LIPIDS • Parent HC + -oic acid

- "lipos" = fats or lard Ex: C18 saturated fatty acid C atoms # of double bonds
- collection of organic molecules of varying chemical compositions = octadecane + -oic acid
- grouped together based on solubility in nonpolar solvents = octadecanoic acid (stearic acid) (18:0)
- Carbon chain length Water solubility Melting point C18 monounsaturated fatty acid
- INSOLUBLE in water = octadecene + -oic acid
- HIGHLY SOLUBLE in aprotic organic solvents such as: = octadecenoic acid (oleic acid) (18:1)
○ diethyl ether ○ acetone
○ chloroform ○ methylene chloride C18 unsaturated fatty acid (2 double bonds)
- Open Chain Forms: = octadecadienoic acid (linoleic acid) (18:2)
• Fatty acids • Triacylglycerols • Phosphoacylglycerols C18 unsaturated fatty acid (3 double bonds)
• Sphingolipids • Glycolipids • Lipid-soluble vitamins = octadecatrienoic acid (linolenic acid) (18:3)
• Prostaglandins • Leukotrienes • Thromboxanes
- Cyclic Forms: • If fatty acid is ionized (COOH part), change to -ate (COO-)
• Cholesterol • Steroid hormones • Bile acids Ex: Palmitic acid palmitate
- BIOLOGIC FUNCTIONS: Oleic acid Oleate
• Energy Source - when oxidized, each gram of fat releases 9 kcal
of energy or more than twice the energy
released by carbohydrates(=4 kcal)
• Energy Storage - in the form of triglycerides (TAG) in adipocytes
• Cell Membrane Structural Compounds
- phospholipid bilayer
- phosphoglycerides, sphingolipids and steroids make up the
basic structure of cell membranes
• Digestion - Bile
• Hormones - steroid hormones - CLASSIFICATION:
- Ex: sex hormones, adrenal hormones (corticoids) • Length of Carbon chain
• Vitamins - lipid-soluble vitamins (vitamin A,D,E and K) - long-chain fatty acids - >12 carbons
• Vitamin Absorption - Dietary fat serves as a carrier of lipid- - medium-chain fatty acids - 6-10 carbons
soluble vitamins - short-chain fatty acids - <6 carbons
• Protection - fats as shock absorber • Degree of Unsaturation
• Insulation - prevention of the release of heat - Saturated Fatty Acids
- subcutaneous fat - Genera Formula: CH3(CH2)nCOOH
- obtained from animal sources (SOLID at room temp.)
- SOLID @ RT due to its linear structure of single bonds,
allowing it to be packed tightly
- higher melting point
- NO DOUBLE BONDS - each carbon is being "saturated" w/ H
- Ex: • Capric Acid (10 carbons)
• Lauric Acid (12 carbons) • Palmitic Acid (16 carbons)
• Myristic Acid (14 carbons) • Stearic Acid (18 carbons)

- Oily or greasy nonpolar molecules stored in adipose tissue of the body

- Heterogenous compounds mainly composed of hydrocarbon chains
- Energy-rich organic molecules - Unsaturated Fatty Acids
• more energy than carbohydrates - obtained from plant sources (LIQUID at room temp.)
• long-term; used when all carbohydrates have been exhausted - LIQUID @ RT due to its bent structure of double bonds,
NOT allowing it to be packed tightly
- lower melting point
• Fatty Acids - Saturated - AT LEAST 1 CARBON-CARBON DOUBLE BOND
- Unsaturated - almost all are in CIS configuration
• Glycerides - Neutral glycerides - 2 TYPES:
- Phosphoglycerides 1. Monounsaturated Fatty Acids (MUFA)
• Complex Lipids - Lipolipids - ONLY 1 carbon-carbon double bond
• Nonglyceride - Steroids
- Waxes
- Sphingolipids - Spingomyelin
- Glycolipids
Fatty Acids 2. Polyunsaturated Fatty Acids (PUFA)
- building blocks of lipids - > 1 carbon-carbon double bonds
- naturally occurring monocarboxylic acid
- an unbranched-chain carboxylic acid 18:3 (Δ9,12,15)
- have EVEN # of carbon atoms, usually between 12-20
*2 Double bonds are separated by at least 1 hydrocarbon*
• Acetyl CoA - adds 2 C atoms as it lengthens lipid chain
- AMPHIPATHIC - has both polar and nonpolar
- hydrocarbon chain + terminal carboxyl group

Nonpolar End
O Polar/Hydrophilic End
Hydrophobic End
(Fat-soluble Tail)
R C OH (ACIDIC PROPERTY)

- NOMENCLATURE: • Location of Double Bonds

 - The body CANNOT form C=C before 9th Carbon, making fatty • NO!!!
acids W/ double bonds before 9th Carbon ESSENTIAL - Trans-vaccenic acid - can LOWER risk of heart disease, diabetes
- The body CAN form C=C before 9th Carbon, making fatty & obesity
acids W/O double bonds before 9th Carbon NONESSENTIAL - Omega-3
- in Polyunsaturated Fatty Acids (PUFA): - essential fatty acids
• identified by position of double bond nearest the methyl • body can ONLY make some EPA & DHA from ALA
end (CH3) or omega end (ω) - Eicosopentanoic acid (EPA)
• Δ - shows location of double bonds - Docohexanoic acid (DHA)
- start counting from carboxyl end (COOH as C1) - Alpha-linolenic acid (ALA)
• first = 3 carbons away from methyl end Omega-3 • from flaxseed–most, canola (rapeseed), soybean, walnut,
• first = 6 carbons away from methyl end Omega-6 wheat germ
STEP 1: Find the nearest double bond near omega end - Omega-6
2: Start counting from the omega end - corn, safflower, cottonseed, sesame, sunflower
(Terminal methyl as C1) - Ex: Linoleic acid

OMEGA END (ω) - CHEMICAL REACTIONS OF FATTY ACIDS

/METHYL END • Esterification
- Fatty acids (acid) react with alcohols to form esters and water

• Acid Hydrolysis
- fatty acids are produced from esters
- reverse of esterification
- acid medium

• Saponification
- base-catalyzed hydrolysis of an ester
- alkaline medium
- PRODUCTS: Ionized Salt (SOAP) and Alcohol
- Soaps have a long uncharged hydrocarbon tail and a
negatively-charged terminus (carboxylate terminus)
- form Micelles that dissolve oil and dirt particles

- Omega-3 fatty acid

• unsaturated fatty acid with its endmost double bond 3
carbons away from its methyl end
- Omega-6 fatty acid
• unsaturated fatty acid with its endmost double bond 6
carbons away from its methyl end
- Reaction at Double bonds: (Unsaturated Fatty Acids)
• Hydrogenation
- food industry converts polyunsaturated vegetable oils into
saturated solid fats
- Unsaturated fatty acids converted to saturated fatty acids
- increase degree of saturation as double bonds are converted to
single bonds, melting point

• Partial Hydrogenation
- NOT ALL BONDS are broken
- add H to some but NOT ALL.
- Double bonds in polyunsaturated oil

- CIS-TRANS ISOMERISM
• Cis- Fatty Acid
- Hs are on the same side of double bond
- fold into U-like formation
- naturally occurring
• Trans- Fatty Acid
- Hs are on the opposite sides of double bond
- occur in partially hydrogenated food
- BAD!!! It can lead to CVD by promoting
deposition of fat plaques to blood vessels
= ATHEROSCLEROSIS

- ARE ALL TRANS-FAT BAD?