1. 9 Octadecenoic Acid
2. 9-octadecenoic Acid
3. Cis 9 Octadecenoic Acid
4. Cis-9-octadecenoic Acid
5. Oleate
1. 112-80-1
2. Cis-9-octadecenoic Acid
3. Oleate
4. (z)-octadec-9-enoic Acid
5. Elaidoic Acid
6. Cis-oleic Acid
7. Wecoline Oo
8. Vopcolene 27
9. Glycon Wo
10. Pamolyn 100
11. Glycon Ro
12. Metaupon
13. Oelsauere
14. Groco 5l
15. Groco 2
16. Groco 4
17. Groco 6
18. Tego-oleic 130
19. Emersol 211
20. 9z-octadecenoic Acid
21. Cis-octadec-9-enoic Acid
22. Industrene 105
23. Industrene 205
24. Industrene 206
25. Pamolyn
26. Z-9-octadecenoic Acid
27. 9-octadecenoic Acid (z)-
28. Oleinic Acid
29. Emersol 210
30. Emersol 213
31. 9-octadecenoic Acid (9z)-
32. L'acide Oleique
33. Century Cd Fatty Acid
34. Emersol 6321
35. Extraolein 90
36. Oleine 7503
37. 9-octadecenoic Acid, (z)-
38. Emersol 205
39. Emersol 233ll
40. Hy-phi 1055
41. Hy-phi 1088
42. Hy-phi 2066
43. Hy-phi 2088
44. Hy-phi 2102
45. Elaic Acid
46. Priolene 6906
47. 9-octadecenoic Acid
48. White Oleic Acid
49. Wochem No. 320
50. Emersol 220 White Oleic Acid
51. Fema No. 2815
52. Extra Oleic 80r
53. Extra Oleic 90
54. Extra Oleic 99
55. Extra Olein 80
56. Extra Olein 90r
57. Lunac O-ca
58. Lunac O-ll
59. Lunac O-p
60. Neo-fat 92-04
61. Priolene 6907
62. Priolene 6928
63. Priolene 6930
64. Priolene 6933
65. Elainic Acid
66. Emersol 6313nf
67. Cis-oleate
68. Delta9-cis-oleic Acid
69. (9z)-octadec-9-enoic Acid
70. (9z)-octadecenoic Acid
71. Fema Number 2815
72. D 100 (fatty Acid)
73. Emersol 221 Low Titer White Oleic Acid
74. K 52
75. Oelsaeure
76. 9-cis-octadecenoic Acid
77. Hsdb 1240
78. Red Oil
79. D 100
80. (9z)-9-octadecenoic Acid
81. Oleic Acid [nf]
82. 9-octadecylenic Acid
83. Emersol 233
84. Oleicacid
85. 18:1delta9cis
86. Priolene 6936
87. Chebi:16196
88. Nsc-9856
89. 9,10-octadecenoic Acid
90. C18:1n-9
91. Neo-fat 90-04
92. .delta.9-cis-oleic Acid
93. 9-(z)-octadecenoic Acid
94. (z)-9-octadecanoic Acid
95. 9-octadecenoic Acid, Cis-
96. Cis-.delta.9-octadecenoate
97. 2umi9u37cp
98. Chembl8659
99. Cis-.delta.9-octadecenoic Acid
100. Cis-delta(9)-octadecenoic Acid
101. Nsc9856
102. Oleic Acid (nf)
103. Osteum
104. Mfcd00064242
105. C18:1 N-9
106. Fa 18:1
107. Octadec-9-enoic Acid
108. Ncgc00091119-02
109. 18:1 N-9
110. C18:1
111. Cis-9-octadecenoate
112. (9z)- Octadecenoic Acid
113. Dsstox_cid_5809
114. 18:1(n-9)
