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Chemistry

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Also known as: 60-33-3, Linolic acid, (9z,12z)-octadeca-9,12-dienoic acid, Telfairic acid, Cis,cis-linoleic acid, Linoleate
Molecular Formula
C18H32O2
Molecular Weight
280.4  g/mol
InChI Key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
FDA UNII
9KJL21T0QJ

Linoleic Acid
A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed)
1 2D Structure

Linoleic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(9Z,12Z)-octadeca-9,12-dienoic acid
2.1.2 InChI
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
2.1.3 InChI Key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
2.1.4 Canonical SMILES
CCCCCC=CCC=CCCCCCCCC(=O)O
2.1.5 Isomeric SMILES
CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
9KJL21T0QJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9 Trans,12 Trans Octadecadienoic Acid

2. 9,12 Octadecadienoic Acid

3. 9,12-octadecadienoic Acid

4. 9-trans,12-trans-octadecadienoic Acid

5. Acid, 9,12-octadecadienoic

6. Cis,cis-9,12-octadecadienoic Acid

7. Linoelaidic Acid

8. Linoelaidic Acid, (e,z)-isomer

9. Linoleate

10. Linoleic Acid, (e,e)-isomer

11. Linoleic Acid, (z,e)-isomer

12. Linoleic Acid, (z,z)-isomer

13. Linoleic Acid, (z,z)-isomer, 14c-labeled

14. Linoleic Acid, Ammonium Salt, (z,z)-isomer

15. Linoleic Acid, Calcium Salt, (z,z)-isomer

16. Linoleic Acid, Potassium Salt, (z,z)-isomer

17. Linoleic Acid, Sodium Salt, (e,e)-isomer

18. Linoleic Acid, Sodium Salt, (z,z)-isomer

19. Linolelaidic Acid

20. Trans,trans-9,12-octadecadienoic Acid

2.3.2 Depositor-Supplied Synonyms

1. 60-33-3

2. Linolic Acid

3. (9z,12z)-octadeca-9,12-dienoic Acid

4. Telfairic Acid

5. Cis,cis-linoleic Acid

6. Linoleate

7. 9,12-linoleic Acid

8. Grape Seed Oil

9. Cis,cis-9,12-octadecadienoic Acid

10. Emersol 315

11. Unifac 6550

12. Polylin 515

13. Cis-9,cis-12-octadecadienoic Acid

14. 9z,12z-linoleic Acid

15. (z,z)-9,12-octadecadienoic Acid

16. 9z,12z-octadecadienoic Acid

17. Extra Linoleic 90

18. 9-cis,12-cis-linoleic Acid

19. Emersol 310

20. All-cis-9,12-octadecadienoic Acid

21. Polylin No. 515

22. Oils, Grape

23. Linoleic

24. Acide Linoleique

25. 9,12-octadecadienoic Acid (9z,12z)-

26. 9-cis,12-cis-octadecadienoic Acid

27. Alpha-linoleic Acid

28. Acido Linoleico

29. 8024-22-4

30. 9,12-octadecadienoic Acid

31. Leinoleic Acid

