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Fatty Acid

Aka: Fatty Acid, Dietary Fat, Cooking Oil, Unsaturated Fatty Acid, Saturated Fatty Acid, Monounsaturated Fatty Acid, Essential Fatty Acid, Dietary Fatty Acid, Fatty Acid Metabolism
  1. See Also
    1. Omega-3 Fatty Acid
    2. Omega-6 Fatty Acid
    3. Lipid
    4. Triglyceride
    5. Cholesterol
  2. Definitions
    1. Lipid
      1. Organic molecules containing Hydrocarbons
      2. Poorly soluble in water, but soluble in organic solvents
      3. Examples include free Fatty Acids, Triglycerides, phospholipids
    2. Fatty Acids
      1. Aliphatic hydrocarbon chain with a terminal COOH group
      2. Chains vary in length of 6 to 30 carbons (even numbers, sythesized and broken down in 2 carbon increments)
      3. Major component of fats, with Triglycerides composed of 3 Fatty Acid chains linked to a gylcerol molecule
      4. Fatty Acids may be saturated, monounsaturated or polyunsaturated
    3. Saturated Fatty Acids
      1. Saturated with hydrogen atoms and contain only single bonds between carbons
      2. Palmitic Acid (16 carbons) to stearic Acid (18 carbons) are common saturated fats in humans
    4. Monounsaturated Fatty Acids
      1. Carbon chain with a single pair of missing hydrogens (1 double bond)
      2. Oleic Acid (e.g. Olive oil) is a 18 carbon chain
    5. Polyunsaturated Fatty Acids
      1. Carbon chain with more than 1 pair of missing hydrogens (more than 1 double bond)
      2. Linoleic Acid (e.g. Safflower oil) and Linolenic Acid (e.g. Soybean oil) each are 18 carbon chains
    6. Essential Fatty Acids
      1. Long chain Fatty Acids (18 carbon chains) that cannot be synthesized in humans (specific double bond locations)
      2. Examples include Linoleic Acid and linolenic acid
    7. Triglyceride
      1. Lipid composed of three molecules of Fatty Acid esterified to glycerol
      2. Triglycerides are a non-polar fat synthesized from Carbohydrates or ingested
      3. Triglycerides are High Energy Molecules that are stored for later use in animal adipose cells (fat cells)
    8. Diglyceride
      1. Lipid composed of two Fatty Acid chains esterified to glycerol
    9. Monoglyceride
      1. Lipid composed of a single Fatty Acid chain esterified to glycerol
    10. Phosphoglyceride
      1. Diglyceride with the one free OH group on glycerol attached to a phosphate (Phosphatidate)
      2. Phosphate in turn is attached to serine, Ethanolamine, choline or Inositol
      3. Includes Phosphatidyl Serine, Phosphatidyl Ethanolamine, Phosphatidyl choline, Phosphatidyl Inositol
  3. Physiology: Fatty Acid Metabolism
    1. fatMetabolism.png
    2. Fatty Acids are stored for later energy use, bound to glycerol, as Triglycerides
      1. Insulin promotes Fatty Acid and Triglyceride synthesis (as well as that of glycogen and Proteins)
      2. Insulin promotes fat cell uptake of Glucose, which may be used to synthesize Fatty Acids
      3. Fatty Acids are synthesized by adding, in repeated cycles, 2 carbon atoms (from acetyl CoA) at a time
      4. Three Fatty Acid chains in turn, are bound to one glycerol to form Triglycerides which are stored in fat cells
      5. Insulin reduces fat cell intracellular cAMP, thereby reducing Lipase activity (and Triglyceride breakdown)
    3. Fatty Acids are burned as fuel in the Kreb Cycle (TCA Cycle)
      1. Hypoglycemia triggers ephinephrine, Norepinephrine and Glucagon release
      2. Ephinephrine, Norepinephrine and Glucagon bind cell receptors, trigger cAMP to activate Lipase within fat cells
      3. Lipase breaks down Triglyceride into its glycerol backbone and three Fatty Acid chains
      4. Fatty Acids are degraded (oxidized) by removing, in repeated cycles, 2 carbon atoms at a time (acetyl CoA)
      5. Glycerol may also enter Glycolysis (via Glycerol-3P to Dihydroxyacetone Phosphate to Glyceraldehyde-3P)
