506-26-3

Basic information

• Product Name: gamma-Linolenic acid
• Synonyms: (Z,Z,Z)-6,9,12-Octadecatrienoic acid;OCTADECA-6Z,9Z,12Z-TRIENOIC ACID;6Z,9Z,12Z-OCTADECATRIENOIC ACID;6,9,12-OCTADECATRIENOIC ACID;ALL CIS-6,9,12-OCTADECATRIENOIC ACID;C18:3 (ALL CIS-6,9,12) ACID;CIS,CIS,CIS-6,9,12-OCTADECATRIENOIC ACID;DELTA 6 CIS 9 CIS 12 CIS OCTADECATRIENOIC ACID
• CAS NO: 506-26-3
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.43
• Product Categories: Miscellaneous Natural Products;Biochemistry;Higher Fatty Acids & Higher Alcohols;Unsaturated Higher Fatty Acids;Biological and chemical
• Mol File: 506-26-3.mol
• Article Data: 221

Chemical Properties

• Melting Point: -12～-11℃
• Boiling Point: 379.5°Cat760mmHg
• Flash Point: 110 °C
• Appearance: /liquid
• Density: 0.92
• Vapor Pressure: 8.26E-07mmHg at 25°C
• Refractive Index: n20/D 1.471
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.74±0.10(Predicted)
• Stability: Light Sensitive
• Merck: 14,5507
• BRN: 1712253
• CAS DataBase Reference: gamma-Linolenic acid(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-Linolenic acid(506-26-3)
• EPA Substance Registry System: gamma-Linolenic acid(506-26-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 506-26-3(Hazardous Substances Data)

Usage

Description

Gamma-Linolenic acid (GLA) is an omega-6 fatty acid primarily found in vegetable oils. It is known for its potential immune-regulating and anti-inflammatory effects, and is sold as a dietary supplement for treating inflammation and autoimmune diseases. GLA has a chemical structure with an 18-carbon chain and three cis double bonds, making it an isomer of alpha-linolenic acid, a polyunsaturated omega-3 fatty acid.

Uses

Used in Pharmaceutical Industry:
Gamma-Linolenic acid is used as an anti-inflammatory and immune-regulating agent for the treatment of various inflammation-related conditions and autoimmune diseases. It may also be used in the treatment of atopic eczema, although its efficacy is disputed.
Used in Analytical Chemistry:
GLA is used as an analytical standard in gas chromatography, which is a technique used to separate and analyze compounds that can be vaporized without decomposition.
Used in Nutritional Studies:
Gamma-Linolenic acid is used in nutritional studies regarding weight regain and as a possible tumor suppression agent. It is also used in research on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.
Used in Food Industry:
GLA is found in various vegetable oils such as GLA safflower oil, evening primrose oil, blackcurrant seed oil, borage oil, and hemp seed oil. It is also present in edible hemp seeds, oats, barley, and spirulina. These sources can be used in the food industry to provide a dietary source of GLA for consumers.
Used in Genetically Modified Products:
GLA safflower oil, a novel concentrated form of GLA, is a genetically modified oil that has been available in commercial quantities since 2011. This oil contains 40% GLA, making it a valuable source for the production of GLA-rich products in the food and pharmaceutical industries.

History

GLA was first isolated from the seed oil of evening primrose. This herbal plant was grown by Native Americans to treat swelling in the body. In the 17th century, it was introduced to Europe and became a popular folk remedy, earning the name king's cure-all. in 1919, Heiduschka and Lüft extracted the oil from evening primrose seeds and described an unusual linolenic acid, which they name γ-. Later, the exact chemical structure was characterized by Riley. Although there are α- and γ- forms of linolenic acid, there is no β- form. One was once identified, but it turned out to be an artifact of the original analytical process.

