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Chemistry

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Also known as: Alpha-linolenic acid, 463-40-1, Linolenate, (9z,12z,15z)-octadeca-9,12,15-trienoic acid, A-linolenic acid, Cis,cis,cis-9,12,15-octadecatrienoic acid

Molecular Formula

C₁₈H₃₀O₂

Molecular Weight

278.4 g/mol

InChI Key

DTOSIQBPPRVQHS-PDBXOOCHSA-N

FDA UNII

0RBV727H71

A fatty acid that is found in plants and involved in the formation of prostaglandins.

1 2D Structure

Alpha-Linolenic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

2.1.2 InChI

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-

2.1.3 InChI Key

DTOSIQBPPRVQHS-PDBXOOCHSA-N

2.1.4 Canonical SMILES

CCC=CCC=CCC=CCCCCCCCC(=O)O

2.1.5 Isomeric SMILES

CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

0RBV727H71

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alpha Linolenic Acid

2. Alpha Linolenic Acid, Ammonium Salt

3. Alpha Linolenic Acid, Calcium Salt

4. Alpha Linolenic Acid, Lithium Salt

5. Alpha Linolenic Acid, Magnesium Salt

6. Alpha Linolenic Acid, Potassium Salt

7. Alpha Linolenic Acid, Sodium Salt

8. Alpha Linolenic Acid, Zinc Salt

9. Alpha-linolenic Acid

10. Alpha-linolenic Acid, (e,e,e)-isomer

11. Alpha-linolenic Acid, (e,e,z)-isomer

12. Alpha-linolenic Acid, (e,z,e)-isomer

13. Alpha-linolenic Acid, (e,z,z)-isomer

14. Alpha-linolenic Acid, (z,e,e)-isomer

15. Alpha-linolenic Acid, (z,e,z)-isomer

16. Alpha-linolenic Acid, (z,z,e)-isomer

17. Alpha-linolenic Acid, Ammonium Salt

18. Alpha-linolenic Acid, Calcium Salt

19. Alpha-linolenic Acid, Lithium Salt

20. Alpha-linolenic Acid, Magnesium Salt

21. Alpha-linolenic Acid, Potassium Salt

22. Alpha-linolenic Acid, Sodium Salt

23. Alpha-linolenic Acid, Tin(2+) Salt

24. Alpha-linolenic Acid, Zinc Salt

25. Linolenate

2.3.2 Depositor-Supplied Synonyms

1. Alpha-linolenic Acid

2. 463-40-1

3. Linolenate

4. (9z,12z,15z)-octadeca-9,12,15-trienoic Acid

5. A-linolenic Acid

6. Cis,cis,cis-9,12,15-octadecatrienoic Acid

7. All-cis-9,12,15-octadecatrienoic Acid

8. Alpha-lnn

9. (z,z,z)-9,12,15-octadecatrienoic Acid

10. 9-cis,12-cis,15-cis-octadecatrienoic Acid

11. 9,12,15-octadecatrienoic Acid, (z,z,z)-

12. (9,12,15)-linolenic Acid

13. .alpha.-linolenic Acid

14. (9z,12z,15z)-octadecatrienoic Acid

15. 9z,12z,15z-octadecatrienoic Acid

16. Industrene 120

17. Ccris 656

18. 9,12,15-octadecatrienoic Acid

19. Chembl8739

20. Cis-delta9,12,15-octadecatrienoic Acid

21. Ai3-23986

22. Cis-delta(9,12,15)-octadecatrienoic Acid

23. (z,z,z)-octadeca-9,12,15-trienoic Acid

24. 68424-45-3

25. Chebi:27432

26. 0rbv727h71

27. Nsc-2042

28. Linolenic Acid (18:3 N-3)

29. Fa 18:3

30. 9,12,15-all-cis-octadecatrienoic Acid

31. Ncgc00091058-04

32. Linolenic Acid 10 Microg/ml In Methanol

33. Cis-9,cis-12,cis-15-octadecatrienoic Acid

34. Dsstox_cid_5506

35. Cis-9, Cis-12, Cis-15-octadecatrienoic Acid

36. Dsstox_rid_77815

37. Dsstox_gsid_25506

38. 29857-63-4

39. 9,12,15-octadecatrienoic Acid, (9z,12z,15z)-, Dimer

40. 9,12,15-octadecatrienoic Acid, (9z,12z,15z)-

41. Alpha-la

42. Cas-463-40-1

43. Smr000857336

44. C18:3n-3,6,9

45. Alpha Linolenic Acid

46. (9z,12z,15z)-octadecatrienoate

47. Linolenic Acid, Crude

48. Linseed Oil Fatty Acids

49. Linolenic Acid (8ci)

50. Cis,cis,cis-9,12,15-octadecatrienoate

51. Unii-0rbv727h71

52. A-linolenate

53. Cis-9,12,15-octadecatrienoic Acid

54. Cis,cis-9,12,15-octadecatrienoic Acid

55. (9z,12z,15z)-9,12,15-octadecatrienoic Acid

56. Nsc 2042

57. Alpha-linolenic-acid

58. Einecs 207-334-8

59. Mfcd00065720

60. Alpha -linolenic Acid

61. C18:3

62. Linolenic Acid, >=99%

63. Alpha-linolenic Acid Tech.

64. Linolenic Acid [mi]

65. (9z,12z,15z)octadeca-9,12,15-trienoic Acid

66. Schembl15282

67. 9,12,15-octadecatrienoate