32. (9z,12z)-octadecadienoic Acid

33. Ronacare Asc 3

34. 9,12-octadecadienoic Acid (z,z)-

35. Acide Cis-linoleique

36. (9z,12z)-9,12-octadecadienoic Acid

37. Chebi:17351

38. Cis-9, Cis-12-octadecadienoic Acid

39. Cis-delta(9,12)-octadecadienoic Acid

40. Nsc-281243

41. 9kjl21t0qj

42. Chembl267476

43. 9-cis,12-cis-octadecadienoate

44. C18:2

45. Cis,cis-linoleate

46. Ncgc00091049-04

47. C18:2 (n-6)

48. Fema No. 3380, Linoleic Acid-

49. Vespula Pensylvanica B708568k063

50. Dsstox_cid_5505

51. Dsstox_rid_77814

52. Dsstox_gsid_25505

53. Mfcd00064241

54. Oils, Grape Seed

55. Cas-60-33-3

56. 8016-21-5

57. Ccris 650

58. 14c-linoleic Acid

59. Linoleic Acid, Pure

60. Hsdb 5200

61. (14c)-linoleic Acid

62. Sr-01000944790

63. Cis-delta9,12-octadecadienoic Acid

64. Einecs 200-470-9

65. Unii-9kjl21t0qj

66. 9,12-octadecadienoic Acid, (z,z)-

67. Nsc 281243

68. (14c)alpha-linolenic Acid

69. Acidelinoleique

70. 7552p0k6pn

71. Linolate

72. Grapeseed Oil

73. Linoleic-acid

74. Leinolic Acid

75. Ai3-11132

76. Trans-9,trans-12-octadecadienoic Acid

77. 9z,12z-linoleate

78. Linoleic Acid 315

79. N-6,9 All-cis

80. Linoleic Acid, 95%

81. 9z,12z-octadecadienoate

82. 9-cis,12-cis-linoleate

83. Linoleic Acid, >=95%

84. Linoleic Acid, >=99%

85. Bmse000497

86. Bmse000604

87. Epitope Id:117705

88. Linoleic Acid [mi]

89. Linoleic And Linolenic Acids

90. Schembl7067

91. (9z,12z)-9,12-octadecadienoic-1-13c Acid

92. Cis,12-octadecadienoic Acid

93. Linoleic Acid [fcc]

94. Pamolyn 125 (salt/mix)

95. Cis-d9,12-octadecadienoate

96. Bspbio_001374

97. Linoleic Acid [hsdb]

98. Linoleic Acid [inci]

99. 80969-37-5

100. Ccris 652

101. Linoleic Acid [vandf]

102. Unii-7552p0k6pn

103. Linoleic Acid [mart.]

104. All-cis-9,12-octadecadienoate

105. Bml3-c03

106. Cis-9,cis-12-octadecadienoate

107. Gtpl1052

108. Linoleic Acid, >=95%, Fg

109. Linoleic Acid, Puriss., 90%

110. Delta9,12-octadecadienoic Acid

111. Linoleic Acid [who-dd]

112. (z,z)-9,12-octadecadienoate

113. Dtxsid2025505

114. Acon1_000270

115. Bdbm22231

116. C18:2, N-6,9 All-cis

117. Cis-d9,12-octadecadienoic Acid

118. Linoleic Acid, >=93% (gc)

119. Chebi:137735

120. 9,12-octadecadienoic Acid, (z,z)-, Labeled With Carbon-14

121. Hms1361e16

122. Hms1791e16

123. Hms1989e16

124. Hms3402e16

125. Hms3649f07

126. Hms3886f05

127. Linoleic Acid, Analytical Standard

128. 9,12-octadecadienoic Acid (van)