Biochem/physiol Actions

Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds.

references

[1] yagaloff k a, franco l, simko b, et al. essential fatty acids are antagonists of the leukotriene b4 receptor[j]. prostaglandins, leukotrienes and essential fatty acids, 1995, 52(5): 293-297.[2] crooks s w, stockley r a. leukotriene b4[j]. the international journal of biochemistry & cell biology, 1998, 30(2): 173-178.[3] tasset-cuevas i, fernández-bedmar z, lozano-baena m d, et al. protective effect of borage seed oil and gamma linolenic acid on dna: in vivo and in vitro studies[j]. plos one, 2013, 8(2): e56986.[4] jamal g a, carmichael h. the effect of γ‐linolenic acid on human diabetic peripheral neuropathy: a double‐blind placebo‐controlled trial[j]. diabetic medicine, 1990, 7(4): 319-323.[5] andreassi m, forleo p, dilohjo a, et al. efficacy of γ-linolenic acid in the treatment of patients with atopic dermatitis[j]. journal of international medical research, 1997, 25(5): 266-274.

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-

Synthetic route

methyl linoleate (16326-32-2) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With lithium hydroxide; water In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) r.t., 12 h;	98%

eicosatetraynoic acid (4184-93-4) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With quinoline; Lindlar's catalyst; ethanol Hydrogenation;
With quinoline; hydrogen; Lindlar's catalyst In ethanol at 20℃;

9(Z),12(Z)-octadecadien-6-ynoic acid (56795-52-9) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With quinoline; hydrogen; Lindlar's catalyst; Lindlar's catalyst; Piperonyl butoxide In Petroleum ether

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + heptadeca-5c,8c,11c-trienyl magnesium bromide → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With diethyl ether

5-bromopentanoic acid (2067-33-6) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: ammonia 2: acid 3: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 12 h 4: 92 percent / CBr4, PPh3 / CH2Cl2 / 1 h / Ambient temperature 5: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 40 °C 6: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 7: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme

hept-6-ynoic acid (30964-00-2) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: acid 2: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 12 h 3: 92 percent / CBr4, PPh3 / CH2Cl2 / 1 h / Ambient temperature 4: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 40 °C 5: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 6: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme
Multi-step reaction with 2 steps 1: ethyl magnesium bromide; tetrahydrofuran / anschliessend mit 1-Brom-undeca-2,5-diin und Kupfer(I)-cyanid 2: Lindlar-catalyst; quinoline; ethanol / Hydrogenation View Scheme
Multi-step reaction with 2 steps 2: H2, quinoline / Pb, Pd, CaCO3 / light petroleum View Scheme

methyl hept-6-ynoate (56909-02-5) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 12 h 2: 92 percent / CBr4, PPh3 / CH2Cl2 / 1 h / Ambient temperature 3: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 40 °C 4: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 5: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme

Octadeca-6,9,12-triinsaeure-methylester (16326-31-1) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 2: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme

11-Bromo-undeca-6,9-diynoic acid methyl ester (209860-40-2) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 40 °C 2: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 3: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme

methyl 11-hydroxyundeca-6,9-diynoate (209860-37-7) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / CBr4, PPh3 / CH2Cl2 / 1 h / Ambient temperature 2: 89 percent / K2CO3, NaI, CuI / dimethylformamide / 40 °C 3: 65 percent / H2, (CH2NH2)2 / P-2 Ni / ethanol 4: 98 percent / LiOH, H2O / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h View Scheme

3-hex-5-ynyl-2,4,10-trioxa-adamantane (131867-44-2) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl magnesium bromide; tetrahydrofuran / Erwaermen des Reaktionsgemisches mit 1-Brom-undeca-2,5-diin und Kupfer(I)-chlorid und Erwaermen einer Loesung des danach isolierten Reaktionsprodukts in Aethanol und Tetrahydrofuran mit wss.Schwefelsaeure 2: Lindlar-catalyst; quinoline; ethanol / Hydrogenation View Scheme

undeca-2,5-diyn-1-ol (35378-79-1) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2, quinoline / Pd, Pb, CaCO3 / light petroleum 4: H2, quinoline / Pb, Pd, CaCO3 / light petroleum View Scheme
Multi-step reaction with 3 steps 1: PBr3, Py / diethyl ether / 3 h / Heating 2: (i) EtMgBr, THF, (ii) /BRN= 1754010/, CuCN 3: H2, quinoline / Lindlar catalyst / ethanol / 20 °C View Scheme

