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Octadecanedioic acid
CAS
871-70-5
PubChem ID
70095
Molecular formula
C18H34O4

Octadecanedioic acid, also known as 1,18-Octadecanedioic acid is a long chain aliphatic saturated fatty acid with terminal –COOH groups at both ends. It is normally not found in humans, but can be used as a molecular biomarker in patients with Reye’s syndrome. This long chain fatty acid is biodegradable, making it a suitable candidate for drug-carrier technologies. This long chain fatty acid, Octadecanedioic acid intermediate is a chemical for manufacture of important biomolecules. 1,18-Octadecanedioic acid intermediate is used extensively in drug delivery systems.

Synonyms: 

Physical, Chemical and Biological Characteristics

1,18-Octadecanedioic acid exists as solid white crystals and has a molecular mass of 314.46 grams per mole. It is slightly soluble in water and remains as an uncharged molecule in physiological pH. It shows FTIR peaks at 2910 cm-1 with Potassium Bromide wafer technique and at 1.25 ppm with one-dimensional 1H NMR Spectra.

Since this long chain fatty acid is slightly soluble in water and is weakly acidic (pKa = 4.65). It is normally not present even at miniscule amounts but can be detected in feces samples of patients with Colorectal Cancer. The toxic effects of Octadecanedioic acid are skin corrosion/irritation and serious eye damage. However, this fatty acid is not labeled as a serious toxic chemical like other dicarboxylic acids.

Industrial Applications

Over 52 vendor companies are present globally which manufacturers Octadecanedioic acid or 1,18-Octadecanedioic acid. The concentration of chemical suppliers and distributors for Octadecanedioic acid is mainly in China and United States with a small presence in Germany, UK, and Switzerland. Some of the chemical manufacturing units in the US specialize in bulk supplies and laboratory specific customization of Octadecanedioic acid for use in R&D. It is used primarily as a biodegradable compound for functionalization or coating on nanoparticles for drug delivery of Paclitaxel, a commonly prescribed chemotherapeutic drug against breast cancer and ovarian cancer. Another reason for Octadecanedioic acid huge application and demand is its use in manufacturing micro or nano-sized parts of surgical devices that are implantable or decomposable. The list of chemical suppliers of 1,18-Octadecanedioic acid has names from Japan, Hong Kong and India as well. Because of its increased pharmaceutical significance, various R&D groups are exploring microbial biocatalysts and substrates for the chemical synthesis of this unbranched lipid. Higher chain dicarboxylic acids such as Octadecanedioic acid are applied in the chemical synthesis of metal-acting fluids, detergents & surfactants, lubricants, oiling agents, emulsifiers, wetting agents, textile treatments and emollients. Since it has the potential to be used for various lipid derivatives and biochemical formulations, it has an increased demand in most developing and developed countries.

Octadecanedioic acid has been used in studying effect of antibiotics, developing Insulin analogs and studying disorders of lipid metabolism including Reye’s syndrome as a molecular biomarker. It has become an extensive molecule for testing the effect of different storage lipids on the plasma lipoprotein levels, different routes of fatty acid oxidation and to evaluate the toxicity of implantable medical devices.

References
  1. Candida guilliermondii as a potential biocatalyst for the production of long-chain ?,?-dicarboxylic acids, Nicole Werner, Miriam Dreyer, Wenke Wagner, Nicolas Papon, Steffen Rupp, Susanne Zibek; Biotechnology Letters

We identified the major ?- and ?-oxidation pathway genes in C. guilliermondii and performed first steps in the strain improvement. A double pox disruption mutant was created that slowed growth with oleic acid but showed accelerated DCA degradation. Increase in DCA production was achieved by homologous overexpression of a plasmid borne cytochrome P450 monooxygenase gene.

  1. Synthesis and study of novel biodegradable oligo (ester amide) s based on sebacic acid, octadecanedioic acid, 1, 6-hexanediamine and ?-caprolactone: 2; I Arvanitoyannis, A Nakayama, N Kawasaki… - Polymer, 1995 – Elsevier

Two series of novel oligo(ester amide)s based on sebacic acid/1,6-hexanediamine/?-caprolactone and octadecanedioic acid/1,6-hexanediamine/?-caprolactone were synthesized. The determination of the molecular weights with both gel permeation chromatography and 1H nuclear magnetic resonance (n.m.r.) showed that they vary from 1000 to 6000. Differential scanning calorimetry and thermogravimetric analysis were employed for determining glass transitions, melting points, heats of melting and decomposition temperatures of the oligo(ester amide)s.

