Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets

Stearic acid is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin.In general, the applications of stearic acid exploit its bifunctional character, with a polar head group that can be attached to metal cations and a nonpolar chain that confers solubility in organic solvents. The combination leads to uses as a surfactant and softening agent. Stearic acid undergoes the typical reactions of saturated carboxylic acids, a notable one being reduction to stearyl alcohol, and esterification with a range of alcohols. This is used in a large range of manufactures, from simple to complex electronic devices.

The fatty acids are absorbed in the regular diet the same as the free fatty acids. Low acute toxicity is shown. There was in 2017 no evidence at doses up to 10% in the diet for toxic effects.Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Soaps are not made directly from stearic acid, but indirectly by saponification of triglycerides consisting of stearic acid esters. Esters of stearic acid with ethylene glycol, glycol stearate, and glycol distearate are used to produce a pearly effect in shampoos, soaps, and other cosmetic products. They are added to the product in molten form and allowed to crystallize under controlled conditions. Detergents are obtained from amides and quaternary alkylammonium derivatives of stearic acid.In view of the soft texture of the sodium salt, which is the main component of soap, other salts are also useful for their lubricating properties. Lithium stearate is an important component of grease. The stearate salts of zinc, calcium, cadmium, and lead are used to soften PVC. Stearic acid is used along with castor oil for preparing softeners in textile sizing. They are heated and mixed with caustic potash or caustic soda. Related salts are also commonly used as release agents, e.g. in the production of automobile tires.

1. Schwab, U. S., Maliranta, H. M., Sarkkinen, E. S., Savolainen, M. J., Kesäniemi, Y. A., & Uusitupa, M. I. Different effects of palmitic and stearic acid-enriched diets on serum lipids and lipoproteins and plasma cholesteryl ester transfer protein activity in healthy young women[J]. Metabolism, 1996, 45(2): 143-149.

2. Rijnkels J M, van der Reijden A C, Alink G M. Effects of vegetables–fruit extracts and indole-3-carbinol on stearic acid-modulated intercellular communication and cytochrome P450-IA activity[J]. Environmental toxicology and pharmacology, 1998, 6(2): 103-109.

3. Lu, H., Hao, L., Li, S., Lin, S., Lv, L., Chen, Y., Sun, C. Elevated circulating stearic acid leads to a major lipotoxic effect on mouse pancreatic beta cells in hyperlipidaemia via a miR-34a-5p-mediated PERK/p53-dependent pathway[J]. Diabetologia, 2016, 59(6): 1247-1257.

4. Hirabara S M, Curi R, Maechler P. Saturated fatty acid‐induced insulin resistance is associated with mitochondrial dysfunction in skeletal muscle cells[J]. Journal of cellular physiology, 2010, 222(1): 187-194.

5. Sawada, K., Kawabata, K., Yamashita, T., Kawasaki, K., Yamamoto, N., & Ashida, H. Ameliorative effects of polyunsaturated fatty acids against palmitic acid-induced insulin resistance in L6 skeletal muscle cells[J]. Lipids in health and disease, 2012, 11(1): 36.

6. Zhang, Y., Dong, L., Yang, X., Shi, H., & Zhang, L.α-Linolenic acid prevents endoplasmic reticulum stress-mediated apoptosis of stearic acid lipotoxicity on primary rat hepatocytes[J]. Lipids in health and disease, 2011, 10(1): 81.

7. Pérez-Vich B, Garcés R, Fernández-Martínez J M. Epistatic interaction among loci controlling the palmitic and the stearic acid levels in the seed oil of sunflower[J]. Theoretical and Applied Genetics, 2000, 100(1): 105-111.

8. Gillman, J. D., Tetlow, A., Hagely, K., Boersma, J. G., Cardinal, A., Rajcan, I., & Bilyeu, K. Identification of the molecular genetic basis of the low palmitic acid seed oil trait in soybean mutant line RG3 and association analysis of molecular markers with elevated seed stearic acid and reduced seed palmitic acid[J]. Molecular breeding, 2014, 34(2): 447-455.

