotoxicity of glyceryl monooleate- and phytantriol-based lipid liquid crystalline nanoparticles. Journal of nanobiotechnology. 2021 Jun; 19(1):168. doi: 10.1186/s12951-021-00913-5. [PMID: 34082768]
Yue Wei, Yanping Xie, Zhixiang Cai, Yalong Guo, Hongbin Zhang. Interfacial rheology, emulsifying property and emulsion stability of glyceryl monooleate-modified corn fiber gum. Food chemistry. 2021 May; 343(?):128416. doi: 10.1016/j.foodchem.2020.128416. [PMID: 33127225]
Sarigama Rajesh, Jiali Zhai, Calum J Drummond, Nhiem Tran. Synthetic ionizable aminolipids induce a pH dependent inverse hexagonal to bicontinuous cubic lyotropic liquid crystalline phase transition in monoolein nanoparticles. Journal of colloid and interface science. 2021 May; 589(?):85-95. doi: 10.1016/j.jcis.2020.12.060. [PMID: 33450463]
Katherine Miranda-Cadena, Marisol Dias, Augusto Costa-Barbosa, Tony Collins, Cristina Marcos-Arias, Elena Eraso, Célia Pais, Guillermo Quindós, Paula Sampaio. Development and Characterization of Monoolein-Based Liposomes of Carvacrol, Cinnamaldehyde, Citral, or Thymol with Anti-Candida Activities. Antimicrobial agents and chemotherapy. 2021 03; 65(4):. doi: 10.1128/aac.01628-20. [PMID: 33468460]
Catarina Costa, Isabel S Oliveira, João P N Silva, Sandra G Silva, Cláudia Botelho, M Luísa C do Vale, Maria Elisabete C D Real Oliveira, Andreia C Gomes, Eduardo F Marques. Effective cytocompatible nanovectors based on serine-derived gemini surfactants and monoolein for small interfering RNA delivery. Journal of colloid and interface science. 2021 Feb; 584(?):34-44. doi: 10.1016/j.jcis.2020.09.077. [PMID: 33039681]
Sampa Sarkar, Nhiem Tran, Sarvesh Kumar Soni, Zeyad Nasa, Calum J Drummond, Charlotte E Conn. Cuboplex-Mediated Nonviral Delivery of Functional siRNA to Chinese Hamster Ovary (CHO) Cells. ACS applied materials & interfaces. 2021 Jan; 13(2):2336-2345. doi: 10.1021/acsami.0c20956. [PMID: 33410653]
Shen Yu Helvig, Laura Woythe, Simon Pham, Gizem Bor, Helene Andersen, Seyed Moein Moghimi, Anan Yaghmur. A structurally diverse library of glycerol monooleate/oleic acid non-lamellar liquid crystalline nanodispersions stabilized with nonionic methoxypoly(ethylene glycol) (mPEG)-lipids showing variable complement activation properties. Journal of colloid and interface science. 2021 Jan; 582(Pt B):906-917. doi: 10.1016/j.jcis.2020.08.085. [PMID: 32919118]
Elżbieta Jabłonowska, Dorota Matyszewska, Ewa Nazaruk, Marlena Godlewska, Damian Gaweł, Renata Bilewicz. Lipid membranes exposed to dispersions of phytantriol and monoolein cubosomes: Langmuir monolayer and HeLa cell membrane studies. Biochimica et biophysica acta. General subjects. 2021 01; 1865(1):129738. doi: 10.1016/j.bbagen.2020.129738. [PMID: 32956751]
Peipei Ma, Ruiteng Li, Lin Zhu, Xiang Yu, Siqing Zhu, Lulu Pang, Jinqiu Ma, Lina Du, Yiguang Jin. Wound healing of laser injured skin with glycerol monooleicate cubic liquid crystal. Burns : journal of the International Society for Burn Injuries. 2020 09; 46(6):1381-1388. doi: 10.1016/j.burns.2020.03.016. [PMID: 32305138]
Qingtao Liu, Yunxin Xiao, Adrian Hawley, Ben J Boyd. Lipid-based lyotropic liquid crystalline phase transitions as a novel assay platform using birefringence as the visual signal output. Journal of materials chemistry. B. 2020 08; 8(29):6277-6285. doi: 10.1039/d0tb00355g. [PMID: 32227064]
Juliane Riewe, Peer Erfle, Sebastian Melzig, Arno Kwade, Andreas Dietzel, Heike Bunjes. Antisolvent precipitation of lipid nanoparticles in microfluidic systems - A comparative study. International journal of pharmaceutics. 2020 Apr; 579(?):119167. doi: 10.1016/j.ijpharm.2020.119167. [PMID: 32087265]
Dorota K Flak, Vivian Adamski, Grzegorz Nowaczyk, Kosma Szutkowski, Michael Synowitz, Stefan Jurga, Janka Held-Feindt. AT101-Loaded Cubosomes as an Alternative for Improved Glioblastoma Therapy. International journal of nanomedicine. 2020; 15(?):7415-7431. doi: 10.2147/ijn.s265061. [PMID: 33116479]
Fatma Mohamed Elsenosy, Ghada Ahmed Abdelbary, Ahmed Hassen Elshafeey, Ibrahim Elsayed, Ahmed Roshdy Fares. Brain Targeting of Duloxetine HCL via Intranasal Delivery of Loaded Cubosomal Gel: In vitro Characterization, ex vivo Permeation, and in vivo Biodistribution Studies. International journal of nanomedicine. 2020; 15(?):9517-9537. doi: 10.2147/ijn.s277352. [PMID: 33324051]
Edi Simoni, Filippo Valente, Lukas Boge, Mimmi Eriksson, Erica Gentilin, Mariarita Candito, Diego Cazzador, Laura Astolfi. Biocompatibility of glycerol monooleate nanoparticles as tested on inner ear cells. International journal of pharmaceutics. 2019 Dec; 572(?):118788. doi: 10.1016/j.ijpharm.2019.118788. [PMID: 31676341]
