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6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)- (gamma--Linolenic acid)

Delta notation: 18:3-delta-6c,9c,12c

Other Names: 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-; -gamma--Linolenic acid; (Z,Z,Z)-6,9,12-Octatrienoic acid; 6(Z),9(Z),12(Z)-Octadecatrienoic acid; 6,9,12-all-cis-Octadecatrienoic acid; 6-cis,9-cis,12-cis-Octadecatrienoic acid; Gamma-linolenic acid; Gamolenic acid; all-cis-6,9,12-Octadecatrienoic acid; cis,cis,cis-6,9,12-Octadecatrienoic acid; cis-6,cis-9,cis-12-Octadecatrienoic acid

Formula: C18 H30 O2

Mass: 278.43

IUPAC name: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

6,9,12 octadecatrienoic acid, (6z,9z,12z)
Structure drawn at OPSIN (opsin.ch.cam.uk)

External Database IDs:
CAS registry: 506-26-3
SOFA Mol: M_094
Lipid Maps: LMFA01030141
PubChem: 5280933
ChEBI:

inchi: InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-/f/h19H

stdinchi: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-

stdinchikey: VZCCETWTMQHEPK-QNEBEIHSSA-N

smiles: C(CCCC\C=C/C\C=C/C\C=C/CCCCC)(=O)O

Results

Displaying datapoints 51 - 100 of 962 in total
PlantSort off PublicationSort off ValueSort off UnitSort off
Symphytum caucasicum Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 20.1 GLC-Area-%
Borago officinalis Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 20.0 GLC-Area-%
Onosmodium molle Search for new industrial oils. XI. Oils of boraginaceae Kleiman, R.; Earle, F. R.; Wolff, I. A.; Jones, Q. Journal of the American Oil Chemists' Society (1964) 41 459-460 20.0 GLC-Area-%
Borago officinalis Book: Manual of Gas-liquid Chromatography of Organic Acids (in Russian) Gorjaev, M. I. Evdakova, N. A. Book: Spravočnik po gazožidkostnoj chromatografii organičeskich kislot (1977) Nauka Alma-Ata None 20.0 GLC-Area-%
Oenothera biennis Evening primrose (Oenothera spp.) oil and seed Hudson, B. J. F. Journal of the American Oil Chemists' Society (1984) 61 540-543 20.0
Anemone sylvestris Unpublished unpublished results MRI (1997) 20.0 GLC-Area-%
Borago officinalis Search for new industrial oils. XI. Oils of boraginaceae Kleiman, R.; Earle, F. R.; Wolff, I. A.; Jones, Q. Journal of the American Oil Chemists' Society (1964) 41 459-460 20.0 GLC-Area-%
Echium decaisnei Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 19.92 GLC-Area-%
Borago officinalis L. 长白山区野果种子脂肪酸的研究_赵淑春 . Study on Fatty Acids of Seed of Wild Fruit Trees of Changbai Mountain Area Shuchun Zhao; Li Fu; Ying Yu; Minti Liu Chinese Wild Plant Resource (1994) (1) 10-15 19.92 weight-%
Paeonia suffruticosa var. papaveracea (Andrews) A. Kern. 紫草籽油的超临界CO_2萃取及其脂肪酸含量分析_戴震安 . Supercritical-CO_2 fluid extraction and fatty acid contents analysis of lithospermum seeds oil DAI Zhen-an; ZHOU Yong-chuan; DENG Xiu China Oils and Fats (2004) 29(11) 49-50 19.89 weight-%
Anemone crinita Unpublished unpublished results MRI (1991) 19.8 GLC-Area-%
Borago officinalis Fatty acid profiles and sn -2 fatty acid distribution of γ-linolenic acid-rich Borago species Guil-Guerrero, José Luis; Gómez-Mercado, Francisco; Ramos-Bueno, Rebeca Pilar; González-Fernández, María José; Urrestarazu, Miguel; Jiménez-Becker, Silvia; de Bélair, Gérard Journal of Food Composition and Analysis (2018) 66 74-80 19.8 weight-%
