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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 901 - 950 of 962 in total
PlantSort off PublicationSort off ValueSort off UnitSort off
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-%
Anemone crinita Unpublished unpublished results MRI (1991) 19.8 GLC-Area-%
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-%
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-%
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 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-%
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
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-%
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-%
Symphytum caucasicum Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 20.1 GLC-Area-%
Onosmodium hispidissimum Stereospecific analysis of Onosmodium hispidissimum Mack. seed oil triglycerides MacKenzie, S. L.; Giblin, E. M.; Mazza, G. Journal of the American Oil Chemists' Society (1993) 70 629-631 20.1 GLC-Area-%
Echium pininana Unpublished Aitzetmueller, K. unpublished results (1999) 20.2 GLC-Area-%
Borago officinalis Unpublished unpublished results MRI (1991) 20.2 GLC-Area-%
Lithodora moroccana Gamma-linolenic and stearidonic acids from Moroccan Boraginaceae Guil-Guerrero, J. L.; López-Martínez, J. C.; Gómez-Mercado, F.; Campra-Madrid, P. European Journal of Lipid Science and Technology (2006) 108 43-47 20.2 weight-%
Hevea brasiliensis (Willd. ex A. Juss.) Müll. Arg. 橡胶种子油的脂肪酸组成和含量分析（GC) . Analysis of fatty acid compositions of rubber seed oil by GC YIN Gui-hao; CAO Jian-hua; ZHANG Shi-rui GUANGDONG AGRICULTURAL SCIENCES (2009) (11) 157-158 20.4 weight-%
Borago officinalis Lipid components of borage (Borago officinalis L.) seeds and their changes during germination Senanayake, S. P. J. Namal; Shahidi, Fereidoon Journal of the American Oil Chemists' Society (2000) 77 55-61 20.5 GLC-Area-%
Echium virescens 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 21.6 GLC-Area-%
Echium giganteum 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 21.68 GLC-Area-%
Borago officinalis Urea-based fractionation of seed oil samples containing fatty acids and acylglycerols of polyunsaturated and hydroxy fatty acids Hayes, Douglas G.; Van Alstine, James M.; Setterwall, Fredrik Journal of the American Oil Chemists' Society (2000,2) 77 207-213 21.7 GLC-Area-%
Borago officinalis Fatty acid profiles of 80 vegetable oils with regard to their nutritional potential Dubois, V.; Breton, S.; Linder, M.; Fanni, J.; Parmentier, M. European Journal of Lipid Science and Technology (2007) 109 710-732 21.9 GLC-Area-%
Pentaglottis sempervirens Chemotaxonomic significance of fatty acids and tocopherols in Boraginaceae Velasco, L.; Goffman, F. D. Phytochemistry (1999) 52 423-426 22.1 GLC-Area-%
Symphytum orientale Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 22.2 GLC-Area-%
Echium aculeatum 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 22.29 GLC-Area-%
Echium leucophaeum 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 22.48 GLC-Area-%
Borago officinalis Screening of lipases for enzymatic concentration of γ-linolenic acid (GLA) from seed oils López-Martínez, J. C.; Campra-Madrid, P.; Ramírez-Fajardo, A.; Esteban-Cerdán, L.; Guil-Guerrero, J. L. Journal of Food Lipids (2006) 13 362-374 22.5 GLC-Area-%
Borago officinalis Donnees Chimiotaxinomiques sur les Boraginacees P. Tetenyi Acta Botanica Academiae Scientiarum Hungaricae (1974) 20 159-167 22.9 GLC-Area-%
Borago pygmaea 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 22.9 weight-%
Borago officinalis OENOTHERA SPECIES AND BORAGO-OFFICINALIS - SOURCES OF GAMMA-LINOLENIC ACID Muuse, B. G.; Essers, M. L.; Vansoest, L. J. M. Netherlands Journal of Agricultural Science (1988) 36 357-363 22.93 GLC-Area-%
Borago officinalis Unpublished unpublished results MRI (1994) 23.0 GLC-Area-%
Borago morisiana 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 23.1 weight-%
Echium nervosum Unpublished Aitzetmueller, K. unpublished results (1999) 23.2 GLC-Area-%
Echium onosmifolium 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 23.44 GLC-Area-%
Echium candicans 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 23.66 GLC-Area-%
Echium fastuosum 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 23.77 GLC-Area-%
Lithospermum latifolium 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 23.9 GLC-Area-%
Astelia banksii SEED FATS OF ASTELIA AND COLLOSPERMUM FAMILY LILIACEAE Morice, I. M. Journal of the Science of Food and Agriculture (1967) 18 343-& 23.9 GLC-Area-%
Astelia solandri SEED FATS OF ASTELIA AND COLLOSPERMUM FAMILY LILIACEAE Morice, I. M. Journal of the Science of Food and Agriculture (1967) 18 343-& 24.1 GLC-Area-%
Echium sventenii 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 24.39 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 24.4 GLC-Area-%
Borago officinalis Chemotaxonomic significance of fatty acids and tocopherols in Boraginaceae Velasco, L.; Goffman, F. D. Phytochemistry (1999) 52 423-426 24.4 GLC-Area-%
Echium acanthocarpum 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 24.51 GLC-Area-%
Echium nervosum 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 24.52 GLC-Area-%
Astelia trinervia SEED FATS OF ASTELIA AND COLLOSPERMUM FAMILY LILIACEAE Morice, I. M. Journal of the Science of Food and Agriculture (1967) 18 343-& 24.8 GLC-Area-%
Astelia nadeaudii Seed fats of further species of Astelia Morice, I. M. Phytochemistry (1975) 14 1315-1318 24.8 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 24.8 GLC-Area-%
Echium fastuosum Screening of lipases for enzymatic concentration of γ-linolenic acid (GLA) from seed oils López-Martínez, J. C.; Campra-Madrid, P.; Ramírez-Fajardo, A.; Esteban-Cerdán, L.; Guil-Guerrero, J. L. Journal of Food Lipids (2006) 13 362-374 24.9 GLC-Area-%
Borago officinalis Estudio de Ia presencia del acido gamma-linolenico en los aceites vegetales Pedro Mario, Fernandez San Juan Alimentaria (1992) 29 49-52 24.9 GLC-Area-%
Borago pygmaea BORAGO-PYGMEA - A NEW SOURCE OF GAMMA-LINOLENIC ACID Ucciani, E.; Mallet, G.; Gamisans, J. Revue Francaise Des Corps Gras (1992) 39 135-138 25.1 GLC-Area-%