129. Hy-n0729

130. Zinc4474613

131. Tox21_111067

132. Tox21_202171

133. Tox21_303080

134. (9z,12z)-9,12-octadecadienoate

135. C18:2 9c

136. Cis,cis-octadeca-9,12-dienoic Acid

137. Cis-9,cis-12-octadecadienoic Acid,

138. Lmfa01030120

139. Nsc281243

140. S5821

141. (z,z)-octadeca-9, 12-dienoic Acid

142. 9,12-octadecadienoic Acid, (e,e)-

143. 9,12-octadecadienoic Acid, Cis,cis-

144. Akos015951293

145. Db14104

146. Rans, Trans-9,12-octadecadienoic Acid

147. 9-(z), 12-(z)-octadecadienoic Acid

148. Cis-.delta.9,12-octadecadienoic Acid

149. Idi1_033844

150. Ncgc00091049-01

151. Ncgc00091049-02

152. Ncgc00091049-03

153. Ncgc00091049-05

154. Ncgc00091049-06

155. Ncgc00091049-07

156. Ncgc00257024-01

157. Ncgc00259720-01

158. Vitamin F Component Linoleic Acid

159. 12c Omega6 Todos Cis-9,12-octadienoico

160. Ac-33770

161. As-12672

162. Bp-31121

163. Fa(18:2(9z,12z))

164. Linoleic Acid, Technical, 60-74% (gc)

165. Octadeca-9,12-dienoic Acid, (cis,cis)-

166. Ai3-36448

167. 9,z)-

168. Cs-0009742

169. L0053

170. L0124

171. C01595

172. 9, (z)-

173. A832696

174. Q407426

175. Sr-01000944790-1

176. Sr-01000944790-3

177. Brd-k08973992-001-03-9

178. C18:2 9c, 12c Omega6 Todos Cis-9,12-octadienoico

179. Linoleic Acid (constituent Of Spirulina) [dsc]

180. 5ce5e1f3-8859-4c5b-9afe-e44a7076df6e

181. Linoleic Acid (constituent Of Flax Seed Oil) [dsc]

182. Linoleic Acid (constituent Of Saw Palmetto) [dsc]

183. Linoleic Acid (constituent Of Borage Seed Oil) [dsc]

184. Linoleic Acid, Liquid, Bioreagent, Suitable For Cell Culture

185. Linoleic Acid (c18:2) (constituent Of Krill Oil) [dsc]

186. Linoleic Acid, 2.0 Mg/ml In Ethanol, Certified Reference Material

187. Cis,cis-9,12-octadecadienoic Acid; Linoleate; Emersol315; Linoleic; Unifac6550;

188. 30175-49-6

189. 85594-37-2

190. Lin

191. Linoleic Acid, Pharmagrade, Manufactured Under Appropriate Controls For Use As A Raw Material In Pharma Or Biopharmaceutical Production

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 280.4 g/mol
Molecular Formula C18H32O2
XLogP36.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count14
Exact Mass280.240230259 g/mol
Monoisotopic Mass280.240230259 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity267
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ To determine the effect of low doses of linoleic acid and calcium on prostaglandin (PG) levels and the efficacy of this treatment in the prevention of preeclampsia. In a randomized, double-blind, placebo-controlled study we treated 86 primigravidas with risk factors for preeclampsia (high biopsychosocial risk [above 3 points], positive roll-over test, and high mean blood pressure [above 85 mmHg)] with daily doses of either 450 mg linoleic acid and 600 mg calcium (n=43) or 450 mg starch and 600 mg lactose placebo (n=43) during the third trimester of pregnancy. Four women in the experimental group (9.3%) developed preeclampsia compared with 16 (37.2%) controls (relative risk 0.25, 95% confidence interval 0.09, 0.69, P < .001). The median serum levels of PGE2 after 4 weeks of treatment increased by 106% in the experimental group (P=.03) and decreased by 33% in the control group (P=.02). The median ratio between thromboxane B2 and PGE2 decreased by 40% in the experimental group (P=.02) and increased by 18% in the control group (P=.14). No significant differences were observed in the median ratio between thromboxane B2 and 6-keto PGF1alpha in either group. No serious maternal or neonatal side effects of treatment occurred in either group. The administration of low daily doses of linoleic acid and calcium during the third trimester of pregnancy reduced the incidence of preeclampsia significantly in women at high risk, possibly by correcting the PGE2 levels.

PMID:9540946 Herrera JA et al; Obstet Gynecol 91 (4): 585-90 (1998)


/EXPL THER/ Abdominal obesity is strongly related to metabolic disorders. Recent research suggests that dietary conjugated linoleic acid (CLA) reduces body fat and may improve metabolic variables in animals. The metabolic effects of CLA in abdominally obese humans have not yet been tested. To investigate the short-term effect of CLA on abdominal fat and cardiovascular risk factors in middle-aged men with metabolic disorders, twenty-five abdominally obese men (waist-to-hip ratio (WHR), 1.05+/-0.05; body mass index (BMI), 32+/-2.7 kg/m(2) (mean+/-s.d.)) who were between 39 and 64-y-old participated in a double-blind randomised controlled trial for 4 weeks. Fourteen men received 4.2 g CLA/day and 10 men received a placebo. The main endpoints were differences between the two groups in sagittal abdominal diameter (SAD), serum cholesterol, low-density lipoprotein, high-density lipoprotein, triglycerides, free fatty acids, glucose and insulin. At baseline, there were no significant differences between groups in anthropometric or metabolic variables. After 4 weeks there was a significant decrease in SAD (cm) in the CLA group compared to placebo (P=0.04, 95% CI; -1.12, -0.02). Other measurements of anthropometry or metabolism showed no significant differences between the groups. These results indicate that CLA supplementation for 4 weeks in obese men with the metabolic syndrome may decrease abdominal fat, without concomitant effects on overall obesity or other cardiovascular risk factors. /Conjugated linoleic acid/

