Carbohydrates and their Classification

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Questions and Answers

What is the general ratio of hydrogen and oxygen in carbohydrates?

  • Twice the hydrogen as oxygen
  • Same as in lipids
  • Same as in water (correct)
  • Equal parts hydrogen and oxygen

Which of the following carbohydrates yields two monosaccharide molecules upon hydrolysis?

  • Disaccharides (correct)
  • Monosaccharides
  • Polysaccharides
  • Trisaccharides

Which term describes a monosaccharide with 6 carbon atoms?

  • Pentose
  • Hexose (correct)
  • Triose
  • Tetrose

Which polysaccharide, composed of glucose units joined by beta-1,4 linkages, forms the primary cell walls in plants?

<p>Cellulose (D)</p> Signup and view all the answers

What is the name of the monosaccharide that results from the hydrolysis of inulin?

<p>Fructose (B)</p> Signup and view all the answers

Which of the following best describes the structural difference between glucose and fructose?

<p>Glucose is an aldohexose while fructose is a ketohexose. (D)</p> Signup and view all the answers

What is the primary source of sucrose?

<p>Sugar cane and sugar beets (A)</p> Signup and view all the answers

What is the function of lime in sucrose production from sugar cane?

<p>To neutralize plant acids (D)</p> Signup and view all the answers

Which of the following is a major use of sucrose in the pharmaceutical industry?

<p>As a preservative (D)</p> Signup and view all the answers

How is dextrose typically obtained for pharmaceutical use?

<p>Controlled enzymatic hydrolysis of starch (A)</p> Signup and view all the answers

What is the typical purity range of crystalline dextrose used for parenteral applications?

<p>99.5% to 100% (B)</p> Signup and view all the answers

Which of the following is a common use of dextrose in pharmaceutical preparations?

<p>Anticoagulant (A)</p> Signup and view all the answers

What are the two main structural components of starch?

<p>Amylose and amylopectin (A)</p> Signup and view all the answers

What type of glycosidic bond links the glucopyranose units in amylose?

<p>Alpha 1,4-glycosidic bonds (A)</p> Signup and view all the answers

Which agent is used to complex with amylose to effect its separation from amylopectin?

<p>Iodine (A)</p> Signup and view all the answers

What is the effect of alpha-amylase on starch?

<p>Random splitting of alpha-1,4-glucosidic linkages (C)</p> Signup and view all the answers

Which of these statements best describes how starch forms a translucent sol?

<p>Starch granules swell and rupture in boiling water. (C)</p> Signup and view all the answers

Which family of plants are corn and wheat, sources of starch, classified under?

<p>Gramineae (B)</p> Signup and view all the answers

What term is used to describe starch that has been chemically or mechanically processed to rupture all or part of the granules in the presence of water?

<p>Pregelatinized starch (C)</p> Signup and view all the answers

What is the primary use of hetastarch, characterized by approximately 90% amylopectin?

<p>As a plasma expander (B)</p> Signup and view all the answers

What is the main carbohydrate present in liquid glucose?

<p>Dextrose (B)</p> Signup and view all the answers

From what source is fructose usually obtained commercially?

<p>Enzymatic isomerization of glucose (C)</p> Signup and view all the answers

In what primary application is fructose used due to its lower urinary secretion compared to glucose?

<p>As a food for diabetic patients (A)</p> Signup and view all the answers

What is a significant characteristic of lactose regarding its composition?

<p>Composed of glucose and galactose (C)</p> Signup and view all the answers

What enzyme is required to hydrolyze lactose into its constituent monosaccharides?

<p>Lactase (B)</p> Signup and view all the answers

Which of the following describes the primary pharmaceutical use of lactose?

<p>Tablet diluent (B)</p> Signup and view all the answers

For what diagnostic purpose is xylose approved by the FDA?

<p>Evaluating intestinal absorption (D)</p> Signup and view all the answers

How is xylose typically obtained for commercial use?

<p>Boiling corn cobs with dilute acid (C)</p> Signup and view all the answers

Which of the following describes the primary use of inulin?

<p>Evaluation of renal function (A)</p> Signup and view all the answers

What type of linkage characterizes the residues in inulin?

<p>Beta-2,1-glycosidic bonds (A)</p> Signup and view all the answers

What enzyme leads to the formation of dextran?

