1. (z)-octadec-9-enol
2. Cis-9-octadecen-1-ol
3. Oleol
4. Oleyl Alcohol, (z)-isomer
1. (z)-octadec-9-en-1-ol
2. 143-28-2
3. Cis-9-octadecen-1-ol
4. Ocenol
5. Dermaffine
6. Lancol
7. Novol
8. Oceol
9. Oleol
10. Satol
11. Oleic Alcohol
12. Oleo Alcohol
13. (z)-9-octadecen-1-ol
14. Crodacol-o
15. Conditioner 1
16. Loxanol M
17. Atalco O
18. Siponol Oc
19. Sipol O
20. Cachalot O-1
21. Cachalot O-3
22. Cachalot O-8
23. H.d. Eutanol
24. Hd-ocenol K
25. Loxanol 95
26. Unjecol 50
27. Unjecol 70
28. Unjecol 90
29. Oleoyl Alcohol
30. Olive Alcohol
31. Cachalot O-15
32. Crodacol A.10
33. Unjecol 110
34. Hd Oleyl Alcohol Cg
35. Cis-9-octadecenyl Alcohol
36. Adol 34
37. Adol 80
38. Adol 85
39. Adol 90
40. Witcohol 85
41. Witcohol 90
42. Hd-ocenol 90/95
43. 9-octadecen-1-ol, (z)-
44. Z-9-dodecen-1-ol
45. Hd Oleyl Alcohol 70/75
46. Hd Oleyl Alcohol 80/85
47. Hd Oleyl Alcohol 90/95
48. (z)-octadec-9-enol
49. Adol 320
50. Adol 330
51. Adol 340
52. (9z)-octadec-9-en-1-ol
53. Cis-9-octadecenol
54. Cis-octadecen-1-ol
55. 9-octadecen-1-ol
56. (z)-9-octadecenol
57. Oleylalcohol
58. Polyoxyl 10 Oleyl Ether
59. Hd-eutanol
60. Octadec-9z-enol
61. (9z)-9-octadecen-1-ol
62. 9z-octadecen-1-ol
63. Oleyl Alcohol (nf)
64. Oleyl Alcohol [nf]
65. ( Z)-9-octadecenol
66. Witcohol 85 (tn)
67. 9-octadecen-1-ol, (9z)-
68. Nsc-10999
69. 9-octadecen-1-ol, Cis-
70. 172f2wn8dv
71. Fema No. 4363
72. Chebi:73504
73. Mfcd00002993
74. 0leyl Alcohol
75. 9-octadecenol
76. Poly(oxy-1,2-ethanediyl), Alpha-((z)-9-octadecenyl)-omega-hydroxy-
77. Hsdb 6484
78. Einecs 205-597-3
79. Nsc 10999
80. Unii-172f2wn8dv
81. Ai3-07620
82. Genapol O
83. Lipocol O
84. Cis-oleyl Alcohol
85. Anjecol 90n
86. Unjecol 90n
87. (z)-oleyl Alcohol
88. Anjecol 90nr
89. Unjecol 90nr
90. Francol Oa-95
91. Fancol Oa-95
92. Cis 9 Octadecen-1-ol
93. Cis-9-0ctadecen-1-ol
94. 9(z)-octadecen-1-ol
95. Hd-echelon 90/95
96. Cis-octadec-9-en-1-ol
97. Dsstox_cid_2010
98. Octadeca-9-cis-en-1-ol
99. Ec 205-597-3
100. Cis-.delta.9-octadecenol
101. Hd-ocenol 90/95 V
102. Oleyl Alcohol [ii]
103. Oleyl Alcohol [mi]
104. Schembl5668
105. (z)-octadeca-9-en-1-ol
106. Dsstox_rid_76459
107. Dsstox_gsid_22010
108. Oleyl Alcohol [inci]
109. Oleyl Alcohol [vandf]
110. Oleyl Alcohol [mart.]
111. (9z)-9-octadecen-1-ol #
112. Octadec-9-en-1-ol, (z)-
113. Oleyl Alcohol [usp-rs]
114. Oleyl Alcohol [who-dd]
115. Chembl2105350
116. Dtxsid0022010
117. Oleyl Alcohol, >=99% (gc)
118. Cis-9-octadecenol [fhfi]
119. Oleyl Alcohol, Analytical Standard
120. Cis-laquo Deltaraquo 9-octadecenol
121. Nsc10999
122. Oleyl Alcohol [ep Impurity]
123. Zinc8214634
124. Tox21_200111
125. (9z)-9-octadecen-1-ol, 85%
126. Lmfa05000213
127. Oleyl Alcohol [ep Monograph]
128. Oleyl Alcohol, Technical Grade, 85%
129. Akos004910411
130. (9z)-9-octadecen-1-ol, 85per Cent
131. Oleyl Alcohol, Technical, ~60% (gc)
132. Ncgc00164365-01
133. Ncgc00164365-02
134. Ncgc00257665-01
135. Bs-42539
136. Cas-143-28-2
137. Db-007794
138. O0058
139. D05245
140. A884989
141. Q7086489
142. W-109512
143. 3164d881-7e14-4979-9e60-58ddc0468323
144. Oleyl Alcohol, United States Pharmacopeia (usp) Reference Standard
| Molecular Weight | 268.5 g/mol |
|---|---|
| Molecular Formula | C18H36O |
| XLogP3 | 7.4 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 15 |
| Exact Mass | 268.276615768 g/mol |
| Monoisotopic Mass | 268.276615768 g/mol |
| Topological Polar Surface Area | 20.2 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 175 |
| 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 |
Long-chain alcohols have been detected in lipid extracts of bovine and porcine brain and heart muscle at levels of approximately 0.002% (w/w) of the total lipids. Hexadecanol, octadecanol, octadecenol and, in the bovine tissues, docosanol were identified as major constituents.
