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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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Also known as: Trioctanoin, 538-23-8, Tricaprilin, Glycerol trioctanoate, Glycerol tricaprylate, Rato

Molecular Formula

C₂₇H₅₀O₆

Molecular Weight

470.7 g/mol

InChI Key

VLPFTAMPNXLGLX-UHFFFAOYSA-N

FDA UNII

6P92858988

Glycerol tricaprylate is a metabolite found in the aging mouse brain.

1 2D Structure

Tricaprylin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,3-di(octanoyloxy)propyl octanoate

2.1.2 InChI

InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3

2.1.3 InChI Key

VLPFTAMPNXLGLX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)OC(=O)CCCCCCC

2.2 Other Identifiers

2.2.1 UNII

6P92858988

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-ethylhexanoic Acid, 1,2,3-propanetriyl Ester

2. Glycerol Tricaprylate

3. Glycerol Trioctanoate

4. Glyceryl Tricaprylate

5. Glyceryl Trioctanoate

6. Octanoic Acid, 1,2,3- Propanetriyl Ester

7. Panasate 800

8. Triethylhexanoin

9. Trioctanoin

10. Trioctanoylglyceride

2.3.2 Depositor-Supplied Synonyms

1. Trioctanoin

2. 538-23-8

3. Tricaprilin

4. Glycerol Trioctanoate

5. Glycerol Tricaprylate

6. Rato

7. Caprylin

8. Glyceryl Trioctanoate

9. Trioctanoylglycerol

10. Tricaprylic Glyceride

11. Maceight

12. Propane-1,2,3-triyl Trioctanoate

13. Glyceryl Tricaprylate

14. Caprylic Acid Triglyceride

15. Caprylic Triglyceride

16. Octanoin, Tri-

17. Axona

18. 1,2,3-tri-n-octanoylglycerol

19. Trioctanoin Oil

20. Octanoic Acid Triglyceride

21. Tricaprylyl Glycerin

22. 2,3-di(octanoyloxy)propyl Octanoate

23. Octanoic Acid, 1,2,3-propanetriyl Ester

24. Panacete 800

25. Glycerol Tri-n-octanoate

26. Miglyol 808

27. Nsc 4059

28. Tricapryloylglycerol

29. Tricaprylyl Glycerol

30. Glycerin Tricaprylate

31. Ac-1202

32. 1,2,3-propanetriol Trioctanoate

33. Cer-0001

34. Nsc-4059

35. Caprylic Acid, 1,2,3-propanetriyl Ester

36. Octanoic Acid, 1,1',1''-(1,2,3-propanetriyl) Ester

37. Trioctanoin;glyceryl Trioctanoate

38. Chebi:76978

39. Ac-1204

40. Ncgc00091285-01

41. Dsstox_cid_1375

42. Dsstox_rid_76119

43. Dsstox_gsid_21375

44. Tg(8:0/8:0/8:0)

45. Tricaprilin [jan]

46. 6p92858988

47. Sefsol 800

48. Caprylidene

49. Tri-n-octanoin

50. Trioctanoylglyceride

51. Cas-538-23-8

52. Einecs 208-686-5

53. 1,2,3-tricapryloylglycerol

54. Brn 1717202

55. Tricaprylm

56. Tri-octanoin

57. Tri-n-caprylin

58. Hsdb 7829

59. Emalex Ktg

60. Glycerol Trioctanoin

61. Mfcd00036236

62. Unii-6p92858988

63. Sefsol 810

64. Captex 8000

65. Axona [vandf]

66. Glycerol Trioctanoic Acid

67. Tricaprylin [ii]

68. Tricaprilin [inn]

69. Tricaprilin (jan/usan)

70. Tricaprilin [usan:jan]

71. Tricaprilin [hsdb]

72. Tricaprilin [usan]

73. Tricaprylin [inci]

74. 1,2,3-trioctanoylglycerol

75. Tricaprylin [mart.]

76. Schembl61958

77. Tricaprilin [who-dd]

78. 4-02-00-00991 (beilstein Handbook Reference)