(2Z,5Z)-1-bromo-2,5-undecadiene (75817-51-5) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: H2, quinoline / Pb, Pd, CaCO3 / light petroleum View Scheme

undeca-2c,5c-dien-1-ol (75817-50-4) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 3 steps 3: H2, quinoline / Pb, Pd, CaCO3 / light petroleum View Scheme

1-bromooct-2-yne (18495-27-7) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) EtMgBr, THF, (ii) /BRN= 1744118/, CuCl 2: PBr3, Py / diethyl ether / 3 h / Heating 3: (i) EtMgBr, THF, (ii) /BRN= 1754010/, CuCN 4: H2, quinoline / Lindlar catalyst / ethanol / 20 °C View Scheme

1-bromo-2,5-undecadiyne (34498-24-3) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) EtMgBr, THF, (ii) /BRN= 1754010/, CuCN 2: H2, quinoline / Lindlar catalyst / ethanol / 20 °C View Scheme

C4 + linoleic acid (60-33-3) → γ-linolenic + all-cis-6,9,12-octadecatrienoic acid (506-26-3)

C4 + linoleic acid (60-33-3) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

linoleic acid (60-33-3) → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With Saccharomyces cerevisiae expressing Δ6 fatty acid desaturase at 30℃; for 48h; Microbiological reaction; Enzymatic reaction;

cis-6,cis-9,cis-12-octadecatrienoic acid ethyl ester → all-cis-6,9,12-octadecatrienoic acid (506-26-3)

Conditions	Yield
With water; sodium hydroxide In ethanol at 30 - 50℃; for 0.5h; Inert atmosphere;	500 g

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → cis,cis,cis-6,9,12-octadecatrienol (24149-05-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 23℃;	100%
Stage #1: all-cis-6,9,12-octadecatrienoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 18℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0 - 15℃; Inert atmosphere; Sealed tube;	97.4%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	94%
With lithium aluminium tetrahydride In diethyl ether at 25 - 35℃; Inert atmosphere;	90%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 1-hydroxy-cis,cis,cis-6,9,12-octadecatriene + Z,Z,Z-OCTADECA-6,9,12-TRIENOL (GAMMA-LINOLENOL)

Conditions	Yield
With sulfuric acid In diethyl ether; water	A n/a B 94%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6) → 3-γ-linolenoyl-1,2-isopropylidene-sn-glycerol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane for 3h;	93%

N-hydroxyphthalimide (524-38-9) + all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 1,3-dioxoisoindolin-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 14h;	93%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + β-sitosterol (83-46-5) → (6Z,9Z,12Z)-Octadeca-6,9,12-trienoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With pseudomonas lipase In water at 40℃; for 24h; Esterification; Enzymatic reaction;	91.5%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + Coprostanol (80-97-7, 360-68-9, 516-92-7, 516-95-0, 566-84-7, 14615-12-4, 16720-60-8, 17608-41-2, 18769-46-5, 27409-41-2, 56193-35-2, 57759-49-6, 73465-18-6, 103365-91-9, 105119-51-5) → (6Z,9Z,12Z)-Octadeca-6,9,12-trienoic acid (3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With pseudomonas lipase In water at 40℃; for 24h; Esterification; Enzymatic reaction;	90.6%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + cholesterol (57-88-5) → (6Z,9Z,12Z)-Octadeca-6,9,12-trienoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With pseudomonas lipase In water at 40℃; for 24h; Esterification; Enzymatic reaction;	89.5%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + serotonin hydrochloride (153-98-0) → C28H40N2O2 (1002100-41-5)

