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| CAS No.: | 57-11-4 |
|---|---|
| Name: | Stearic acid |
| Molecular Structure: | |
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| Formula: | C18H36O2 |
| Molecular Weight: | 284.47700 |
| Synonyms: | Stearic acid;n-octadecanoic acid;naa173;groco58;groco59;groco55;groco54;C18;pd185;NAA180;steraic acid;kam1000; |
| EINECS: | 266-928-5 |
| Density: | 0.84 |
| Melting Point: | 67-72°C(lit.) |
| Boiling Point: | 361°C(lit.) |
| Flash Point: | >230°F |
| Solubility: | 0.1-1 g/100 mL at 23 ºC |
| Appearance: | White solid with a mild odor |
| Hazard Symbols: | R11:; R36/37/38:; |
| Risk Codes: | F:Flammable; F:Flammable; |
| Safety: | |
| Transport Information: | |
| PSA: | 37.30000 |
| LogP: | 6.33250 |
| Conditions | Yield |
|---|---|
| With hydrogen; palladium In ethyl acetate at 25℃; under 760.051 Torr; for 12h; | 100% |
| With hydrogen; palladium in polystyrene In tetrahydrofuran at 25℃; under 760.051 Torr; for 12h; | 100% |
| With hydrogen; 5%-palladium/activated carbon In ethyl acetate under 2585.81 Torr; for 6h; | 100% |
1-(tert-butyldimethylsilyloxy)octadecan
stearic acid
| Conditions | Yield |
|---|---|
| With potassium fluoride; jones reagent In acetone at 0℃; for 2h; | 100% |
stearic acid
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid for 15h; Product distribution; | 100% |
| Conditions | Yield |
|---|---|
| With hydrogen In methanol at 20℃; for 5h; | 99.4% |
| Multi-step reaction with 2 steps 1: KOH; butyl alcohol / Zusatz von Wasser und weiteres kurzes Erwaermen des Reaktionsgemisches 2: PtO2; glacial acetic acid / 2206.5 Torr / Hydrogenation View Scheme |
Sb(C6H5)4(OOC(CH2)16CH3)
A
tetraphenylantimony(V) chloride
B
stearic acid
| Conditions | Yield |
|---|---|
| With aq. HCl | A 99% B n/a |
| Conditions | Yield |
|---|---|
| Stage #1: 10-bromodecanoic acid With 1-methyl-pyrrolidin-2-one; tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: n-octylmagnesium chloride With buta-1,3-diene; nickel dichloride In tetrahydrofuran under 760.051 Torr; for 1h; Inert atmosphere; Cooling with ice; | 97% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In N,N-dimethyl-formamide for 0.75h; Ambient temperature; | 96% |
| With water; indium (III) iodide; silica gel for 0.533333h; Hydrolysis; Irradiation; | 90% |
| With potassium hydroxide In methanol at 35℃; for 1h; | 73% |
| Conditions | Yield |
|---|---|
| With hydrogen; Rhodium chloride tri(triphenylphosphine-meta-trisulfonate) In water for 18h; Ambient temperature; | 95% |
| With selenium at 300℃; | |
| With platinum(IV) oxide; acetic acid under 2206.5 Torr; Hydrogenation; | |
| hoher Wasserstoffdruck.Hydrogenation; | |
| With palladium/alumina; hydrogen In methanol at 80℃; under 15001.5 Torr; Catalytic behavior; Kinetics; Reagent/catalyst; Autoclave; |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol for 1h; Reflux; | 94% |
| With Mg-Al hydrotalcite; hydrogen at 325℃; under 21446.5 Torr; | |
| With aluminum oxide; dilauryl thiodipropionate; 2,6-di-tert-butyl-4-methyl-phenol; Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate; magnesium oxide In water at 100 - 130℃; under 5250.53 Torr; for 0.75h; Temperature; |
N-methylstearylamide
stearic acid
| Conditions | Yield |
|---|---|
| With sodium hydroxide; Glyoxal; copper dichloride Heating; | 93% |
| Conditions | Yield |
|---|---|
| With carbon monoxide; 1,5-bis-(diphenylphosphino)pentane; acetic anhydride; potassium iodide; iron(II) chloride at 240℃; under 15201 Torr; for 3h; | 93% |
| Conditions | Yield |
|---|---|
| With benzotriazole*CrO3 In acetone for 5h; Heating; | 91% |
| With benzotriazole*CrO3 In acetone for 5h; Product distribution; Heating; other primary and secondary alcohols (steroids), other solvents and substrate ratios; | 91% |