79. Mls002454452

80. Glyceryl Trioctanoate, >=99%

81. Chembl1406148

82. Dtxsid6021375

83. Nsc4059

84. Propane-1,2,3-triyltrioctanoate

85. Glyceryl Tricaprylate [nf]

86. Hms3039h17

87. Hy-b1804

88. Zinc8214697

89. Tox21_111110

90. Tox21_201480

91. Tox21_302762

92. Caprylic Triglyceride [vandf]

93. S6342

94. Who 10584

95. Octanoic Acid,2,3-propanetriyl Ester

96. Akos015899778

97. Glyceryl Tricaprylate [usp-rs]

98. Tox21_111110_1

99. Ccg-214786

100. Db12176

101. 2,3-bis(octanoyloxy)propyl Octanoate #

102. Ncgc00091285-02

103. Ncgc00091285-03

104. Ncgc00256431-01

105. Ncgc00259031-01

106. As-75522

107. Smr001372028

108. Db-071745

109. Cs-0013846

110. Ft-0720359

111. T0365

112. D01587

113. Glyceryl Trioctanoate, Technical, >=90% (gc)

114. Sr-01000854712

115. Q2747851

116. Sr-01000854712-2

117. 3-(2-chlorophenyl)-1-(3,4-dichlorophenyl)-1-hydroxyurea

118. Tricaprylin, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₅₀O₆
Molecular Weight	470.7 g/mol
XLogP3	8.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	26
Exact Mass	470.36073931 g/mol
Monoisotopic Mass	470.36073931 g/mol
Topological Polar Surface Area	78.9 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	461
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

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Excipients

Usually inert substances added to a prescription in order to provide suitable consistency to the dosage form. These include binders, matrix, base or diluent in pills, tablets, creams, salves, etc. (See all compounds classified as Excipients.)

4.2 Absorption, Distribution and Excretion

In the small intestine, most triglycerides are split into monoglycerides, free fatty acids, and glycerol, which are absorbed by the intestinal mucosa. Within the epithelial cells, resynthesized triglycerides collect into globules along with cholesterol and phospholipids and are encased in a protein coat as chylomicrons. Chylomicrons are transported in the lymph to the thoracic duct and eventually to the venous system. The chylomicrons are removed from the blood as they pass through the capillaries of adipose tissue. Fat is stored in adipose cells until it is transported to other tissues as free fatty acids which are used for cellular energy or incorporated into cell membranes. When 14C-labeled long-chain triglycerides are administered intravenously, 25% to 30% of the radiolabel is found in the liver within 30 to 60 minutes, with less than 5% remaining after 24 hours. Lesser amounts of radiolabel are found in the spleen and lungs. After 24 hours, nearly 50% of the radiolabel has been expired in carbon dioxide, with 1% of the carbon label remaining in the brown fat. The concentration of radioactivity in the epididymal fat is less than half that of the brown fat.

Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Trilaurin, Triarachidin, Tribehenin, Tricaprin, Tricaprylin, Trierucin, Triheptanoin, Triheptylundecanoin, Triisononanoin, Triisopalmitin, Triisostearin, Trilinolein, Trimyristin, Trioctanoin, Triolein, Tripalmitin, Tripalmitolein, Triricinolein, Tristearin, Triundecanoin, Glyceryl Triacetyl Hydroxystearate, Glyceryl Triacetyl Ricinoleate, and Glyceryl Stearate; Scientific Regulatory Reference CD-ROM (2006). Cosmetic, Toiletry, and Fragrance Association, Washington D.C.

After absorption, long- chain saturated fatty acids are transported mainly via the intestinal lymph as triglycerides. Fatty acids with 10 or less carbon atoms are transported mainly from the intestine via the portal blood vessels. There are also data indicating that unsaturated long-chain fatty acids are absorbed mainly via the lymph vessels.

The skin penetration enhancement of drugs by tricaprylin has been demonstrated in vivo using Wistar rats and in vitro using hairless female mice. ... The drug permeation ratio in the presence of triglycerides increased in the following order: Tricaprylin (C8) > Triolein (CI8) > Tributyrin (C4) > Triacetin (C2).

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