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Stearic acid

Stearic acid (/ˈstɪərɪk/ STEER-ik, /stiˈærɪk/ stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain.[9] The IUPAC name is octadecanoic acid.[9] It is a soft waxy solid with the formula CH3(CH2)16CO2H.[9] The triglyceride derived from three molecules of stearic acid is called stearin.[9] Stearic acid is a prevalent FA in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.[11]

Stearic acid[1]
Names
Preferred IUPAC name
Octadecanoic acid
Other names
Stearic acid
C18:0 (Lipid numbers)
Identifiers
  • 57-11-4 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL46403 Y
ChemSpider
  • 5091 Y
DrugBank
  • DB03193 Y
ECHA InfoCard 100.000.285
EC Number
  • 200-313-4
  • 3377
KEGG
  • C01530
  • 5281
RTECS number
  • WI2800000
UNII
  • 4ELV7Z65AP Y
  • DTXSID8021642
  • CCCCCCCCCCCCCCCCCC(=O)O
Properties
C18H36O2
Molar mass 284.484 g·mol−1
Appearance White solid
Odor Pungent, oily
Density 0.9408 g/cm3 (20 °C)[2]
0.847 g/cm3 (70 °C)
Melting point 69.3 °C (156.7 °F; 342.4 K)[2]
Boiling point 361 °C (682 °F; 634 K)
decomposes
232 °C (450 °F; 505 K)
at 15 mmHg[2]
0.00018 g/100 g (0 °C)
0.00029 g/100 g (20 °C)
0.00034 g/100 g (30 °C)
0.00042 g/100 g (45 °C)
0.00050 g/100 g (60 °C)[3]
Solubility Soluble in alkyl acetates, alcohols, HCOOCH3, phenyls, CS2, CCl4[4]
Solubility in dichloromethane 3.58 g/100 g (25 °C)
8.85 g/100 g (30 °C)
18.3 g/100 g (35 °C)[4]
Solubility in hexane 0.5 g/100 g (20 °C)
4.3 g/100 g (30 °C)
19 g/100 g (40 °C)
79.2 g/100 g (50 °C)
303 g/100 g (60 °C)[4]
Solubility in ethanol 1.09 g/100 mL (10 °C)
2.25 g/100 g (20 °C)
5.42 g/100 g (30 °C)
22.7 g/100 g (40 °C)
105 g/100 g (50 °C)
400 g/100 g (60 °C)[3]
Solubility in acetone 4.73 g/100 g[5]
Solubility in chloroform 15.54 g/100 g[5]
Solubility in toluene 13.61 g/100 g[5]
Vapor pressure 0.01 kPa (158 °C)[2]
0.46 kPa (200 °C)
16.9 kPa (300 °C)[6]
−220.8·10−6 cm3/mol
Thermal conductivity 0.173 W/m·K (70 °C)
0.166 W/m·K (100 °C)[7]
1.4299 (80 °C)[2]
Structure
B-form = Monoclinic[8]
B-form = P21/a[8]
B-form = Cs
2h
[8]
a = 5.591 Å, b = 7.404 Å, c = 49.38 Å (B-form)[8]
α = 90°, β = 117.37°, γ = 90°
Thermochemistry
501.5 J/mol·K[2][6]
435.6 J/mol·K[2]
−947.7 kJ/mol[2]
−11342.4 kJ/mol[9]
Hazards
NFPA 704 (fire diamond)
1
1
0
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
4640 mg/kg (rats, oral)[10]
21.5 mg/kg (rats, intravenous)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates.[9] As its ester, stearic acid is one of the most common saturated fatty acids found in nature and in the food supply, following palmitic acid.[12][13] Dietary sources of stearic acid include meat, poultry, fish, eggs, dairy products, and foods prepared with fats; beef tallow, lard, butterfat, cocoa butter, and shea butter are rich fat sources of stearic acid.[9][12]

Occurrence and production

Dietary intake

Of the saturated fatty acids consumed in the United States, stearic acid consumption is second (26% of total saturated fatty acid intake) to palmitic acid (56% of total saturated fatty acid intake).[12] Stearic acid is more abundant in animal fat (up to 33% in beef liver[14]: 739 ) than in vegetable fat (typically less than 5%).[12] The important exceptions are the foods cocoa butter (34%) and shea butter, where the stearic acid content (as a triglyceride) is 28–45%.[9][14] Examples of the use of stearic acid in food manufacturing include baked goods, frozen dairy products, gelatins, puddings, hard candy, and nonalcoholic beverages.[9]

Biosynthesis and manufacturing

In biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks.[9]

Stearic acid is obtained from fats and oils by the saponification of the triglycerides using hot water (about 100 °C). The resulting mixture is then distilled.[15] Commercial stearic acid is often a mixture of stearic and palmitic acids, although purified stearic acid is available. Commercially, oleic acid, as found in palm and soy, can be hydrogenated to give stearic acid.

