Aspirin-Presentation.pptx

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Chronicles of

Starring: Acetic Anhydride and Salicylic Acid

Guest appearance by: Ferric Chloride

Cameo appearances by: Sulfuric Acid and Hydrochloric Acid

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History

Charlotte Whittaker and Karen Tong

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The Beginning

•

Aspirin (acetylsalicylic acid) is frequently used to relieve minor aches and pains, as an antipyretic to reduce fever as well as an anti-inflammatory medication

•

Isolated by Felix Hoffman (Bayer Aspirin)

•

Aspirin research prompted Hoffmann’s rheumatic father encouraging his son to produce a medicine devoid of

the unpleasant effects of sodium salicylate.

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Scientists

Felix

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The Beginning cont'd

• Originally planned to research propionyl, butyryl,

valeryl, benzoyl and acetyl salicylic acids

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Fantastical Alternative Applications

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Salicylic Acid into The Sunlight

• _{Aspirin can be used for almost anything!}

• _{Practical uses range from a cleansing facial wash to a sweat-stain}

remover to a bug-bite and sting ointment.

• _{Salicylic acid is able to penetrate and break-down fats and lipids,}

making it capable of causing chemical burns on the skin if contained at very high concentrations.

• _{It is capable of damaging the lining of pores in such cases if the}

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Preservative Issues

•

When ingested, salicylic acid has a possible ototoxic

effect by constraining the flow of prestin.

•

It can induce transitory hearing loss in zinc-deficient

people. Salicylic acid can also be used as a preservative

but much controversy over whether it should be used is a

hot topic right now.

•

Claims of such negative externalities are common.

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Acne Treatment

• Salicylic acid is one of the active ingredients in the topical lotion for acne treatment, and it is as stated previously; a major component of aspirin.

•

Similar benefit as AHA (alpha-hydroxy) treatment which encourages the

peeling of old, damaged surface skin cells.

• Salicylic acid is especially helpful in treating acne because of its ability to penetrate through the epidermis to the follicle.

• In this way, it decreases the number of pore blockages and breakouts on the skin.

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Sweat-Destainer

• 6 pints of sweat every hour from over 2.6 million sweat glands that are located all over our bodies.

• The main component of sweat is the leftover minerals our bodies excrete that are too heavy to evaporate with the escaping water; we have a hard time bleaching these minerals because minerals don’t have a color to remove or a material to bleach and they don’t come out with just water when they have been embedded into the fabric of our clothing.

• Aluminum chloride hexahydrate along with salicylic acid is often found in antiperspirants and is considered the initial treatment for patients with average hyperhidrosis (extreme sweating) because it works on preventing nasty buildup.

• Our sweat contains a compound called urea, which causes sweat to yellow on our clothing.

• While deodorants may seem to help, many also contain aluminum compounds, which mix with the perspiration and cause those white stains on dark clothing, which unfortunately are waterproof. Salicylic acid, however, can remove these.

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Dandruff Ointment

•

Dandruff or sebhorreic dermatitis, is a common

epidermal problem affecting around fifty percent of the world population lending no favorites to any certain

gender or race.

•

Malassezia globosa (see right) is the fungus responsible for this, levels of such rise by a factor of 1.5 to 2 times through dandruff.

•

Although incurable there are many supposed

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Daandruff Ointment cont'd

•

Keratolytic agents such as salicylic acid and sulphur loosen the attachments between the corneocytes and allow them to flow freely; this stops the skin cells from clumping together and producing huge flakes the people often mistake for snow.

•

Shampoos used to tackle these white, itchy symptoms usually contain acrylates copolymer, sodium laureth sulfate, trolamine, quaternium 26 and propylene glycol, cocamidopropyl betaine, behentrimonium

methosulphate and cetearyl alcohol, propylparaben, methylparaben, and some other really complicated

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•

Reduces the severity of hangovers after long periods of drinking and there is much truth to that.