<p>Dextran sucrase (D)</p> Signup and view all the answers

What is the typical use of dextrans with average molecular weights of 40,000 to 75,000?

<p>As a plasma expander (B)</p> Signup and view all the answers

What is the primary use of iron dextran injection?

<p>Treatment of iron deficiency (C)</p> Signup and view all the answers

How is caramel primarily produced?

<p>Heating sucrose or glucose (B)</p> Signup and view all the answers

What is the primary industrial use of caramel?

<p>Colorant (A)</p> Signup and view all the answers

What makes powdered cellulose a suitable excipient in self-binding tablets?

<p>Its ability to act as a diluent and disintegrant (A)</p> Signup and view all the answers

What is the primary application of methylcellulose in ophthalmic solutions?

<p>Topical protectant (A)</p> Signup and view all the answers

Which of the following is most likely a property of gums with linear polymer structures compared to those with branched structures?

<p>Lower solubility (D)</p> Signup and view all the answers

From what source is tragacanth obtained?

<p>Plant exudate (D)</p> Signup and view all the answers

What is the property of tragacanth that makes it useful in acidic conditions?

<p>It is the most resistant hydrocolloid to acid hydrolysis (A)</p> Signup and view all the answers

What characteristic makes branched hydrocolloids more suitable for immediate drug use after reconstitution compared to linear hydrocolloids?

<p>They readily rehydrate. (A)</p> Signup and view all the answers

What polysaccharide is the main component of Acacia/gum arabic?

<p>Arabin (C)</p> Signup and view all the answers

Which property makes acacia particularly useful as an emulsifying agent compared to other hydrocolloids?

<p>Good stability over a wide pH range (A)</p> Signup and view all the answers

From what source is sodium alginate typically extracted?

<p>Brown seaweeds (C)</p> Signup and view all the answers

Which of the following is a common application of sodium alginate due to its properties?

<p>Suspending agent (B)</p> Signup and view all the answers

From what is Agar extracted?

<p>Red algae (C)</p> Signup and view all the answers

What makes agar useful as a gel in bacteriologic culture media?

<p>It is non-toxic and stable at sterilization temperatures (C)</p> Signup and view all the answers

What substances yield the gelling power and viscosity of Pectin

<p>The number of galacturonjc acid units in the molecules (C)</p> Signup and view all the answers

A researcher is investigating novel carbohydrate-based excipients for a new drug formulation aimed at sustained release. They discover a complex polysaccharide that exhibits strong intermolecular hydrogen bonding and is poorly soluble in most solvents. When this polysaccharide is used in tablet formulation, what primary challenge would the researcher most likely encounter?

<p>Difficulty in achieving consistent drug distribution within the tablet matrix. (C)</p> Signup and view all the answers

Flashcards

What are Carbohydrates?

Aldehyde or ketone alcohols containing carbon, hydrogen, and oxygen.

What are Monosaccharides?

Cannot be hydrolyzed into simpler carbohydrates.

What are Disaccharides?

Yields two monosaccharide molecules on hydrolysis.

What are Sugars?

Sugars are crystalline, soluble in water, and sweet tasting.

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What are Polysaccharides?

Complex carbohydrates represented by starch, inulin, and cellulose; can be hydrolyzed.

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What are Pentoses?

General formula CHO; products resulting from hydrolysis of pentosans.

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What is Cellulose?

The plant's structural skeleton from carbohydrate material. Cell walls in plant cells for example.

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What is a Glucosan?

Hexose yielding glucose when broken down.

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What is a Fructosan?

Hexose yielding fructose when broken down.

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What are monosaccharides?

Simple sugar that is chemically a ketonic or aldehydic substitution product of a polyhydroxy alcohol.

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What is glyceraldehyde?

An aldehydic or ketonic type of triose usually in the form of phosphate esters

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What monosaccharides occur freely in plants?

Fructose (levulose) and glucose (dextrose)

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What happens when Sucrose is hydrolyzed?

Sucrose yields invert sugar (glucose and fructose).

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What is Maltose?

Produced by hydrolysis of starch during barley and other grain germination; yields 2 glucose molecules.

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Where does Sucrose come from?

From Saccharum officinarum (sugar cane) and Beta vulgaris (sugar beets).

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What are the USES of Sucrose?

Pharmaceutical necessity for syrups, demulcent, and nutrient.

