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Tox21_300562
Also known as: Octadecanoic acid, 57-11-4, N-octadecanoic acid, Stearophanic acid, Cetylacetic acid, Pearl stearic
Molecular Formula
C18H36O2
Molecular Weight
284.5  g/mol
InChI Key
QIQXTHQIDYTFRH-UHFFFAOYSA-N
FDA UNII
4ELV7Z65AP

Stearic Acid is a saturated long-chain fatty acid with an 18-carbon backbone. Stearic acid is found in various animal and plant fats, and is a major component of cocoa butter and shea butter.
1 2D Structure

Tox21_300562

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
octadecanoic acid
2.1.2 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)
2.1.3 InChI Key
QIQXTHQIDYTFRH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
4ELV7Z65AP
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aluminum Monostearate

2. Aluminum Tristearate

3. Ammonium Stearate

4. Calcium Stearate

5. Magnesium Stearate

6. Octadecanoic Acid

7. Sodium Stearate

8. Zinc Stearate

2.3.2 Depositor-Supplied Synonyms

1. Octadecanoic Acid

2. 57-11-4

3. N-octadecanoic Acid

4. Stearophanic Acid

5. Cetylacetic Acid

6. Pearl Stearic

7. Stearex Beads

8. 1-heptadecanecarboxylic Acid

9. Octadecansaeure

10. Stearinsaeure

11. Vanicol

12. Hydrofol Acid 150

13. Century 1240

14. Industrene R

15. Glycon Dp

16. Glycon Tp

17. Humko Industrene R

18. Dar-chem 14

19. Formula 300

20. Hydrofol 1895

21. Hystrene 7018

22. Hystrene 9718

23. Glycon S-80

24. Glycon S-90

25. Hydrofol Acid 1655

26. Hydrofol Acid 1855

27. Tegostearic 254

28. Tegostearic 255

29. Tegostearic 272

30. Hystrene 80

31. Octadecoic Acid

32. Industrene 5016

33. Hystrene S-97

34. Hystrene T-70

35. Emersol 120

36. Emersol 132

37. Hystrene 4516

38. Hystrene 5016

39. Groco 54

40. Groco 55

41. Groco 55l

42. Groco 58

43. Groco 59

44. Glycon S-70

45. Industrene 8718

46. Industrene 9018

47. Kam 1000

48. Emersol 150

49. Fema No. 3035

50. Steric Acid

51. C18:0

52. Neo-fat 18-53

53. Neo-fat 18-54

54. Neo-fat 18-59

55. Neo-fat 18

56. Acidum Stearinicul

57. Barolub Fta

58. Caswell No. 801d

59. Hy-phi 1199

60. Hy-phi 1205

61. Hy-phi 1303

62. Hy-phi 1401

63. Neo-fat 18-s

64. Kam 2000

65. Kam 3000

66. Oktadekansaeure

67. Neo-fat 18-55

68. Neo-fat 18-61

69. Acide Stearique

70. Century 1210

71. Pd 185

72. Stearic Acid 50

73. Acide Octadecanoique

74. Naa 173

75. Hydrofol Acid 150 (van)

76. Ccris 2305

77. Prifac 2918

78. Hsdb 2000

79. Vis-plus

80. Prodhygine

81. Epa Pesticide Chemical Code 079082

82. Stearic Acid Cherry

83. Edenor C18

84. Stearic Acid (tn)

85. Purified Stearic Acid

86. Dervacid 3155

87. Ch3-[ch2]16-cooh

88. Loxiol G 20

89. Adeka Sa 300

90. Century 1220

91. Century 1230

92. Emersol 6349

93. Ai3-00909

94. Lunac S 20

95. Lunac S 40

96. Wo 2 (fatty Acid)

97. Hydrofol Acid 1895

98. Octadecanoic Acid, Dimer

99. Bonderlube 235

100. Mfcd00002752

101. Nsc-25956

102. 4elv7z65ap

103. Adeka Fatty Acid Sa 910

104. Chembl46403

105. Chebi:28842

106. Nsc25956

107. Nsc-261168

108. Ncgc00091596-02

109. Dsstox_cid_1642

110. Dsstox_rid_76256

111. Dsstox_gsid_21642

