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Chemistry

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Also known as: Hexadecanoic acid, 57-10-3, Cetylic acid, Palmitate, N-hexadecanoic acid, Hexadecylic acid
Molecular Formula
C16H32O2
Molecular Weight
256.42  g/mol
InChI Key
IPCSVZSSVZVIGE-UHFFFAOYSA-N
FDA UNII
2V16EO95H1

Palmitic Acid Chloride
A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.
1 2D Structure

Palmitic Acid Chloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
hexadecanoic acid
2.1.2 InChI
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
2.1.3 InChI Key
IPCSVZSSVZVIGE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
2V16EO95H1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Hexadecanoic

2. Acid, Palmitic

3. Calcium Palmitate

4. Hexadecanoic Acid

5. Palmitate, Calcium

6. Palmitate, Sodium

7. Sodium Palmitate

2.3.2 Depositor-Supplied Synonyms

1. Hexadecanoic Acid

2. 57-10-3

3. Cetylic Acid

4. Palmitate

5. N-hexadecanoic Acid

6. Hexadecylic Acid

7. Hydrofol

8. N-hexadecoic Acid

9. 1-pentadecanecarboxylic Acid

10. Palmitinic Acid

11. Pentadecanecarboxylic Acid

12. C16 Fatty Acid

13. Hexadecanoate

14. Hexaectylic Acid

15. 1-hexyldecanoic Acid

16. Hexadecoic Acid

17. Industrene 4516

18. Emersol 140

19. Emersol 143

20. Hystrene 8016

21. Hystrene 9016

22. Palmitinsaeure

23. Palmitic Acid, Pure

24. Fema No. 2832

25. Palmitic Acid 95%

26. Kortacid 1698

27. Loxiol Ep 278

28. Palmitic Acid (natural)

29. Hydrofol Acid 1690

30. Prifac 2960

31. Fatty Acids, C14-18

32. Pristerene 4934

33. Edenor C16

34. Lunac P 95kc

35. C16:0

36. Lunac P 95

37. Lunac P 98

38. Cetyl Acid

39. Hsdb 5001

40. Ai3-01594

41. Nsc 5030

42. Pristerene-4934

43. Palmitic Acid (nf)

44. Glycon P-45

45. Chebi:15756

46. Nsc5030

47. Prifac-2960

48. Nsc-5030

49. Hexadecanoic Acid (9ci)

50. Mfcd00002747

51. Palmitic Acid (7ci,8ci)

52. Chembl82293

53. Ch3-[ch2]14-cooh

54. Imex C 1498

55. 2v16eo95h1

56. N-hexadecoate

57. Lmfa01010001

58. Pa 900

59. 67701-02-4

60. Fa 16:0

61. Fa 1695

62. 1-hexyldecanoate

63. Ncgc00164358-01

64. Dsstox_cid_1602

65. Pentadecanecarboxylate

66. Hexadecanoic Acid 10 Microg/ml In Acetonitrile

67. Dsstox_rid_76229

68. Dsstox_gsid_21602

69. C16h32o2

70. Plm

71. Palmic Acid

72. Hexadecanoate (n-c16:0)

73. Cas-57-10-3

74. Ccris 5443

75. Sr-01000944716

76. Einecs 200-312-9

77. Palmitic Acid [usan:nf]

78. Brn 0607489

79. Palmitoate

80. Hexadecoate

81. Palmitinate

82. Palmitic-acid

83. Palmitoic Acid

84. Hexadecanoicacid

85. Aethalic Acid

86. Unii-2v16eo95h1

87. Hexadecanoic Acid Palmitic Acid

88. 2hmb

89. 2hnx

90. Fatty Acid Pathway

91. Palmitic Acid_jeyam

92. Palmitic Acid, Fcc

93. Kortacid 1695

94. Palmitic Acid_ragusa

95. Univol U332

96. Prifrac 2960

97. Hexadecanoic Acid Anion

98. 3v2q

99. Palmitic Acid, >=99%

100. Bmse000590

101. Epitope Id:141181

102. Ec 200-312-9

103. Cetyl Acid [vandf]

104. Palmitic Acid [ii]

105. Palmitic Acid [mi]

106. Schembl6177

107. Palmitic Acid [dsc]

108. Palmitic Acid [fcc]

109. Palmitic Acid [fhfi]

110. Palmitic Acid [hsdb]

111. Palmitic Acid [inci]

112. Palmitic Acid [usan]

113. 4-02-00-01157 (beilstein Handbook Reference)

