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    Dihomo-Gamma-Linolenate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    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

    2D Structure

    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 Weight 306.5 g/mol
    Molecular Formula C20H34O2
    XLogP37.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count15
    Exact Mass306.255880323 g/mol
    Monoisotopic Mass306.255880323 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity327
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count3
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.