112. 18639-67-3

113. Stearic Acid, Pure

114. Stearicacid

115. Lunac

116. Stearic Acid (powder/beads/flakes)

117. Cas-57-11-4

118. Isostearic Acid Ex

119. Nsc 25956

120. Haimaric Mkh(r)

121. Prisorine 3501

122. Prisorine 3502

123. Prisorine 3508

124. Emersol 153nf

125. Emersol 871

126. Emersol 875

127. Emery 875d

128. Emery 871

129. Unimac 5680

130. C-lube 10

131. Einecs 200-313-4

132. Stearic Acid [jan:nf]

133. Fatty Acids, C16-20

134. Unii-4elv7z65ap

135. Brn 0608585

136. Stearophanate

137. Promulsin

138. Stearex

139. Tsubaki

140. N-octadecanoate

141. Bassinic Acid

142. Lactaric Acid

143. Proviscol Wax

144. Talgic Acid

145. Kolliwax S Fine

146. Edenor Htict-n

147. 1hmr

148. 1hmt

149. 4fnn

150. Kiri Stearic Acid

151. Lunac Ya

152. N-octadecylic Acid

153. Palmitostearic Acid

154. Stearic Acid 70

155. Stearic Acid, Cp

156. Sterene 60b

157. Sterene 60r

158. Einecs 250-178-0

159. F 3 (lubricant)

160. Industrene 4518

161. Nonsoul Sk 1

162. Pristerene 4900

163. Pristerene 4904

164. Pristerene 4910

165. Pristerene 4916

166. Pristerene 4963

167. Pristerene 4981

168. Pristerene 9429

169. Pristerene 9559

170. Pristerine 4989

171. Hystrene S 97

172. Hystrene T 70

173. Edenor St 1

174. Sunfat 18s

175. Emersol 153

176. Selosol 920

177. Sterene 460

178. Industrene 5016k

179. Stearic Acid 110

180. Stearic Acid 120

181. Stearic Acid 420

182. Hystrene 9718nf

183. Kortacid 1895

184. Radiacid 0427

185. Edenor St 20

186. Lunac 30

187. Serfax Mt 90

188. Stearic Acid_ravikumar

189. Unister Naa 180

190. Century 1224

191. Edenor Ht-jg 60

192. Lunac S 90kc

193. Stearic Acid (8ci)

194. Stearic Acid, Puriss.

195. Hyfac 410

196. Hyfac 420

197. Hyfac 421

198. Hyfac 422

199. Hystrene 7018 Fg

200. Hystrene 9718nffg

201. Lunac S 30

202. Lunac S 50

203. Lunac S 90

204. Lunac S 98

205. Prifac 5905

206. 3v2p

207. 875d

208. 1-heptadecanecarboxylate

209. Hydrogenated Tallow Acid

210. Industrene 7018 Fg

211. Stearic Acid Nf Powder

212. Afco-chem B 65

213. Hydrogenated Tallow Acids

214. Stearic Acid - 65%

215. Stearic Acid - 70%

216. Stearic Acid 153 Nf

217. Heptadecanecarboxylic Acid

218. Stearic Acid & Glycerin

219. Edenor C 18/98

220. Tallow Acid, Hydrogenated

221. Neo-fat 18-57

222. Neo-fat 18-58

223. S 300 (fatty Acid)

224. Octadecanoic Acid (9ci)

225. Stearic Acid, >=98%

226. Schembl659

227. Hystrene 9718 Nf Fg

228. Sa 400 (fatty Acid)

229. Bmse000485

230. Stearic Acid [ii]

231. Stearic Acid [mi]

232. Stearic Acid, High Purity

233. Stearic Acid-[13c18]

234. Stearic Acid-2-[13c]

235. Ec 200-313-4

236. Emery 400 (salt/mix)

237. Stearic Acid [dsc]

238. Stearic Acid [jan]

239. Tallow, Acids, Hydrogenated

240. Stearic Acid (jp15/nf)

241. Stearic Acid (jp17/nf)

242. Stearic Acid Triple-pressed

243. Triple Pressed Stearic Acid

244. Emersol 110 (salt/mix)

245. Stearic Acid - High Purity

246. Stearic Acid [fhfi]

247. Stearic Acid [hsdb]

248. Stearic Acid [inci]

249. Stearic Acid (reagent Grade)

250. Stearic Acid [vandf]

251. 4-02-00-01206 (beilstein Handbook Reference)

