Lipids Brochure
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Please inquire for pricing and availability of listed products to our local sales representatives. 1 Lipids Fatty Acyls Lipids form a broad category of biomolecules which constitute an O O essential part of living organisms in addition to carbohydrates CH3 OH CH3 ONa and proteins. This brochure introduces lipids and related Fatty Acids Fatty Acid Sodium Salts O O O substances such as fatty acids and their derivatives. The CH3 Cl OH OH biosynthesis of fatty acids involves the condensation of malonyl- Fatty Acid Halides Fatty Dicarboxylic Acids 1) CoA (or methylmalonyl CoA) with acyl CoA as a primer. O Carboxylic acids with chains of 4 or more carbons are referred to CH3 H CH3 OH Fatty Aldehydes Fatty Alcohols as fatty acids while those with 10 or more carbons are called O O 2) 3) higher fatty acids. Lipids are classified as the below. CH3 OCH3 CH3 OCH2CH3 Fatty Acid Methyl Esters Fatty Acid Ethyl Esters CH3 CH3 Saturated/Unsaturated Fatty Acids CH3 H Fatty Acid Sodium Salts CH3 CH H Fatty Acyls Fatty Acids Fatty Acid Halides 3 O Fatty Aldehydes Fatty Dicarboxylic Acids H H Fatty Alcohols CH3 O Fatty Acid Esters Fatty Acid Methyl Esters Fatty Acid Cholesteryl Esters Eicosanoids Fatty Acid Ethyl Esters O Fatty Acid Cholesteryl Esters CH3 O CH3 Waxes Waxes Glycerolipids Glycerides O Phospholipids Glycerophospholipids COOH CH3 Glycolipids HO OH Eicosanoids Sphingolipids Lipid Extracts Glycerolipids O O CH3 O O CH3 CH3 O O Glycerides Phospholipids O CH CH O 3 3 N CH3 O O P O CH3 CH3 O O O Glycerophospholipids Glycolipids HO OH O O HN CH HO 3 OH HO O CH3 OH Sphingoglycolipids Sphingolipids OH CH CH O 3 3 N CH3 O P O CH3 CH3 NH O O Sphingophospholipids Figure 1. Classification of Lipids 2 Please inquire for pricing and availability of listed products to our local sales representatives. Lipids ● Functional Roles ● Analysis Fatty acids exist in living organisms mainly as esters of glycerol GC is the most frequently used technique for the analysis of fatty and triacylglycerols which occur as a major form of energy acids. However, their direct analysis appears to be difficult owing storage in adipose tissue. Triacylglycerols are found in living to their low volatility in electron impact (EI) ionization mass organisms as mixtures of acyl groups with different number of spectrometry under normal condition. They can however be carbons and are difficult in most cases to isolate as a single easily detected by GC-MS method upon derivatization to their substance. Moreover, fatty acids also exist in living organisms in methyl esters. the form of cholesteryl esters which constitute an essential The several methylation methods include the treatment of the component of cell membranes where it is required to establish free fatty acids with boron trifluoride-ether complex in methanol proper membbrane permeability and fluidity. or with trimethylsilyldiazomethane, etc. Free fatty acids are known to suppress cell-growth at an order of The GC on-column method is a simple method that uses a 0.1mM and above, therefore considerable attention should be methanolic solution of trimethylsulfonium hydroxide or paid during their