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Questions and Answers
Which of the following are sources of lipids?
Which of the following are sources of lipids?
What is the primary function of fixed oils in the lipid classification?
What is the primary function of fixed oils in the lipid classification?
What process involves converting liquid oils to solid fats?
What process involves converting liquid oils to solid fats?
Which of the following describes the reaction of heating lipids?
Which of the following describes the reaction of heating lipids?
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Which lipid classification is typically liquid at room temperature?
Which lipid classification is typically liquid at room temperature?
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What are waxes primarily composed of?
What are waxes primarily composed of?
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What is a common application of sulfated oils?
What is a common application of sulfated oils?
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Which type of fatty acids dominate in the composition of fats?
Which type of fatty acids dominate in the composition of fats?
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What is produced during the saponification process?
What is produced during the saponification process?
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What does a high iodine value indicate about an oil?
What does a high iodine value indicate about an oil?
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Which of the following represents a non-drying oil?
Which of the following represents a non-drying oil?
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How is the ester value calculated?
How is the ester value calculated?
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What does the acid value measure in lipid analysis?
What does the acid value measure in lipid analysis?
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In the context of lipid chemistry, what does a higher Koettsdorfer number indicate?
In the context of lipid chemistry, what does a higher Koettsdorfer number indicate?
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What is the outcome of hydrolyzing acetylated fats?
What is the outcome of hydrolyzing acetylated fats?
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Which chemical reaction is responsible for the rancidity of fats?
Which chemical reaction is responsible for the rancidity of fats?
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Which of the following saturated fatty acids has the highest number of carbon atoms?
Which of the following saturated fatty acids has the highest number of carbon atoms?
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What is the primary source of Azelaic acid?
What is the primary source of Azelaic acid?
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Which of the following fatty acids is a dietary precursor of prostaglandins?
Which of the following fatty acids is a dietary precursor of prostaglandins?
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In terms of lipid classification, what distinguishes a monounsaturated fatty acid?
In terms of lipid classification, what distinguishes a monounsaturated fatty acid?
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Which fatty acid is considered the most abundant?
Which fatty acid is considered the most abundant?
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What is a primary use of sodium morrhuate?
What is a primary use of sodium morrhuate?
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What active constituent is derived from castor oil that acts as a stimulant laxative?
What active constituent is derived from castor oil that acts as a stimulant laxative?
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Which saturated fatty acid has a trivial name 'Capric acid'?
Which saturated fatty acid has a trivial name 'Capric acid'?
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Timnodonic acid, also known as eicosapentaenoic acid (EPA), is classified as which type of ω fatty acid?
Timnodonic acid, also known as eicosapentaenoic acid (EPA), is classified as which type of ω fatty acid?
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What type of reaction is involved in the formation of lipids from fatty acids?
What type of reaction is involved in the formation of lipids from fatty acids?
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Which oil contains 75% oleic acid and 25% linoleic acid?
Which oil contains 75% oleic acid and 25% linoleic acid?
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Which unsaturated fatty acid is an immediate precursor of prostaglandins?
Which unsaturated fatty acid is an immediate precursor of prostaglandins?
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Which of the following is responsible for the male sterility associated with cottonseed oil?
Which of the following is responsible for the male sterility associated with cottonseed oil?
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Which lipid is derived from the pyrolysis of ricinoleic acid?
Which lipid is derived from the pyrolysis of ricinoleic acid?
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Study Notes
Lipids
- Lipids are esters of long-chain fatty acids & alcohols (Lipoids/Lipins)
- General uses
- Emollients (soften the skin)
- Lubricant laxatives as emulsions
- Solvents for IM injections
- Manufacture of soaps (Saponification/Alkali-catalyzed esterification of FA = FA + KOH/NaOH)