9. Allen, E., Johnson, A. R., Fogerty, A. C., Pearson, J. A., & Shenstone, F. S. Inhibition by cyclopropene fatty acids of the desaturation of stearic acid in hen liver[J]. Lipids, 1967, 2(5): 419-423.

10. Lyman, R. L., Fosmire, M. A., Giotas, C., & Miljanich, P. Inhibition of desaturation of stearic acid in livers of rats fed ethionine[J]. Lipids, 1970, 5(7): 583-589.

11. Joshy, K. S., George, A., Jose, J., Kalarikkal, N., Pothen, L. A., & Thomas, S. Novel dendritic structure of alginate hybrid nanoparticles for effective anti-viral drug delivery[J]. International journal of biological macromolecules, 2017, 103: 1265-1275.

12. Bougnoux, P., Chajes, V., Lanson, M., Hacene, K., Body, G., Couet, C., & Le Floch, O. Prognostic significance of tumor phosphatidylcholine stearic acid level in breast carcinoma[J]. Breast cancer research and treatment, 1991, 20(3): 185-194.

13. Liu, Z., Zhang, W., Fan, S., Wang, L., & Jiao, L.Changes in the electron paramagnetic resonance spectra of albumin-associated spin-labeled stearic acid as a diagnostic parameter of colorectal cancer (Retraction of vol 11, 223, 2013)[J]. 2016.

14. Liu, Z., Zhang, W., Fan, S., Wang, L., & Jiao, L.Retraction Note: Changes in the electron paramagnetic resonance spectra of albumin-associated spin-labeled stearic acid as a diagnostic parameter of colorectal cancer[J]. World journal of surgical oncology, 2016, 14(1): 156.

15. Fogerty A C, Johnson A R, Pearson J A. Ring position in cyclopropene fatty acids and stearic acid desaturation in hen liver[J]. Lipids, 1972, 7(5): 335-338.

16. Tsao F H C. Selective use of palmitic acid over stearic acid for synthesis of phosphatidylcholine and phosphatidylglycerol in lung[J]. Lipids, 1986, 21(11): 724-725.

17. Pai T, Yeh Y Y. Stearic acid unlike shorter‐chain saturated fatty acids is poorly utilized for triacylglycerol synthesis and β‐oxidation in cultured rat hepatocytes[J]. Lipids, 1996, 31(2): 159-164.

18. Huang, S. T., Du, Y. Z., Yuan, H., Zhang, X. G., Miao, J., Cui, F. D., & Hu, F. Q. Synthesis and anti-hepatitis B virus activity of acyclovir conjugated stearic acid-g-chitosan oligosaccharide micelle[J]. Carbohydrate polymers, 2011, 83(4): 1715-1722.

19. Jubie, S., Ramesh, P. N., Dhanabal, P., Kalirajan, R., Muruganantham, N., & Antony, A. S.Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues[J]. European journal of medicinal chemistry, 2012, 54: 931-935.

20. Vishnyakov, V., Kelly, P. J., Humblot, J., Kriek, R. J., Allen, N. S., & Mahdjoub, N.Use of ion-assisted sputtering technique for producing photocatalytic titanium dioxide thin films: Influence of thermal treatments on structural and activity properties based on the decomposition of stearic acid[J]. Polymer Degradation and Stability, 2018, 157: 1-8.

21. https://en.wikipedia.org/wiki/Stearic_acid

22. Gunstone F D, Harwood J L, Dijkstra A J. The lipid handbook with CD-ROM[M]. CRC press, 2007.

23. EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS), Mortensen A, Aguilar F, et al. Re‐evaluation of fatty acids (E 570) as a food additive[J]. EFSA Journal, 2017, 15(5): e04785.

24. Rahman S M, Takagi Y, Kinoshita T. Genetic control of high stearic acid content in seed oil of two soybean mutants[J]. Theoretical and Applied Genetics, 1997, 95(5-6): 772-776.