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1. Acid, Myristic
2. Acid, Tetradecanoic
3. Myristate
4. Tetradecanoic Acid
1. Tetradecanoic Acid
2. 544-63-8
3. N-tetradecanoic Acid
4. N-tetradecan-1-oic Acid
5. Crodacid
6. N-tetradecoic Acid
7. 1-tridecanecarboxylic Acid
8. Myristate
9. Tetradecoic Acid
10. Hydrofol Acid 1495
11. Univol U 316s
12. Emery 655
13. Myristinsaeure
14. Hystrene 9014
15. Neo-fat 14
16. C14 Fatty Acid
17. Fema No. 2764
18. Myristic Acid, Pure
19. N-myristic Acid
20. Myristic Acid (natural)
21. Tetradecanoate
22. Acide Tetradecanoique
23. Nsc 5028
24. Ccris 4724
25. Ch3-[ch2]12-cooh
26. Hsdb 5686
27. C14:0
28. Philacid 1400
29. Chebi:28875
30. Ai3-15381
31. Prifac 2942
32. Nsc-5028
33. 1-tetradecanecarboxylic Acid
34. Philacid-1400
35. Prifrac-2942
36. 0i3v7s25aw
37. Chembl111077
38. Nsc5028
39. Dsstox_cid_1666
40. N-tetradecan-1-oate
41. Dsstox_rid_76274
42. Dsstox_gsid_21666
43. 32112-52-0
44. Cas-544-63-8
45. Myristic Acid [nf]
46. Einecs 208-875-2
47. Brn 0508624
48. Myristoate
49. Unii-0i3v7s25aw
50. Myristoic Acid
51. N-tetradecanoate
52. Tetradecanoicacid
53. 3usx
54. Myristic Acid Pure
55. Myristic Acid Flake
56. Mfcd00002744
57. Hystrene 9514
58. Edenor C 14
59. Myristic Acid 655
60. 1-tridecanecarboxylate
61. Magnesiumarsenate
62. Myristic Acid, 95%
63. Myristic Acid, Natural
64. Tridecanecarboxylic Acid
65. Myristic Acid (8ci)
66. Myristic Acid, Reagent
67. 3v2n
68. 3w9k
69. Myristic Acid, Puriss.
70. Tetradecanoic Acid (9ci)
71. Bmse000737
72. Epitope Id:176772
73. Myristic Acid [ii]
74. Myristic Acid [mi]
75. Schembl6374
76. Myristic Acid [fcc]
77. Myristic Acid-[14-13c]
78. Myristic Acid [fhfi]
79. Myristic Acid [hsdb]
80. Myristic Acid [inci]
81. 4-02-00-01126 (beilstein Handbook Reference)
82. Mls002152942
83. Wln: Qv13
84. Tetradecanoic (myristic) Acid
85. Myristic Acid [mart.]
86. Gtpl2806
87. Myristic Acid [usp-rs]
88. Dtxsid6021666
89. Hms3039e15
90. Hms3648o20
91. Myristic Acid, Analytical Standard
92. Hy-n2041
93. Zinc1530417
94. Einecs 250-924-5
95. Myristic Acid, >=98.0% (gc)
96. Tox21_201852
97. Tox21_302781
98. Bdbm50147581
99. Lmfa01010014
100. S5617
101. Stl185697
102. Myristic Acid, >=95%, Fcc, Fg
103. Myristic Acid, Sigma Grade, >=99%
104. Akos009156714
105. Ccg-266785
106. Db08231
107. Ds-3833
108. Fa 14:0
109. Nsc 122834
110. Ncgc00091068-01
111. Ncgc00091068-02
112. Ncgc00091068-03
113. Ncgc00256547-01
114. Ncgc00259401-01
115. Ac-34674
116. Bp-27915
117. Smr001224536
118. Cs-0018531
119. Ft-0602832
120. Ft-0770860
121. M0476
122. En300-78099
123. C06424
124. Myristic Acid, Vetec(tm) Reagent Grade, 98%
125. Q422658
126. Sr-01000854525
127. Sr-01000854525-3
128. W-109088
129. F8889-5016
130. Edae4876-c383-4ad4-a419-10c0550931db
131. Myristic Acid (constituent Of Saw Palmetto) [dsc]
132. Myristic Acid, United States Pharmacopeia (usp) Reference Standard
133. Tetradecanoic Acid; 1-tridecanecarboxylic Acid; N-tetradecanoic Acid
134. Myristic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
| Molecular Weight | 228.37 g/mol |
|---|---|
| Molecular Formula | C14H28O2 |
| XLogP3 | 5.3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 12 |
| Exact Mass | 228.208930132 g/mol |
| Monoisotopic Mass | 228.208930132 g/mol |
| Topological Polar Surface Area | 37.3 Ų |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Complexity | 155 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
/EXPL THER/ The antitumor activity of some fatty acids was studied in vivo using Ehrlich ascites and solid carcinomas implanted into Swiss albino mice of Strain ddY. Suspensions of the fatty acids in Tween 80 and distilled water were admin 24 hr after tumor implantation and were continued for 5 consecutive days. Doses of 8 mg/mouse/day of myristic aicd were effective inhibitors against Ehrlich ascites tumor, more than doubling the survival time of treated versus control mice.