| With α,α,α-trifluorotoluene; oxygen; Ru*Co(2+)*2OH(1-)*CeO2 at 60℃; for 5h; atmospheric pressure; | 78% |
(+/-)-threo-9,10-dibromo-octadecanoic acid
stearic acid
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.25h; | 88% |
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide In water at 100℃; for 6h; Catalytic behavior; Green chemistry; | 87% |
| Conditions | Yield |
|---|---|
| With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere; | 86% |
| Conditions | Yield |
|---|---|
| Pt/Sn/C Product distribution / selectivity; | A 85% B 5.9% |
| With glycerol In water at 25 - 300℃; under 10351 Torr; Kinetics; Mechanism; Reagent/catalyst; Inert atmosphere; | A 24% B 75% |
| With 5% platinum on carbon; water at 330℃; for 1.5h; Autoclave; | A 9.2% B 36.1% |
| With palladium on activated carbon; glycerol In water at 250℃; for 20h; Catalytic behavior; |
Octadecanoic acid 3-cyano-benzyl ester
stearic acid
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile Irradiation; | 78% |
methyl 5-thiastearate
A
cis-9-hexadecenoic acid
B
cis-Octadecenoic acid
C
1-hexadecylcarboxylic acid
D
stearic acid
| Conditions | Yield |
|---|---|
| With Saccharomyces cerevisiae NR2335 In ethanol at 30℃; for 48h; | A 62% B 27% C 8% D 3% |
Octadecanoic acid pentafluorobenzyl ester
stearic acid
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile Irradiation; | 62% |
| Conditions | Yield |
|---|---|
| With nickel(II) iodide; SmI2/Sm In various solvent(s) at 25℃; for 2h; Reduction; dimerization; | A 57% B 34% |
Octadecanoic acid 4-cyano-benzyl ester
stearic acid
| Conditions | Yield |
|---|---|
| With triethylamine In acetonitrile Irradiation; | 54% |
B
cis-Octadecenoic acid
C
linoleic acid
D
(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid
E
stearic acid
| Conditions | Yield |
|---|---|
| With hydrogen; mineral malachite at 165℃; under 3102.97 Torr; for 4h; Conversion of starting material; | A 16.23% B 37.82% C 41.48% D 2.92% E 5.39% |
stearic anhydride
3-benzoyl-5-fluorouracil
A
stearic acid
B
3-benzoyl-5-fluoro-1-octadecanoyl-1H-pyrimidine-2,4-dione
| Conditions | Yield |
|---|---|
| With pyridine In 1,4-dioxane; acetone | A n/a B 40% |
methyl 5-thiastearate
A
cis-9-hexadecenoic acid
B
cis-Octadecenoic acid
D
1-hexadecylcarboxylic acid
E
stearic acid
| Conditions | Yield |
|---|---|
| With Saccharomyces cerevisiae NRC2335 In ethanol at 30℃; for 48h; Product distribution; | A 38% B 16% C 25% D 6% E 1% |
methyl 5-thiastearate
A
cis-9-hexadecenoic acid
C
1-hexadecylcarboxylic acid
D
stearic acid
| Conditions | Yield |
|---|---|
| With Saccharomyces cerevisiae NR2335 In ethanol at 30℃; for 48h; Further byproducts given; | A 33% B 31% C 4% D n/a |
cis-Octadecenoic acid
isopropyl alcohol
A
isopropyl oleate
B
isopropyl stearate
C
stearic acid
| Conditions | Yield |
|---|---|
| With cobalt at 200℃; for 4h; Reagent/catalyst; | A n/a B n/a C 23.9% |
| Conditions | Yield |
|---|---|
| at 150 - 170℃; under 3 - 4 Torr; Decarboxylation; |
ethanol
1,2-di-O-stearoyl-rac-3-glycerophosphate
A
glycerol 2-phosphate, free acid
B
lysophosphatidic acid
C
stearic acid
| Conditions | Yield |
|---|---|
| bei Raumtemperatur; |
| Conditions | Yield |
|---|---|
| With palladium Hydrogenation; |
| Conditions | Yield |
|---|---|
| Gel-0.5percent DVB at 65 - 67℃; under 760.051 Torr; for 2h; Conversion of starting material; Molecular sieves 3A; Canola oil; | 100% |
| Gel-1percent DVB at 65 - 67℃; under 760.051 Torr; for 2h; Conversion of starting material; Molecular sieves 3A; Canola oil; | 100% |
| Gel-1.5percent DVB at 65 - 67℃; under 760.051 Torr; for 2h; Conversion of starting material; Molecular sieves 3A; Canola oil; | 100% |