Takahashi, T, Schmid, HHO; Chem Physics of Lipids 4 (2): 243-246 (1970)
Long chain alcohols were detected in developing rat brain at highest level of 0.0109% of the total lipids at the age of 10 days and decreased to 0.0036% at the age of 40 days. They consisted mainly of hexadecanol, octadecanol, octadecenol, eicosanol, docosanol, and tetracosanol.
PMID:834119 Natarajan V, Schmid HH; Lipids 12 (1): 128-30 (1977)
A mixture of cis-9[1(-14)C] octadecenol and [1(-14)C] docosanol was injected into the brains of 19-day-old rats, and incorporation of radioactivity into brain lipids was determined after 3, 12, and 24 hr. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid, but oleic acid was more readily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated into 18:1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18:1 alkyl moieties of the choline phosphoglycerides. Even after the disappearance of the 18:1 alcohol from the substrate mixture (12 hr), the 22:0 alcohol was not used to any measurable extent for alkyl and alk-1-enylglycerol formation.
PMID:916829 Natarajan V, Schmid HH; Lipids 12 (10): 872-5 (1977)
The distribution of radioactivity from intravenously administered cis-9[1-14C]octadecenol into various tissues of the rat was studied as a function of time. The pattern of incorporation of radioactivity into alkyl, alk-1-enyl and acyl moieties of the lipids in heart, lungs, liver, intestine, kidney, brain and plasma revealed that oxidation of the long-chain alcohol and esterification of the resulting fatty acid to a wide variety of lipids are by far the most predominant reactions. Acylation of the long-chain alcohol is observed especially in liver, which appears to be the major site of biosynthesis of wax esters. Alkylation of the long-chain alcohol to alkoxylipids occurs in most tissues, most predominantly in the heart.
PMID:7398637 Mukherjee KD et al; Eur J Biochem 107 (1): 289-94 (1980)
cis-9-Octadecenyl alcohol (oleyl alcohol), orally administered, increased the relative concentration of 18:1 alkyl and alk-1-enyl moieties in alkoxylipids of the small intestine of rats.
Bandi ZL et al; Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 239 (3): 357-367 (1971)
A mixture of cis-9[1(-14)C] octadecenol and [1(-14)C] docosanol was injected into the brains of 19-day-old rats, Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid, but oleic acid was more readily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated into 18:1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18:1 alkyl moieties of the choline phosphoglycerides.
PMID:916829 Natarajan V, Schmid HH; Lipids 12 (10): 872-5 (1977)
cis-9-[1-(14)C]Octadecenol, cis,cis-9,12-[1-(14)C]octadecadienol, and cis,cis,cis-9,12,15-[1-(14)C]octadecatrienol were administered intracerebrally to 18-day-old rats. Incorporation of radioactivity into the constituent alkyl, alk-1-enyl, and acyl moieties of the ethanolamine phosphatides of brain was determined after 3, 6, 24, and 48 hr. Incorporation of radioactivity from each precursor proceeded at approximately the same rate leading to mono-, di-, and triunsaturated alkyl and alk-1-enyl glycerols. In addition, the labeled alcohols were found to be oxidized to the corresponding fatty acids which were incorporated into acyl groups; radioactivity derived from di- and triunsaturated alcohols was found mainly in acyl moieties produced through chain elongation and desaturation reactions of di- and triunsaturated fatty acids.
PMID:5041271 Su KL, Schmid HH; J Lipid Res 13 (4): 452-7 (1972)
Farnesol (FOH) inhibits the CDP-choline pathway for PtdCho (phosphatidylcholine) synthesis, an activity that is involved in subsequent induction of apoptosis /SRP: programmed cell death/. Interestingly, the rate-limiting enzyme in this pathway, CCTalpha (CTP:phosphocholine cytidylyltransferase alpha), is rapidly activated, cleaved by caspases and exported from the nucleus during FOH-induced apoptosis. The purpose of the present study was to determine how CCTalpha activity and PtdCho synthesis contributed to induction of apoptosis by FOH and oleyl alcohol. Contrary to previous reports, /the authors/ show that the initial effect of FOH and oleyl alcohol was a rapid (10-30 min) and transient activation of PtdCho synthesis. During this period, the mass of DAG (diacylglycerol) decreased by 40%, indicating that subsequent CDP-choline accumulation and inhibition of PtdCho synthesis could be due to substrate depletion. At later time points (>1 h), FOH and oleyl alcohol promoted caspase cleavage and nuclear export of CCTalpha, which was prevented by treatment with oleate or DiC8 (dioctanoylglycerol). Protection from FOH-induced apoptosis required CCTalpha activity and PtdCho synthesis since (i) DiC8 and oleate restored PtdCho synthesis, but not endogenous DAG levels, and (ii) partial resistance was conferred by stable overexpression of CCTalpha and increased PtdCho synthesis in CCTalpha-deficient MT58 cells. These results show that DAG depletion by FOH or oleyl alcohol could be involved in inhibition of PtdCho synthesis. However, decreased DAG was not sufficient to induce apoptosis provided nuclear CCTalpha and PtdCho syntheses were sustained.
PMID:16097951 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1316283 Lagace TA, Ridgway ND; Biochem J 392 (Pt 3): 449-56 (2005)
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