      6. Energy from each extracted acetyl coA enters the Kreb Cycle
      7. Each Kreb Cycle generates NADH and FADH2 (total energy 17 ATP per Fatty Acid chain)
    4. Fats offer high energy stores (9 KCals/g) compared with Carbohydrates and Proteins (4 kcals/g)
      1. Triglycerides are non-polar and bind less water (more compact than Carbohydrates, Proteins)
      2. Each triglcyeride contains 3 Fatty Acids, each with 16 to 18 carbons (fueling 24-27 Kreb Cycles)
      3. In addition, glycerol, the Triglyceride backbone, may also fuel Glycolysis and the Kreb Cycle
    5. Fatty Acid Metabolism may also yield Ketones
      1. gluconeogenesis.png
      2. Fatty Acid chains are broken down into multiple acetyl-CoA molecules and a final acetoacetyl CoA
      3. Acetoacetyl CoA may be further broken down into acetyl-CoA for the Kreb Cycle or converted to Ketones
      4. Ketones include Acetoacetate, acetone and hydroxybutyrate
      5. Ketones may be used as fuel by the brain, heart and Muscle
      6. Ketones are typically generated at times of starvation or with Insulin deficiency (Diabetic Ketoacidosis)
  4. Approach: Oils
    1. Use olive oil in non-high heat preparation (cold salads, roasting)
    2. Safflower oil, canola oil and peanut oil are safer oils for cooking, able to withstand high heat
  5. Types: Saturated Fatty Acid
    1. Carbon chain with a maximum number of attached hydrogens (no double bonds)
    2. Risks
      1. Increases LDL Cholesterol (esp. long chain Fatty Acids with >10 carbons)
      2. Increased Coronary Artery Disease risk
    3. Examples
      1. Palmitic Acid (e.g. Palm oil): 16 carbon chain
      2. Stearic Acid (e.g. Animal fat): 18 carbon chain
  6. Types: Monounsaturated Fatty Acids
    1. Carbon chain with a single pair of missing hydrogens (1 double bond)
    2. Benefits
      1. Decreased risk of cardiovascular disease
      2. Lowers LDL Cholesterol
    3. Examples
      1. Oleic Acid (e.g. Olive oil): 18 carbon chain
  7. Types: Polyunsaturated Fatty Acids
    1. Carbon chain with more than 1 pair of missing hydrogens (more than 1 double bond)
    2. Benefits
      1. Specific to Omega-3 Fatty Acids (sub-type of polyunsaturated fats)
    3. Risks
      1. Increased weight gain
      2. Gallstone formation
    4. Examples
      1. Linoleic Acid (e.g. Safflower oil): 18 carbon chain (Essential Fatty Acid)
      2. Linolenic Acid (e.g. Soybean oil): 18 carbon chain (Essential Fatty Acid)
      3. Arachidonic Acid (e.g. Meat and dairy products): 20 carbon chain (Essential Fatty Acid)
      4. Eicosapentaenoic Acid (e.g. Fish Oil): 20 carbon chain (Essential Fatty Acid)
      5. Docosahexaenoic Acid (e.g. Fish Oil): 22 carbon chain (Essential Fatty Acid)
  8. Types: Trans-Fatty Acids
    1. Double bond of unsaturated fat is in trans-configuration
      1. Hydrogens are on opposite sides of the double bonds
      2. Contrast with cis-configuration where the hydrogens are on same side of the bond
    2. Synthesized via hydrogenation (artificial addition of hydrogens)
      1. Converts liquid vegetable oils to semi-solids or solid fats
    3. Risks
      1. Directly associated with increased risk of heart disease
      2. Increase LDL Cholesterol and Serum Triglycerides
      3. Decreases HDL Cholesterol
    4. Examples
      1. Elaidic Acid (e.g. margarines): 18 carbon chain (this is the trans form of oleic acid)
  9. Prevention: Dietary Recommendations
    1. Keep Fatty Acid intake less than 30% of total daily calories
    2. Limit saturated fat to less than 7% of total daily calories
    3. Limit trans-fats to less than 1% of total daily calories
  10. References
    1. Goldberg (2001) Clinical Biochemistry, Medmasters, Miami, p. 17-23
    2. Guyton and Hall (2006) Medical Physiology, 7th Ed, Elsevier Saunders, Philadelphia, p. 829-58
    3. Hu (2001) J Am Coll Nutr 20(1): 5-19 [PubMed]
    4. White (2009) Am Fam Physician 80(4): 345-50 [PubMed]

