Stearic Acid

• CAT Number: R019980
• CAS Number: 57-11-4
• Molecular Formula: CH3(CH2)16COOH
• Molecular Weight: 284.484
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: octadecanoic acid
• InChI: InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
• InChIKey: QIQXTHQIDYTFRH-UHFFFAOYSA-N
• SMILES: CCCCCCCCCCCCCCCCCC(=O)O

Stearic acid(CAT: R019980) is a long-chain saturated fatty acid that can be derived from either animal fats or vegetable oils. Compared to other long-chain saturated fatty acids that are hypercholesterolemic, experimental diets high in stearic acid (9.3-11.8% of energy) do not raise plasma total cholesterol or LDL-cholesterol concentrations but may slightly reduce HDL-cholesterol concentrations. Stearic acid can be used as a hardening agent for vegetable oils and due to its negligible effect on cholesterol metabolism may be used as an alternative to modification of fatty acids by partial hydrogenation.

Reference

[1]. J Gerontol A Biol Sci Med Sci. 2019 Sep 15;74(10):1564-1572. doi: 10.1093/gerona/glx246.
Stearic Acid Supplementation in High Protein to Carbohydrate (P:C) Ratio Diet Improves Physiological and Mitochondrial Functions of Drosophila melanogaster parkin Null Mutants.
Bajracharya R(1), Bustamante S(2), O Ballard JW(1).
Author information: (1)School of Biotechnology and Biomolecular Sciences, Sydney, Australia. (2)Bioanalytical Mass Spectrometry Facility, Mark Wainwright Analytical Center, University of New South Wales, Sydney, Australia.
Optimizing dietary macronutrients benefits the prevention and management of many human diseases but there is conflicting dietary advice for Parkinson's disease (PD), and no single strategy is universally recommended. Recently, it was shown that dietary stearic acid (C18:0) improves survival and mitochondrial functions in the parkin null Drosophila model of PD. Here, we incorporate stearic acid into high protein and high carbohydrate diets and study survival, climbing ability, mitochondrial membrane potential, respiration, basal reactive oxygen species, and conduct lipidomics assays. We observed that parkin null flies showed improvement in all assays tested when stearic acid was added to the high protein diet but not to the high carbohydrate diet. When lipid proportion was examined, we observed higher levels in flies fed the high protein diet with stearic acid diet and the high carbohydrate diet. Unexpectedly, free levels of fatty acids exhibited opposite trend. Combined, these data suggest that dietary Protein: Carbohydrate ratio and stearic acid influences levels of bound fatty acids. The mechanisms that influence free and bound fatty-acid levels remain to be explored, but one possible explanation is that breakdown products can bind to membranes and improve the mitochondrial functions of parkin null flies.
DOI: 10.1093/gerona/glx246 PMID: 29236963 [Indexed for MEDLINE]

[2]. J Endocrinol. 2020 Jul;246(1):13-27. doi: 10.1530/JOE-20-0055.
miRNA-mRNA profile and regulatory network in stearic acid-treated β-cell dysfunction.
Yu Y(1), Guo R(1), Zhang Y(1), Shi H(2), Sun H(2), Chu X(1), Wu X(1), Lu H(1), Sun C(1).
Author information: (1)Department of Nutrition and Food Hygiene (National Key Discipline), Public Health College, Harbin Medical University, Harbin, China. (2)College of Bioinformatics Science and Technology, Harbin Medical University, Harbin, China.
Chronic exposure of pancreatic β-cells to saturated fatty acid (palmitic or stearic acid) is a leading cause of impaired insulin secretion. However, the molecular mechanisms underlying stearic-acid-induced β-cell dysfunction remain poorly understood. Emerging evidence indicates that miRNAs are involved in various biological functions. The aim of this study was to explore the differential expression of miRNAs and mRNAs, specifically in stearic-acid-treated- relative to palmitic-acid-treated β-cells, and to establish their co-expression networks. β-TC-6 cells were treated with stearic acid, palmitic acid or normal medium for 24 h. Differentially expressed miRNAs and mRNAs were identified by high-throughput sequencing and bioinformatic analysis. Co-expression network, gene ontology (GO) and pathway analyses were then conducted. Changes in the expression of selected miRNAs and mRNAs were verified in β-TC-6 cells and mouse islets. Sequencing analysis detected 656 known and 1729 novel miRNAs. miRNA-mRNA network and Venn-diagram analysis yielded two differentially expressed miRNAs and 63 mRNAs exclusively in the stearic-acid group. miR-374c-5p was up-regulated by a 1.801 log2(fold-change) and miR-297b-5p was down-regulated by a -4.669 log2(fold-change). We found that miR-297b-5p and miR-374c-5p were involved in stearic-acid-induced lipotoxicity to β-TC-6 cells. Moreover, the effects of miR-297b-5p and miR-374c-5p on the alterations of candidate mRNAs expressions were verified. This study indicates that expression changes of specific miRNAs and mRNAs may contribute to stearic-acid-induced β-cell dysfunction, which provides a preliminary basis for further functional and molecular mechanism studies of stearic-acid-induced β-cell dysfunction in the development of type 2 diabetes.
DOI: 10.1530/JOE-20-0055 PMID: 32302972 [Indexed for MEDLINE]

