20701-68-2

Usage

Uses

Used in Personal Care Industry:
Octadecenedioic acid is used as an ingredient in skincare products for its ability to promote skin exfoliation and enhance skin hydration. Its anti-inflammatory and antioxidant properties also contribute to the overall effectiveness of these products.
Used in Polymer Production:
Octadecenedioic acid is used as a component in the production of polymers, resins, and coatings due to its chemical properties and versatility.
Used in Metabolic Disorders Treatment:
Octadecenedioic acid has potential uses in the treatment of certain metabolic disorders, although further research may be required to fully understand its therapeutic potential in this area.

InChI:InChI=1/C18H32O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-2H,3-16H2,(H,19,20)(H,21,22)/b2-1-

Upstream product

• 132973-20-7 cis-16-bromo-9-hexadecenoic acid methyl ester 
• 996-82-7 sodium diethylmalonate 
• 53246-86-9 8-hexadecyne-1,16-dicarboxylic acid 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 
• 112-80-1 cis-Octadecenoic acid 
• 24753-49-9 Dimethyl (E)-octadec-9-enedioate 
• 533-87-9 DL-erythro-aleuritic acid 
• 123-99-9 azelaic acid 
• 1732-10-1 Dimethyl azelate 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 2104-19-0 azelaic monomethyl ester 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 

Downstream Products

• 123-99-9 azelaic acid 
• 18287-34-8 meso-9,10-dihydroxy-octadecanedioic acid 
• 41194-37-0 (Z)-Octadec-9-enedioyl dichloride 
• 61549-41-5 (Z)-Octadec-9-enedioic acid dibutyl ester 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 
• 25601-41-6 methyl 9-decenoate 
• 1046470-12-5 methyl 10-cyano-dec-9-enoate 
• 854401-56-2 10-cyano-9-decenoate 
• 1732-10-1 Dimethyl azelate 
• 1620950-95-9 C₂₄H₃₆O₄ 

Relevant academic research and scientific papers

Stereochemistry of C18 monounsaturated cork suberin acids determined by spectroscopic techniques including 1H-NMR multiplet analysis of olefinic protons

Introduction Suberin is a biopolyester responsible for the protection of secondary plant tissues, and yet its molecular structure remains unknown. The C18:1 ω-hydroxyacid and the C18:1 α,ω-diacid are major monomers in the suberin structure, but the configuration of the double bond remains to be elucidated. Objective To unequivocally define the configuration of the C18:1 suberin acids. Methods Pure C18:1 ω-hydroxyacid and C18:1 α,ω-diacid, isolated from cork suberin, and two structurally very close C18:1 model compounds of known stereochemistry, methyl oleate and methyl elaidate, were analysed by NMR spectroscopy, Fourier transform infrared (FTIR) and Raman spectroscopy, and GC-MS. Results The GC-MS analysis showed that both acids were present in cork suberin as only one geometric isomer. The analysis of dimethyloxazoline (DMOX) and picolinyl derivatives proved the double bond position to be at C-9. The FTIR spectra were concordant with a cis-configuration for both suberin acids, but their unambiguous stereochemical assignment came from the NMR analysis: (i) the chemical shifts of the allylic 13C carbons were shielded comparatively to the trans model compound, and (ii) the complex multiplets of the olefinic protons could be simulated only with 3JHH and long-range 4JHH coupling constants typical of a cis geometry. Conclusion The two C18:1 suberin acids in cork are (Z)-18-hydroxyoctadec-9-enoic acid and (Z)-octadec-9-enedoic acid. Copyright 2013 John Wiley & Sons, Ltd. The two C18:1 cork suberin ω-hydroxyacid and α,ω-diacid were proved to have a cis configuration: (Z)-18-hydroxyoctadec-9-enoic acid and (Z)-octadec-9-enedoic acid. Their double bond stereochemistry was elucidated by spectroscopic techniques, namely 1H-NMR and 13C-NMR. The chemical shifts of the olefinic and allylic protons and of the allylic carbons were diagnostic, and the 1H-NMR multiplets of the olefinic protons could only be simulated using 3JHH and long-range 4J HH coupling constants typical of the cis configuration. The revealed stereochemistry of this two major suberin monomers brings a new insight into the mostly unknown suberin macromolecular structure. Copyright

METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS

The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).

ESTERAMINES AND DERIVATIVES FROM NATURAL OIL METATHESIS

Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

ESTERS FOR USE AS A BASE STOCK AND IN LUBRICANT APPLICATIONS

This invention relates to base ester compounds and complex ester compounds that can be used as a base stock for lubricant applications or a base stock blend component for use in a finished lubricant or for particular applications, and methods of making the same. The base ester compounds and complex esters described herein comprise dimer and/or trimer esters, and their respective branched derivatives.