Uses

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.[9] 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.[9] This is used in a large range of manufactures, from simple to complex electronic devices.[9]

As food additive

Stearic acid (E number E570) is found in some foods.[9][16]

Soaps and cosmetics

Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products.[9] Stearate soap, such as sodium stearate, could be made from stearic acid but instead are usually produced by saponification of stearic acid-containing triglycerides. 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.[9]

Lubricants, softening and release agents

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 as heat stabilisers 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. As an example, it can be used to make castings from a plaster piece mold or waste mold, and to make a mold from a shellacked clay original. In this use, powdered stearic acid is mixed in water and the suspension is brushed onto the surface to be parted after casting. This reacts with the calcium in the plaster to form a thin layer of calcium stearate, which functions as a release agent.[17]

Steric acid can be converted to zinc stearate, which is used as a lubricant for playing cards (fanning powder) to ensure a smooth motion when fanning. Stearic acid is a common lubricant during injection molding and pressing of ceramic powders.[18]

Niche uses

Being inexpensive, nontoxic, and fairly inert, stearic acid finds many niche applications.[9][15] Varied examples of stearic acid use in manufacturing include soaps and greases, household soap products, synthetic rubber, cosmetic and pharmaceutical creams and lotions, candles, phonograph records, lubricants, shoe and metal polishes, food packaging, and rubber compounds.[9]

Stearic acid is used as a negative plate additive in the manufacture of lead-acid batteries.[citation needed] It is added at the rate of 0.6 g per kg of the oxide while preparing the paste. It is believed to enhance the hydrophobicity of the negative plate, particularly during dry-charging process. It also reduces the extension of oxidation of the freshly formed lead (negative active material) when the plates are kept for drying in the open atmosphere after the process of tank formation. As a consequence, the charging time of a dry uncharged battery during initial filling and charging (IFC) is comparatively lower, as compared to a battery assembled with plates which do not contain stearic acid additive. Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies.[9]

Metabolism

An isotope labeling study in humans[19] concluded that the fraction of dietary stearic acid that oxidatively desaturates to oleic acid is 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also, stearic acid is less likely to be incorporated into cholesterol esters. In epidemiologic and clinical studies, stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids.[12]

Examples

Salts
Esters

References

  1. ^ Susan Budavari, ed. (1989). Merck Index (11th ed.). Rahway, New Jersey: Merck & Co., Inc. p. 8761. ISBN 978-0-911910-28-5.
  2. ^ a b c d e f g h Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  3. ^ a b Ralston, A.W.; Hoerr, C.W. (1942). "The Solubilities of the Normal Saturated Fatty Acids". The Journal of Organic Chemistry. 7 (6): 546–555. doi:10.1021/jo01200a013. PMID 20280727.
  4. ^ a b c d "stearic acid". Chemister.ru. 2007-03-19. Retrieved 2017-06-30.
  5. ^ a b c Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). D. Van Nostrand Company. p. 677.
  6. ^ a b Octadecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-15)
  7. ^ Vargaftik, Natan B.; et al. (1993). Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 318. ISBN 978-0-8493-9345-7.
  8. ^ a b c d von Sydow, E. (1955). "On the structure of the crystal form B of stearic acid". Acta Crystallographica. 8 (9): 557–560. doi:10.1107/S0365110X55001746.
  9. ^ a b c d e f g h i j k l m n o p q r s "Stearic acid". PubChem, US National Library of Medicine. 29 April 2023. Retrieved 5 May 2023.
  10. ^ Science Lab.com. "Stearic acid MSDS" (PDF). Retrieved 2020-09-30.
  11. ^ Loften, J.R.; Linn, J.G.; Drackley, J.K.; Jenkins, T.C.; Soderholm, C.G.; Kertz, A.F. (August 2014). "Invited review: Palmitic and stearic acid metabolism in lactating dairy cows". Journal of Dairy Science. 97 (8): 4661–4674. doi:10.3168/jds.2014-7919. ISSN 0022-0302.
  12. ^ a b c d e Hunter, J. E.; Zhang, J.; Kris-Etherton, P. M. (2009). "Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: A systematic review". American Journal of Clinical Nutrition. 91 (1): 46–63. doi:10.3945/ajcn.2009.27661. PMID 19939984.
  13. ^ Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra "The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN 0849396883 | ISBN 978-0849396885
  14. ^ a b Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
  15. ^ a b Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_245.pub2.
  16. ^ Aguilar, Fernando; Crebelli, Riccardo; Di Domenico, Alessandro; et al. (2017). "Re-evaluation of fatty acids (E 570) as a food additive". EFSA Journal. 15 (5): 4785. doi:10.2903/j.efsa.2017.4785. PMC 7009963. PMID 32625490.
  17. ^ Angelo Nora; Alfred Szczepanek; Gunther Koenen (2005). "Metallic Soaps". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_361.
  18. ^ Tsenga, Wenjea J.; Mo Liua, Dean; Hsub, Chung-King (1999). "Influence of stearic acid on suspension structure and green microstructure of injection-molded zirconia ceramics". Ceramics International. 25 (2): 191–195. doi:10.1016/S0272-8842(98)00024-8.
  19. ^ Emken, Edward A. (1994). "Metabolism of dietary stearic acid relative to other fatty acids in human subjects". American Journal of Clinical Nutrition. 60 (6): 1023S–1028S. doi:10.1093/ajcn/60.6.1023S. PMID 7977144.