•

Aspirin counteracts the prostaglandin inhibitors which come from the alcoholic beverages.

o Prostaglandins: group of lipid compounds that are derived enzymatically from fatty acids, each one

contains 20 carbon atoms, including a 5-carbon ring.

o They are autocrine and paracrine lipid mediators that act upon platelets, endothelium, uterine and mast

cells, are synthesized in the cell from the essential fatty acids.

•

Sensitize spinal neurons to pain and control hormone regulation.

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The Hangover Part II

•

Only be reached if the prostaglandins can be released as chemical transmitters.

•

If this process is stalled, excess pain and pressure will be released when the chemicals can finally start flowing again after the disruption from the alcoholic beverage has ceased, a.k.a, the hangover begins.

•

Aspirin counteracts this breach of circuit and

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Procedu

re

Karen Tong and Charlotte Whittaker

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The Creation

•

Acetylsalicylic acid --> a weaker acid than salicylic acid --> has the medicinal properties of salicylic acid without having an unbearable taste or producing stomach

problems.

•

The acetyl group, shown by COH₃, effectively hides the acidity of the drug during ingestion.

• ASA passes into the small intestine, converted back into

salicylic acid, where it enters the bloodstream in order to relieve pain

• _{"a" for acetyl, and "-spir" -->}_{Spiraea ulmaria}_{, a sweet}

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Formulas

Salicylic acid

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The Creation Cont'd

•

Esterification

•

Carboxyl (-COOH) group and an -OH group of an alcohol or phenol form a carboxylate ester

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• Presence of an excess of acetic anhydride

forces the equilibrium towards the desired

product, aspirin (7).

• Salicylic acid has a higher pH than stomach

acid --> diprotic, carboxylic acid and phenol

• Acetylsalicylic acid is less acidic than

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• Create a suspension of salicylic acid, a solid

at room temperature, in an excess of acetic

anhydride, which is a liquid at room

temperature

• Acetic anhydride: solvent and reactant

• Phosphoric acid, H

₃

PO

₄

donates a H

+

, which

binds to the reaction complex and H

+

is

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•

Solid salicylic acid disappears and the acetylsalicylic acid product is dissolved in the hot solution.

•

Excess acetic anhydride is hydrolyzed to become acetic acid. Acetic anhydride is very reactive and soluble in water, so the hydrolysis must be done slowly drop by drop.

•

Flask is placed in an ice bath to lower the solubility and precipitate the ASA product.

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Trials and

Tribulations

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I'm Melting!

• Melting point

--> unique to the identity of the

substance, dependent on the ratio of substances

present in sample

• The purer the substance, the smaller the melting

range.

• The more impurities, the lower the melting point.

• Freezing point depression

.

• Melting point range of pure aspirin:138-140 °C.

•

If impurities are present in the crude sample, the

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Just a little TLC...

•

Thin layer chromatography (TLC)

•

Silica --> stationary phase

•

Organic solvent--> mobile phase

•

Adsorption of the molecules: adhesion of atoms, ions, or molecules from a gas, liquid, or dissolved solid to a surface

•

Speed depends on intermolecular interaction between polar silica plate and less polar solvent: polar compounds adsorb more strongly to the silica and do not move as far up the TLC plate

•

Less polar components will favor the solvent, or elutant, and move higher

•

Distance to which the elutant travels --> unique to the compound.

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Movie Time

Directed by:

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Ferric Chloride

• The oxygen atoms of the acid group COOH,

and of the -OH group on the salicylic acid

form with the complex ion Fe(H

₂

O)

₆3+

-->

PURPLE!

• White light that contains wavelengths from

400 nm to 700 nm passes through a

Fe(H

₂

O)

₆3+

-SA solution --> green light

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Beer...

•

The intensity of light of the absorbed wavelengths is reduced when they pass through the solution.

•

Beer's Law: amount of reduction of intensity is dependent on the concentration of the absorbing species and the

path length of the light traveling through the solution.

•

If the optical path length and molar absorptivity coefficient are constant in an experiment, the absorbance varies

with concentration alone.

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Demo

Time

Karen Tong and Charlotte Whittaker

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Who wants to

be the next

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Notice reduced redness in the

area marked by the circles