PMID:11477497 Riserus U et al; Int J Obes Relat Metab Disord 25 (8): 1129-35 (2001)


/EXPL THER/ Conjugated linoleic acid (CLA) refers to a group of positional and geometric isomers of the omega-6 essential fatty acid linoleic acid (cis-9, cis-12, octadecadienoic acid). In humans evidence is currently ambiguous as to whether CLA supplementation has a significant effect on body composition. Despite favorable changes in lipid levels in animal models, a beneficial effect in humans has not yet been established. While some of the changes reported are consistent with an improved lipid profile, declines in HDL and increases in lipoprotein (a) have also been observed in some subjects. Available evidence suggests CLA supplementation has no impact on immune system performance in healthy subjects. /Conjugated linoleic acid/

PMID:11578253 Kelly GS; Altern Med Rev 6 (4): 367-82 (2001)


/EXPL THER/ Melasma is an acquired symmetric hypermelanosis characterized by irregular light-to gray-brown macules and patches on sun-exposed areas. Many therapeutic agents are available but are unsatisfactory. Recently, it has been demonstrated that lincomycin (LM) and linoleic acid (LA) can inhibit melanogenesis in vitro. /The authors/ investigated the clinical efficacy of topical application of LM and LA in combination with betamethasone valerate (BV) in melasma patients. Forty-seven Korean female adults with clinically diagnosed melasma were enrolled in a 6-week, double-blind, randomized clinical trial. Patients were treated with one application of the vehicle (group A), 2% LM mixed with 0.05% BV (group B), or 2% LM mixed with 0.05% BV and 2% LA (group C) on the face every night. Determination of efficacy was based on the Melasma Area and Severity Index (MASI) score and objective assessment (no effect, mild, moderate, or excellent) at intervals of 2 weeks until the end of the study at 6 weeks. After 6 weeks, in comparison with the pre-treatment MASI score, the average MASI score of group C decreased to 68.9%, compared with 98% in group A (p<0.05) and 85.4% in group B. There was no statistically significant difference between group A and group B. Seven patients (43.7%) in group C revealed more than moderate improvement in objective assessment, compared with none in group A and two patients (12.5%) in group B. There were no significant side effects. Topical application of linoleic acid is considered to be effective in the treatment of melasma patients.

PMID:12172049 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3054896 Lee MH et al; J Korean Med Sci 17 (4): 518-23 (2002)


For more Therapeutic Uses (Complete) data for LINOLEIC ACID (11 total), please visit the HSDB record page.


4.2 Drug Warning

Because of lack of long-term safety data, /conjugated linoleic acid/ CLA supplements should be avoided by children, pregnant women and nursing mothers. /Conjugated linoleic acid

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 160


At doses of up to 2 g /Conjugated linoleic acid/ daily, occasional gastointestinal complaints, such as nausea, have been noted. /Conjugated linoleic acid/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 160


4.3 Minimum/Potential Fatal Human Dose

1. Practically nontoxic: probable oral lethal dose (human) above 15 g/kg, more than 1 qt (2.2 lb) for 70 kg person (150 lb).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-199


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

... The objectives of the study were to 1) use the whole body fatty acid balance method to quantify whole-body concentrations of linoleate in humans, 2) estimate the distribution of linoleate between adipose and lean tissue, and 3) assess the effect of weight loss on linoleate stores and beta-oxidation in obese humans. Nine healthy obese men underwent supervised weight loss for 112 d (16 wk). Magnetic resonance imaging data and fatty acid profiles from fat biopsies were both used to determine linoleate stores in adipose and lean tissue and in the whole body. Linoleate beta-oxidation was calculated as intake - (accumulation + excretion). Mean weight loss was 13 kg and linoleate intake was 24 +/- 6 mmol/d over the study period. Whole-body loss of linoleate was 37 +/- 18 mmol/d, or 28% of the level before weight loss. Combining the intake and whole-body loss of linoleate resulted in linoleate beta-oxidation exceeding intake by 2.5-fold during the weight-loss period. All dietary linoleate is beta-oxidized and at least an equivalent amount of linoleate is lost from the body during moderate weight loss in obese men. The method studied permits the assessment of long-term changes in linoleate homeostasis in obese humans and may be useful in determining the risk of linoleate deficiency in other conditions. /Linoleate/