External links

  • NIST Chemistry WebBook Entry

stearic, acid, ɪər, steer, stee, saturated, fatty, acid, with, carbon, chain, iupac, name, octadecanoic, acid, soft, waxy, solid, with, formula, 16co2h, triglyceride, derived, from, three, molecules, stearic, acid, called, stearin, prevalent, nature, found, ma. Stearic acid ˈ s t ɪer ɪ k STEER ik s t i ˈ aer ɪ k stee ARR ik is a saturated fatty acid with an 18 carbon chain 9 The IUPAC name is octadecanoic acid 9 It is a soft waxy solid with the formula CH3 CH2 16CO2H 9 The triglyceride derived from three molecules of stearic acid is called stearin 9 Stearic acid is a prevalent FA in nature found in many animal and vegetable fats but is usually higher in animal fat than vegetable fat It has a melting point of 69 4 C and a pKa of 4 50 11 Stearic acid 1 NamesPreferred IUPAC name Octadecanoic acidOther names Stearic acidC18 0 Lipid numbers IdentifiersCAS Number 57 11 4 Y3D model JSmol Interactive imageChEMBL ChEMBL46403 YChemSpider 5091 YDrugBank DB03193 YECHA InfoCard 100 000 285EC Number 200 313 4IUPHAR BPS 3377KEGG C01530PubChem CID 5281RTECS number WI2800000UNII 4ELV7Z65AP YCompTox Dashboard EPA DTXSID8021642SMILES CCCCCCCCCCCCCCCCCC O OPropertiesChemical formula C 18H 36O 2Molar mass 284 484 g mol 1Appearance White solidOdor Pungent oilyDensity 0 9408 g cm3 20 C 2 0 847 g cm3 70 C Melting point 69 3 C 156 7 F 342 4 K 2 Boiling point 361 C 682 F 634 K decomposes 232 C 450 F 505 K at 15 mmHg 2 Solubility in water 0 00018 g 100 g 0 C 0 00029 g 100 g 20 C 0 00034 g 100 g 30 C 0 00042 g 100 g 45 C 0 00050 g 100 g 60 C 3 Solubility Soluble in alkyl acetates alcohols HCOOCH3 phenyls CS2 CCl4 4 Solubility in dichloromethane 3 58 g 100 g 25 C 8 85 g 100 g 30 C 18 3 g 100 g 35 C 4 Solubility in hexane 0 5 g 100 g 20 C 4 3 g 100 g 30 C 19 g 100 g 40 C 79 2 g 100 g 50 C 303 g 100 g 60 C 4 Solubility in ethanol 1 09 g 100 mL 10 C 2 25 g 100 g 20 C 5 42 g 100 g 30 C 22 7 g 100 g 40 C 105 g 100 g 50 C 400 g 100 g 60 C 3 Solubility in acetone 4 73 g 100 g 5 Solubility in chloroform 15 54 g 100 g 5 Solubility in toluene 13 61 g 100 g 5 Vapor pressure 0 01 kPa 158 C 2 0 46 kPa 200 C 16 9 kPa 300 C 6 Magnetic susceptibility x 220 8 10 6 cm3 molThermal conductivity 0 173 W m K 70 C 0 166 W m K 100 C 7 Refractive index nD 1 4299 80 C 2 StructureCrystal structure B form Monoclinic 8 Space group B form P21 a 8 Point group B form Cs2h 8 Lattice constant a 5 591 A b 7 404 A c 49 38 A B form 8 a 90 b 117 37 g 90 ThermochemistryHeat capacity C 501 5 J mol K 2 6 Std molarentropy S 298 435 6 J mol K 2 Std enthalpy offormation DfH 298 947 7 kJ mol 2 Std enthalpy ofcombustion DcH 298 11342 4 kJ mol 9 HazardsNFPA 704 fire diamond 110Flash point 113 C 235 F 386 K Lethal dose or concentration LD LC LD50 median dose 4640 mg kg rats oral 10 21 5 mg kg rats intravenous 4 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Its name comes from the Greek word stear stear which means tallow The salts and esters of stearic acid are called stearates 9 As its ester stearic acid is one of the most common saturated fatty acids found in nature and in the food supply following palmitic acid 12 13 Dietary sources of stearic acid include meat poultry fish eggs dairy products and foods prepared with fats beef tallow lard butterfat cocoa butter and shea butter are rich fat sources of stearic acid 9 12 Contents 1 Occurrence and production 1 1 Dietary intake 1 2 Biosynthesis and manufacturing 2 Uses 2 1 As food additive 2 2 Soaps and cosmetics 2 3 Lubricants softening and release agents 2 4 Niche uses 3 Metabolism 3 1 Examples 4 References 5 External linksOccurrence and production EditDietary intake Edit Of the saturated fatty acids consumed in the United States stearic acid consumption is second 26 of total saturated fatty acid intake to palmitic