18427-44-6

Basic information

• Product Name: 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID
• Synonyms: 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID;CIS-PARINARIC ACID;parinaric acid;OCTODECATETRAENOICACID;Octadeca-9,11,13,15-tetrenoic acid;9,11,13,15-Octadecatetraenoic acid;Paranaric acid;IJTNSXPMYKJZPR-ZSCYQOFPSA-N
• CAS NO: 18427-44-6
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.41
• EINECS: 242-409-9
• Mol File: 18427-44-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 400.2°Cat760mmHg
• Flash Point: 297°C
• Appearance: /
• Density: 0.937g/cm³
• Vapor Pressure: 1.6E-07mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID(18427-44-6)
• EPA Substance Registry System: 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID(18427-44-6)

Safety Data

• Hazardous Substances Data: 18427-44-6(Hazardous Substances Data)

Usage

Description

9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID, also known as cis-Parinaric acid, is a naturally occurring polyunsaturated fatty acid with a unique conjugated (Z,E,E,Z) tetraene structure. This chromophore allows for natural fluorescence at 432 nm with an excitation wavelength at 320 nm. It is found in the seeds of the Makita tree, a tropical rainforest tree native to Fiji. The acid has been utilized for various scientific applications, including the measurement of phospholipase and lipase activities, as well as an indicator of lipid peroxidation.

Uses

Used in Biomedical Research:
9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID is used as a research tool for studying phospholipase and lipase activities. Its natural fluorescence allows for the easy detection and measurement of these enzyme activities, which are crucial for understanding various biological processes and potential therapeutic targets.
Used in Lipid Peroxidation Studies:
9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID is used as an indicator of lipid peroxidation, a process that occurs during oxidative stress and can lead to cell damage. By monitoring the levels of this acid, researchers can gain insights into the extent of oxidative stress and the potential for cell damage in various conditions.
Used in Analytical Chemistry:
9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID is used as a reference compound in analytical chemistry for the identification and quantification of similar conjugated fatty acids. Its unique fluorescence properties make it an ideal candidate for developing and validating analytical methods.
Used in Pharmaceutical Industry:
9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID may be used as a starting material or intermediate in the synthesis of pharmaceutical compounds targeting various diseases, including those related to lipid metabolism and oxidative stress. Its unique structure and properties can provide valuable insights for drug discovery and development.
Used in Food Industry:
Although the Makita seeds containing 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID are toxic and inedible, the understanding of the properties of this acid could potentially lead to the development of new food additives or preservatives that leverage its unique characteristics to improve food quality and safety.

InChI:InChI=1/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)/b4-3-,6-5+,8-7+,10-9-

Upstream product

• 96823-14-2 (9E,13E,15E)-12-(Pyrrolidine-1-carbothioylsulfanyl)-octadeca-9,13,15-trienoic acid 
• 593-38-4 (9Z,11E,13E,15Z)-octadecatetraenoic acid 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 85235-81-0 Pyrrolidine-1-carbodithioic acid (2E,4E)-hepta-2,4-dienyl ester 
• 86826-33-7 pentadienyldithiocarbamate 
• 96823-09-5 2-(7-Iodo-heptyl)-[1,3]dioxolane 
• 96823-16-4 2-((E)-10-Bromo-dec-8-enyl)-[1,3]dioxolane 
• 96823-15-3 2-((E)-10-Iodo-dec-8-enyl)-[1,3]dioxolane 
• 85235-56-9 Pyrrolidine-1-carbodithioic acid (E)-1-ethyl-penta-2,4-dienyl ester 
• 96823-11-9 Pyrrolidine-1-carbodithioic acid (E)-10-[1,3]dioxolan-2-yl-dec-2-enyl ester 
• 96823-10-8 Pyrrolidine-1-carbodithioic acid 8-[1,3]dioxolan-2-yl-1-vinyl-octyl ester 
• 96823-13-1 Pyrrolidine-1-carbodithioic acid (E)-1-((1E,3E)-hexa-1,3-dienyl)-12-oxo-dodec-3-enyl ester 
• 96823-12-0 Pyrrolidine-1-carbodithioic acid (E)-11-[1,3]dioxolan-2-yl-1-((1E,3E)-hexa-1,3-dienyl)-undec-3-enyl ester 
• 1005452-45-8 C₈H₁₃BO₂ 

Downstream Products

• 123-99-9 azelaic acid 
• 144-62-7 oxalic acid 
• 802294-64-0 propionic acid 
• 57-11-4 stearic acid 

Relevant articles and documents

Synthesis of four isomers of parinaric acid

A simple and reliable method for synthesizing four isomers of parinaric acid from α-linolenic acid (ALA) in high yields is described. The methylene-interrupted, cis triene system (1,4,7-octatriene) of ALA and common to other naturally occurring polyunsaturated fatty acids was transformed to a conjugated tetraene system (1,3,5,7-octatetraene). The synthesis involves bromination of ALA using 0.l M Br2 in a saturated solution of NaBr in methanol, esterification of the fatty acid dibromides, double dehydrobromination by 1,8-diazabicyclo[5.4.0]undec-7-ene and saponification of the conjugated esters to a mixture of free conjugated acids. Addition of one molecule of bromine to the 12,13-double bond of ALA and subsequent dehydrobromination produces α-parinaric acid (9Z,11E,13E,15Z- octadecatetraenoic acid); addition of Br2 to the 9,10-double bond or 15,16-double bond and then dehydrobromination and rearrangement yields 9E,11E,13E,15Z-octadecatetraenoic or 9E,11E,13E,15Z-octadecatetraenoic acids, respectively. The mixture of parinaric acid isomers is obtained in 65% yield, and the isomers can be purified by preparative HPLC; alternatively, the isomers can be converted by base catalyzed cis-trans isomerization (or by treatment with I2) to exclusively β-parinaric acid (9E,11E,13E,15E- octadecatetraenoic acid). The various parinaric acid isomers were characterized by 1H NMR, 13C NMR, UV, GLC, HPLC and mass spectrometry.

A NEW, GENERAL, AND STEREOSELECTIVE SYNTHESIS OF LONG CHAIN TETRAENOIC ACIDS EXAMPLIFIED BY β-PARINARIC ACID

All trans-9,11,13,15-octadecatetraenoic acid was first synthesized in a stereoselective manner, using pentadienyl and allyl dithiocarbamates as the starting materials.This synthesis confirmed that β-parinaric acid has all trans configurations about the four double bonds.

Synthesis of conjugated polyenes via sequential condensation of sulfonylphosphonates and aldehydes

Selective metalation of sulfonylphosphonates results in sufficiently stable carbanions that undergo chemoselective Julia-Kocienski condensation with various aldehydes to provide (E)-allylic phosphonates in good yields and selectivities. The subsequent Horner-Wadsworth-Emmons condensation with aldehydes is used to synthesize various unsymmetrical trans-dienes, trienes, and tetraenes. This methodology is utilized for the concise synthesis of a naturally occurring fluorescent probe for membrane properties, β-parinaric acid.

SYSTEM FOR CONTROLLING THE REACTIVITY OF BORONIC ACIDS

A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.