Echium hierrense Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 19.75 GLC-Area-%
Symphytum uplandicum Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 19.6 GLC-Area-%
Anemone crinita Unpublished unpublished results MRI (1991) 19.5 GLC-Area-%
Borago officinalis L. 两种海桐属植物种子油脂肪酸组成的分析评价_翁德宝 . Analysis and Evaluation of Fatty Acids in the Seed Oils of Two Species of Pittosporum Banks ex Soland.apud Gaertn WENG De-bao; HUANG Xie-fang; WANG Hai-feng AMINO ACIDS AND BIOTIC RESOURCES (2000) 22（3） 6-8 19.42 weight-%
Pulmonaria mollis Chemotaxonomic significance of fatty acids and tocopherols in Boraginaceae Velasco, L.; Goffman, F. D. Phytochemistry (1999) 52 423-426 19.4 GLC-Area-%
Anemone altaica Unpublished unpublished results MRI (1991) 19.3 GLC-Area-%
Echium simplex Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 19.28 GLC-Area-%
Anemone cylindrica Unusual olefinic fatty acids in seed oils from two genera in the ranunculaceae Spencer, G. F.; Kleiman, R.; Earle, F. R.; Wolff, I. A. Lipids (1970) 5 277-278 19.0 GLC-Area-%
Ribes nigrum Fatty acid patterns in organ lipids in response to dietary black currant seed oil rich in gamma-linolenic acid Traitler, H.; Winter, H. Progress in Lipid Research (1986) 25 255-261 19.0 GLC-Area-%
Borago officinalis Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 19.0 GLC-Area-%
Borago longifolia Fatty acid profiles and sn -2 fatty acid distribution of γ-linolenic acid-rich Borago species Guil-Guerrero, José Luis; Gómez-Mercado, Francisco; Ramos-Bueno, Rebeca Pilar; González-Fernández, María José; Urrestarazu, Miguel; Jiménez-Becker, Silvia; de Bélair, Gérard Journal of Food Composition and Analysis (2018) 66 74-80 19.0 weight-%
Anemone cylindrica Unusual olefinic fatty acids in seed oils from two genera in the ranunculaceae Spencer, G. F.; Kleiman, R.; Earle, F. R.; Wolff, I. A. Lipids (1970) 5 277-278 19.0 GLC-Area-%
Borago trabutii Fatty acid profiles and sn -2 fatty acid distribution of γ-linolenic acid-rich Borago species Guil-Guerrero, José Luis; Gómez-Mercado, Francisco; Ramos-Bueno, Rebeca Pilar; González-Fernández, María José; Urrestarazu, Miguel; Jiménez-Becker, Silvia; de Bélair, Gérard Journal of Food Composition and Analysis (2018) 66 74-80 18.9 weight-%
Borago officinalis L. 几种早实核桃坚果中蛋白质_脂肪酸组成成分分析_郝艳宾 . Analysis of Protein and Fatty Acid Composition in Several Kinds of precocious Walnut Nuts Yanbin Hao; Kejian Wang; Shulan Wang; Yanling Zhuang Food Science (2002) 23(10) 123-125 18.78 weight-%
Borago officinalis L. 超临界CO_2流体萃取南瓜籽油的质量研究_李全宏 . Study on Pumpkin Seed Oil Extraction by Supercritical CO_2 Fluid LI Quan-Hong; YAN Hong; WANG Shao-Xiao; CAI Tong-Yi Food Science (2002) 23(4) 22-25 18.78 weight-%
Echium strictum Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 18.75 GLC-Area-%
Borago officinalis BORAGO-PYGMEA - A NEW SOURCE OF GAMMA-LINOLENIC ACID Ucciani, E.; Mallet, G.; Gamisans, J. Revue Francaise Des Corps Gras (1992) 39 135-138 18.5 GLC-Area-%