| Conditions | Yield |
|---|---|
| With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 100% |
| In benzene | |
| In hexane for 5h; Reflux; Inert atmosphere; |
(2S)-3-(benzyloxy)propane-1,2-diol
stearic acid
1-O-benzyl-2,3-dioctadecanoyl-sn-glycerol
| Conditions | Yield |
|---|---|
| With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; | 100% |
| With Candida antarctica lipase In neat (no solvent) at 80℃; Enzymatic reaction; | 80% |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine at 20℃; for 6h; Esterification; | |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide | 100% |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide | 100% |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide | 100% |
2-hydroxy-1,1,2-trimethylpropyl ethylcarbamate
stearic acid
A
4,4,5,5-tetramethyl-1,3-dioxolan-2-one
B
stearic acid ethyl ester
| Conditions | Yield |
|---|---|
| With tert.-butylnitrite; 3 A molecular sieve In dichloromethane at 105℃; for 12h; | A n/a B 100% |
stearic acid
| Conditions | Yield |
|---|---|
| With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; | 100% |
| Conditions | Yield |
|---|---|
| With zinc(II) oxide; citric acid In water at 60 - 70℃; for 0.5h; | 100% |
| With zinc(II) oxide; hydroxypropyl methylcellulose; citric acid In water at 65 - 75℃; for 1h; | 100% |
| With Tergitol 15-S-7; zinc(II) oxide; hydroxypropyl methylcellulose; citric acid In water at 55 - 70℃; for 0.25 - 1h; | 99.1% |
| Conditions | Yield |
|---|---|
| toluene-4-sulfonic acid In toluene for 5h; Heating / reflux; | 100% |
2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
stearic acid
C14H22N2O*C18H36O2
| Conditions | Yield |
|---|---|
| for 0.0833333h; Inert atmosphere; Heating; | 100% |
stearic acid
| Conditions | Yield |
|---|---|
| Stage #1: stearic acid With trifluoroacetic anhydride at 50℃; for 0.333333h; Stage #2: glucomannan acetate at 50℃; for 0.5h; Inert atmosphere; | 100% |
| Conditions | Yield |
|---|---|
| Stage #1: stearic acid With thionyl chloride Reflux; Inert atmosphere; Large scale; Stage #2: 3,6-dibromothiophene[3,2-b]thiophene With aluminum (III) chloride In dichloromethane at 10 - 15℃; for 1h; Autoclave; Large scale; | 100% |
| Conditions | Yield |
|---|---|
| Stage #1: stearic acid With thionyl chloride Reflux; Large scale; Stage #2: C28H41BrO2S3 With aluminum (III) chloride In dichloromethane at 10 - 15℃; for 1h; Autoclave; Inert atmosphere; Large scale; | 100% |
| Conditions | Yield |
|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 100% |
| Conditions | Yield |
|---|---|
| Stage #1: stearic acid With sodium hydroxide In water at 90℃; for 1h; Stage #2: copper(II) choride dihydrate In water for 1h; | 100% |
| Conditions | Yield |
|---|---|
| Stage #1: stearic acid With sodium hydroxide In water at 90℃; for 1h; Stage #2: manganese(II) chloride dihydrate In water for 1h; | 100% |
| Conditions | Yield |
|---|---|
| In methanol at 40℃; | 100% |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20 - 40℃; | 100% |
stearic acid
copper(II) stearate
| Conditions | Yield |
|---|---|
| With ammonium acetate In ethanol; water at 27℃; for 4h; Concentration; Reagent/catalyst; Electrochemical reaction; | 99.21% |
| In neat (no solvent) detected by electron diffraction;; | |
| In toluene reaction does not take place if O2 is excluded;; |
stearic acid
| Conditions | Yield |
|---|---|
| With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane for 12h; Ambient temperature; | 99.1% |
| Conditions | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h; | 99% |
| With Zn-MCM-22 catalyst at 80 - 340℃; under 15001.5 Torr; for 6h; Reagent/catalyst; Inert atmosphere; Large scale; | 95.7% |
