106689-24-1

Basic information

• Product Name: 9-THIASTEARIC ACID
• Synonyms: 9-THIASTEARIC ACID;8-Nonylthiooctanoic acid
• CAS NO: 106689-24-1
• Molecular Formula: C17H34O2S
• Molecular Weight: 302.52
• Mol File: 106689-24-1.mol

Chemical Properties

• Boiling Point: 426.012 °C at 760 mmHg
• Flash Point: 211.445 °C
• Appearance: /
• Density: 0.952 g/cm³
• Storage Temp.: 2-8°C
• PKA: 4.77±0.10(Predicted)
• CAS DataBase Reference: 9-THIASTEARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9-THIASTEARIC ACID(106689-24-1)
• EPA Substance Registry System: 9-THIASTEARIC ACID(106689-24-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 106689-24-1(Hazardous Substances Data)

Usage

Uses

Used in Lubricant Production:
9-Thiastearic acid is used as a lubricant additive for enhancing the performance and durability of lubricants. Its unique structure and chemical properties allow it to modify the physical and chemical properties of materials, providing better lubrication and reducing friction.
Used in Plasticizer Production:
In the plastics industry, 9-thiastearic acid is used as a plasticizer to improve the flexibility, workability, and durability of plastic materials. Its ability to modify the properties of materials makes it a valuable component in the production of various plastic products.
Used in Pharmaceutical Research:
9-Thiastearic acid has been investigated for potential use in pharmaceuticals due to its unique structure and chemical properties. It is being studied for its potential as a treatment for various diseases, offering new avenues for drug development and therapeutic applications.
Used in Industrial Product Development:
9-Thiastearic acid is utilized in the development of various industrial products, such as coatings, adhesives, and sealants, due to its ability to modify the physical and chemical properties of materials. Its unique properties make it a valuable component in the creation of innovative and high-performance products across different industries.

Upstream product

• 1455-21-6 Nonane-1-thiol 
• 17696-11-6 8-bromooctanoic acid 
• 693-58-3 1-Bromononane 
• 74328-61-3 8-mercapto-octanoic acid 

Downstream Products

• 148693-68-9 (+/-)-O¹,O²-bis(9-thiastearyl)-O³-(2-nitrobenzyl)glycerol 

Relevant articles and documents

Effects of chain length and sulphur position of thia fatty acids on their incorporation into phospholipids in 7800 C1 hepatoma cells and isolated rat hepatocytes, and their effects on fatty acid composition of phospholipids

Incorporation of thia fatty acids and their effects on the fatty acid composition in phospholipids has been investigated in 7800 C1 hepatoma cells and cultured hepatocytes. 3-Thia fatty acids of chain lengths from dodecyl-to hexadecyl-thioacetic acid were incorporated into phospholipids during a 3-day incubation. Longer and shorter 3-thia fatty acids were barely detectable. Tetradecylthioacetic acid, 3-thia stearate, and their Δ9-desaturated derivatives were maximally incorporated into whole-cell phospholipids. The amount of tetradecylthioacetic acid incorporated into phospholipids of hepatoma cells remained almost identical in cells cultured for 3 days or adapted over a period of 1 year. Δ9-desaturated metabolites of long chain thia fatty acids (C13-to C16-S-acetic acid) were identified by GC-MS in phospholipids. 3-Thia stearate appeared to be the best substrate for Δ9 desaturase. Incubation of hepatoma cells with thia fatty acids led to alterations in the amount of normal fatty acids in total phospholipids. The amounts of 16:0 and 18:1 decreased and 18:2(n-6) and 20:5 (n-3) increased. Changes in the normal fatty acid composition of phospholipids were seen both with thia acids incorporated into phospholipids and those not incorporated. These effects, therefore, may be only partially dependent on displacement of normal fatty acids by thia fatty acids. Morris 7800 C1 hepatoma cell acyl-CoA synthetase (ACS) and peroxisomal acyl-CoA oxidase (AGO) were induced by thia fatty acids of all chain lengths, and with the sulphur atom(s) in different positions. Control experiments with hepatocytes revealed a similar incorporation of thia fatty acids in these physiologically more normal cells.

Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

The stereochemistry of castor stearoyl-ACP Δ9 desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by 19F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.

1H and 13C N.M.R. Studies on the Positional Isomers of Methyl Thialaurate and Methyl Thiastearate

1H N.m.r. analysis of methyl thialaurate and methyl thiastearate shows that the sulphur atom in the alkyl chain has a significant deshilding effect (α-effect) on the chemical shift of the protons of the adjacent methylene and methyl groups, and also on the methyl protons of the methoxycarbonyl (ester) function.It was possible to identify seven of the positional isomers in each series by examining the chemical shifts and the splitting pattern of the signals in the 1H n.m.r. spectra of these fatty acid ester analogues.The 13C n.m.r. results showed that this S atom has an interesting effect (α-, β-, and γ-effect) on the chemical shift of the carbonyl carbon atom of the methoxycarbonyl (ester) function: the sulphur atom exerts a significant shilding effect in the case of the 2-, 3-, and 4-thia isomers.In the remaining isomers the sulphur atom causes a strong deshilding effect on the methylene or methyl carbon atoms on either side of the sulphide linkage.These results permitted all positional isomers of methyl thialaurate to be identified by this technique, while 10 out of the 16 positional isomers of methyl thiastearate could be characterized.