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What is Dextrose/Glucose?

Sugar that occurs in grapes and fruits; obtained by enzymatic hydrolysis of starch.

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What is the use of Dextrose?

It is an ingredient in dextrose injections and nutrient.

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What is Starch?

Mixture of amylose and amylopectin with alpha 1,4 glycosidic bonds.

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What does alpha-Amylase do?

hydrolyzed by a-1,4-glucosidic linkages producing glucose, maltose, and amylopectin.

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What is the Use for Starch?

Starch for dusting powders, tablet filler, binder, disintegrant, antidote for iodine poisoning.

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What is Pregelatinized Starch?

Starch chemically or mechanically processed to rupture granules. Soluble in cold water.

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What is Fructose?

From inversion of sucrose or hydrolysis of inulin, ketone sugar in fruits and honey.

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What is Lactose?

Cow's milk contains lactose

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What is Pectin in medicine?

Derived from lemon peel; used as protectant and in antidiarrheal formulations.

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What is Xylose?

Pentose obtained by boiling corn cobs; used to evaluate intestinal absorption.

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What is Inulin?

D-fructofuranose from family Compositae; used for renal function evaluation.

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What is Dextran?

Used in 6% solutions as plasma expanders in shock; formed from sucrose.

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What is Caramel?

Concentrated aqueous solution from heating sucrose or glucose.

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What is Powdered Cellulose?

Purified, mechanically disintegrated cellulose; used as self-binding tablet diluent.

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What is Microcrystalline Cellulose?

Purified, partially depolymerized cellulose used as a diluent.

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What is Methylcellulose?

Used as artificial tears or contact lens solutions

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What are Gums and Mucilages?

Natural plant hydrocolloids classified as anionic or nonionic polysaccharides; protection after injury.

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Composition of Gums?

Heterogeneous in composition, containing arabinose, galactose, glucose, mannose, xylose, and uronic acids.

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Solubility of Gums?

Linear polymers are less soluble than branched giving more viscosity.

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What is Acacia' Origin?

Shrub or tree exudates.

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What are marine gums?

Marine gums (agar, algin, carrageenan).

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What is Tragacanth?

Derived from Astragalus; suspending agent and resistant to acid hydrolysis.

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What is Acacia?

Gum arabic from African Acacia species; emulsifying and suspending agent.

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What is Sodium Alginate?

Brown seaweed extract; suspending agent in food and cosmetics.

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What is Agar?

Dried hydrophilic colloidal substance extracted from Gelidium cartilagineum, used to make Jello.

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Study Notes

Carbohydrates

  • Carbohydrates are aldehydes or ketone alcohols
  • These contain carbon, hydrogen, and oxygen
  • Hydrogen and oxygen have the same ratio as in water

Classification of Carbohydrates

  • Carbohydrates are classified into sugars and polysaccharides
  • Simple sugars are monosaccharides and cannot be hydrolyzed
  • Disaccharides yield 2 monosaccharide molecules upon hydrolysis
  • Trisaccharides yield 3 monosaccharide molecules
  • Tetrasaccharides yield 4 monosaccharide molecules
  • Monosaccharides are classified based on the number of carbon atoms:
    • Trioses have 3 carbon atoms
    • Tetroses have 4 carbon atoms
    • Pentoses have 5 carbon atoms
    • Hexoses have 6 carbon atoms
  • Sugars are water-soluble, crystalline and they taste sweet
  • Complex polysaccharides include starch, inulin, and cellulose can usually be hydrolyzed

Hexosans and Plant Structure

  • Hexose is called hexosans
  • Starch, which yields glucose, is also called glucosan
  • Inulin, which yields fructose, is a fructosan
  • Cellulose, a glucose polysaccharide with beta -1,4 linkages, forms plant cell walls
  • Hemicelluloses are high-molecular-weight polysaccharides, more soluble and easily hydrolyzed than cellulose
  • Pentose, sugars with formula CHO include arabinose, xylose, and ribose.
  • Pentoses come from hydrolysis of pentosans, like xylan from deciduous tree wood
  • Pentoses can also be a result of gums and mucilages hydrolysis