administration to cells.4) 3-(trifluoromethyl)phenyltrimethylammonium hydroxide to analyze the fatty acid component of lipids such as glycerolipids. ● Storage Precautions Unsaturated fatty acids like oleic acid are known to undergo ● Solubility aerial oxidation to produce peroxides. Opened bottles of In general, the solubility of fatty acids in water decreases as the unsaturated fatty acids and their derivatives should be stored in carbon number increases. the refrigerator or frozen with inert gas such as nitrogen or argon. Fatty acid esters and glycerolipids are insoluble in water but Moreover the tendency to oxidation increases as the degree of soluble in ethanol, chloroform and diethyl ether. They can be unsaturation in the fatty acids increases. added to the buffer solution as a dimethyl sulfoxide solution to examine their activity in living organisms. Please take caution that the solution becomes suspended as the concentration level ● Derivatives of the dissolved substance increases. It is recommended to Fatty acid methyl esters are the most widely used fatty acid define the optimal concentration level and volume of addition in derivatives in analytical chemistry due to their ease of handling in advance. Sodium salts of fatty acid are more water-soluble than organic solvents as compared to the highly polar free fatty acids. the free fatty acids. Long-chain fatty acid salts tend to form Moreover their analysis by TLC, gas chromatography (GC) and micelles. liquid chromatography (LC) can be improvised by suppressing tailing. Although fatty acid ethyl esters are rarely used for analysis as compared to the methyl esters, they offer an advantage since their method of preparation from fatty acids involves the use of the less toxic ethanol instead of methanol. For instance, eicosapentaenoic acid which is used as a hyperlipemia medicine is being supplied as ethyl ester. Ethyl esters of lower to middle- chain fatty acids can be also employed in the fragrance industry. Sodium salts of fatty acids can be obtained as saponification products of lipids and are widely used in daily life as an ingredient of soap owing to their amphiphilicity and surfactant properties. References 1) P. M. Dewick, in Medicinal Natural Products, 3rd ed., John Wiley & Sons, Chichester, 2009, p. 39. 2) Biochemical Nomenclature and Related Documents, 2nd ed., Portland Press, London, 1992, p. 180. 3) E. Fahy, S. Subramaniam, H. A. Brown, C. K. Glass, A. H. Merrill, Jr., R. C. Murphy, C. R. H. Raetz, D. W. Russell, Y. Seyama, W. Shaw, T. Shimizu, F. Spener, G. van Meer, M. S. VanNieuwenhze, S. H. White, J. L. Witztum, E. A. Dennis, J. Lipid Res. 2005, 46, 839. 4) C. W. Sheu, D. Salomon, J. L. Simmons, T. Sreevalsan, E. Freese, Antimicrob. Agents Chemother. 1975, 7, 349. Please inquire for pricing and availability of listed products to our local sales representatives. 