Conditions	Yield
Stage #1: all-cis-6,9,12-octadecatrienoic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h; Stage #2: serotonin hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Further stages.;	81%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + trimethyleneglycol (504-63-2) → C21H36O3 (184686-99-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	80.1%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + (R)-2,3-dihydroxypropyl n-hexadecanoate (19670-51-0, 32899-41-5, 542-44-9, 5309-46-6) → sn-glycerol 1,2-di-γ-linolenate 3-palmitate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane at 20℃; for 0.5h; Acylation;	70.4%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + glycerol (56-81-5) → 1,3-Dicyclohexylurea (2387-23-7) + tri-γ-linolenin (14465-68-0)

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 20℃;	A n/a B 67%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + methyl L-isoleucyl-L-isoleucinate hydrochloride → methyl ((6Z,9Z,12Z)-octadeca-6,9,12-trienoyl)-L-isoleucyl-L-isoleucinate

Conditions	Yield
Stage #1: all-cis-6,9,12-octadecatrienoic acid; methyl L-isoleucyl-L-isoleucinate hydrochloride With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide for 0.166667h; Stage #2: With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 14h;	64%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → (6Z,9Z)-13-hydroxyoctadeca-6,9-dienoic acid

Conditions	Yield
With linoleate C12 Double-Bond Hydratase gene of L. acidophilus NBRC13951 In aq. phosphate buffer; ethanol at 35℃; for 6h; pH=7; Reagent/catalyst; Enzymatic reaction; regioselective reaction;	60%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 7-[(3Z,6Z)-1-iodo-3,6-dodecadienyl]-2-oxepanone (1210473-44-1)

Conditions	Yield
With bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate In dichloromethane at 40℃; for 18h;	48%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + mycophenolate mofetil (115007-34-6) → C41H59NO8

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 43℃; for 3h;	42.4%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + Tacrolimus (104987-11-3) → C62H97NO13

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 43℃; for 3h;	41.4%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → [6,7-3H]9-cis,12-cis octadecatrienoic acid

Conditions	Yield
With tritium; Lindlar's catalyst In 1,4-dioxane	22%

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → methyl linoleate (16326-32-2)

diazomethane (186581-53-3, 908094-01-9) + oxalyl dichloride (79-37-8) + all-cis-6,9,12-octadecatrienoic acid (506-26-3) → nonadeca-7c,10c,13c-trienoic acid methyl ester (13487-45-1)

Conditions	Yield
(i) (COCl)2, benzene, (ii) /BRN= 102415/, ether, (iii) AgOCOPh, Et3N; Multistep reaction;

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + Pentanedioic acid, monomethyl ester (1501-27-5) → all-cis-Heneicosa-9,12,15-triensaeuremethylester (13487-43-9)

Conditions	Yield
With sodium methylate In methanol at 35 - 40℃; for 6h; (electrolysis);

all-cis-6,9,12-octadecatrienoic acid (506-26-3) + adipic acid monomethyl ester (627-91-8) → all-cis-Docosa-10,13,16-triensaeuremethylester (13487-44-0)

Conditions	Yield
With sodium methylate In methanol at 35 - 40℃; for 6h; Irradiation;

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 6,7,9,10,12,13-hexabromo-octadecanoic acid (103386-22-7)

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → z,z,z-octadeca-6,9,12-trienoyl chloride (54562-14-0)

Conditions	Yield
With Dichloromethyl methyl ether; zinc(II) chloride
With oxalyl dichloride
With oxalyl dichloride In dichloromethane at 20℃;

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 6,7,9,10,12,13-Hexahydroxy-octadecansaeure

Conditions	Yield
(oxidation);

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → 13S-hydroperoxy-6Z,9Z,11E-octadecatrienoic acid (121107-97-9)