68. Bspbio_001376

69. Mls001336029

70. Mls001336030

71. Mls002454413

72. Linolenic Acid [inci]

73. Linolenic Acid [vandf]

74. Bml3-b05

75. Gtpl1049

76. Linolenic Acid [mart.]

77. Linolenic Acid, ~70% (gc)

78. Dtxsid7025506

79. Linolenic Acid [who-dd]

80. Cid_5280934

81. Cis-9,12,15-octadecatrienoate

82. Nsc2042

83. Fa005

84. Hms1361e18

85. Hms1791e18

86. Hms1989e18

87. Hms2233c13

88. Hms3402e18

89. Hms3649h05

90. Linolenic Acid, Analytical Standard

91. Cmc_7371

92. Hy-n0728

93. Zinc3802189

94. All-cis-9,15-octadecatrienoic Acid

95. Tox21_111071

96. Tox21_201727

97. Tox21_303322

98. All-cis-9,12,15-octadecatrienoate

99. Bdbm50240347

100. Lmfa01030152

101. Octadeca-9z,12z,15z-trienoic Acid

102. Akos016008598

103. Db00132

104. (z,z,z)-9,12,15-octadecatrienoate

105. 9-cis,12-cis,15-cis-octadecatrienoate

106. Idi1_033846

107. Ncgc00091058-01

108. Ncgc00091058-02

109. Ncgc00091058-05

110. Ncgc00091058-06

111. Ncgc00091058-07

112. Ncgc00091058-08

113. Ncgc00091058-09

114. Ncgc00091058-10

115. Ncgc00257192-01

116. Ncgc00259276-01

117. (all-z)-9,12,15-octadecatrienoic Acid

118. 9,15-octadecatrienoic Acid, (z,z,z)-

119. Ac-33768

120. As-57338

121. Fema No. 3380, Linolenic Acid-

122. Alpha-linolenic Acid (c18:3 N3)

123. 9(z),12(z),15(z)-octadecatrienoic Acid

124. Cs-0009741

125. L0050

126. C18:3 (n-3)

127. Cis,cis,cis-octadeca-9,12,15-trienoic Acid

128. Fa(18:3(9z,12z,15z))

129. Octadecatrienoic Acid, 9,12,15-(z,z,z)-

130. C06427

131. Linolenic Acid, Vetec(tm) Reagent Grade, 98%

132. Vitamin F Component Alpha Linolenic Acid

133. L000707

134. Q256502

135. Sr-01000838327

136. Sr-01000838327-2

137. 18:3(n-3)

138. 2dcd0473-e5cc-47bb-a0a4-95899aff6c4b

139. Brd-k33396764-001-02-0

140. 9,12,15-octadecatrienoic Acid, (9z,12z,15z)- (9ci)

141. Linolenic Acid (constituent Of Saw Palmetto) [dsc]

142. .alpha.-linolenic Acid (constituent Of Flax Seed Oil) [dsc]

143. Linolenic Acid (constituent Of Evening Primrose Oil) [dsc]

144. .alpha.-linolenic Acid (c18:3) (constituent Of Krill Oil) [dsc]

145. Alpha-linolenic Acid, 1.0 Mg/ml In Ethanol, Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₀O₂
Molecular Weight	278.4 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	13
Exact Mass	278.224580195 g/mol
Monoisotopic Mass	278.224580195 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	301
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For nutritional supplementation and for treating dietary shortage or imbalance.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.

5.2 Mechanism of Action

Alpha Linolenic Acid or ALA is considered an essential fatty acid because it is required for human health, but cannot be synthesized by humans. It is in fact a plant-derived fatty acid. Humans can synthesize other omega-3 fatty acids from ALA, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-inflammatory and anti-atherogenic properties. ALA metabolites may also inhibit the production of the pro-inflammatory eicosanoids, prostaglandin E2 (PGE2) and leukotriene B4 (LTB4), as well as the pro-inflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta). Omega-3 fatty acids like ALA and its byproducts can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. They regulate gene expression through their effects on the activity of transcription factors including NF-kappa B and members of the peroxisome proliferator-activated receptor (PPAR) family. Incorporation of ALA and its metabolites in cell membranes can affect membrane fluidity and may play a role in anti-inflammatory activity, inhibition of platelet aggregation and possibly in anti-proliferative actions of ALA. ALA is first metabolized by delta6 desaturease into steridonic acid.

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