PMID:11273844 Cunnane SC et al; Am J Clin Nutr 73 (4): 709-14 (2001)


Human milk fatty acids vary with maternal dietary fat composition. Hydrogenated dietary oils with trans fatty acids may displace cis n-6 and n-3 unsaturated fatty acids or have adverse effects on their metabolism. The effects of milk trans, n-6, and n-3 fatty acids in breast-fed infants are unclear, although n-6 and n-3 fatty acids are important in infant growth and development. /The authors/ sought to determine the relations between trans and cis unsaturated fatty acids in milk and plasma phospholipids and triacylglycerols of breast-fed infants, and to identify the major maternal dietary sources of trans fatty acids. collected milk from 103 mothers with exclusively breast-fed 2-mo-old infants, blood from 62 infants, and 3-d dietary records from 21 mothers. Results: Mean (+/-SEM) percentages of trans fatty acids were as follows: milk, 7.1 +/- 0.32%; infants' triacylglycerols, 6.5 +/- 0.33%; and infants' phospholipids, 3.7 +/- 0.16%. Milk trans fatty acids, a-linolenic acid (18:3n-3), arachidonic acid (20:4n-6), docosahexaenoic acid (22:6n-3) (P < 0.001), and linoleic acid (18:2n-6) (P = 0.007) were each related to the same fatty acid in infant plasma phospholipids. Milk trans fatty acids were inversely related to milk 18:2n-6 and 18:3n-3, but not to milk or infant plasma 20:4n-6 or 22:6n-3. trans Fatty acids represented 7.7% of maternal total fat intake (2.5% of total energy); the major dietary sources were bakery products and breads (32%), snacks (14%), fast foods (11%), and margarines and shortenings (11%). There were comparable concentrations of trans fatty acids in the maternal diet, breast milk, and plasma triacylglycerols of breast-fed infants. Prepared foods were the major dietary source of trans fatty acids.

Innis SM, King J; Am J Clin Nutr 70 (3): 383-390 (1999)


Some /conjugated linoleic acid/ CLA appears to get incorporated into the phospholipids of cell membranes. /Conjugated linoleic acid/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 159


5.2 Metabolism/Metabolites

/OTHER TOXICITY INFORMATION/ The hepatotoxicity of orally administered secondary autoxidation products of linoleic acid in rats was investigated and compared to the effects following administration of a saline solution and linoleic acid as controls. The de novo synthesis of fatty acids was strongly reduced in the secondary products group. The level of nicotine adenine dinucleotide phosphate (NADPH) in the liver significantly decreased whereas that of nicotine adenine dinucleotide (NADH) did not. The activities of glucose 6-phosphate dehydrogenase and phosphogluconate dehydrogenase apparently decreased. The activities of NAD + kinase and NAD + synthetase decreased and that of NAD + nucleosidase increased in the secondary products group. Therefore the depletion of nicotine adenine dinucleotide phosphate can be attributed to the inhibition of two metabolic systems (a nicotine adenine dinucleotide phosphate-supplemental system and a synthetic system of NADP and NAD), and resulted in the reduction of lipogenesis in the liver. /Autooxidation products/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 822


... Linoleic acid stimulated tumor growth because it is converted by hepatoma 7288CTC to the mitogen, 13-hydroxyoctadecadienoic acid (13-HODE). ...