European Chemicals Bureau; IUCLID Dataset, Myristic acid, pure (CAS #544-63-8) p.25 (2000 CD-ROM edition). Available from, as of January 24, 2008: https://esis.jrc.ec.europa.eu/
EXPTL THER: MYRISTIC ACID WAS AMONG 11 FATTY ACIDS TESTED AGAINST EHRLICH ASCITES CARCINOMA. EACH AGENT WAS ADMIN TO MICE BY INTRAPERITONEAL INJECTION AT THE DOSE OF 400 MG/KG/DAY 5 TIMES & THE EFFECT WAS EVALUATED WITH TOTAL PACKED CELL VOLUME RATIO ON THE 7TH DAY AFTER THE TUMOR IMPLANTATION. MYRISTIC ACID WAS HIGHLY EFFECTIVE AGAINST THE TUMOR.
PMID:1021244 NISHIKAWA Y ET AL; CHEM PHARM BULL 24 (3): 387 (1976)
/EXP THER/ Liposomes consisting of dicetyl-phosphate, cholesterol, lecithin and stearic or myristic or oleic acid, exert a protective effect for mice against experimental infection by Salmonella typhimurium, and delay both the onset and mortality B16 melanoma in these animals. Liposomes labelled with 3H-myristic acid were used as probes in the spleen and liver. ... the treatment schedule rather than route of administration of liposomes, is important. The results show that in order to induce protection, preventive treatment must start at least three days before. Longer treatments do not increase the degree of protection, and treatments started at the same time as, or following experimental infection or tumor transplantation, have no effect.
PMID:8041229 Galdiero F et al; Life Sci 55 (7): 499-509 (1994)
/EXPTL THER/ ... The purpose of this study was to examine the effect of moderate intakes of myristic acid (MA) associated with recommended intake of alpha-linolenic acid (ALA) on lecithin-cholesterol acyltransferase (LCAT) activity in humans. Two experimental diets were tested for 3 months each. Diet 1-MA 1.2% of total energy (TE) and ALA 0.9% TE, diet 2-MA 1.8% and ALA 0.9% TE; a control diet (MA 1.2% and ALA 0.4% TE) was given 3 months before diet 1 and diet 2. The endogenous activity of LCAT was determined at completion of each diet. Compared with the control diet (13.2 +/- 3.1 umol CE/(L x h)), LCAT activity increased significantly (P < 0.001) with diet 1 (24.2 +/- 3.6 umol CE/(L x h)) and diet 2 (33.3 +/- 7.4 micromol CE/(L x h)); the increase observed with diet 2 was significantly (P < 0.001) greater than that due to diet 1. These results suggest that ALA (from rapeseed oil, mainly in sn-2 position) and MA (from dairy fat, mainly in sn-2 position) favor LCAT activity, by respective increases of 83 and 38%. When they are supplied together, a complementary effect was observed (average increase of 152%). Moreover, these observations were associated with a decrease of the ratio of total to HDL-cholesterol. In conclusion, /the/results suggest that moderate supply of MA (1.8% TE) associated with the recommended intake of ALA (0.9% TE) contributes to improve LCAT activity.
