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Chemistry

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Also known as: Cetyl alcohol, Hexadecan-1-ol, 36653-82-4, Hexadecanol, Cetanol, Palmityl alcohol
Molecular Formula
C16H34O
Molecular Weight
242.44  g/mol
InChI Key
BXWNKGSJHAJOGX-UHFFFAOYSA-N
FDA UNII
936JST6JCN

Cetyl Alcohol API
Cetyl Alcohol is a synthetic, solid, fatty alcohol and nonionic surfactant. Cetyl alcohol is used as an emulsifying agent in pharmaceutical preparations.
1 2D Structure

Cetyl Alcohol API

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
hexadecan-1-ol
2.1.2 InChI
InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
2.1.3 InChI Key
BXWNKGSJHAJOGX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCCCCO
2.2 Other Identifiers
2.2.1 UNII
936JST6JCN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cetanol

2. Cetyl Alcohol

3. Cetyl Alcohol, 14c-labeled

4. Cetyl Alcohol, Aluminum Salt

5. Hexadecan-1-ol

6. N-hexadecanol

2.3.2 Depositor-Supplied Synonyms

1. Cetyl Alcohol

2. Hexadecan-1-ol

3. 36653-82-4

4. Hexadecanol

5. Cetanol

6. Palmityl Alcohol

7. Hexadecyl Alcohol

8. N-hexadecanol

9. N-1-hexadecanol

10. N-cetyl Alcohol

11. Cetaffine

12. Cetylol

13. Cetal

14. Ethal

15. Ethol

16. Cetylic Alcohol

17. N-hexadecyl Alcohol

18. Loxanwachs Sk

19. Crodacol C

20. Loxanol K Extra

21. 1-hexadecyl Alcohol

22. Elfacos C

23. Loxanol K

24. Crodacol-cas

25. Crodacol-cat

26. Siponol Wax-a

27. Atalco C

28. Cetalol Ca

29. Siponol Cc

30. Lanol C

31. 1-cetanol

32. Hyfatol 16

33. Cachalot C-50

34. Cachalot C-51

35. Cachalot C-52

36. Alcohol C-16

37. Product 308

38. Aldol 54

39. Dytol F-11

40. Adol

41. Palmitic Alcohol

42. Cyclal Cetyl Alcohol

43. Alfol 16

44. Lorol 24

45. Adol 52

46. Adol 54

47. Adol 52 Nf

48. Hyfatol

49. Epal 16nf

50. 1-hexadecyl Alc

51. 16-hexadecanol

52. C16 Alcohol

53. Adol 520

54. N-hexadecan-1-ol

55. Cetylalkohol

56. Isocetyl Alcohol

57. 1-hexanedecanol

58. Fema No. 2554

59. Isohexadecyl Alcohol

60. Cetylalcohol

61. Ssd Rp

62. Normal Primary Hexadecyl Alcohol

63. Co-1670

64. Co-1695

65. Cetyl Alchol

66. Lipocol C

67. Fancol Ca

68. Cetyl Alcohol Nf

69. Crodacol C70

70. Rita Ca

71. 1-hydroxyhexadecane

72. Cetanol (tn)

73. Lanette 16

74. Philcohol 1600

75. Cetyl Alcohol (nf)

76. Cetyl Alcohol [nf]

77. Lorol C16

78. Loroll 24

79. Cachalot C-50 Nf

80. Adol 52nf

81. Alcohols, C14-18

82. Nsc-4194

83. 936jst6jcn

84. 67762-30-5

85. Chebi:16125

86. Nsc4194

87. Ncgc00159368-02

88. Ncgc00159368-05

89. Dsstox_cid_7991

90. Dsstox_rid_78633

91. Dsstox_gsid_27991

92. Hexadecanol (van)

93. Fatty Alcohol(c16)

94. Caswell No. 165d

95. Fema Number 2554

96. Hexadecyl Alcohol, Normal

97. Cas-36653-82-4

98. Hsdb 2643

99. Nsc 4194

100. Einecs 253-149-0

101. Unii-936jst6jcn

102. Epa Pesticide Chemical Code 001508

103. Cetyl Alcohol (hexadecanol)

104. Brn 1748475

105. Hexadecylalcohol

106. Ai3-00755

107. Hexadecanol Nf

108. Alcohol Cetylicus

109. Ceraphyl Ica

110. Crodacol C95nf

111. Dehydag Wax 16

112. Eutanol G16

113. Crodacol C95 Nf

114. Laurex 16

115. Mfcd00004760

116. Alfol 16rd

117. Ssd (salt/mix)

118. Cetanol (jp17)

119. Epal 16

120. Hyfatol 16-95

121. Kalcol 6098

122. Loxiol Vpg 1743

123. 1-hexadecanol, 95%

124. Ssd Rp (salt/mix)

125. Cetanol [jan]

126. Bmse000487

127. Chembl706

128. Michel Xo-150-16

129. Ec 253-149-0

130. Fatty Alcohols(c12-16)

131. 1-hexadecanol, >=99%

132. Cetyl Alcohol [ii]

133. Cetyl Alcohol [mi]

134. Schembl3381

135. Cetyl Alcohol [hsdb]

136. Cetyl Alcohol [inci]

137. 124-29-8

138. 4-01-00-01876 (beilstein Handbook Reference)

139. 1-hexadecanol [fhfi]