[3]. Molecules. 2020 Sep 8;25(18):4097. doi: 10.3390/molecules25184097.
Stearic Acid/Layered Double Hydroxides Composite Thin Films Deposited by Combined Laser Techniques.
Birjega R(1), Matei A(1), Marascu V(1), Vlad A(1), Ionita MD(1), Dinescu M(1), Zăvoianu R(2), Corobea MC(3).
Author information: (1)National Institute for Lasers, Plasma and Radiation Physics, 409 Atomistilor Street, P.O. Box MG-16, 077125 Magurele-Bucharest, Romania. (2)Faculty of Chemistry, Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, 4-12 Regina Elisabeta Av., S3, 030018 Bucharest, Romania. (3)National Institute for Research and Development in Chemistry and Petrochemistry, 202 Spl.Independentei, 060021 Bucharest, Romania.
We report on the investigation of stearic acid-layered double hydroxide (LDH) composite films, with controlled wettability capabilities, deposited by a combined pulsed laser deposition (PLD)-matrix-assisted pulsed laser evaporation (MAPLE) system. Two pulsed lasers working in IR or UV were used for experiments, allowing the use of proper deposition parameters (wavelength, laser fluence, repetition rate) for each organic and inorganic component material. We have studied the time stability and wettability properties of the films and we have seen that the morphology of the surface has a low effect on the wettability of the surfaces. The obtained composite films consist in stearic acid aggregates in LDH structure, exhibiting a shift to hydrophobicity after 36 months of storage.
DOI: 10.3390/molecules25184097 PMCID: PMC7571018 PMID: 32911637 [Indexed for MEDLINE]

[4]. Molecules. 2019 Apr 15;24(8):1482. doi: 10.3390/molecules24081482.
Stearic Acid/Inorganic Porous Matrix Phase Change Composite for Hot Water Systems.
Xu L(1), Yang R(2).
Author information: (1)Department of Chemical Engineering, Tsinghua University, Beijing 100084, China. . (2)Department of Chemical Engineering, Tsinghua University, Beijing 100084, China. .
The storage and utilization of waste heat in low and medium temperature ranges using phase change materials (PCMs) is an effective technology to improve energy utilization efficiency in combined cooling, heating, and power (CCHP) systems. In this paper, stearic acid/inorganic porous matrix phase change composites were developed to store waste heat for hot water systems. Among them, stearic acid/expanded graphite (EG) phase change composite was highlighted and the thermal physical properties, the dynamic response, and the long-term cyclic stability were evaluated. The stearic acid concentrations in the composites were over 95 wt%. The thermal diffusion coefficients were 3-5 times higher than pure stearic acid, independent of composite densities. Accordingly, the heat storage and release times were decreased by up to 41% and 55%, respectively. After 100 cycles, the composites maintained good dynamic response and long-term cyclic stability, with heat storage density of 122-152 MJ/m³. Hence, this stearic acid/EG phase change composite exhibits excellent comprehensive performances. It is also easy to be prepared and flexible for various types of heat exchangers.
DOI: 10.3390/molecules24081482 PMCID: PMC6515142 PMID: 30991751 [Indexed for MEDLINE]
[5]. Am J Clin Nutr. 1994 Dec;60(6 Suppl):1050S-1053S. doi: 10.1093/ajcn/60.6.1050S.
Stearic acid, clotting, and thrombosis.
Hoak JC(1).
Author information: (1)Division of Blood Diseases and Resources, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD.
Stearic acid causes hypercoagulability of the blood by activation of factor XII and by aggregation of blood platelets. Injection of unbound stearic acid (sodium salt) into the systemic circulation of dogs was followed by massive generalized thrombosis and sudden death. Similar infusions into birds, which are deficient in factor XII, did not cause hypercoagulability or thrombosis. The effects of the long-chain saturated fatty acids could be prevented by using albumin to bind the stearic acid at a molar ratio of free fatty acid (FFA) to albumin of < 2. The major issue is whether eating foods rich in stearic acid can cause a thrombogenic effect. We have no experimental evidence to support this concept. If a thrombogenic effect of long-chain saturated fatty acids exists in humans, it is most likely to occur as an aberration of fatty acid transport in which the FFA-albumin molar ratio exceeds 2 either as a result of very high plasma FFA concentrations from lipid mobilization or a low concentration of albumin in the blood as found in disease states such as the nephrotic syndrome.
DOI: 10.1093/ajcn/60.6.1050S PMID: 7977149 [Indexed for MEDLINE]