acid 56 of total saturated fatty acid intake 12 Stearic acid is more abundant in animal fat up to 33 in beef liver 14 739 than in vegetable fat typically less than 5 12 The important exceptions are the foods cocoa butter 34 and shea butter where the stearic acid content as a triglyceride is 28 45 9 14 Examples of the use of stearic acid in food manufacturing include baked goods frozen dairy products gelatins puddings hard candy and nonalcoholic beverages 9 Biosynthesis and manufacturing Edit In biosynthesis stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl CoA contributes two carbon building blocks 9 Stearic acid is obtained from fats and oils by the saponification of the triglycerides using hot water about 100 C The resulting mixture is then distilled 15 Commercial stearic acid is often a mixture of stearic and palmitic acids although purified stearic acid is available Commercially oleic acid as found in palm and soy can be hydrogenated to give stearic acid Uses EditIn 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 9 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 9 This is used in a large range of manufactures from simple to complex electronic devices 9 As food additive Edit Stearic acid E number E570 is found in some foods 9 16 Soaps and cosmetics Edit Stearic acid is mainly used in the production of detergents soaps and cosmetics such as shampoos and shaving cream products 9 Stearate soap such as sodium stearate could be made from stearic acid but instead are usually produced by saponification of stearic acid containing triglycerides 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 9 Lubricants softening and release agents Edit 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 as heat stabilisers 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 As an example it can be used to make castings from a plaster piece mold or waste mold and to make a mold from a shellacked clay original In this use powdered stearic acid is mixed in water and the suspension is brushed onto the surface to be parted after casting This reacts with the calcium in the plaster to form a thin layer of calcium stearate which functions as a release agent 17 Steric acid can be converted to zinc stearate which is used as a lubricant for playing cards fanning powder to ensure a smooth motion when fanning Stearic acid is a common lubricant during injection molding and pressing of ceramic powders 18 Niche uses Edit Being inexpensive nontoxic and fairly inert stearic acid finds many niche applications 9 15 Varied examples of stearic acid use in manufacturing include soaps and greases household soap products synthetic rubber cosmetic and pharmaceutical creams and lotions candles phonograph records lubricants shoe and metal polishes food packaging and rubber compounds 9 Stearic acid is used as a negative plate additive in the manufacture of lead acid batteries citation needed It is added at the rate of 0 6 g per kg of the oxide while preparing the paste It is believed to enhance the hydrophobicity of the negative plate particularly during dry charging process It also reduces the extension of oxidation of the freshly formed lead negative active material when the plates are kept for drying in the open atmosphere after the process of tank formation As a consequence the charging time of a dry uncharged battery during initial filling and charging IFC is comparatively lower as compared to a battery assembled with plates which do not contain stearic acid additive Fatty acids are classic components of candle making Stearic acid is used along with simple sugar or corn syrup as a hardener in candies 9 Metabolism EditAn isotope labeling study in humans 19 concluded that the fraction of dietary stearic acid that oxidatively desaturates to oleic acid is 2 