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Dihomo-Gamma-Linolenate

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Chemistry

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Also known as: 1783-84-2, Dgla, 8,11,14-eicosatrienoic acid, Gamma-homolinolenic acid, Homo-gamma-linolenic acid, Cis-8,11,14-eicosatrienoic acid

Molecular Formula

C₂₀H₃₄O₂

Molecular Weight

306.5 g/mol

InChI Key

HOBAELRKJCKHQD-QNEBEIHSSA-N

FDA UNII

FC398RK06S

A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.

1 2D Structure

Dihomo-Gamma-Linolenate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

2.1.2 InChI

InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-

2.1.3 InChI Key

HOBAELRKJCKHQD-QNEBEIHSSA-N

2.1.4 Canonical SMILES

CCCCCC=CCC=CCC=CCCCCCCC(=O)O

2.1.5 Isomeric SMILES

CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

FC398RK06S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 8,11,14 Eicosatrienoic Acid

2. 8,11,14-eicosatrienoic Acid

3. Dihomo Gamma Linolenic Acid

4. Dihomogammalinolenic Acid

5. Homo Gamma Linolenic Acid

6. Homo-gamma Linolenic Acid

7. Linolenic Acid, Homo-gamma

8. Ro 12 1989

9. Ro 12-1989

10. Ro 121989

2.3.2 Depositor-Supplied Synonyms

1. 1783-84-2

2. Dgla

3. 8,11,14-eicosatrienoic Acid

4. Gamma-homolinolenic Acid

5. Homo-gamma-linolenic Acid

6. Cis-8,11,14-eicosatrienoic Acid

7. Diroleuton

8. (8z,11z,14z)-icosa-8,11,14-trienoic Acid

9. All-cis-8,11,14-eicosatrienoic Acid

10. Bishomo-gamma-linolenic Acid

11. 8z,11z,14z-eicosatrienoic Acid

12. (z,z,z)-8,11,14-eicosatrienoic Acid

13. Ro 12-1989

14. (8z,11z,14z)-icosatrienoic Acid

15. 8,11,14-icosatrienoate

16. 8,11,14-eicosatrienoate

17. (z,z,z)-8,11,14-icosatrienoate

18. Daleuton

19. (z,z,z)-8,11,14-icosatrienoic Acid

20. Cis,cis,cis-8,11,14-eicosatrienoic Acid

21. .gamma.-homolinolenic Acid

22. (z,z,z)-8,11,14-eicosatrienoate

23. 8,11,14-all-cis-eicosatrienoic Acid

24. Dihomo-.gamma.-linolenic Acid

25. All Cis-8,11,14-eicosatrienoic Acid

26. All-cis-icosa-8,11,14-trienoic Acid

27. Ccris 7669

28. 8,11,14-eicosatrienoic Acid, (8z,11z,14z)-

29. (z,z,z)-icosatri-8,11,14-enoic Acid

30. Cis-8,cis-11,cis-14-eicosatrienoic Acid

31. Dihomo-gamma-linolenate

32. 8c,11c,14c-eicosatrienoic Acid

33. 8, 11, 14-eicosatrienoic Acid

34. Ds107

35. Eicosa-8z,11z,14z-trienoic Acid

36. Dihomo-

37. A-linolenic Acid

38. 20:3, N-6,9,12 All-cis

39. All-cis-8,11,14-icosatrienoic Acid

40. Bishomo-.gamma.-linolenic Acid

41. Chembl465183

42. Ds107g

43. Fc398rk06s

44. 8,11-14-eicosatrienoic Acid, (z,z,z)-

45. Chebi:53486

46. Ds-107

47. Ds-107g

48. 20:3 (.omega.-6) Fatty Acid

49. C20:3, N-6,9,12 All-cis

50. All-cis-eicosa-8,11,14-trienoic Acid

51. C20:3n-6,9,12

52. Fa(20:3(8z,11z,14z))

53. 20:3(n-6)

54. All-cis-8,11,14-eicosatrienoate

55. Homo-gamma-linolensaeure

56. 8,11,14-icosatrienoic Acid

57. Unii-fc398rk06s

58. Eicosatrienoate

59. Dihomolinolenate

60. Bml3-b11

61. 8c,11c,14c-eicosatriensaeure

62. Gamma-homolinolenate

63. Einecs 217-233-0

64. Mfcd00065721

65. All-cis-eicosa-8,11,14-triensaeure

66. Homo-gamma-linolenate

67. C 20:3 N-6

68. Bishomo-gamma-linolenate

69. Dihomo-y-linolenic Acid

70. Daleuton [inn]

71. Dihomo-gamma-linolenic-acid

72. Dibromo-gamma-linolenic Acid

73. Di-homo Gamma-linolenic Acid

74. Dihomo -gamma-linolenic Acid

75. Diroleuton [who-dd]

76. Bspbio_001286

77. Schembl842729

78. 8z,11z,14z-eicosatrienoate

79. Cis-8,11,14-eicosatrienoate

80. Gtpl9775

81. Dtxsid00912351

82. Hms1361a08

83. Hms1791a08

84. Hms1989a08

85. Hms3402a08

86. Hms3649h11

87. 8,11,14-all-cis-eicosatrienoate

88. Hy-a0143

89. Zinc4521470

90. Bdbm50269534

91. Lmfa01030158

92. All Cis-8,11,14-icosatrienoic Acid

93. (z,z,z)-icosatri-8,11,14-enoate

94. Cis,cis,cis-8,11,14-eicosatrienoate

95. Cis-8,cis-11,cis-14-eicosatrienoate

96. Db00154

97. Idi1_033756

98. Ncgc00161350-01

99. Ncgc00161350-02

100. Ncgc00161350-03

101. As-65384

102. 20:3n-6

103. Cis-8,11,14-eicosatrienoic Acid, >=99%

104. Cs-0017463

105. E0640

106. C03242

107. Dihomo- Gamma -linolenic Acid (20:3, N-6)

108. (8z,11z,14z)-8,11,14-eicosatrienoic Acid

109. Q415398

110. Sr-01000946659

111. 8,11,14-eicosatrienoic Acid, (z,z,z)- (8ci)

112. Sr-01000946659-1

113. Brd-k20152659-001-02-0

114. Cis-8,11,14-eicosatrienoic Acid, Analytical Standard

115. 8,11,14-eicosatrienoic Acid, (8z,11z,14z)- (9ci)

2.4 Create Date

2005-06-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₄O₂
Molecular Weight	306.5 g/mol
XLogP3	7.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Exact Mass	306.255880323 g/mol
Monoisotopic Mass	306.255880323 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	327
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, also for treating dietary shortage or imbalance

Treatment of atopic dermatitis

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect.

5.2 Mechanism of Action

DHLA (or DGLA) is a precursor in the synthesis of prostaglandin E1 (PGE1) as well as the series-3 prostaglandins. It also serves as a precursor in the synthesis of eicosapentaenoic acid (EPA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-thrombogenic, anti-inflammatory and anti-atherogenic properties. PGE1 inhibits platelet aggregation and has a vasodilation action. DHLA has also been shown to reduce the production/activity of tumor necrosis factor alpha.

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