Key Monosaccharides

  • Monosaccharides are simple sugars, ketonic or aldehydic polyhydroxy alcohol substitution products
  • The simplest monosaccharide is DIOSE, OH-CH2-CHO but it does not occur freely in nature
  • Aldehydic and ketonic trioses, like glyceraldehyde and dihydroxyacetone, exist as phosphate esters
  • Some organisms can oxidize glycerin to dihydroxyacetone
  • Tetroses are rare in the free state
  • Pentoses, are found in nature, from hydrolysis of hemicelluloses, gums, and mucilages
  • Hexoses are vital monosaccharides in plants, the first sugars synthesized, used to build polysaccharides
  • There are 16 possible aldohexoses and 8 ketohexoses, totaling 48 isomers when including alpha and beta forms

Glucose and Fructose

  • Only fructose (levulose) and glucose (dextrose) of monosaccharides occur freely in plants; and found in sweet fruits, honey, and invert sugar
  • Hydrolyzing starch yields glucose while inulin yields fructose
  • Glucose is an aldohexose, or a polyhydroxy alcohol with an aldehyde group
  • Fructose is a ketohexose, having a ketone group
  • These groups have reducing properties
  • Hexoses are open-chain 6-membered compounds with five carbon atoms having alcohol substituents and the sixth as part of an aldehyde or ketone group.
  • Glucose and other hexoses exist in both cyclic and straight-chain forms
  • Fructose is more complex and exists in two cyclic forms: fructopyranose and furanose
  • Fructopyranose is the crystalline sugar structure, and furanose is has a 5-membered ring, mostly present in oligosaccharides and polysaccharides
  • Phosphate esters of heptoses (7-carbon sugars) are essential for glucose metabolism and photosynthesis
  • An 8-carbon sugar, D-glycero-D-marinooctulose, was isolated from avocado pulp and the rock-garden plant Sedu

Disaccharides

  • Sucrose is the only disaccharide occurring abundantly in plants' free state, rarely maltose is also found in cell sap
  • Sucrose is in fruit juices, sugar cane, sugar beet, and maple sap
  • Upon hydrolysis, sucrose yields equal amounts of glucose and fructose
  • Sucrose is a nonreducing sugar
  • Maltose is produced from starch hydrolysis during barley and grain germination via diastatic fermentation
  • It is a reducing sugar and yields 2 glucose molecules upon hydrolysis
  • Commonly occurring sugars in vegetable drugs are glucose, fructose, sucrose, and maltose
  • Mannose (in mannosans) and galactose (in lactose and raffinose) occur to alimited extent in nature
  • Trehalose (in fungi) and lactose (milk sugar) are disaccharides
  • Lactose is a reducing sugar due to having a functional aldehyde group, while trehalose is nonreducing

Sucrose

  • Sucrose, is derived from Saccharum officinarurm Lin (Fam. Gramineae), Beta vulgaris Linn (Chenopodiaceae)
  • It contains no additives, and it is widely distributed in plants
  • Commercially, it is obtained from sugar cane and sugar beets, and it can also be extracted from sugar maple
  • Production of sucrose includes crushing sugar cane stems using heavy iron rollers
  • Lime is used to neutralize plant acids and coagulate albumins
  • The solution is filtered, decolorized with sulfur dioxide, concentrated, and crystallized

Molasses, Uses of Sucrose

  • When sucrose crystals are no longer obtainable, the dark-colored molasses is a residual syrup utilized in foods, animal feed, and ethyl alcohol production
  • Sucrose is obtained from sugar beets which involves washing and slicing them into “cassettes”
  • Soluble constituents are extracted using hot water, and the crude solution is then purified
  • Sucrose is a pharmaceutical necessity for syrups, acting as a demulcent and nutrient
  • In sufficient aqueous concentration, it is bacteriostatic and preservative
  • Sucrose masks tastes in troches and tablets and slows oxidation in preparations

Dextrose/Glucose

  • Dextrose, or D-glucose, occurs naturally in grapes and fruits
  • It is obtained by controlled enzymatic hydrolysis of starch
  • High-conversion hydrolysates undergo rigorous purification to produce 99.5 to 100% pure, crystalline dextrose
  • Dextrose is a nutrient that may be administered orally, by enema, subcutaneously or intravenously
  • It is in dextrose injections, alcohol and dextrose injection, dextrose and sodium chloride tablets, dopamine hydrochloride and dextrose injections, lidocaine hydrochloride and dextrose injections, and potassium chloride and dextrose injections
  • Dextrose is also in anticoagulant citrate dextrose and anticoagulant citrate phosphate dextrose, which is used as an anticoagulant for storing whole blood