  1. Effect of dietary stearic acid on plasma cholesterol and lipoprotein levels, A Bonanome, SM Grundy - New England Journal of Medicine, 1988 - Mass Medical Soc

We studied the metabolic effects of stearic acid (18:0) on plasma lipoprotein levels in 11 subjects during three dietary periods each. The three liquid-formula diets, which were used in random order, were high in palmitic acid (16:0), stearic acid, and oleic acid (18:1), respectively. Caloric intakes were the same during the three periods.

  1. Controlled crystallization of CaCO3 under stearic acid monolayers, S Mann, BR Heywood, S Rajam, JD Birchall - Nature, 1988 - nature.com

The degree of compression of the monolayer dictates the homogeneity of vaterite nucleation. In particular, partially compressed films are optimal for controlled crystallization, suggesting that the mobility of organic surfaces may be of general importance. Our results can be explained by electrostatic and stereochemical interactions at the inorganic–organic interface and these observations support current theories of biomineralization, as well as being of potential significance in the crystal engineering of microscopic inorganic assemblies2.

  1. Effect of saturated and unsaturated fatty acids on the desaturation in vitro of palmitic, stearic, oleic, linoleic, and linolenic acids, RR Brenner, RO Peluffo - Journal of Biological Chemistry, 1966 - ASBMB

Quantitative oxidative desaturation of labeled palmitic, stearic, oleic, linoleic, and linolenic acids to palmitoleic, oleic, octadeca-6, 9-dienoic, ?-linolenic, and octadeca-6, 9, 12, 15-tetraenoic acids, respectively, by liver microsomes of rats was studied by gas-liquid radiochromatography after incubation of the acids in a medium containing adenosine triphosphate, reduced nicotinamide adenine dinucleotide, reduced nicotinamide adenine dinucleotide phosphate, MgCl2, coenzyme A, glutathione, nicotinamide, NaF, and NaCN in oxygen at pH 7 and 35°. The rates of conversion of oleic into octadeca-6,9-dienoic, linoleic into ?-linolenic, and linolenic into octadeca-6,9,12, 15-tetraenoic acids were measured, and Lineweaver-Burk plots showed the existence of competitive reactions among the three acids.

  1. Hydrogenation alternatives: effects of trans fatty acids and stearic acid versus linoleic acid on serum lipids and lipoproteins in humans, P L Zock and M B Katan; Journal of Lipid Research

The objective of this study was to compare the effects of linoleic acid (cis,cis-C18:2(n-6)) and its hydrogenation products elaidic (trans-C18:1(n-9)) and stearic acid (C18:0) on serum lipoprotein levels in humans. Twenty-six men and 30 women, all normolipemic and apparently healthy, completed the trial. Three experimental diets were supplied to every subject for 3 weeks each, in random order (multiple cross-over). The Linoleate-diet provided 12.0% of total energy intake as linoleic acid, 2.8% as stearic acid, and 0.1% as trans fatty acids. The Stearate-diet supplied 3.9 energy % as linoleic acid, 11.8% stearic acid, and 0.3% trans fatty acids.

  1. FTIR-ATR studies on Langmuir-Blodgett films of stearic acid with 1-9 monolayers, F Kimura, J Umemura, T Takenaka - Langmuir, 1986 - ACS Publications

Fourier transform infrared (FTIR–attenuated total reflection (ATR) spectra have been recorded of Langmuir-Blodgett (LB) films of stearic acid deposited on a germanium plate with 1, 2, 3, 5, and 9 monolayers. Examination of the CH2 scissoring band suggests that the hydrocarbon chain of stearic acid in the first monolayer is in a hexagonal or pseudohexagonal subcell packing where each hydrocarbon chain is freely rotated around its axis oriented approximately perpendicular to the surface.

  1. Infrared study of adsorption in situ at the liquid-solid interface. V. Adsorption of octadecanol, octadecylamine, and octadecanedioic acid on silica, and a criterion for considering competitive adsorption, MJD Low, PL Lee - Journal of Colloid and Interface Science, 1973 - Elsevier

Infrared spectra were recorded in situ of octadecanol (A), 1,18-Octadecanedioic acid (B), and octadecanedioic acid (C) adsorbed from CC1 4 solutions onto highly degassed silica. Adsorbed A interacted with silanols and caused a shift, ?v OH, of the silanol band of~ 275 cm-1; ; the data suggest that A dimers interacted with silanols but also adsorbed without such an interaction. B interacted extensively and strongly with silanols, causing a ?vOH ~ 750 cm?1.