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Chemistry

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Also known as: Tetradecanoic acid, 544-63-8, N-tetradecanoic acid, N-tetradecan-1-oic acid, Crodacid, N-tetradecoic acid
Molecular Formula
C14H28O2
Molecular Weight
228.37  g/mol
InChI Key
TUNFSRHWOTWDNC-UHFFFAOYSA-N
FDA UNII
0I3V7S25AW

Myristic Acid Chloride
A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed)
1 2D Structure

Myristic Acid Chloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
tetradecanoic acid
2.1.2 InChI
InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
2.1.3 InChI Key
TUNFSRHWOTWDNC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
0I3V7S25AW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Myristic

2. Acid, Tetradecanoic

3. Myristate

4. Tetradecanoic Acid

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 228.37 g/mol
Molecular Formula C14H28O2
XLogP35.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count12
Exact Mass228.208930132 g/mol
Monoisotopic Mass228.208930132 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count16
Formal Charge0
Complexity155
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/ 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.


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

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.


5.2 Metabolism/Metabolites

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


5.3 Mechanism of Action

... 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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05-Jan-2022
30-Jun-2025
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Looking for 544-63-8 / Myristic Acid Chloride API manufacturers, exporters & distributors?

Myristic Acid Chloride manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Myristic Acid Chloride API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Myristic Acid Chloride manufacturer or Myristic Acid Chloride supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Myristic Acid Chloride manufacturer or Myristic Acid Chloride supplier.

PharmaCompass also assists you with knowing the Myristic Acid Chloride API Price utilized in the formulation of products. Myristic Acid Chloride API Price is not always fixed or binding as the Myristic Acid Chloride Price is obtained through a variety of data sources. The Myristic Acid Chloride Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Myristic Acid Chloride

Synonyms

Tetradecanoic acid, 544-63-8, N-tetradecanoic acid, N-tetradecan-1-oic acid, Crodacid, N-tetradecoic acid

Cas Number

544-63-8

Unique Ingredient Identifier (UNII)

0I3V7S25AW

About Myristic Acid Chloride

A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed)

Tetradecanoic Acid Manufacturers

A Tetradecanoic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Tetradecanoic Acid, including repackagers and relabelers. The FDA regulates Tetradecanoic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Tetradecanoic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Tetradecanoic Acid manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Tetradecanoic Acid Suppliers

A Tetradecanoic Acid supplier is an individual or a company that provides Tetradecanoic Acid active pharmaceutical ingredient (API) or Tetradecanoic Acid finished formulations upon request. The Tetradecanoic Acid suppliers may include Tetradecanoic Acid API manufacturers, exporters, distributors and traders.

click here to find a list of Tetradecanoic Acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Tetradecanoic Acid USDMF

A Tetradecanoic Acid DMF (Drug Master File) is a document detailing the whole manufacturing process of Tetradecanoic Acid active pharmaceutical ingredient (API) in detail. Different forms of Tetradecanoic Acid DMFs exist exist since differing nations have different regulations, such as Tetradecanoic Acid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Tetradecanoic Acid DMF submitted to regulatory agencies in the US is known as a USDMF. Tetradecanoic Acid USDMF includes data on Tetradecanoic Acid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Tetradecanoic Acid USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Tetradecanoic Acid suppliers with USDMF on PharmaCompass.

Tetradecanoic Acid GMP

Tetradecanoic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Tetradecanoic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Tetradecanoic Acid GMP manufacturer or Tetradecanoic Acid GMP API supplier for your needs.

Tetradecanoic Acid CoA

A Tetradecanoic Acid CoA (Certificate of Analysis) is a formal document that attests to Tetradecanoic Acid's compliance with Tetradecanoic Acid specifications and serves as a tool for batch-level quality control.

Tetradecanoic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Tetradecanoic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Tetradecanoic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Tetradecanoic Acid EP), Tetradecanoic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Tetradecanoic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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