114. Fat

115. Wln: Qv15

116. P5585_sigma

117. Palmitic Acid [vandf]

118. Palmitic Acid [mart.]

119. Gtpl1055

120. Qspl 166

121. Palmitic Acid [usp-rs]

122. Palmitic Acid [who-dd]

123. (1(1)(3)c)hexadecanoic Acid

124. Dtxsid2021602

125. 1b56

126. Hms3649n08

127. Palmitic Acid, Analytical Standard

128. Palmitic Acid, Bioxtra, >=99%

129. Palmitic Acid, Grade Ii, ~95%

130. Hy-n0830

131. Palmitic Acid, Natural, 98%, Fg

132. Zinc6072466

133. Tox21_112105

134. Tox21_201671

135. Tox21_302966

136. Ac9381

137. Bbl011563

138. Bdbm50152850

139. Palmitic Acid [ep Monograph]

140. S3794

141. Stl146733

142. Edenor C 16-98-100

143. Palmitic Acid, >=95%, Fcc, Fg

144. Akos005720983

145. Tox21_112105_1

146. Ccg-267027

147. Cr-0047

148. Db03796

149. Palmitic Acid, For Synthesis, 98.0%

150. Surfaxin Component Palmitic Acid

151. Ncgc00164358-02

152. Ncgc00164358-03

153. Ncgc00256424-01

154. Ncgc00259220-01

155. Bp-27917

156. Lucinactant Component Palmitic Acid

157. Palmitic Acid, Purum, >=98.0% (gc)

158. Sy006518

159. Cs-0009861

160. Ft-0626965

161. Ft-0772579

162. N2456

163. P0002

164. P1145

165. Palmitic Acid, Saj First Grade, >=95.0%

166. A14813

167. C00249

168. D05341

169. Palmitic Acid, Vetec(tm) Reagent Grade, 98%

170. Palmitic Acid, >=98% Palmitic Acid Basis (gc)

171. A831313

172. Hexadecanoic Acid-13c16 (algal Source) (

173. Q209727

174. Sr-01000944716-1

175. Sr-01000944716-2

176. Ba71c79b-c9b1-451a-a5be-b480b5cc7d0c

177. Palmitic Acid (constituent Of Spirulina) [dsc]

178. F0001-1488

179. Z955123552

180. Palmitic Acid (constituent Of Flax Seed Oil) [dsc]

181. Palmitic Acid (constituent Of Saw Palmetto) [dsc]

182. Palmitic Acid, Certified Reference Material, Tracecert(r)

183. Palmitic Acid (constituent Of Borage Seed Oil) [dsc]

184. Palmitic Acid, European Pharmacopoeia (ep) Reference Standard

185. Palmitic Acid (constituent Of Evening Primrose Oil) [dsc]

186. Palmitic Acid, United States Pharmacopeia (usp) Reference Standard

187. Palmitic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

188. Sodium Palmitate, Palmitic Acid Sodium Salt, Sodium Hexadecanoate, Sodium Pentadecanecarboxylate, Hsdb 759

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 256.42 g/mol
Molecular Formula C16H32O2
XLogP36.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count14
Exact Mass256.240230259 g/mol
Monoisotopic Mass256.240230259 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count18
Formal Charge0
Complexity178
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/ Recent studies indicate that lipid metabolic changes affect the survival of multiple myeloma (MM) cells. Time-of-flight secondary ion mass spectrometry (TOF-SIMS), an imaging mass spectrometry technique, is used to visualize the subcellular distribution of biomolecules including lipids. We therefore applied this method to human clinical specimens to analyze the membrane fatty acid composition and determine candidate molecules for MM therapies. We isolated MM cells and normal plasma cells (PCs) from bone marrow aspirates of MM patients and healthy volunteers, respectively, and these separated cells were analyzed by TOF-SIMS. Multiple ions including fatty acids were detected and their ion counts were estimated. In MM cells, the mean intensity of palmitic acid was significantly lower than the mean intensity in PCs. In a cell death assay, palmitic acid reduced U266 cell viability dose-dependently at doses between 50 and 1000 uM. The percentage of apoptotic cells increased from 24 hr after palmitic acid administration. In contrast, palmitic acid had no effect on the viability of normal peripheral blood mononuclear cells (PBMCs). The results of this study indicated that palmitic acid is a potential candidate for novel therapeutic agents that specifically attack MM cells.

