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PMOC LAB > EXERCISE 9 > Flashcards

EXERCISE 9 Flashcards

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1
Q
  • a white crystalline compound isolated from natural sources or synthetically produced from methyl salicylate
  • this drug falls under the category analgesic, antipyretic, and inti-inflammatory agent
A

SALICYLIC ACID

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2
Q

SALICYLIC ACID

NATURAL salicylic acid is obtained from what plants

A

Wintergreen leaves
Sweet Birch Tree bark

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3
Q

SALICYLIC ACID

SYNTHETIC saliyclic acid is chemically known as ____ or ____

A

2-hydroxybenzoic acid or o-hydroxybenzoic acid

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4
Q

SALICYLIC ACID | HISTORY

an Italian chemist he is the FIRST to synthesize salicylic acid

A

Raffaele Piria

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5
Q

SALICYLIC ACID | HISTORY

Raffaele Piria split SALICIN into a ____ and an aromatic component ____

A

sugar and an aromatic component salicylaldehyde

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6
Q

SALICYLIC ACID | HISTORY

RAFFAELE PIRIA:
converted salicylaldehyde by ____ and ____

A

hydrolysis and oxidation

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7
Q

SALICYLIC ACID | HISTORY

RAFFAELE PIRIA:
converted salicylaldehyde by hydrolysis and oxidation, to an acid of crystallized colorless needles, which he named ____

A

salicylic acid

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8
Q

SALICYLIC ACID | USES

systemically, salicylic acid produces these effects similar to those of aspirin

A

analgesic and antipyretic

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9
Q

SALICYLIC ACID | USES

it possess this activity due to its ability to inhibit cyclooxygenase

A

anti-inflammatory

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10
Q

SALICYLIC ACID | USES

salicylic acid salt (sodium saalicylate) has known ____, the reason why salicylic acid is found in toothpastes and mouthwashes

A

ANTIBACTERIAL

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11
Q

SALICYLIC ACID | USES

salicylic has mild antiseptic action which makes it a good ____ but only in SMALL doses

A

FOOD PRESERVATIVE

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12
Q

SALICYLIC ACID | USES

dose of salicylic acid as a food preservative

A

SMALL DOSES only

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13
Q

SALICYLIC ACID | USES

it facilitates desquamation by solubilizing the intercellular cement that binds scales in the stratum corneum, thereby loosening the keratin

A

KERATOLYTIC

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14
Q

SALICYLIC ACID | USES

the removal of stratum corneum suppresses fungal growth. also used for treatment of dandruff, acne, psoriasis, calluses, corns, keratosis pilaris, and warts

A

ANTIFUNGAL

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15
Q

SALICYLIC ACID | USES

different ____ contain salicylic acid for:
* seborrheic dermatitis
* mild to moderate acne vulgaris
* ichthyosis
* psoriasis
* warts, corns, and calluses
* dandruff

A

cosmetic preparations

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16
Q

SALICYLIC ACID | SIDE EFFECTS

INTERNALLY

A

GI irritation
salicylism toxicity

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17
Q

SALICYLIC ACID | SIDE EFFECTS

EXTERNALLY

A

skin irritation
rashes
skin itching or swelling

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18
Q

SALICYLIC ACID | SIDE EFFECTS

SALICYLATE POISONING:
severe toxicity

A

metabolic acidosis
seizures

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19
Q

SALICYLIC ACID | SIDE EFFECTS

SALICYLATE POISONING:
hyperventilation leads to

A

respiratory alkalosis

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20
Q

SALICYLIC ACID | SIDE EFFECTS

SALICYLATE POISONING:
toxic level fora 30lb child

A

12 adult aspirin or 48 baby aspirin

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21
Q

SALICYLIC ACID | REAGENTS

  • LIMITING REACTANT
  • precursor for the synthesis
  • the methyl group on its structure is replaced with a hydrogen upon reaction
  • this is achieved through hydrolysis
A

METHYL SALICYLATE

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22
Q

SALICYLIC ACID | REAGENTS

METHYL SALICYLATE:
the methyl group on its structure is replaced with a ____ upon reaction

A

HYDROGEN

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22
Q

SALICYLIC ACID | REAGENTS

METHYL SALICYLATE:
the replacement of methyl group with a hydrogen upon reaction is achieved through ____

A

hydrolysis

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23
Q

SALICYLIC ACID | REAGENTS

  • CORROSIVE
  • used to HYDROLYZE methyl salicylate forming disodium salicylate salt, methanol and water
  • the volume used for the reaction is A LOT MORE than that of methyl salicylate
  • this it to ensure that ALL ester groups present would easily separate
A