Starch: Chemistry and Properties

  • Starch is a mix of two structurally different polysaccharides
    • Amylose is a linear molecule of 250-300 D-glucopyranose units, uniformly linked by alpha 1,4 glycosidic bonds
    • Ainylopectin consists of 1000+ glucose units connected with alpha 1,4 linkages
  • Amylose is more water-soluble than amylopectin, making it possible to separate the two components
  • Complexing and precipitating amylose with agents such as alcohols or nitroparaffins improves separation efficiency
  • Amylose reacts with iodine to form a deep blue complex; amylopectin yields a blue-violet or purple color
  • Most starches consist of 25% amylose and 75% amylopectin
  • Certain waxy or glutinous starches are made of no amylose or small amounts (less than 6%)

Breakdown and Uses of Starch

  • Alpha-amylase, an enzyme in saliva and pancreatic juice, hydrolyzes starch by randomly cleaving α-1,4-glucosidic linkages
  • This yields a mix of glucose, maltose, amylopectin and branched/unbranched oligosaccharides
  • Starch forms colloidal solutions rather than true ones
  • A cold water suspension of starch swells and ruptures in boiling water, forming a translucent sol that sets to a firm jelly upon cooling
  • Cold concentrate of caustic alkalies, chloral hydrate, ammonium thiocyanate, or hydrochloric acid causes starch granules to swell/rupture creating pastes
  • Pharmaceutically, corn (Zea mays L), wheat (Triticum aestivum L), or potato tubers (Solanum tuberosum) can turn into Starch
  • Uses as dusting powders/pharmaceutical aid, tablet filler, binder, and disintegrant
  • Purified starch amylose is useful for tablet functions and can be swallowed as an antidote for iodine poisoning
  • Has commercial applications like paper sizing, cloth sizing, and laundry starching
  • Serves as the starting material for liquid glucose (corn syrup), dextrose, dextrins, and high-fructose sweeteners

Modified Starches

  • Pregelatinized is starch processed chemically/mechanically in water to rupture all/part of the granules, and then dried
  • This is done to enhance compressibility, flow, making it slightly soluble/soluble in water for use in tablets
  • Sodium starch glycolate is a semisynthetic carboxymethyl ether sodium salt of starch
  • This has a function to disintegrate in tablet formulas
  • Heta starch is 90% amylopectin that can be used as a plasma expander (6% solution)
  • Heta starch can have adjunct therapy to address shock from hemorrhage, burns, surgery, sepsis, or other trauma.

Liquid Glucose Composition and Production

  • Liquid glucose comes from incomplete hydrolysis of starch
  • The result is a thick syrup, colorless/yellowish, odorless and sweet
  • Includes dextrose, dextrins, maltose, and water and uses as an agent of pharmaceutic necessity
  • In the USA washing with diluted hydrochloric acid in corn-starch
  • Heated for 22 minutes at 30 lb pressure
  • The acid that results gets neutralized, centrifuged, filtered and evaporated to syrupy condition

Fructose: Production and Uses

  • Fructose is obtained by inverting aqueous solutions of sucrose and separating fructose from glucose
  • During sucrose hydrolysis, equal amounts of fructose and dextrose are formed
  • It occurs naturally in sweet fruits and honey
  • Fructose is primarily sourced from enzymatically prepared high fructose syrup but also from inulin hydrolysis
  • Fructose food for diabetics, often in infant formulas
  • Given parenterally, produces less urinary secretion than glucose
  • It is present in fructose injection and fructose and sodium chloride injection
  • These preparations are fluid, nutrient, and electrolyte replenishers administered intravenously or subcutaneously
  • Fructose is about half as sweet as glucose, of interest to those who are calorie-conscious
  • High-fructose sweeteners are made by controlled enzymatic isomerization of glucose using immobilized glucose isomerase from Streptomyces
  • High fructose corn syrups with up to 90% fructose are commercially available

Lactose: Composition and Properties

  • Cow's milk is either fresh or pasteurized from Bos taurus Linn (Fam. Bovidae) without changes
  • Its a opaque, white fluid contains little fat globules in it, and also albumen, casein, lactose, and inorganic salts
  • An 80-90% water, a 3% casein, and a 5% lactose
  • Contained in milk: 0.1 - 1% salt, and fat 2.5 - 5 %. Rich in vitamins, too