PMID:25846050 Nagata Y et al; Leuk Res 39 (6): 638-45 (2015)


/EXPL THER/ Approximately 80% of all new HIV-1 infections are acquired through sexual contact. Currently, there is no clinically approved microbicide, indicating a clear and urgent therapeutic need. We recently reported that palmitic acid (PA) is a novel and specific inhibitor of HIV-1 fusion and entry. Mechanistically, PA inhibits HIV-1 infection by binding to a novel pocket on the CD4 receptor and blocks efficient gp120-to-CD4 attachment. Here, we wanted to assess the ability of PA to inhibit HIV-1 infection in cervical tissue ex vivo model of human vagina, and determine its effect on Lactobacillus (L) species of probiotic vaginal flora. Our results show that treatment with 100-200 uM PA inhibited HIV-1 infection in cervical tissue by up to 50%, and this treatment was not toxic to the tissue or to L. crispatus and jensenii species of vaginal flora. In vitro, in a cell free system that is independent of in vivo cell associated CD4 receptor; we determined inhibition constant (Ki) to be ~2.53 uM. These results demonstrate utility of PA as a model molecule for further preclinical development of a safe and potent HIV-1 entry microbicide inhibitor.

PMID:21949756 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3176227 Lin X et al; PLoS One 6 (9): e24803 (2011)


/EXPL THER/ In a recent laboratory study, a fatty acid from seaweed reduced the ability of HIV-1 viruses to enter immune system cells. The study was reported in the journal AIDS Research and Human Retroviruses. Drug-resistant strains of HIV-1 have been on the rise, prompting the need for new therapeutic agents. Previous studies have demonstrated that products derived from natural sources have the potential to inhibit HIV-1 infection. In this laboratory study, researchers evaluated palmitic acid (from Sargassum fusiforme, a type of seaweed that grows off the coasts of Japan and China) to see if palmitic acid reduced the ability of HIV-1 viruses to enter CD4+ T-cells (white blood cells that are HIV-1's main target). Palmitic acid blocked both X4-tropic and R5-tropic viruses, the HIV viruses that use a particular receptor (X4 or R5) to enter a cell. In addition, the study's findings showed that palmitic acid protected other cells against HIV-1, reducing X4 infection in primary peripheral blood lymphocytes and R5 infection in primary macrophages (white blood cells). In all cases, the extent of the blocking effect depended on the concentration of palmitic acid, and most cells remained viable (alive) after treatment. The researchers noted that understanding the relationship between palmitic acid and CD4 may lead to development of an effective microbicide product for preventing sexual transmission of HIV.

NIH; National Center for Complimentary and Integrative Health; Laboratory Study Explores Anti-HIV Potential of Palmitic Acid (January, 2012); Available from, as of October 18, 2017: https://nccih.nih.gov/research/results/spotlight/121409.htm