3 Lipids A2035 300mL O Fatty Acyls Fatty Acids Saturated Fatty Acids CH3 OH Acetic Acid CAS RN: 64-19-7 P0500 25mL 500mL B0754 25mL 500mL V0003 25mL 500mL H0105 25mL 500mL H0030 25mL 500mL O O O O O CH3 CH3 CH3 OH CH3 OH OH CH3 OH OH Propionic Acid Butyric Acid Valeric Acid Hexanoic Acid Heptanoic Acid CAS RN: 79-09-4 CAS RN: 107-92-6 CAS RN: 109-52-4 CAS RN: 142-62-1 CAS RN: 111-14-8 O0027 25mL 500mL P0952 25mL 100mL 500mL D0017 25g 400g U0004 25g 250g L0011 25g 500g O O O O O CH3 CH3 CH3 OH OH CH3 OH OH CH3(CH2)10 C OH n-Octanoic Acid Nonanoic Acid Decanoic Acid Undecanoic Acid Lauric Acid CAS RN: 124-07-2 CAS RN: 112-05-0 CAS RN: 334-48-5 CAS RN: 112-37-8 CAS RN: 143-07-7 T0412 25g 100g 500g M0476 25g 500g P0035 25g 100g 500g P0002 25g 500g P1145 5g O O O O O CH3(CH2)11 C OH CH3(CH2)12 C OH CH3(CH2)13 C OH CH3(CH2)14 COH CH3(CH2)14 COH Tridecanoic Acid Myristic Acid Pentadecanoic Acid Palmitic Acid (>97.0%) Palmitic Acid (>99.5%) CAS RN: 638-53-9 CAS RN: 544-63-8 CAS RN: 1002-84-2 CAS RN: 57-10-3 CAS RN: 57-10-3 H0019 25g 100g 500g S0163 25g 500g N0283 10g 25g E0006 1g 25g H0010 1g 10g O O O O O CH3(CH2)15 C OH CH3(CH2)16 C OH CH3(CH2)17 C OH CH3(CH2)18 C OH CH3(CH2)19 C OH Heptadecanoic Acid Stearic Acid Nonadecanoic Acid Arachidic Acid Heneicosanoic Acid CAS RN: 506-12-7 CAS RN: 57-11-4 CAS RN: 646-30-0 CAS RN: 506-30-9 CAS RN: 2363-71-5 D0963 25g 500g B1248 5g 25g B1747 5g T0402 1g 10g T0076 1g 5g 25g O O O O O CH3(CH2)20 COH CH3(CH2)20 COH CH3(CH2)20 COH CH3(CH2)21 C OH CH3(CH2)22 C OH Behenic Acid (>80.0%) Behenic Acid (>95.0%) Behenic Acid (>99.0%) Tricosanoic Acid Lignoceric Acid CAS RN: 112-85-6 CAS RN: 112-85-6 CAS RN: 112-85-6 CAS RN: 2433-96-7 CAS RN: 557-59-5 P0882 1g 5g C0829 1g 10g H0971 100mg 1g 5g M1342 100mg N0662 1g 5g O O O O O CH3(CH2)23 C OH CH3(CH2)24 C OH CH3(CH2)25 C OH CH3(CH2)26 C OH CH3(CH2)27 COH Pentacosanoic Acid Cerotic Acid Heptacosanoic Acid Octacosanoic Acid Nonacosanoic Acid CAS RN: 506-38-7 CAS RN: 506-46-7 CAS RN: 7138-40-1 CAS RN: 506-48-9 CAS RN: 4250-38-8 M0595 100mg 1g 5g C0416 25g 100g P0345 5mL 25mL P1072 5mL 25mL O O O O Unsaturated CH CH CH (CH ) C OH 3 3 3 2 28 Fatty Acids CH3 OH OH OH Melissic Acid Crotonic Acid trans-2-Pentenoic Acid trans-3-Pentenoic Acid CAS RN: 506-50-3 CAS RN: 107-93-7 CAS RN: 13991-37-2 CAS RN: 1617-32-9 4 Please inquire for pricing and availability of listed products to our local sales representatives. Lipids H0383 25g 250g H0077 25g H0426 5mL H0427 5mL 25mL O0004 10mL O O O O O CH3 OH CH3 OH CH3(CH2)3CH CH C OH CH3(CH2)2CH CHCH2 C OH CH3 OH 2-Heptenoic Acid trans-2-Hexenoic Acid trans-3-Hexenoic Acid (contains 3-Heptenoic Acid) 3-Heptenoic Acid trans-2-Octenoic Acid CAS RN: 13419-69-7 CAS RN: 1577-18-0 CAS RN: 18999-28-5 CAS RN: 29901-85-7 CAS RN: 1871-67-6 O0070 5mL 25mL N0426 25mL N0312 1mL 5mL D0098 5mL 25mL D1186 5mL O O O O O CH (CH ) CH CHCH COH CH3(CH2)3CH CHCH2 COH CH3(CH2)5CH CH COH CH3(CH2)4CH CHCH2 C OH CH3 OH 3 2 5 2 3-Octenoic Acid 2-Nonenoic Acid 3-Nonenoic Acid trans-2-Decenoic Acid 3-Decenoic Acid CAS RN: 1577-19-1 CAS RN: 3760-11-0 CAS RN: 4124-88-3 CAS RN: 334-49-6 CAS RN: 15469-77-9 D4449 5mL 25mL U0032 5g U0007 25g 400g T0759 5g 25g H0428 1g 5g O O O O O CH2 OH CH3(CH2)4CH CH(CH2)2 C OH CH3(CH2)7CH CH COH CH3(CH2)9CH CH C OH CH3(CH2)12CH CH C OH 4-Decenoic Acid 2-Undecenoic Acid 10-Undecenoic Acid 2-Tridecenoic Acid Gaidic Acid CAS RN: 26303-90-2 CAS RN: 4189-02-0 CAS RN: 112-38-9 CAS RN: 6969-16-0 CAS RN: 629-56-1 H0072 100mg 1g O0010 5g 25g O0009 1g O0011 25mL 500mL O0180 5mL 25mL COOH COOH COOH COOH COOH CH3