Milk By-Products

  • If waiting a few hours after milk production small fat globules increase
  • Fats turn to butter if churned , turning into buttermilk
  • Skim milk: liquid left after skimming fat, containing rennin and forms curd, treated to form a liquid coagum and whey: lactose and inorganic salts results
  • Created to make cheese
  • Condensed milk: made from autoclaving a vacuum of partially evaporating milk sterilization
  • Malted milk: extracts made from evaporating and using low-heat to avoid destroying enzymes

Lactose: Hydrolysis and Uses

  • Milk is a main source of the nutrient: Lactose ( sugar)
  • The description of how lactose hydrolyzes and what happens
  • Its hydrolyzed through a certain enzyme: LACTASE ( other enzymes do not work)
  • Lactose easily has lactic and butyric fermentations
  • The usages
  • Uses to dilute tablets, less-sweeter that can dissolve
  • Nutrients for infants
  • Good for flora because causes the perfect substrate for lactobacilli.
  • Inert mixing of pills
  • Lactulose is formed after synthesis for an alkaline version. Gives fructose, lactose upon being broken. Colon-bacteria can ferment lactulose and therefore release acids and laxative.

Lactulose

  • A 10-20g Lactulose daily is an effect constipation treatment, mostly decrease ammonia volume in bloodstream
  • A 20-30g dosage should be taken with water, 3-4 times daily

Xylose

  • Xylose or Xylan (wood/sugar) is a pentose made by diluting with wood parts. Its not processed by most mammilian bodies
  • FDA, can be used in intestinal disorders. Is shown through excretions from urination (malabsorptions)
  • This causes disease (celiac, pellagra etc (sprue, Croho's disease(regional ileitis))

Inulin

  • Inulin (hydrous), D-fructofuranose, residues linked. Found is family Compostiae
  • High amount in chicory. Is from sap
  • Its usually formed to to Spherite through time in alcohol mediums
  • Used to know about special lab tests in renals
  • Absorbs through only glomeruli.
  • Its injected with a 10g, into 100ml sodium chloride through IV's

Dextran Production and Use

  • an a-1,6-links sucrose is made of the enzyme polyglucan transglucosylase (dextran sucrase)
  • By controlling Depolymerization an average weigh range (40,000-75,000) can be maintained for Dextran
  • In an a6% this is a blood thickener if in trauma situations
  • Dextran is good for using because it doesn't thicken much from plasmas viscosity and is prolonged in 1,6 linkage, if slowly cleaving

Dextran: Additional Properties and Applications

  • Dextrans can cross space with other molecules and excretes. 10 percent is to treat shocks
  • Functions to have thickness/increase flow to clots through interferences
  • Colloidal solution mix's the water with the hydrolyzed version
  • Only through IV and intramuscular usage

CARAMEL

  • Heated in water for a while until taste is gone, makes brown syrup with alkali. Some compounds make it work like NaCl
  • Used in drinks, beverages, medicines and colorings

Modified Celluloses

  • Powdered cellulose processed after plant fibers are alpha-cellulose
  • It can be used as diluents and self binders
  • Microcrystalline cellulose makes minerals in the material, used in acids

Cellulose Derivatives

  • Methylcellulose(cellulose ether) is a chloride mix that's white
  • Ophthal solutions (0.5-1%) topical applications because artificial tears
  • Ethylcellulose(cellulose ethers) film coating binders
  • Hydroxyethyl cellulose is thickening applications
  • Hydroxypropyl cellulose(cellulose ethers) contains thickeners and liquid applications

Hydroxypropyl Methylcellulose

  • PG- ether, cellulose groups connected from links
  • Suspending applications topical

Gums and Mucilages

  • Gum is a hydrocolloid for herbs. Can be a salt
  • They are protective fluids/substances after injured
  • Derivatives can be for properties a number hydrocolloids exist

Gum Structure and Properties

  • Gums contain Galactose, arabinose etc. A methyl ether is an application for polymers
  • Pharmacy applications tablet binders/laxatives (for adhesives)
  • Precipitated from alcohol and leads
  • Mucilage and gums are made to be sticky but mucilage are normal and gums are for pathology

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