115. Oleic Acid, Pure
116. Dsstox_rid_77930
117. Dsstox_gsid_25809
118. Oleic Acid (natural)
119. Caswell No. 619
120. Wecoline Oo (van)
121. Acide Oleique [french]
122. Acide Oleique
123. Cis-delta9-octadecenoic Acid
124. L'acide Oleique [french]
125. Cas-112-80-1
126. Smr000326739
127. Ccris 682
128. Naa 35
129. Sulfurized Oleic Acid
130. Sulphurized Oleic Acid
131. Oleic Acid, Sulfurized
132. Cis-delta(sup 9)-octadecenoic Acid
133. Nsc 9856
134. Einecs 204-007-1
135. Unii-2umi9u37cp
136. Epa Pesticide Chemical Code 031702
137. Brn 1726542
138. Distoline
139. Oleinate
140. Oleaic Acid
141. Rapinic Acid
142. Ai3-01291
143. 1gni
144. 1hms
145. 1vyf
146. 2lkk
147. Oleic Acid Liquid
148. Lunac Oa
149. Edenor Atio5
150. Edenor Ftio5
151. Industrene 104
152. Z-9-octadecenoate
153. Einecs 270-164-8
154. Oleic Acid, P.a.
155. Emersol 213nf
156. Emersol 214nf
157. Pamolyn 125
158. Priolene 6900
159. 9,10-octadecenoate
160. 9-octadecenoic Acid (z)-, Sulfurized
161. Oleic Acid (8ci)
162. Oleic Acid Extra Pure
163. Cis-octadec-9-enoate
164. Pamolyn 100 Fg
165. Pamolyn 100 Fgk
166. 9-(z)-octadecenoate
167. Emersol 7021
168. 9-octadecenoic Acid (9z)-, Sulfurized
169. (z)-9-octadecanoate
170. Emersol 6313 Nf
171. Emersol 6333 Nf
172. Oleic Acid-9,10-t
173. (9z)-9-octadecenoate
174. Z-octadeca-9-enoic Acid
175. Oleic Acid [ii]
176. Oleic Acid [mi]
177. Oleic Acid [fcc]
178. Epitope Id:187036
179. Oleic Acid [fhfi]
180. Oleic Acid [hsdb]
181. Oleic Acid [inci]
182. Oleic Acid, Natural, Fcc
183. Emersol 220 White Oleate
184. Oleic Acid [vandf]
185. Oleic Acid, Technical Grade
186. Schembl1138
187. Delta9-cis-octadecenoic Acid
188. Oleic Acid [mart.]
189. Wln: Qv8u9-c
190. Oleic Acid [usp-rs]
191. Oleic Acid [who-dd]
192. 4-02-00-01641 (beilstein Handbook Reference)
193. 99148-48-8
194. Mls001056779
195. Mls002153498
196. Mls002454427
197. 9-octadecenoic Acid, (9z)-
198. (9z)-9-octadecenoic Acid #
199. Gtpl1054
200. Oleic Acid, Analytical Standard
201. Dtxsid1025809
202. Oleic Acid, >=93% (gc)
203. Oleic Acid, >=99% (gc)
204. Regid_for_cid_445639
205. 1g74
206. Oleic Acid [ep Monograph]
207. Hms2234o13
208. Hms3649h21
209. Hms3885h18
210. Oleic Acid, Technical Grade, 90%
211. Hy-n1446
212. Zinc6845860
213. Endocine Component Oleic Acid
214. Tox21_111086
215. Tox21_201967
216. Tox21_303324
217. Bdbm50150484
218. Cis-9-octadecenoic Acid;elainic Acid
219. Hsci1_000362
220. Lmfa01030002
221. S4707
222. 9-octadecenoic Acid (9z)- (9ci)
223. Cis-9-octadecenoic-9,10-3h2 Acid
224. Emersol 221 Low Titer White Oleate
225. Akos017343225
226. Cis-.delta.(sup 9)-octadecenoic Acid
227. At13415
228. Ccg-267270
229. 9-octadecenoic-9,10-t2 Acid, (z)-
230. Ncgc00091119-01
231. Ncgc00091119-03
232. Ncgc00257233-01
233. Ncgc00259516-01
234. 68412-07-7
235. Ac-33767
236. As-16066
237. Bp-24023
238. Fa(18:1(9z))
239. Oleic Acid, Saj First Grade, >=70.0%
240. Oleic Acid, Selectophore(tm), >=99.0%
241. Cs-0016886
242. O0011
243. O0180
244. C00712
245. D02315
246. Oleic Acid, From Suet, Natural, >=60% (gc)
247. Ab00641912_08
248. 9-octadecenoic-9,10-t2 Acid, (9z)- (9ci)
249. A894525
250. Oleic Acid, Suitable For Cell Culture, Bioreagent
251. Q207688
252. Sr-01000780573
253. Oleic Acid (constituent Of Spirulina) [dsc]
254. Sr-01000780573-6
255. 9-octadecenoic Acid(z)-,oxidized,sulfonated,sodium Salts
256. F0001-0262
257. Oleic Acid (constituent Of Flax Seed Oil) [dsc]
258. Oleic Acid (constituent Of Saw Palmetto) [dsc]
259. Oleic Acid, Certified Reference Material, Tracecert(r)
260. Oleic Acid (constituent Of Borage Seed Oil) [dsc]
261. Oleic Acid, European Pharmacopoeia (ep) Reference Standard
262. 459ce4c0-c836-4249-8e2d-69874b714e9c
263. Oleic Acid (c18:1) (constituent Of Krill Oil) [dsc]
264. Oleic Acid (constituent Of Evening Primrose Oil) [dsc]
265. Oleic Acid, United States Pharmacopeia (usp) Reference Standard
266. Oleic Acid, Meets Analytical Specification Of Ph, Eur., 65.0-88.0% (gc)
267. Oleic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
268. Oleic Acid-water Soluble, Powder, Bioreagent, Suitable For Cell Culture
269. Ole
270. Oleic Acid, Pharmagrade, Manufactured Under Appropriate Controls For Use As Raw Material In Pharma Or Biopharmaceutical Production.