4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid Also stearic acid is less likely to be incorporated into cholesterol esters In epidemiologic and clinical studies stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids 12 Examples Edit SaltsCalcium stearate Cobaltous stearate Lithium stearate Magnesium stearate Mercuric stearate Sodium stearate Zinc stearateEstersEstradiol stearate Glycol stearate Stearin Testosterone stearateReferences Edit Susan Budavari ed 1989 Merck Index 11th ed Rahway New Jersey Merck amp Co Inc p 8761 ISBN 978 0 911910 28 5 a b c d e f g h Lide David R ed 2009 CRC Handbook of Chemistry and Physics 90th ed Boca Raton Florida CRC Press ISBN 978 1 4200 9084 0 a b Ralston A W Hoerr C W 1942 The Solubilities of the Normal Saturated Fatty Acids The Journal of Organic Chemistry 7 6 546 555 doi 10 1021 jo01200a013 PMID 20280727 a b c d stearic acid Chemister ru 2007 03 19 Retrieved 2017 06 30 a b c Seidell Atherton Linke William F 1919 Solubilities of Inorganic and Organic Compounds 2nd ed D Van Nostrand Company p 677 a b Octadecanoic acid in Linstrom Peter J Mallard William G eds NIST Chemistry WebBook NIST Standard Reference Database Number 69 National Institute of Standards and Technology Gaithersburg MD retrieved 2014 06 15 Vargaftik Natan B et al 1993 Handbook of Thermal Conductivity of Liquids and Gases illustrated ed CRC Press p 318 ISBN 978 0 8493 9345 7 a b c d von Sydow E 1955 On the structure of the crystal form B of stearic acid Acta Crystallographica 8 9 557 560 doi 10 1107 S0365110X55001746 a b c d e f g h i j k l m n o p q r s Stearic acid PubChem US National Library of Medicine 29 April 2023 Retrieved 5 May 2023 Science Lab com Stearic acid MSDS PDF Retrieved 2020 09 30 Loften J R Linn J G Drackley J K Jenkins T C Soderholm C G Kertz A F August 2014 Invited review Palmitic and stearic acid metabolism in lactating dairy cows Journal of Dairy Science 97 8 4661 4674 doi 10 3168 jds 2014 7919 ISSN 0022 0302 a b c d e Hunter J E Zhang J Kris Etherton P M 2009 Cardiovascular disease risk of dietary stearic acid compared with trans other saturated and unsaturated fatty acids A systematic review American Journal of Clinical Nutrition 91 1 46 63 doi 10 3945 ajcn 2009 27661 PMID 19939984 Gunstone F D John L Harwood and Albert J Dijkstra The Lipid Handbook with Cd Rom 3rd ed Boca Raton CRC Press 2007 ISBN 0849396883 ISBN 978 0849396885 a b Beare Rogers J Dieffenbacher A Holm J V 2001 Lexicon of lipid nutrition IUPAC Technical Report Pure and Applied Chemistry 73 4 685 744 doi 10 1351 pac200173040685 S2CID 84492006 a b Anneken David J Both Sabine Christoph Ralf Fieg Georg Steinberner Udo Westfechtel Alfred 2006 Fatty Acids Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a10 245 pub2 Aguilar Fernando Crebelli Riccardo Di Domenico Alessandro et al 2017 Re evaluation of fatty acids E 570 as a food additive EFSA Journal 15 5 4785 doi 10 2903 j efsa 2017 4785 PMC 7009963 PMID 32625490 Angelo Nora Alfred Szczepanek Gunther Koenen 2005 Metallic Soaps Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a16 361 Tsenga Wenjea J Mo Liua Dean Hsub Chung King 1999 Influence of stearic acid on suspension structure and green microstructure of injection molded zirconia ceramics Ceramics International 25 2 191 195 doi 10 1016 S0272 8842 98 00024 8 Emken Edward A 1994 Metabolism of dietary stearic acid relative to other fatty acids in human subjects American Journal of Clinical Nutrition 60 6 1023S 1028S doi 10 1093 ajcn 60 6 1023S PMID 7977144 External links Edit Wikimedia Commons has media related to Stearic acid NIST Chemistry WebBook Entry Retrieved from https en wikipedia org w index php title Stearic acid amp oldid 1154903607, wikipedia, wiki, book, books, library,

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