Fatty Acids (C0015684)

Definition (CHV) a major component of fats
Definition (CHV) a major component of fats
Definition (NCI) Monobasic, aliphatic acids with varying chain lengths between 6 and 30. Fatty acids are a major constituent in all fats and can be either saturated, monounsaturated, or polyunsaturated. Saturated and monounsaturated fatty acids are synthesized by the body, whereas polyunsaturated fatty acids are not and must be obtained in the diet. (NCI)
Definition (NCI_NCI-GLOSS) A major component of fats that are used by the body for energy and tissue development.
Definition (MSH) Organic, monobasic acids derived from hydrocarbons by the equivalent of oxidation of a methyl group to an alcohol, aldehyde, and then acid. Fatty acids are saturated and unsaturated (FATTY ACIDS, UNSATURATED). (Grant & Hackh's Chemical Dictionary, 5th ed)
Definition (CSP) organic, monobasic acids derived from hydrocarbons by the equivalent of oxidation of a methyl group to an alcohol, aldehyde, and then acid; chemically R COOH where R is an aliphatic moiety; the common fatty acids of biological origin are linear chains with an even number of carbon atoms.
Concepts Lipid (T119)
MSH D005227
SnomedCT 31979005
LNC LP14488-8, MTHU010738
English Fatty Acids, Acids, Fatty, Fatty Acids [Chemical/Ingredient], fatty acid, fatty acids, Fatty acids, Fatty acid, Fatty acid (substance), Fatty acid, NOS, Fatty Acid, FATTY ACID
Swedish Fettsyror
Czech kyseliny mastné, mastné kyseliny
Finnish Rasvahapot
Japanese 脂肪酸, 脂肪族カルボン酸
Polish Kwasy tłuszczowe, Kwasy tłuszczowe nasycone
Norwegian Fettsyrer
Spanish ácido graso (sustancia), ácido graso, Ácidos Grasos
French Acides gras
German Fettsäuren
Italian Acidi grassi
Portuguese Ácidos Graxos
Derived from the NIH UMLS (Unified Medical Language System)

Fatty Acids, Essential (C0015686)

Definition (NCI) Used to indicate a fatty acid that is not efficiently synthesized by humans and must be included in the diet.
Definition (MSH) Long chain organic acid molecules that must be obtained from the diet. Examples are LINOLEIC ACIDS and LINOLENIC ACIDS.
Definition (CSP) long chain organic acid molecules that must be obtained from the diet.
Concepts Lipid (T119)
MSH D005228
English Acids, Essential Fatty, Fatty Acids, Essential, essential fatty acid, Essential Fatty Acids, Essential_Fatty_Acid, Fatty Acids, Essential [Chemical/Ingredient], acids essential fatty, Essential fatty acids, Essential Fatty Acid, essential fatty acids
Swedish Fettsyror, essentiella
Czech kyseliny mastné esenciální, EFAs, esenciální mastné kyseliny
Finnish Välttämättömät rasvahapot
Polish Kwasy tłuszczowe eteryczne
French Acides gras essentiels, Acides gras indispensables
German Fettsäuren, essentielle
Italian Acidi grassi essenziali
Portuguese Ácidos Graxos Essenciais
Spanish Ácidos Grasos Esenciales
Derived from the NIH UMLS (Unified Medical Language System)

Fatty Acids, Monounsaturated (C0015687)

Definition (NCI_CRCH) A class of dietary fatty acids containing one double bond.
Definition (MSH) Fatty acids which are unsaturated in only one position.
Concepts Lipid (T119) , Biologically Active Substance (T123)
MSH D005229
SnomedCT 102718001
LNC LP33081-8, MTHU016383
English Acids, Monounsaturated Fatty, Fatty Acids, Monounsaturated, Monounsaturated Fatty Acids, MUFA - Monounsat fatty acid, Fatty Acid, Total Monounsaturated, Monounsaturated Fatty Acid, Fatty Acids, Monounsaturated [Chemical/Ingredient], monounsaturated fatty acid, monounsaturated fatty acids, Fatty acids.monounsaturated, MUFA, Monounsaturated fatty acid, MUFA - Monounsaturated fatty acid, Monounsaturated fatty acid (substance)
Swedish Fettsyror, enkelomättade
Czech kyseliny mastné mononenasycené
Finnish Yksittäistyydyttymättömät rasvahapot
Croatian Not Translated[Fatty Acids, Monounsaturated]
Polish Kwasy tłuszczowe mononienasycone
Spanish ácido graso monosaturado (sustancia), ácido graso monosaturado, Ácidos Grasos Monoinsaturados
French Acides gras monoinsaturés
German Einfach ungesättigte Fettsäuren, Fettsäuren, einfach ungesättigte
Italian Acidi grassi monoinsaturi
Portuguese Ácidos Graxos Monoinsaturados
Derived from the NIH UMLS (Unified Medical Language System)