METHOD FOR PREPARING LONG-CHAIN HYDROXYACIDS, DIACIDS AND OLIGOMERS AND POLYLMERS THEREOF

A method and process for the preparation of ricinoleic acid analogs and oligomers and polymers containing such ricinoleic acid analogs.

Two-step biocatalytic route to biobased functional polyesters from ω-carboxy fatty acids and diols

Biobased ω-carboxy fatty acid monomers 1,18-cis-9-octadecenedioic, 1,22-cis-9-docosenedioic, and 1,18-cis-9,10-epoxy-octadecanedioic acids were synthesized in high conversion yields from oleic, erucic and epoxy stearic acids by whole-cell biotransformations catalyzed by C. tropicalis ATCC20962. Maximum volumetric yields in shake-flasks were 17.3, 14.2, and 19.1 g/L after 48 h conversion for oleic acid and 72 h conversions for erucic and epoxy stearic acids, respectively. Studies in fermentor with better control of pH and glucose feeding revealed that conversion of oleic acid to 1,18-cis-9-octadecenedioic acid by C. tropicalis ATCC20962 occurred with productivities up to 0.5 g/L/h. The conversion of ω-carboxy fatty acid monomers to polyesters was then studied using immobilized Candida antarctica Lipase B (N435) as catalyst. Polycondensations with diols were performed in bulk as well as in diphenyl ether. The retension of functionality from fatty acid, to ω-carboxy fatty acid monomer and to corresponding polyesters resulted in polymers with with unsaturated and epoxidized repeat units and Mw values ranging from 25000 to 57000 g/mol. These functional groups along chains disrupted crystallization giving materials that are low melting (23-40 °C). In contrast, saturated polyesters prepared from 1,18-octadecanedioic acid and 1,8-octanediol have correspondingly higher melting transitions (88 °C). TGA results indicated that all synthesized polyesters showed high thermal stabilities. Thus, the preparation of functional monomers from C. tropicalis ω-oxidation of fatty acids provides a wide range of new monomer building blocks to construct functional polymers.

Synthesis and characterization of highly functionalized symmetric aromatic hexa-ol intermediates from oleic acid

A novel highly functionalized aromatic hexa-ol was synthesized by palladium-catalyzed cyclotrimerization of an alkyne fatty acid ester followed by LAH reduction. This polyol product is a novel monomer made from a renewable lipid raw material for the production of polyurethanes, polyesters and polyamides.

Suberin structure in potato periderm: Glycerol, long-chain monomers, and glyceryl and feruloyl dimers

Suberin in extractive-free potato periderm amounts to 25% determined by NaOCH3 methanolysis. Monomeric composition is characterized by glycerol (20% of monomers), long-chain α,ω-diacids, ω-hydroxyacids, alkanoic acids, and alkan-1-ols, with predominance of octadec-9-enodioic acid and 18-hydroxyoctadec-9-enoic acid (39 and 15% of long-chain monomers, respectively). Aromatic hydroxycinnamyl monomers were also present (2-catalyzed methanolysis solubilized ~10% of suberin aliphatics. GC-MS analysis showed the presence of monomers, dimers, and trimers (87, 12, and 1% of identified compounds, respectively). A total of 26 dimers were identified by EIMS: monoacylglyceryl esters of α,ω-diacids, ω-hydroxyacids, and alkanoic acids (with predominance of the 1- and 2-isomers of the monoacylglyceryl ester of the octadec-9-enodioic acid), as well as feruloyl esters of ω-hydroxyacids and alkan-1-ols and a small quantity of a monoferuloylglycerol. Following a discussion of suberin macromolecular structure, it is proposed that in suberized cell walls, the polyaliphatic polymers have a three-dimensional development ensured by glycerol and exist independently from the associated polyaromatics.

Aleuritic acid in the preparation of (Z)-9-octadecene-1,18-dioic acid (intermediate in civetone synthesis) and queen substance of honey-bee utilizing phosphonate carbanions

Wittig-Horner-Emmons olefination on aldehydes derived from aleuritic acid leading to the formation of both pure Z and E isomers of 9-octadecene-1,18 dioic acid, in good yield (valuable intermediate for musk perfume civetone) and a synthesis of 9-oxo-(E)-2-decenoic acid (queen bee substance) are reported.

A Synthesis of (Z)-Octadec-9-enedioic Acid

The monomethyl ester of azelaic acid was transformed into two fragments, namely triphenylphosphonium bromide and methyl 9-oxononanoate.A Wittig reaction between these two fragments produced dimethyl (Z)-octadec-9-enedioate and subsequent hydrolysis gave the title diacid.Interestingly, the same acid was available directly from oleic acid in a published procedure which utilized a mutant strain of Candida tropicalis.