Conditions	Yield
With ammonium sulfate soybean lipoxygenase;

all-cis-6,9,12-octadecatrienoic acid (506-26-3) → (5Z,8Z,11Z)-heptadecatrienal

Conditions	Yield
With 2,4-dinitrophenylhydrazone; LCA(long chain aldehydes)-forming activity in Ulva pertusa fronds solubilized by Triton X-100 at 35℃; for 0.25h; Yield given;

Upstream product

• 35378-79-1 undeca-2,5-diyn-1-ol 
• 75817-51-5 (2Z,5Z)-1-bromo-2,5-undecadiene 
• 18495-27-7 1-bromooct-2-yne 
• 34498-24-3 1-bromo-2,5-undecadiyne 
• 31450-14-3 cis-6,cis-9,cis-12-octadecatrienoic acid ethyl ester 
• 60-33-3 linoleic acid 
• 75817-50-4 undeca-2c,5c-dien-1-ol 
• 131867-44-2 3-hex-5-ynyl-2,4,10-trioxa-adamantane 
• 209860-37-7 methyl 11-hydroxyundeca-6,9-diynoate 
• 209860-40-2 11-Bromo-undeca-6,9-diynoic acid methyl ester 
• 16326-31-1 Octadeca-6,9,12-triinsaeure-methylester 
• 56909-02-5 methyl hept-6-ynoate 
• 30964-00-2 hept-6-ynoic acid 
• 2067-33-6 5-bromopentanoic acid 

Downstream Products

• 13487-45-1 all-cis-Nonadeca-7,10,13-triensaeuremethylester 
• 16326-32-2 methyl linoleate 
• 142-62-1 hexanoic acid 
• 60187-52-2 γ-linolenyl mesylate 
• 7324-41-6 cis-8,11,14-eicosatrienoic acid 
• 104926-32-1 N-vanillyl-6Z,9Z,12Z-octadecatrienamide 
• 212843-13-5 C₃₆H₅₈O₃ 
• 2387-23-7 1,3-Dicyclohexylurea 
• 14465-68-0 tri-γ-linolenin 

Relevant articles and documents

PROCESS FOR INCREASING THE STABILITY OF A COMPOSITION COMPRISING POLYUNSATURATED OMEGA-6 FATTY ACIDS

The present invention relates to processes for increasing the stability of compositions comprising polyunsaturated omega-6 fatty acids against oxidation. The processes comprise the following steps: (i) providing a starting composition comprising at least one polyunsaturated omega-6 fatty acid component; (ii) providing a lysine composition; (iii) admixing aqueous, aqueous-alcoholic or alcoholic solutions of starting composition and lysine composition, and subjecting resulting admixture to spray drying conditions subsequently, thus forming a solid product composition comprising at least one salt of a cation derived from lysine with an anion derived from a polyunsaturated omega-6 fatty acid; the product composition exhibiting a solvent content SC selected from the following: SC 5 wt%, SC 3 wt%, SC 1 wt%, SC 0.5 wt%. Compositions obtainable by such spray drying processes and use of such compositions for the manufacture of food, nutritional and pharmaceutical products are further comprised by the present invention.

SOYBEAN VARIETY A1024175

The invention relates to the soybean variety designated A1024175. Provided by the invention are the seeds, plants and derivatives of the soybean variety A1024175. Also provided by the invention are tissue cultures of the soybean variety A1024175 and the plants regenerated therefrom. Still further provided by the invention are methods for producing soybean plants by crossing the soybean variety A1024175 with itself or another soybean variety and plants produced by such methods.

SOYBEAN VARIETY A1025921

The invention relates to the soybean variety designated A1025921. Provided by the invention are the seeds, plants and derivatives of the soybean variety A1025921. Also provided by the invention are tissue cultures of the soybean variety A1025921 and the plants regenerated therefrom. Still further provided by the invention are methods for producing soybean plants by crossing the soybean variety A1025921 with itself or another soybean variety and plants produced by such methods.