Fatty Acids, Unsaturated (C0015690)

Definition (CSP) fatty acids in which the carbon chain contains one or more douple or triple carbon-carbon bonds.
Definition (MSH) FATTY ACIDS in which the carbon chain contains one or more double or triple carbon-carbon bonds.
Concepts Lipid (T119)
MSH D005231
SnomedCT 21625008
English Acids, Unsaturated Fatty, Fatty Acids, Unsaturated, Unsaturated Fatty Acids, unsaturated fatty acid, unsaturated fatty acids, unsaturated fatty acids (medication), dietary supplements fatty acids (unsaturated), Fatty Acids, Unsaturated [Chemical/Ingredient], Unsaturated fatty acids, Unsaturated fatty acid, Unsaturated fatty acid (substance), Unsaturated fatty acid, NOS
Swedish Fettsyror, omättade
Finnish Tyydyttymättömät rasvahapot
Japanese 脂肪酸-不飽和, 多価不飽和脂肪酸, 不飽和脂肪族カルボン酸, 不飽和脂肪酸, 脂肪酸-多価不飽和
Spanish Ácidos Grasos Insaturados, Ácidos Grasos no Saturados, ácido graso insaturado (sustancia), ácido graso insaturado
Portuguese Ácidos Graxos Insaturados, Ácidos Graxos não Saturados
Polish Kwasy tłuszczowe nienasycone, Witamina F
Czech kyseliny mastné nenasycené, nenasycené mastné kyseliny
Norwegian Fettsyrer, umettede, Umettede fettsyrer
French Acides gras insaturés
German Ungesättigte Fettsäuren
Italian Acidi grassi insaturi
Derived from the NIH UMLS (Unified Medical Language System)

Saturated fat (C0597423)

Definition (NCI_NCI-GLOSS) A type of fat with certain chemical properties that is usually solid at room temperature. Most saturated fats come from animal food products, but some plant oils, such as palm and coconut oil, also contain high levels. Eating saturated fat increases the level of cholesterol in the blood and the risk of heart disease.
Definition (NCI_CRCH) A class of dietary fatty acids containing no double bonds.
Definition (CSP) fatty acid with no double or triple bonds.
Definition (CSP) fat with no double or triple bonds.
Concepts Lipid (T119) , Food (T168)
MSH D005227
SnomedCT 436841000124103, 102719009
LNC LP33079-2, MTHU016382
English Acids, Saturated Fatty, Saturated Fatty Acids, saturated fatty acid, Saturated Fatty Acid, Saturated fat, fats saturated, acids fatty saturated, saturated fatty acids, fat saturated, saturated fat, Saturated fat (substance), Fatty acids.saturated, Saturated fatty acid, Saturated fatty acid (substance), Saturated fatty acid, NOS, Fatty Acids, Saturated
Portuguese Ácidos Graxos Saturados
Spanish Ácidos Grasos Saturados, ácido graso saturado (sustancia), ácido graso saturado
German Fettsäuren, gesättigte
French Acides gras saturés
Italian Acidi grassi saturi
Czech nasycené mastné kyseliny
Norwegian Fettsyrer, mettede, Mettede fettsyrer
Derived from the NIH UMLS (Unified Medical Language System)

Study of Nutrition, Fats (C1527016)

Definition (NCI) Role of dietary fats in cancer causation or prevention and in general health.
Concepts Research Activity (T062)
English Dietary Fat, Lipid Nutrition, Fats, Nutrition, Fats, Study of Nutrition, Fats
Derived from the NIH UMLS (Unified Medical Language System)

Dietary Fatty Acid (C2348264)

Definition (NCI_CRCH) Compound found in food containing from 4 to 24 carbons in a hydrocarbon chain, including a carboxyl group (-COOH) at one end and a methyl group (-CH3) at the other end.
Definition (NCI) A class of organic compound that is found in various foods, comprising an alkyl chain with a carboxylic acid end. Naturally occurring dietary fatty acids have a carbon backbone that ranges in length from 4 to 24 units.
Concepts Lipid (T119)
English Dietary Fatty Acid, Total Dietary Fatty Acid
Derived from the NIH UMLS (Unified Medical Language System)

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