140. Cetyl Alcohol [vandf]

141. Cetyl Alcohol [mart.]

142. Cetyl Alcohol [usp-rs]

143. Cetyl Alcohol [who-dd]

144. Cetyl Alcohol [who-ip]

145. Dtxsid4027991

146. Amy6070

147. Cetyl Alcohol, Analytical Standard

148. Cetyl Alcohol, Puriss., 95.0%

149. Hms3652h05

150. Cs-d1348

151. Hy-b1465

152. Zinc8214519

153. Einecs 252-964-9

154. Tox21_111609

155. Tox21_300325

156. Cetyl Alcohol [ep Monograph]

157. Lmfa05000061

158. S4173

159. Stl283943

160. Unii-1800h64066

161. Akos005287456

162. Tox21_111609_1

163. 1-hexadecanol, Reagentplus(r), 99%

164. Ccg-266894

165. Db09494

166. Alcohol Cetylicus [who-ip Latin]

167. Ncgc00159368-03

168. Ncgc00159368-04

169. Ncgc00159368-06

170. Ncgc00254286-01

171. Bs-16666

172. Cetyl Alcohol, Puriss., >=99.0% (gc)

173. Ft-0701357

174. Ft-0707360

175. H0071

176. Sw219201-1

177. Cetyl Alcohol, Saj Special Grade, >=98.0%

178. Cetyl Alcohol, Selectophore(tm), >=99.0%

179. En300-19351

180. 1-hexadecanol, Vetec(tm) Reagent Grade, 94%

181. C00823

182. D00099

183. Ab01566915_01

184. Q161632

185. Sr-01000944409

186. Sr-01000944409-1

187. 1800h64066

188. 810f139f-c57e-4df1-916a-a320ad0daf4d

189. F0001-1047

190. Cetyl Alcohol, European Pharmacopoeia (ep) Reference Standard

191. Cetyl Alcohol, United States Pharmacopeia (usp) Reference Standard

192. Cetyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 242.44 g/mol
Molecular Formula C16H34O
XLogP37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count14
Exact Mass242.260965704 g/mol
Monoisotopic Mass242.260965704 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count17
Formal Charge0
Complexity123
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

A synthetic surfactant (Exosurf), and its non-surface-active components tyloxapol and cetyl alcohol, can function as antioxidants, and their in vivo instillation is associated with decreased hyperoxic injury in rats.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 3:669


4.2 Minimum/Potential Fatal Human Dose

1(?). 1= Practically nontoxic: Probable oral lethal dose (human) above 15 g/kg; more than 1 quart (2.2 lb) for 70 kg person (150 lb).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-174


4.3 Drug Indication

No therapeutic indications in medicinal products. Indicated to be used as an indirect additive in food contact substances, or an ingredient in commercial or cosmetic products.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cetyl alcohol exhibits skin protect properties against skin irritations caused by bites, rashes and stings. The inhibitory action of cetyl alcohol against the growth of _Mycoplasma gallisepticum_ and _Mycopiasma pneumoniae_ has been reported.


5.2 Absorption, Distribution and Excretion

Absorption

Following ingestion at a dose level of 2.0 g/kg in rats, cetyl alcohol was partly absorbed. Administration of 0.2 mg cetyl alcohol in rat by stomach tube indicated good absorption as 63-96 % of radiolabeled cetyl alcohol was detected in the lymph. About 15% of total cetyl alcohol was unchanged during its passage through the mucosal cells of the small intestine but mostly underwent oxidation to palmitic acid. The extent of absorption was reported to be 26% in poultry.


Route of Elimination

Following ingestion at a dose level of 2.0 g/kg in rats, about 20% of the dose was recovered as unchanged molecule in the feces. This may be due to the interconvertibility of fatty acids and alcohols, resulting in the conversion of palmitic acid to cetyl alcohol during its passage through the intestinal mucosal cells into the intestinal lumen. In rats, cetyl Alcohol was also excreted in the urine as conjugated glucuronic acid and as expired carbon dioxide.


Following ingestion at a dose level of 2.0 g/kg bw /in rats/, 1-hexadecanone is partly absorbed and metabolized, about 20% of the dose being recovered unchanged in the feces.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 486


5.3 Metabolism/Metabolites

Following ingestion at a dose level of 2.0 g/kg in rats, cetyl alcohol was partly metabolized to palmitic acid. After administration of 0.2 mg cetyl alcohol in rat by stomach tube, cetyl alcohol was mostly oxidized to palmitic acid and incorporated into triglycerides and phospholipids during its passage through the mucosal cells of the small intestine.


Cetyl alcohol is oxidized in rats to the corresponding fatty acid, palmitic 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. 6:494


The primary aliphatic alcohols undergo two general reactions in vivo, namely oxidation to carboxylic acids and direct conjugation with glucuronic acid. The first reaction proceeds with the intermediate formation of an aldehyde, and the carboxylic acid from this may be either oxidized completely to carbon dioxide or excreted as such or combined with glucuronic acid as an ester glucuronide. The extent to which as alcohol undergoes the second reaction, i.e. direct conjugation to an ether glucuronide, appears to depend upon the speed of the first reaction, for alcohols which are rapidly oxidized from very little ether glucuronide unless given in high doses.

European Chemicals Bureau; IUCLID Dataset, Cetyl Alcohol (36653-82-4) (2000 CD-ROM edition). Available from, as of April 14, 2006: https://esis.jrc.ec.europa.eu/


5.4 Mechanism of Action

Cetyl alcohol has hydrating properties that makes it a suitable emulsifier and stabilizer in pharmaceutical formulations. It is also present in washable ointment base due to its dispersant abilities and stabilizing properties. Potential antimicrobial activity of cetyl alcohol may be due to a change in cell membrane permeability that either blocks absorption of essential nutrients and induction of outward diffusion vital cellular components. This proposed mechanism of action is thought to be similar for other long-chain aliphatic alcohols with same antimicrobial activity, such as myristyl alcohol and behenyl alcohol.


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