2716-53-2

Basic information

• Product Name: MONOELAIDIN
• Synonyms: DELTA 9 TRANS MONOELAIDIN;GLYCEROL ALPHA-MONOELAIDATE;1-MONO-TRANS-9-OCTADECENOYL GLYCEROL;MONOELAIDIN;monoelaidin (C18:1;MONOELAIDIN (C18:1 (TRANS)-9);1-(trans-9-Octadecenoyl)-rac-glycerol;(9E)-9-Octadecenoic acid 2,3-dihydroxypropyl ester
• CAS NO: 2716-53-2
• Molecular Formula: C₂₁H₄₀O₄
• Molecular Weight: 356.54
• Mol File: 2716-53-2.mol
• Article Data: 48

Chemical Properties

• Melting Point: 58 °C
• Boiling Point: 483.3°C at 760 mmHg
• Flash Point: 155.4°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 2.27E-11mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: −20°C
• PKA: 13.16±0.20(Predicted)
• CAS DataBase Reference: MONOELAIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOELAIDIN(2716-53-2)
• EPA Substance Registry System: MONOELAIDIN(2716-53-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2716-53-2(Hazardous Substances Data)

Usage

Description

MONOELAIDIN, also known as 1-Monoelaidin, is a naturally occurring compound derived from the monounsaturated fatty acid, elaidic acid. It is structurally similar to the compound found in chili peppers, capsaicin, and is known to activate the transient receptor potential vanilloid subtype 1 (TRPV1) receptor. This activation has been linked to various physiological effects and potential therapeutic applications.

Uses

Used in Pharmaceutical Applications:
MONOELAIDIN is used as an activator for the TRPV1 receptor, which is also known as the capsaicin receptor. The activation of this receptor has been associated with various physiological effects, including pain relief, anti-inflammatory actions, and potential neuroprotective properties. As a result, MONOELAIDIN may be utilized in the development of novel pharmaceuticals targeting these areas.
Used in Pain Management:
MONOELAIDIN is used as a pain-relieving agent due to its ability to activate the TRPV1 receptor. This activation can lead to the desensitization of pain-sensing neurons, providing relief from various types of pain, including chronic and neuropathic pain.
Used in Anti-Inflammatory Applications:
MONOELAIDIN is used as an anti-inflammatory agent, as the activation of the TRPV1 receptor can help reduce inflammation by modulating the release of pro-inflammatory mediators. This property makes MONOELAIDIN a potential candidate for the treatment of various inflammatory conditions, such as arthritis and other autoimmune diseases.
Used in Neuroprotection:
MONOELAIDIN is used as a neuroprotective agent, as the activation of the TRPV1 receptor has been shown to provide neuroprotective effects against various neurodegenerative diseases, such as Alzheimer's and Parkinson's disease. The potential neuroprotective properties of MONOELAIDIN make it a promising candidate for the development of therapeutics targeting these conditions.

InChI:InChI=1/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+

Upstream product

• 112-62-9 Methyl oleate 
• 112-80-1 cis-Octadecenoic acid 
• 56-81-5 glycerol 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 122-32-7 trioleoylglycerol 
• 111-62-6 oleic acid ethyl ester 
• 3896-58-0 vinyl oleate 
• 33001-45-5 (+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 506-24-1 Stearolic acid 
• 1120-32-7 stearolic acid methyl ester 
• 50816-19-8 8-bromooctanol 
• 168136-39-8 2-(octadec-9-yn-1-yloxy)tetrahydro-2H-pyran 

Downstream Products

• 20299-66-5 1,2-bis-lauroyloxy-3-oleoyloxy-propane 
• 18985-53-0 silicic acid tetrakis-(2-hydroxy-3-oleoyloxy-propylester) 
• 120831-58-5 (+/-)-1,2-bis-octadeca-9c,11t,13t-trienoyloxy-3-oleoyloxy-propane 
• 2465-32-9 1,3-diolein 
• 3443-84-3 2-Oleoylglycerol 
• 101200-99-1 1-oleoyl-3-acetyl-rac-glycerol 
• 55401-64-4 (Z)-9-octadecenoic acid 2,3-bis(acetyloxy)propyl ester 
• 124109-45-1 (+/-)-O¹-butyryl-O³-oleoyl-glycerol 
• 121235-57-2 (+/-)-1,2-bis-butyryloxy-3-oleoyloxy-propane 
• 1867-91-0 1,2-dipalmitoyl-3-oleoyl-rac-glycerol 
• 2190-29-6 (+-)-1-oleoyloxy-2,3-bis-stearoyloxy-propane 
• 20299-65-4 1,2-bis-decanyloxy-3-oleoyloxy-propane 
• 74160-01-3 1,2-bis-myristoyloxy-3-oleoyloxy-propane 
• 2190-29-6 1-oleoyloxy-2,3-bis-stearoyloxy-propane 

Relevant articles and documents

Synthesis and physical properties of EOE and EEO, triacylglycerols containing elaidic and oleic fatty acids

Symmetrical and non-symmetrical triacylglycerols (TAG) containing oleic (O; 9c-18:1) and elaidic (E; 9t-18:1) acids were required as part of a study relating the physical characteristics and functionality of trans-containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils-a significant part of frying oils prepared by partial hydrogenation of vegetable oils-without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans-containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p-toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3- and 1,2-isomers). The DAG fraction was separated by silica gel chromatography, the 1,3-dielaidylglycerol (1,3EE-DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O-MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi-gram quantities of EOE and EEO, in 80-85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more-stable MAG or DAG precursors, the symmetrical EOE and non-symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined. AOCS 2007.

Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2

The invention belongs to the field of fatty acid glyceride synthesis and nano powder preparation, relates to a method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2,and particularly relates to a method for synthesizing fatty acid monoglyceride and co-producing the nano SiO2 by long-chain fatty acid and glycerinum. The method comprises the following steps of: using silicon tetrachloride to react with the glycerinum, so as to enable the glycerinum to be partially esterified to generate silicic acid glyceride; and performing an esterification reaction with fatty acid to generate fatty acid silicic acid glyceride; finally using high-activity (instability) of silicate ester, hydrolyzing in a mild condition, synthesizing the high-content fatty acid monoglyceride, and by-producing SiO2 powder in a nano state. So that a fatty acid monoglyceride product is high-selectively obtained and nano SiO2 powder is co-produced by a simple technology in the mild condition.

Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids

Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.