/EXPL THER/ The high rate of HIV-1 mutation and the frequent sexual transmission highlight the need for novel therapeutic modalities with broad activity against both CXCR4 (X4) and CCR5 (R5)-tropic viruses. We investigated a large number of natural products, and from Sargassum fusiforme we isolated and identified palmitic acid (PA) as a natural small bioactive molecule with activity against HIV-1 infection. Treatment with 100 uM PA inhibited both X4 and R5 independent infection in the T cell line up to 70%. Treatment with 22 uM PA inhibited X4 infection in primary peripheral blood lymphocytes (PBL) up to 95% and 100 uM PA inhibited R5 infection in primary macrophages by over 90%. Inhibition of infection was concentration dependent, and cell viability for all treatments tested remained above 80%, similar to treatment with 10(-6)M nucleoside analogue 2',3'-dideoxycytidine (ddC). Micromolar PA concentrations also inhibited cell-to-cell fusion and specific virus-to-cell fusion up to 62%. PA treatment did not result in internalization of the cell surface CD4 receptor or lipid raft disruption, and it did not inhibit intracellular virus replication. PA directly inhibited gp120-CD4 complex formation in a dose-dependent manner. We used fluorescence spectroscopy to determine that PA binds to the CD4 receptor with K(d) approximately 1.5 +/- 0.2 uM, and we used one-dimensional saturation transfer difference NMR (STD-NMR) to determined that the PA binding epitope for CD4 consists of the hydrophobic methyl and methelene groups located away from the PA carboxyl terminal, which blocks efficient gp120-CD4 attachment. These findings introduce a novel class of antiviral compound that binds directly to the CD4 receptor, blocking HIV-1 entry and infection. Understanding the structure-affinity relationship (SAR) between PA and CD4 should lead to the development of PA analogs with greater potency against HIV-1 entry.

PMID:20001317 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2828184 Lee DY et al; AIDS Res Hum Retroviruses 25 (12): 1231-41 (2009)


5 Pharmacology and Biochemistry
5.1 Pharmacology

Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 Absorption, Distribution and Excretion

Added (14)C-labeled palmitate was more significantly incorporated into lipid fractions of muscle fibers from fetal and neonatal monkeys than those from adults. /Palmitate/

Beatty CH, Bocek RM; Amer J Physiol 219 (5): 1311 (1970)


More (14)C-labeled palmitate was incorporated into lipid by adipose tissue of genetically obese rats than by controls. /Palmitate/

PMID:5506400 Bray et al; Metab Clin Exp 19 (10): 839 (1970)


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, or 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. 341 J Am Col Toxicol 6 (3): 321-401 (1987). Available from, as of November 22, 2017: https://www.cir-safety.org/ingredients


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

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. 341 J Am Col Toxicol 6 (3): 321-401 (1987). Available from, as of November 22, 2017: https://www.cir-safety.org/ingredients


For more Absorption, Distribution and Excretion (Complete) data for Palmitic acid (7 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Palmitic acid is rapidly metabolized, primarily by beta-oxidation. In addition to oxidative breakdown, palmitic acid undergoes a variety of conversion reactions in the liver and intestinal mucosa to stearic, oleic, palmitoleic, and myristic acids. omega-Oxidation, prior to beta-oxidation, may account for 5 to 10% of the hepatic metabolism of palmitic acid in the starved rat. After oxidation or conversion to other long-chain fatty acids or phospholipids, the carbon skeleton of palmitic acid is stored in the form of esterified cholesterol or returned to the plasma, depending upon the nutritional state of the organism.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 743


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. /Fatty 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. 341 J Am Col Toxicol 6 (3): 321-401 (1987). Available from, as of November 22, 2017: https://www.cir-safety.org/ingredients


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). /fatty 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. 341 J Am Col Toxicol 6 (3): 321-401 (1987). November 22, 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. /Fatty 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. 341 J Am Col Toxicol 6 (3): 321-401 (1987). Available from, as of November 22, 2017: https://www.cir-safety.org/ingredients


Palmitic acid has known human metabolites that include 15-Hydroxy-hexadecanoic acid.

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


5.5 Mechanism of Action

... Excessive palmitoylcarnitine formation and exhausted L-carnitine stores leading to energy depletion, attenuated acetylcholine synthesis and oxidative stress to be main mechanisms behind PA-induced neuronal loss.High PA exposure is suggested to be a factor in causing diabetic neuropathy and gastrointestinal dysregulation.

PMID:24312551 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3849255 Voss U et al; PLoS One 8 (12): e81413 (2013)


... First phase insulin release response was lost in these islets. FFAs slightly increased the insulin output of normal fresh pancreas beta-cells. However, chronic exposure to FFAs resulted in loss of first phase insulin release and blunted insulin secretion response to various levels of D-glucose stimulation.

PMID:12688627 Ayvaz G et al; Diabetes Metab 28 (6 Pt 2): 3S7-12 (2002)


API Reference Price

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05-Jan-2021
31-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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