Name: Docosanedioic acid
Brand: BOC Sciences
Price: 629 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

5 g

$629

In stock

Synonyms

Felogenic acid; Phellogenic acid; 1,22-Docosanedioic acid; 1,20-Eicosanedicarboxylic acid; Docosan-1,22-dioic acid

IUPAC Name

docosanedioic acid

Canonical SMILES

C(CCCCCCCCCCC(=O)O)CCCCCCCCCC(=O)O

InChI

InChI=1S/C22H42O4/c23-21(24)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(25)26/h1-20H2,(H,23,24)(H,25,26)

InChIKey

DGXRZJSPDXZJFG-UHFFFAOYSA-N

Density

0.972 g/cm3

Melting Point

130 - 131°C

Flash Point

Not applicable

Appearance

White solid.

Quantity

Data not available, please inquire.

Storage

2-8°C

Boiling Point

527°C at 760 mmHg

Docosanedioic acid, a long-chain dicarboxylic acid with diverse applications, is utilized across various fields of bioscience and industry. Here are four key applications of docosanedioic acid:

Polymer Production: Acting as a fundamental unit for building polymers, docosanedioic acid plays a vital role in the synthesis of polyamides and polyesters. These polymers boast exceptional thermal and mechanical properties, making them ideal for high-performance applications. From engineering plastics to specialty coatings, the uses of these polymers are extensive and varied.

Lubricant Formulation: Within the lubricant industry, docosanedioic acid functions as an additive that enhances the viscosity and thermal stability of lubricants and greases. This enhancement is crucial for maintaining optimal machinery performance in extreme conditions, ultimately reducing wear and extending the longevity of mechanical components. Its versatile properties make it a valuable ingredient in lubricant formulations.

Cosmetic Industry: Embraced by the cosmetic industry, docosanedioic acid plays a key role in skincare and cosmetic product formulations. Its incorporation enhances the emollient properties of creams and lotions, providing lasting moisture to the skin. Additionally, it serves as a thickening agent, enhancing the texture and spreadability of cosmetic formulations. The multifaceted benefits of this acid contribute to creating luxurious and effective cosmetic products.

Pharmaceutical Applications: In the realm of pharmaceuticals, docosanedioic acid is being extensively researched for its potential in drug delivery systems. Its unique chemical structure enables the formation of biodegradable polymers that facilitate controlled drug release. This targeted delivery system ensures efficient administration of therapeutic agents at specific sites, improving treatment efficacy and patient adherence. The versatility of docosanedioic acid holds promise for advancing pharmaceutical innovations.

1.Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes.

Sanders RJ1, Ofman R, Valianpour F, Kemp S, Wanders RJ. J Lipid Res. 2005 May;46(5):1001-8. Epub 2005 Feb 16.

We studied the omega-oxidation of docosanoic acid (C22:0) in rat liver microsomes. C22:0 and 22-hydroxy-docosanoic acid (omega-hydroxy-C22:0) were used as substrates, and the reaction products were analyzed by electrospray ionization mass spectrometry. In the presence of NADPH, omega-oxidation of C22:0 produced not only the hydroxylated product, omega-hydroxy-C22:0, but also the dicarboxylic acid of C22:0, docosanedioic acid (C22:0-DCA). When rat liver microsomes were incubated with omega-hydroxy-C22:0 in the presence of either NAD+ or NADPH, C22:0-DCA was formed readily. Formation of C22:0-DCA from either C22:0 or omega-hydroxy-C22:0 with NADPH as cofactor was inhibited strongly by miconazole and disulfiram, whereas no inhibition was found with NAD+ as cofactor. Furthermore, omega-oxidation of C22:0 was reduced significantly when molecular oxygen was depleted. The high sensitivity toward the more specific cytochrome P450 inhibitors ketoconazole and 17-octadecynoic acid suggests that hydroxylation of C22:0 and omega-hydroxy-C22:0 may be catalyzed by one or more cytochrome P450 hydroxylases belonging to the CYP4A and/or CYP4F subfamily.

2.Bicyclic alpha,omega-dicarboxylic acid derivatives from a colonial tunicate of the family Polyclinidae.

Bao B1, Dang HT, Zhang P, Hong J, Lee CO, Cho HY, Jung JH. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6205-8. doi: 10.1016/j.bmcl.2009.08.094. Epub 2009 Sep 3.

In the course of our search for bioactive metabolites from a colonial tunicate of the family Polyclinidae, six new (1-6) cyclic fatty acid derivatives were isolated. Their planar structures were established on the basis of NMR and MS spectroscopic analyses. The relative configuration was determined by NOESY experiment. Compounds 1-6 represent a fused bicyclic skeleton possibly derived from alpha,omega-dicarboxylic acids such as eicosanedioic acid or docosanedioic acid via a Diels-Alder type of cyclization. Compounds 1-4 and 6 showed mild cytotoxicity against a panel of five human solid tumor cell lines.