252. Wln: Qv17

253. Agar Agar Type K-100 Nf

254. Stearic Acid [mart.]

255. Hydrogenated Tallow Acid, Beef

256. Hydrogenated Tallow Fatty Acids

257. Stearic Acid - Triple Pressed

258. Stearic Acid [usp-rs]

259. Stearic Acid [who-dd]

260. 17fa

261. Gtpl3377

262. Wo 2

263. Stearic Acid (fragrance Grade)

264. Stearic Acid High Purity 90%

265. Stearic Acid-1,2-[13c2]

266. Dtxsid8021642

267. Fatty Acids, Hydrogenated Tallow

268. Tallow Fatty Acids, Hydrogenated

269. Tallow, Hydrogenated Fatty Acids

270. Unii-x33r8u0062

271. Nonsoul Sn 1 (*sodium Salt*)

272. S 30c S 30c (fatty Acid)

273. Sna-2000 (*sodium Salt*)

274. Stearic Acid, Analytical Standard

275. Vlz 200

276. Stearic Acid High Purity 90% V

277. Purified Stearic Acid [nf]

278. Stearic Acid Flake 132 Nf Flake

279. Stearic Acid, Reagent Grade, 95%

280. Hy-b2219

281. Stearic Acid [ep Monograph]

282. Stearic Acid 400 (rubber Grade)

283. Zinc4978673

284. Tox21_111154

285. Tox21_201887

286. Tox21_300562

287. Bbl012224

288. Bdbm50240485

289. Lmfa01010018

290. S5733

291. Sa 200

292. Stearic Acid, >=95%, Fcc, Fg

293. Stl163565

294. Akos005716958

295. Tox21_111154_1

296. Ccg-267314

297. Db03193

298. Fa 1655

299. Fa 18:0

300. T16-55f

301. X33r8u0062

302. Ncgc00091596-01

303. Ncgc00091596-03

304. Ncgc00091596-04

305. Ncgc00091596-05

306. Ncgc00254456-01

307. Ncgc00259436-01

308. 68937-76-8

309. E570

310. Vs-03242

311. Stearic Acid, Puriss., >=98.5% (gc)

312. Stearic Acid, Saj First Grade, >=90.0%

313. Bb 0268543

314. Cs-0021598

315. Ft-0674650

316. Ft-0689088

317. G 270

318. S 300

319. S0163

320. Stearic Acid, Saj Special Grade, >=95.0%

321. Stearic Acid, Vetec(tm) Reagent Grade, 94%

322. 400jb9103-88

323. A 1760

324. C01530

325. D00119

326. Ec 250-178-0

327. F70008

328. Stearic Acid 50, Tested According To Ph.eur.

329. Vegetable Stearic Acid 7036 Fg, Kosher, Nf

330. Q209685

331. Sr-01000944717

332. Melting Point Standard 69-71c, Analytical Standard

333. Sr-01000944717-1

334. Stearic Acid, Grade I, >=98.5% (capillary Gc)

335. Stearic Acid, Saj First Grade, >=90.0%, Powder

336. F0001-1489

337. Stearic Acid (constituent Of Saw Palmetto) [dsc]

338. Stearic Acid, Certified Reference Material, Tracecert(r)

339. Z955123678

340. Stearic Acid (constituent Of Flax Seed Oil) [dsc]

341. Cd7993ea-ad14-452a-a907-33376cc98790

342. Stearic Acid, European Pharmacopoeia (ep) Reference Standard

343. Stearic Acid (constituent Of Evening Primrose Oil) [dsc]

344. Stearic Acid, United States Pharmacopeia (usp) Reference Standard

345. Stearic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 284.5 g/mol
Molecular Formula C18H36O2
XLogP37.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count16
Exact Mass284.271530387 g/mol
Monoisotopic Mass284.271530387 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity202
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ Stearic acid is known as a potent anti-inflammatory lipid. This fatty acid has profound and diverse effects on liver metabolism. The aim of this study was to investigate the effect of stearic acid on markers of hepatocyte transplantation in rats with acetaminophen (APAP)-induced liver damage. Wistar rats were randomly assigned to 10-day treatment. Stearic acid was administered to the rats with APAP-induced liver damage. The isolated liver cells were infused intraperitoneally into rats. Blood samples were obtained to evaluate the changes in the serum liver enzymes, including activities of aspartate aminotransferase (AST), alanine aminotransferase (ALT) and alkaline phosphatase (ALP) and the level