| Stage #1: stearic acid With triethylamine; methyl chloroformate In dichloromethane at 20℃; for 2h; Cooling with ice; Stage #2: diethylamine In dichloromethane at 20℃; | 71% |
| at 200 - 250℃; | |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 36h; |
| Conditions | Yield |
|---|---|
| With thionyl chloride In toluene at 20℃; Reflux; | 99% |
| With phosgene; pentabutyl propyl guanidinium chloride; silica gel In neat (no solvent) at 100 - 120℃; | 98% |
| With phosgene; N,N-dimethyl-formamide In toluene at 50℃; | 98.5% |
| Conditions | Yield |
|---|---|
| With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature; | 99% |
| With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature; | 98% |
| With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 92% |
2-Amino-2-methyl-1-propanol
stearic acid
4,4-dimethyl-2-heptadecyl-2-oxazoline
| Conditions | Yield |
|---|---|
| With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h; | 99% |
| at 170℃; for 0.666667h; Microwave irradiation; Neat (no solvent); open vessel; | 73% |
| With potassium hydroxide 1.) 150 deg C; 2.) 180 deg C; Multistep reaction; | |
| 14.1 g (79.7%) | |
| 14.1 g (79.7%) |
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Stearic Acid, with the cas number 57-11-4, also called Octadecanoic Acid, one of the most common long-chain fatty acids, found in combined form in natural animal and vegetable fats. Commercial “stearic acid” is a mixture of approximately equal amounts of stearic and palmitic acids and small amounts of oleic acid. It is employed in the manufacture of candles, cosmetics, shaving soaps, lubricants, and pharmaceuticals.Stearic acid is prepared by treating these fats and oils with water at a high pressure and temperature (above 200 °C), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled. Commercial stearic acid is often a mixture of stearic and palmitic acids, although purified stearic acid is available.
Physical properties about Stearic Acid are:
(1)ACD/LogP: 7.83; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.03; (4)ACD/LogD (pH 7.4): 5.24; (5)ACD/BCF (pH 5.5): 84062.82; (6)ACD/BCF (pH 7.4): 1348.58; (7)ACD/KOC (pH 5.5): 69237.45; (8)ACD/KOC (pH 7.4): 1110.74; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 16; (12)Index of Refraction: 1.456; (13)Molar Refractivity: 87.005 cm3; (14)Molar Volume: 320.283 cm3; (15)Polarizability: 34.491 10-24cm3; (16)Surface Tension: 33.4189987182617 dyne/cm; (17)Density: 0.888 g/cm3; (18)Flash Point: 162.369 °C; (19)Enthalpy of Vaporization: 63.841 kJ/mol; (20)Boiling Point: 359.44 °C at 760 mmHg;
Uses of Stearic Acid:
Generally 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, notably reduction to stearyl alcohol, and esterification with a range of alcohols.
Safety information of Stearic Acid:
When you are using this chemical, please be cautious about it as the following: Wear suitable gloves and eye/face protection; In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; Keep away from sources of ignition - No smoking.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)CCCCCCCCCCCCCCCCC;
(2)Std. 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); (3)Std. InChIKey:QIQXTHQIDYTFRH-UHFFFAOYSA-N
The toxicity data of Stearic Acid is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 23mg/kg (23mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Acta Pharmacologica et Toxicologica. Vol. 18, Pg. 141, 1961. |
| rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 17, Pg. 383, 1979. | |
| rat | LD50 | intravenous | 21500ug/kg (21.5mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Acta Pharmacologica et Toxicologica. Vol. 18, Pg. 141, 1961. |
| rat | LDLo | oral | 4640mg/kg (4640mg/kg) | Journal of the American College of Toxicology. Vol. 6(3), Pg. 321, 1987. |