PMID:11377374 Sauer LA et al; Biochem Pharmacol 61 (12): 1455-62 (2001)


13-hydroxyoctadecadienoic acid (13-HODE) synthesis is enhanced by cyclic AMP. Gamma-linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation. /gamma-Linolenic acid/

PMID:9561154 Horrobin DF et al; Adv Exp Med Biol 433: 291-4 (1997)


Linoleic acid has known human metabolites that include Isoleukotoxin and Leukotoxin.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.3 Mechanism of Action

/The objective of this work was/ to study the gene expression of the resistin and the effects of conjugated linoleic acid on its expression in white adipose tissue of obese rats fed with high fat diet during the formation of insulin resistance. Male Wistar rats were randomly separated in control group, high-fat group and high fat + conjugated linoleic acid (CLA) group (0.75 g, 1.50 g, 3.00 g per 100 g diet weight), using reverse transcription polymerase chain reaction (RT-PCR) technique to measure the expression level of resistin and peroxisome proliferator-activated receptor-gamma (PPARgamma) mRNA expression. The serum insulin and glucose levels of obese rats were (11.11 +/- 2.73) mIU/L, (5.09 +/- 0.66) mmol/L, and supplement of CLA might decrease hyperinsulinemia and hyperglycemia, in CLA group (0.75 g, 1.50 g, 3.00 g per 100 g diet weight) the serum insulin levels were (6.99 +/- 1.77) mIU/L, (7.36 +/- 1.48) mIU/L, (7.85 +/- 1.60) mIU/L, and glucose levels were (4.28 +/- 0.72) mmol/L, (4.18 +/- 0.55) mmol/L, (4.06 +/- 0.63) mmol/L. The expression of resistin in adipose tissue of obese rat fed with high fat diet was increased as compared with those fed with basic diet. CLA might increase the expression of resistin and PPARgamma in adipose tissue of obese rat. The expression of resistin mRNA of obese rat fed with high fat diet was higher than those fed with basic diet, and CLA might improve the insulin resistance in obese rats and possibly upregulate the expression of resistin through activing PPARgamma. /Conjugated linoleic acid/

PMID:15938854 Zhou XR et al; Zhonghua Yu Fang Yi Xue Za Zhi 39 (3): 191-4 (2005)


Conjugated linoleic acid (CLA) is a mixture of positional (e.g. 7,9; 9,11; 10,12; 11,13) and geometric (cis or trans) isomers of octadecadienoic acid. This compound was first shown to prevent mammary carcinogenesis in murine models. Later investigations uncovered a number of additional health benefits, including decreasing atherosclerosis and inflammation while enhancing immune function. The mechanisms of action underlying these biological properties are not clearly understood. The aim of this review is to highlight recent advances in CLA research related to experimental inflammatory bowel disease. In addition, two possible mechanisms of action (i.e. endoplasmic and nuclear) were discussed in detail in the context of enteric inflammatory disorders. Conjugated linoleic acid was first implicated in down-regulating the generation of inducible eicosanoids (i.e. PGE(2) and LTB(4)) involved in early micro-inflammatory events (endoplasmic). More recently, CLA has been shown to modulate the expression of genes regulated by peroxisome proliferator-activated receptors (PPARs; nuclear). In pigs, prolonged dietary CLA treatment stimulated the expression of PPAR-gamma in the muscle. Thus, evidence supporting both mechanistic theories of CLA acting through eicosanoid synthesis and PPAR activity is available. The further understanding of the anti-inflammatory mechanisms of action of CLA may yield novel nutritional therapies for enteric inflammation. /Conjugated linoleic acid/

PMID:12468364 Bassaganya-Riera J et al; Clin Nutr 21 (6): 451-9 (2002)


/Conjugated linoleic acid/ CLA may modulate eicosanoid activity as well as the activity... of tumor necrosis factor-alpha. /Conjugated linoleic acid/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 159


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USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX
Not Confirmed
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USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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26th North American ISSX
Not Confirmed
USDMF Inactive-api CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT
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02

Waitaki Biosciences

New Zealand

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

26th North American ISSX
Not Confirmed
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Waitaki Biosciences

New Zealand

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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26th North American ISSX
Not Confirmed
USDMF Inactive-api CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT
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USDMF

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01

26th North American ISSX
Not Confirmed

01

26th North American ISSX
Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 6706

Submission : 1986-12-04

Status : Inactive

Type : II

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02

Pharmaglobe Laboratories Ltd

Country

USDMF

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26th North American ISSX
Not Confirmed

02

Pharmaglobe Laboratories Ltd

Country
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26th North American ISSX
Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 9288

Submission : 1991-08-13

Status : Inactive

Type : II

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API Reference Price

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04-Mar-2021
23-Aug-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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