of serum albumin. To assess the engraftment of infused hepatocytes, rats were euthanized, and the liver DNA was used for PCR using sex-determining region Y (SRY) primers. The levels of AST, ALT and ALP in the serum of rats with APAP-induced liver injury were significantly increased and returned to the levels in control group by day six. The APAP-induced decrease in albumin was significantly improved in rats through cell therapy, when compared with that in the APAP-alone treated rats. SRY PCR analysis showed the presence of the transplanted cells in the liver of transplanted rats. Stearic acid-rich diet in combination with cell therapy accelerates the recovering of hepatic dysfunction in a rat model of liver injury.

PMID:27090202 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4983676 Hashemi Goradel N et al; Iran Biomed J 20 (4): 217-22 (2016)


/EXPL THER/ Because of their reported antiviral and anti-inflammatory activities, cream formulations containing n-docosanol (docosanol) or stearic acid were tested for effects on chemically-induced burns in mice. In this model, injury was induced by painting the abdomens of mice with a chloroform solution of phenol. This was followed by the topical application of test substances 0.5, 3, and 6 hr later. Progression of the wounds was assessed by a single evaluator after 8 hr, using a numerical score of gross morphology. Docosanol- and stearic acid-containing creams substantially and reproducibly lessened the severity and progression of skin lesions compared to untreated sites with a 76% and 57% reduction in mean lesion scores, respectively. Untreated wounds appeared red and ulcerated; docosanol cream-treated wounds showed only slight erythema.

PMID:10945745 Khalil MH et al; Contact Dermatitis 43 (2): 79-81 (2000)


4.2 Minimum/Potential Fatal Human Dose

LD100 Human oral 14286 mg/kg; practically nontoxic: probable oral lethal dose (human) more than 1 qt (2.2 lb) for 70 kg person (150 lb).

USEPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. HPV Data Set for Cobalt Stearate and Fatty Acids, Tall Oil, Cobalt Salts p.14 (2003)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

A mild moisturizing body wash with stearic acid, a key component of corneum lipids, and emollient soybean oil has been introduced in the market place. The objectives of this study are to determine the amount and the location of the stearic acid in the corneum after in vivo cleansing by the formulation. Clinical cleansing studies for one and five consecutive days were carried out with the formulation containing soybean oil or petroleum jelly (PJ). The free stearic acid in it was replaced by the fully deuterated variant. The amounts of stearic acid in 10 consecutive corneum tape strips were measured by liquid chromatograph-mass spectroscopy. Separately, electron paramagnetic resonance (EPR) measurements were taken with a porcine skin after a wash by the soybean oil formulation with its free fatty acid replaced by its spin probe analogue, 5-doxyl stearic acid. Deuterated stearic acid was detected in all 10 consecutive layers of stratum corneum and the total amount after five washes with the soybean oil formulation was 0.33 ug/sq cm. The spin probe in cleanser-treated skin was incorporated in a partially ordered hydrophobic region similar to corneum lipids. The probe mobility increased in the temperature region where lipid disorder was expected. The estimated total fatty acid delivered to skin from cleansing is comparable to the amount of fatty acid in a corneum layer. The delivered fatty acid is most likely incorporated in the corneum lipid phase.