PMID:17564735 Vayse-Boue C et al; Lipids 42 (8): 717-22 (2007)
For more Therapeutic Uses (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.
IN NORMAL RATS, HIGHER RADIOACTIVITY WAS FOUND IN HEART, LIVER, SPLEEN & ADRENALS 2 HR AFTER ADMIN OF PALMITIC ACID THAN AFTER ADMIN OF MYRISTIC ACID. IN GRANULOMA POUCH-BEARING RATS, RADIOACTIVITY SHOWED HIGHER DISTRIBUTION IN ADRENALS & POUCH EXUDATE 2 HR AFTER PALMITIC ACID ADMIN, COMPARED TO THOSE GIVEN MYRISTIC ACID. RADIOACTIVITY IN THE POUCH WALL WAS GREATER IN RATS GIVEN MYRISTIC ACID.
PMID:660439 MIMURA T ET AL; YAKUGAKU ZASSHI 98 (5): 660 (1978)
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. 15, June 2005.
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 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.
IN RATS FED COCONUT OIL, MYRISTIC ACID WAS ONE OF THE PRINCIPAL FATTY ACIDS PRESENT IN HEPATIC AND ADIPOSE TISSUE TRIGLYCERIDES. ETHANOL INCR THE PROPORTIONS OF MYRISTIC ACID.
PMID:5362513 MENDENHALL CL ET AL; BIOCHEM BIOPHYS ACTA 187 (4): 510 (1969)
IN ADDITION TO METABOLISM BY BETA-OXIDATION, MYRISTIC ACID HAS BEEN SHOWN TO UNDERGO CHAIN ELONGATION TO PALMITIC & STEARIC ACIDS, DESATURATION TO MYRISTOLEIC ACID & INCORPORATION INTO HEPATIC NEUTRAL LIPIDS (& TO A LESSER EXTENT, PHOSPHOLIPIDS).
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4931
THE CONVERSION OF SATURATED FATTY ACIDS TO MONOUNSATURATED FATTY ACIDS BY THE 9000 X G SUPERNATANT RAT LIVER HOMOGENATE WAS LESS FOR MYRISTIC ACID THAN FOR PALMITIC ACID. THESE FATTY ACIDS PRODUCED ONLY DELTA9-MONOENOIC ACIDS OF THE SAME CHAIN LENGTH.
NAKAGAWA M, UCHIYAMA M; J BIOCHEM (TOKYO) 66 (1): 95 (1969)
MYRISTATE INCORPORATED FROM (14)C-LABELED ACETATE WAS PREFERENTIALLY ESTERIFIED INTO TRIGLYCERIDE, WHEREAS THE LABELED STEARATE WAS CONVERTED INTO PHOSPHOLIPIDS IN THE ISOLATED RAT ADIPOSE CELLS.
PMID:4330331 WINAND J ET AL; BIOCHIM BIOPHYS ACTA 239 (2): 142 (1971)
For more Metabolism/Metabolites (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.
Tetradecanoic acid has known human metabolites that include 13-Hydroxytetradecanoic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
... The specific hypothesis tested was that free fatty acid association with CD36, a class B scavenger receptor, induces the activation of endothelial nitric-oxide synthase (eNOS). A human microvascular endothelial cell line and a transfected Chinese hamster ovary cell system were used to determine which free fatty acids stimulate eNOS. Surprisingly, only myristic acid, and to a lesser extent palmitic acid, stimulated eNOS. The stimulation of eNOS was dose- and time-dependent. Competition experiments with other free fatty acids and with a CD36-blocking antibody demonstrated that the effects of myristic acid on eNOS required association with CD36. Further mechanistic studies demonstrated that the effects of myristic acid on eNOS function were not dependent on PI 3-kinase, Akt kinase, or calcium. Pharmacological studies and dominant negative constructs were used to demonstrate that myristic acid/CD36 stimulation of eNOS activity was dependent on the activation of AMP kinase. These data demonstrate an unexpected link among myristic acid, CD36, AMP kinase, and eNOS activity.
PMID:15970594 Zhu W, Smart EJ; J Biol Chem 280 (33): 29543-50 (2005)
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