| Molecular Weight | 282.5 g/mol |
|---|---|
| Molecular Formula | C18H34O2 |
| XLogP3 | 6.5 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 15 |
| Exact Mass | 282.255880323 g/mol |
| Monoisotopic Mass | 282.255880323 g/mol |
| Topological Polar Surface Area | 37.3 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 234 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
/EXPTL THER/ Ten Japanese boys with childhood adrenoleukodystrophy (ALD), one adult patient with adrenomyeloneuropathy (AMN), and two presymptomatic ALD boys were treated with dietary erucic acid (C22:1) for more than 12 months; except in a case of childhood ALD patient who died 7 months after beginning erucic acid therapy. During erucic acid therapy, the serum levels of very long-chain fatty acid (VLCFA) (C24:0/C22:0) decreased within 1-2 months in all patients, and these levels in four of the patients decreased to the normal range. Neurological examination and MRI findings in all 10 of the childhood ALD patients showed progression of the disease while they were receiving the dietary therapy. However, the mean interval between the onset of awkward gait and a vegetative state in diet-treated patients was significantly longer than that in the untreated patients. One AMN patient showed slight improvement of spastic gait and lessened pain in the lower limbs due to spasticity. The two presymptomatic ALD boys remained intact on clinical examination and on MRI findings for 38 and 23 months, respectively, after starting the diet.
PMID:7694994 Asano J et al; Brain Dev 16 (6): 454-8 (1994)
/EXPL THER/ An open 2 yr trial of oleic and erucic acids (Lorenzos oil) included 14 men with adrenomyeloneuropathy, 5 symptomatic heterozygous women and 5 boys with preclinical adrenomyeloneuropathy. No evidence of a clinically relevant benefit from dietary treatment in patients with adrenomyeloneuropathy (accumulation of very-long-chain fatty acids) could be found. /Lorenzos oil/
European Chemicals Bureau; IUCLID Dataset, (Z)-docos-13-enoic acid (CAS # 112-86-7) p.78 (2000 CD-ROM edition). Available from, as of January 29, 2008: https://esis.jrc.ec.europa.eu/
40 male and 6 female patients with adrenoleukodystrophy received Lorenzos oil (20% erucic acid and 80% oleic acid). In 19 of these patients the platelet count decr significantly. In 6 patients with thrombocytopenia, platelet counts became normal within 2 to 3 mo after erucic acid was omitted from the diet. Observations suggested that strategies for the dietary management of adrenoleukodystrophy requiring the admin of large amt of erucic acid may be associated with thrombocytopenia and that the erucic acid component of Lorenzos oil is the cause of the thrombocytopenia. Patients treated with erucic acid should be followed closely with determinations of the platelet count. /Lorenzos oil: 20% erucic acid and 80% oleic acid/
European Chemicals Bureau; IUCLID Dataset, (Z)-docos-13-enoic acid (CAS # 112-86-7) p.78 (2000 CD-ROM edition). Available from, as of January 30, 2008: https://esis.jrc.ec.europa.eu/
15 men with adrenoleukodystrophy and 3 symptomatic heterozygous women were admin oleic and erucic acids (Lorenzos oil). Asymptomatic thrombocytopenia developed in 5 patients (platelet counts ranged between 37000 and 84000 per cu mm) but was reversed within 2 to 3 wk after erucic acid was omitted. In addition, long-term treatment with Lorenzos oil (for 24 to 43 mo) was associated with lymphocytopenia in these 5 patients. The observations suggested that the long-term treatment of adrenoleukodystrophy with Lorenzos oil can induce severe lymphocytopenia with immunosuppression and recurrent infections. /Lorenzos oil/
European Chemicals Bureau; IUCLID Dataset, (Z)-docos-13-enoic acid (CAS # 112-86-7) p.79 (2000 CD-ROM edition). Available from, as of January 30, 2008: https://esis.jrc.ec.europa.eu/
1. 1= PRACTICALLY NONTOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) ABOVE 15 G/KG, MORE THAN 1 QT (2.2 LB) FOR 70 KG PERSON (150 LB).
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-134
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 of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 15, June 2005.
Simultaneous ingestion of trace amounts of 14C-triolein (10 uCi) and 3H-oleic acid (20 uCi) in 42 g of carrier fat by patients with normal fecal fat excretion resulted in estimated fecal excretion of less than 10% of both substances. Gastrointestinal transit times for 14C-triolein, 3H-oleic acid, and a nonabsorbable marker, CrCl3, did not differ significantly.
Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 16, June 2005.
Oleic Acid has been reported to penetrate the skin of rats. On histological examination, fluorescence from absorbed oleic acid was found in epidermal cell layers of skin removed from treated rats within 10 min of its application. The path of penetration was suggested to be via the hair follicles. Only minute amounts of oleic acid were visualized in the blood vessels throughout the experiment. Skin permeability was shown to increase with the lipophilic nature of a compound.
Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 15, June 2005.
METABOLISM OF TRITIATED OLEIC ACID WAS STUDIED IN RATS DURING 600 DAYS. DURING FIRST 4 DAYS, HALF ACTIVITY IS FIXED TO WATER & HALF IS STORED IN ADIPOSE TISSUE WHICH IT LEAVES QUICKLY, THEN MORE SLOWLY WITH T/2 OF ABOUT 200 DAYS.
JEANMAIRE L ET AL; REPORT ISS CEA-R-4975 34 (1979)
For more Absorption, Distribution and Excretion (Complete) data for OLEIC ACID (10 total), please visit the HSDB record page.
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 of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 15, June 2005.
The beta-oxidation of fatty acids occurs in most vertebrate 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 of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 15, June 2005.
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 of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; p. 15, June 2005.
The normal metabolic pathway of palmitic and stearic acids in mammals produces oleic acid. Oleic acid, on a series of elongation and desaturation steps, may be converted into longer chain eicosatrienoic and nervonic acid.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 829
Weanling rats were fed diets containing rapeseed, canbra or ground nut oils for 8 or 60 days. They received simultaneously (14)C erucate and (3)H2 oleate by iv application. Animals were killed 2 or 19 hr after injection, lungs were removed and the distribution of (14)C and (3)H radioactivities was determined in pulmonary lipid fractions and in fatty acids of phospholipids and neutral lipids. More (14)C than (3)H radioactivity was recovered in lung lipids 3 and 19 hr after admin of labelled fatty acids. (14)C and (3)H radioactivity in the phospholipid fraction was larger than in the triglyceride fraction, the inverse was observed after 19 hr. The main part of (14)C radioactivity was present in the monounsaturated fatty acids, in decr order: 18:1, 24:1, 16:1 and 20:1. Erucic acid was slightly esterified in phospholipids.
European Chemicals Bureau; IUCLID Dataset, (Z)-docos-13-enoic acid (CAS # 112-86-7) p.76 (2000 CD-ROM edition). Available from, as of January 29, 2008: https://esis.jrc.ec.europa.eu/
Oleic acid has known human metabolites that include 17-Hydroxyoleic acid and 18-Hydroxyoleic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
METABOLISM OF TRITIATED OLEIC ACID WAS STUDIED IN RATS DURING 600 DAYS. /ELIMINATION OCCURED/ SLOWLY WITH T/2 OF ABOUT 200 DAYS.
JEANMAIRE L ET AL; REPORT ISS CEA-R-4975 34 (1979)
Insulin resistance is linked with a cluster of multiple risk factors and excessive acceleration of atherosclerosis. The underlying mechanism is not, however, fully understood. To determine the link between insulin resistance and altered vascular function, we focused on the effect of various non-esterified fatty acids on diacylglycerol-protein kinase C pathway and mitogen-activated protein kinase activity in cultured aortic smooth muscle cells. Incubation of the cells with saturated non-esterified fatty acids (200 micromol/L) for 24 hr, such as palmitate or stearate, induced a significant increase in diacylglycerol concentrations by about fivefold or eightfold, respectively, whereas oleate induced a slight increase in diacylglycerol concentrations by 1.8-fold and arachidonate induced none. In addition, the increased diacylglycerol concentrations induced by palmitate were completely restored to control concentrations by triacsin C, acyl-CoA synthetase inhibitor. These results suggest that saturated non-esterified fatty acids may increase diacylglycerol concentrations through de novo pathway by stepwise acylation. In parallel with the increased diacylglycerol, incubation of the cells with saturated non-esterified fatty acids significantly induced the activation of protein kinase C and mitogen-activated protein kinase. The palmitate-induced increase in mitogen-activated protein kinase activity was restored to control concentrations by GF109203X (5 x 10(-7) mol/L), a specific protein kinase C inhibitor, suggesting a protein kinase C-dependent activation of mitogen-activated protein kinase. Saturated non-esterified fatty acids induced an increase in de novo diacylglycerol synthesis and subsequent activation of protein kinase C and mitogen-activated protein kinase in cultured aortic smooth muscle cells. This could contribute to the altered vascular functions in the insulin resistant state.
PMID:11380080 Yu HY et al; Diabetologia 44 (5): 614-20 (2001)
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