PMID:20883293 Mukherjee S et al; J Cosmet Dermatol 9 (3): 202-10 (2010)


It has been noted by several investigators that increasing fatty acid chain length slightly decreased their digestibility; stearic acid was the most poorly absorbed of the common fatty acids.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


Fatty acids, /including stearic acid/, originating from adipose tissue stores are either bound to serum albumin or remain unesterified in the blood.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


Oleic, palmitic, myristic, and stearic acids are primarily transported via the lymphatic system, and lauric acid is transported by the lymphatic and (as a free fatty acid) portal systems.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


Radioactivity has been traced to the heart, liver, lung, spleen, kidney, muscle, intestine, adrenal, blood, and lymph, and adipose, mucosal, and dental tissues after administration of radioactive oleic, palmitic, and stearic acids.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


5.2 Metabolism/Metabolites

Stearic acid metabolism via beta-oxidation, omega-oxidation, and (omega-1)-oxidation has been demonstrated in rat liver. Removal of a single acetate moiety can occur to produce palmitic acid, and both this and stearic acid may be desaturated, producing oleic and palmitoleic acids, respectively. After (l4)C stearic acid was injected into rats, about 50 percent of the liver (14)C was recovered as oleic acid, indicating that extensive desaturation occurs. Desaturation occurs only to a small extent extrahepatically but has been detected in adipose tissue and in cells of mammary tissue. Stearic acid is also incorporated into phospholipids, di- and triglycerides, cholesterol, cholesterol esters, and other sterol esters.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 746


Proposed mechanisms for fatty acid uptake by different tissues range from passive diffusion to facilitated diffusion or a combination of both. Fatty acids taken up by the tissues can either be stored in the form of triglycerides (98% of which occurs in adipose tissue depots) or they can be oxidized for energy via the beta-oxidation and tricarboxylic acid cycle pathways of catabolism.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


The beta-oxidation of fatty acids occurs in most vertebrae tissues (except the brain) using an enzyme complex for the series of oxidation and hydration reactions resulting in the cleavage of acetate groups as acetyl-CoA (coenzyme A). An additional isomerization reaction is required for the complete catabolism of oleic acid. Alternate oxidation pathways can be found in the liver (omega-oxidation) and in the brain (alpha-oxidation).

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


Fatty acid biosynthesis from acetyl-CoA takes place primarily in the liver, adipose tissue, and mammary glands of higher animals. Successive reduction and dehydration reactions yield saturated fatty acids up to a 16-carbon chain length. Stearic acid is synthesized by the condensation of palmitoyl-CoA and acetyl-CoA in the mitochondria, and oleic acid is formed via a mono-oxygenase system in the endoplasmic reticulum.

Cosmetic Ingredient Review; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid. p.341 Journal of the American College of Toxicology 6 (3): 321-401 (1987). Available from, as of November 15, 2017: https://www.cir-safety.org/ingredients


Animal cells can de novo synthesize palmitic and stearic fatty acid and their n-9 derivatives. However, de novo synthesis requires the utilization of energy. Palmitic acid (C16) is the immediate precursor of stearic acid (C18). In animal cells, oleic acid is created by the dehydrogenation (desaturation) of stearic acid. Oleic acid is further elongated and desaturated into a family of n-9 fatty acids. The demand for energy used to synthesize n-9 fatty acids can be reduced in cell culture by providing palmitic and stearic acids. In addition, since palmitic and stearic acid are saturated, they are not peroxidized during delivery to the cells.

Sigma-Aldrich; Stearic Acid in Cell Culture. Available from, as of November 22, 2017: https://www.sigmaaldrich.com/life-science/cell-culture/learning-center/media-expert/stearic-acid.html


Stearic Acid has known human metabolites that include 17-Hydroxystearic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


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