Leonie van T Hag, Liliana de Campo, Nhiem Tran, Anna Sokolova, Raphael Trenker, Matthew E Call, Melissa J Call, Christopher J Garvey, Anna E Leung, Tamim A Darwish, Anwen Krause-Heuer, Robert Knott, Thomas G Meikle, Calum J Drummond, Raffaele Mezzenga, Charlotte E Conn. Protein-Eye View of the in Meso Crystallization Mechanism. Langmuir : the ACS journal of surfaces and colloids. 2019 06; 35(25):8344-8356. doi: 10.1021/acs.langmuir.9b00647. [PMID: 31122018]
Priya Singh, Veerendra Kumar Sharma, Subhankar Singha, Victoria García Sakai, Ramaprosad Mukhopadhyay, Ranjan Das, Samir Kumar Pal. Unraveling the Role of Monoolein in Fluidity and Dynamical Response of a Mixed Cationic Lipid Bilayer. Langmuir : the ACS journal of surfaces and colloids. 2019 04; 35(13):4682-4692. doi: 10.1021/acs.langmuir.9b00043. [PMID: 30807692]
Haiyu Ni, Shuwen Xu, Pengfei Gu, Adelijiang Wusiman, Yue Zhang, Tianxin Qiu, Zhenguang Liu, Han Ni, Yuanliang Hu, Jiaguo Liu, Yi Wu, Deyun Wang. Optimization of preparation conditions for CTAB-modified Polygonatum sibiricum polysaccharide cubosomes using the response surface methodology and their effects on splenic lymphocytes. International journal of pharmaceutics. 2019 Mar; 559(?):410-419. doi: 10.1016/j.ijpharm.2019.01.060. [PMID: 30738129]
Behnoosh Tajik-Ahmadabad, Lucas Chollet, Jacinta White, Frances Separovic, Anastasios Polyzos. Metallo-Cubosomes: Zinc-Functionalized Cubic Nanoparticles for Therapeutic Nucleotide Delivery. Molecular pharmaceutics. 2019 03; 16(3):978-986. doi: 10.1021/acs.molpharmaceut.8b00890. [PMID: 30648870]
Anne Trivino, Ashwini Gumireddy, Harsh Chauhan. Drug-Lipid-Surfactant Miscibility for the Development of Solid Lipid Nanoparticles. AAPS PharmSciTech. 2019 Jan; 20(2):46. doi: 10.1208/s12249-018-1229-3. [PMID: 30617602]
Ana C N Oliveira, Joana Fernandes, Anabela Gonçalves, Andreia C Gomes, M E C D Real Oliveira. Lipid-based Nanocarriers for siRNA Delivery: Challenges, Strategies and the Lessons Learned from the DODAX: MO Liposomal System. Current drug targets. 2019; 20(1):29-50. doi: 10.2174/1389450119666180703145410. [PMID: 29968536]
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Mohammad Yaser Khani Meynaq, Britta Lindholm-Sethson, Solomon Tesfalidet. Cationic interaction with phosphatidylcholine in a lipid cubic phase studied with electrochemical impedance spectroscopy and small angle X-ray scattering. Journal of colloid and interface science. 2018 Oct; 528(?):321-329. doi: 10.1016/j.jcis.2018.05.065. [PMID: 29860201]
Aaron Eskinazi-Budge, Dharani Manickavasagam, Tori Czech, Kimberly Novak, James Kunzler, Moses O Oyewumi. Preparation of emulsifying wax/glyceryl monooleate nanoparticles and evaluation as a delivery system for repurposing simvastatin in bone regeneration. Drug development and industrial pharmacy. 2018 Oct; 44(10):1583-1590. doi: 10.1080/03639045.2018.1483381. [PMID: 29847182]
Kapilkumar Vithani, Adrian Hawley, Vincent Jannin, Colin Pouton, Ben J Boyd. Solubilisation behaviour of poorly water-soluble drugs during digestion of solid SMEDDS. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 Sep; 130(?):236-246. doi: 10.1016/j.ejpb.2018.07.006. [PMID: 29981444]
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Nhiem Tran, Marion Hocquet, Blandine Eon, Parveen Sangwan, Julian Ratcliffe, Tracey M Hinton, Jacinta White, Berkay Ozcelik, Nicholas P Reynolds, Benjamin W Muir. Non-lamellar lyotropic liquid crystalline nanoparticles enhance the antibacterial effects of rifampicin against Staphylococcus aureus. Journal of colloid and interface science. 2018 Jun; 519(?):107-118. doi: 10.1016/j.jcis.2018.02.048. [PMID: 29486430]
Sanyog Jain, Pooja Yadav, Rajan Swami, Nitin Kumar Swarnakar, Varun Kushwah, Sameer S Katiyar. Lyotropic Liquid Crystalline Nanoparticles of Amphotericin B: Implication of Phytantriol and Glyceryl Monooleate on Bioavailability Enhancement. AAPS PharmSciTech. 2018 May; 19(4):1699-1711. doi: 10.1208/s12249-018-0986-3. [PMID: 29532426]
Nhiem Tran, Xavier Mulet, Adrian M Hawley, Celesta Fong, Jiali Zhai, Tu C Le, Julian Ratcliffe, Calum J Drummond. Manipulating the Ordered Nanostructure of Self-Assembled Monoolein and Phytantriol Nanoparticles with Unsaturated Fatty Acids. Langmuir : the ACS journal of surfaces and colloids. 2018 02; 34(8):2764-2773. doi: 10.1021/acs.langmuir.7b03541. [PMID: 29381863]
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