- Parenteral nutrient in TPN (highest caloric value = 9 kcal/g)
Classification of Lipids
-
Fixed Oils:
- Esters of FA + Glycerol
- Also known as Triglycerides
- Liquid at room temperature except for Myristica, Theobroma oil
- Mainly unsaturated FA (pi-bonds)
- Source: Plants
- Function: Energy source
-
Fats:
- Esters of FA + High MW alcohol (Cetyl alcohol, Stearyl Alcohol)
- Solid at room temperature except for Jojoba oil - Mainly saturated FA (sigma bonds)
- Source: Animals
- Function: Protection
-
Waxes:
- Solid or semi-solid except for Jojoba oil
- Both saturated & unsaturated
- Source: Plants & Animals
Reaction with Lipids
-
Hydrogenation
- Liquid oil → Solid fats
- Addition of Water → breaks down to ALCOHOL + FATTY ACID
- By passing H gas in presence of Nickel / Palladium through the oil heated @ 160-200C
-
Heating:
- Continuous heating of oil forms ACROLEIN/PROPENAL (presence of glycerol, formation of propenal)
- Distinct odor of acrolein
- Black markings in filter paper → confirm presence of acrolein
-
Sulfation:
- Sulfated / Sulfurated oils
- Used as surfactants wherein temperature is kept down by chilling
-
Oxidation:
- Addition of Oxygen → Rancidity (fats become rancid/panis)
-Saponification: Formation of soap
- Fatty acid + Strong alkali
- NaOH, Ca(OH)2 → hard soap
- KOH → soft soap
USP Quantitative Tests for Lipids
-
Acid Value / Number
- no.of mg of KOH to NEUTRALIZE the free acids and to HYDROLYZE THE ESTERS in 1 g of the substance
-
Ester Value
- mg of KOH needed to SAPONIFY 1g of FA
- DIFFERENCE between SV and AV (saponification value- acid value)
- Ester Value Formula: EV = SV - AV
-
Saponification Value
- no.of mg of KOH needed to NEUTRALIZE the FREE ACIDS and SAPONIFY THE ESTERS in 1 g of the substance
- Saponification Value Formula: SV = AV + EV
-
Koettsdorfer number
- no.of mg of KOH needed to NEUTRALIZE the FREE ACIDS and SAPONIFY THE ESTERS in 1 g of the substance
-
Iodine Value
- g of iodine absorbed under prescribed conditions by 100 g of sample
- Measures the DEGREE OF UNSATURATION of the oil (↑ unsaturation, ↑ drying)
- High iodine value oils partially resinify on exposure to air
- Non-drying: < 100 (Olive oil, Peanut oil, Almond oil, Hazelnut oil, Cocoa butter, Palm oil, Fish oil, Tree oil)
- Semi-drying: 100 - 120 (Cottonseed oil, Sesame oil, Corn oil, Soybean oil, Sunflower oil, Safflower oil, Mustard oil)
- Drying: > 120 (Linseed / Flaxseed oil, Cod liver oil)
-
Acetyl value
- no.of mg of KOH required to NEUTRALIZE the ACETIC ACID freed by the hydrolysis of ACETYLATED fat or other substances
-
Peroxide Value
- no.of mg of ACTIVE OXYGEN per kilogram of a substance
Fatty Acids
- Saturated Fatty Acids
- Monocarboxylic FA
- Formic: Methanoic
- Acetic: Ethanoic
- Propionic: Propanoic
- Butyric: Butanoic
- Valeric: Pentanoic
- CaprOic: Hexanoic
- Enenthic: Heptanoic
- CaprYlic: Octanoic
- Pelargonic: nonanoic
- CarprIc: Decanoic
- Lauric: Dodecanoic
- Myristic: Tetradecanoic
- Palmitic : Hexadecanoic (Most abundant FA)
- Stearic: Octadecanoic
- Arachidic: eicosanoic
- Behenic: Docosanoic
- Lignoceric: Tetracosanoic
- Cerotic: Hexacosanoic
- Unsaturated Fatty Acids
- Lipid | Comments | Omega # | # of C / # of = | Δ Double Bond Position
- ----------- | ----------- | ----------- | ----------- | -----------
- Palmitoleic | | 7 | 16:1 | 9
- Oleic | Cis – Oleic acid ; Trans – Elaidic acid | 9 | 18:1 | 9
- Linoleic | Dietary precursor of PG (Vitamin F) | 6 | 18:2 | 9, 12 (Omega 6)
- Linolenic | | 3 | 18:3 | 𝛼-9, 12, 15 (Omega 3) | 6 | 18:3 | 𝛾-6, 9, 12 (Omega 6)
- Arachidonic | Immediate precursor of PG | 6 | 20:4 | 5, 8, 11, 14 (Omega 6)
- Timnodonic | EPA (eicosapentanoic acid) | 3 | 20:5 | 5, 8, 11, 14, 17
- Cervonic | DHA (docusahexaenoic acid) | 3 | 22:6 | 4, 7, 10, 13, 16, 19
- Linolenic (Alpha : ↓ risk of heart disease, maintain normal heart rhythm and pumping)
- Linolenic (Gamma: stimulate skin and hair growth, maintain bone health, regulate metabolism, and reproductive system)
Notable Fatty Acids
- Fatty Acids | Source | Use
- ----------- | ----------- | -----------
- Sodium morrhuate (morrhuic acid) | Atlantic cod, Gadus morhua | Sclerosing agent (varicose)
- Azelaic acid | Ozonolysis of castor oil (Ricinus communis) | Anti-Acne
- Undecyclinic acid | Pyrolysis of ricinoleic acid from castor oil | Anti-Fungal
Fixed Oils
-
Castor Oil
- Source: Ricinus communis
- Origin: Tangan-tangan
- Active Constituent: Triricinolein – converted to ricinoleic acid, Recinoleic acid - stimulant cathartic (laxative), Ricin - toxic principle, Recinine - alkaloid, Oleic acid – pharmaceutic aid
-
Olive Oil / Oil of Europe / Sweet Oil
- Source: Olea europea
- Origin: First grade virgin (Less Pressure), Second gv (More Pressure), Technical grade (Hot Water), Sulfur grade (CS2 (Carbon Disulfide), Inferior Quality), Tournant oil (Fallen, decomposing fruits, High FA (stronger flavor, darker oil))
- Active Constituent:
-
Peanut oil / Arachis oil
- Source: Arachis hypogea
- Active Constituent: 75% Oleic acid, 25% Linoleic acid
-
Sesame / Teel / Benne oil
- Source: Linga Sesamum indicum
- Active Constituent: Oleic acid, Linoleic acid
-
Corn oil
- Source: Zea mays
- Active Constituent: Oleic acid, Linoleic acid
-
Cottonseed oil
-
Source: Gossypium hirsutum
- Active Constituent: 0.6% Gossypol - Male Sterility, Lecithin - control deranged lipid metabolism
-
Soybean oil
- Source: Glycine soja
- Active Constituent: Stigmasterol - precursor of steroid synthesis
-
Almond oil
- Source: Prunus amygdalus
- Active Constituent: Polyunsaturated fixed oil
- Apricot
- Active Constituent:
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