Buglossoides purpureocaeruleum Gamma-linolenic acid from fourteen boraginaceae species Guil-Guerrero, J. L.; García-Maroto, F.; Vilches-Ferrón, M. A.; López-Alonso, D. Industrial Crops and Products (2003) 18 85-89 18.5 GLC-Area-%
Borago officinalis Chemotaxonomic significance of fatty acids and tocopherols in Boraginaceae Velasco, L.; Goffman, F. D. Phytochemistry (1999) 52 423-426 18.5 GLC-Area-%
Aegle marmelos Unique occurrence of unusual fatty acid in the seed oil of Aegle marmelos Corre: Screening the rich source of seed oil for bio-energy production Katagi, Kariyappa S.; Munnolli, Ravindra S.; Hosamani, Kallappa M. Applied Energy (2011) 88 1797-1802 18.4 weight-%
Ribes pauciflorum Turcz. ex Ledeb. 长柄扁桃及6个近缘种营养成分研究GC-MS . Studies on the Nutritional Components of Prunus pedunculata (Pall.) Maxim. and Its Six Related Species Heng Ma Thesis (2013) 18.34 weight-%
Lithospermum officinale Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 18.3 GLC-Area-%
Onosmodium occidentale NATURALLY OCCURRING ALL-CIS 6,9,12,15-OCTADECATETRAEONOIC ACID IN PLANT OILS Craig, B. M.; Bhatty, M. K. Journal of the American Oil Chemists Society (1964) 41 209-& 18.3 GLC-Area-%
Lithospermum purpurocaeruleum Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 18.2 GLC-Area-%
Lithospermum purpurocaeruleum Search for new seed oils. XV. Oils of boraginaceae Miller, R. W.; Earle, F. R.; Wolff, I. A.; Barclay, A. S. Lipids (1968) 3 43-45 18.0 GLC-Area-%
Onosmodium occidentale Search for new seed oils. XV. Oils of boraginaceae Miller, R. W.; Earle, F. R.; Wolff, I. A.; Barclay, A. S. Lipids (1968) 3 43-45 18.0 GLC-Area-%
Onosmodium occidentale Search for new seed oils. XV. Oils of boraginaceae Miller, R. W.; Earle, F. R.; Wolff, I. A.; Barclay, A. S. Lipids (1968) 3 43-45 18.0 GLC-Area-%
Lithospermum purpurocaeruleum Search for new seed oils. XV. Oils of boraginaceae Miller, R. W.; Earle, F. R.; Wolff, I. A.; Barclay, A. S. Lipids (1968) 3 43-45 18.0 GLC-Area-%
Anchusa officinalis Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 17.9 GLC-Area-%
Anchusa riparia Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 17.7 GLC-Area-%
Borago officinalis L. 玻璃苣种子中脂肪酸含量的测定_张红梅（GC） . Determination of Fatty Acid Content in Borage seed ZHANG Hong-mei; LI Si-ying; CAI Bao-hong Journal of Anhui Agricultural Sciences (2014) 42(31) 11223-11224 17.52 weight-%
Echium auberianum Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 17.45 GLC-Area-%
Pulmonaria officinalis Unpublished Aitzetmueller, K. unpublished results (1999) 17.4 GLC-Area-%
Echium triste Occurrence and characterization of oils rich in γ-linolenic acid part I: Echium seeds from Macaronesia Guil-Guerrero, J. L.; Gomez-Mercado, F.; Garcia-Maroto, F.; Campra-Madrid, P. Phytochemistry (2000) 53 451-456 17.19 GLC-Area-%
Anemone cylindrica Unpublished unpublished results MRI (1991) 17.1 GLC-Area-%
Lithospermum erythrorhizon Unpublished unpublished results MRI (1996) 17.1 GLC-Area-%
Anemone cylindrica Unpublished unpublished results MRI (1991) 17.1 GLC-Area-%
Lithospermum officinale Unpublished unpublished results MRI (1992) 16.6 GLC-Area-%