25% SODIUM HYDROXIDE

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24
# **SALICYLIC ACID | REAGENTS** * source of **H+ ions** used to **PROTONATE** the **disodium salicylate** (salt ion) * an **EXCESS** of this strong acid was **added** to **fully convert** the **disodium salicylate** into **salicylic acid** | addition of H2SO4 is until it appears as permanent white ppt
CONC. SULFURIC ACID
25
# **SALICYLIC ACID | SYNTHESIS** ____ and ____ is mixed in an erlenmeyer flask
methyl salicylate & sodium hydroxide
26
# **SALICYLIC ACID | SYNTHESIS** the solution is placed on an **ice bath** while the ____ is **added**
sulfuric acid
27
# **SALICYLIC ACID | SYNTHESIS** the addition of **sulfuric acid** while the solution is placed on an **ice bath** ____ the **disodium salicylate salt**
PROTONATES
28
# **SALICYLIC ACID | SYNTHESIS** the reaction is ____, thus **releasing** heat
exothermic
29
# **SALICYLIC ACID | SYNTHESIS** **sulfuric acid** is added ____ while **swirling**
dropwise
30
# **SALICYLIC ACID | SYNTHESIS** addition of the acid is **stopped** after it **saturated** the solution converting the ____ into ____
disodium salicylate into salicylic acid
31
# **SALICYLIC ACID | SYNTHESIS** BASE HYDROLYSIS: in **METHYL SALICYLATE**, the **benzene ring** is **substituted** by a ____ group and an ____ group
hydroxyl (-OH) and ester (-COOCH3)
32
# **SALICYLIC ACID | SYNTHESIS** BASE HYDROLYSIS: in **SALICYLIC ACID**, the **ester group** has been **replaced** with a ____ group
carboxyl (-COOH)
33
# **SALICYLIC ACID | SYNTHESIS** **reaction** involved in the synthesis of saliycylic acid
BASE HYDROLYSIS / Saponification
34
# **SALICYLIC ACID | SYNTHESIS** BASE HYDROLYSIS: **methyl salicylate** is **HYDROLYZED** using ____ forming the **disodium salicylate salt**
sodium hydroxide
35
# **SALICYLIC ACID | SYNTHESIS** BASE HYDROLYSIS: the **disodium salicylate** salt is ____ using a **strong acid**
protonated
36
# **SALICYLIC ACID | SYNTHESIS** BASE HYDROLYSIS is also known as
saponification
37
# **SALICYLIC ACID | FILTRATION & DRYING** the precipitate is **filtered** and it is washed using ____
COLD distilled water
38
# **SALICYLIC ACID | PHYSICAL TEST** COLOR
WHITE
39
# **SALICYLIC ACID | PHYSICAL TEST** ODOR
ODORLESS
40
# **SALICYLIC ACID | PHYSICAL TEST** APPEARANCE
crystalline powder
41
# **SALICYLIC ACID | CHEMICAL TEST** * detect the presence of **PHENOL** * PRINCIPLE: salicylic acid reacts with ferric chloride (FeCl3) to form ferric salicylate and HCl acid * POSITIVE RESULT: **purple color** of solution (**ferric salicylate**)
FERRIC CHLORIDE TEST
42
# **SALICYLIC ACID | CHEMICAL TEST** POSITIVE RESULT: **Ferric Chloride Test**
PURPLE COLOR
43
# **SALICYLIC ACID | CHEMICAL TEST** * detects presence of **MULTIPLE BONDS** and **PHENOLIC GROUP** * PRINCIPLE: phenols undergo **substitution** reaction with bromine water * POSITIVE RESULT: **decolorized solution (HBr)** with **white precipitate** (**2,4,6-tribromophenol**)
BROMINE WATER TEST
44
# **SALICYLIC ACID | CHEMICAL TEST** POSITIVE RESULT: **Bromine Water Test**
decolorized solution with white ppt
45
# **SALICYLIC ACID | CHEMICAL TEST** END PRODUCT: **Bromine Water Test**
2,4,6-tribromophenol
46
# **SALICYLIC ACID | CHEMICAL TEST** * PRINCIPLE: salicylic acid will undergo **esterification** reaction forming methyl salicylate upon reaction with methanol * POSITIVE RESULT: **minty odor** (**methyl salicylate**)
REACTION WITH METHANOL
47
# **SALICYLIC ACID | CHEMICAL TEST** POSITIVE RESULT: **Reaction with Methanol**
minty odor (methyl salicylate)
48
# **SALICYLIC ACID | CHEMICAL TEST** REACTION WITH METHANOL: **salicylic acid** will **undergo** ____ reaction fofrming **methyl salicylate** upon reaction with **methanol**
ESTERIFICATION
49
# **SALICYLIC ACID | PRODUCT** IUPAC name
2-hyroxybenzoic acid
50
# **SALICYLIC ACID | PRODUCT** synonym
o-hydroxybenzoic acid 2-carboxyphenol acido salicilico
51
# **SALICYLIC ACID | PRODUCT** MOLECULAR FORMULA
C7H6O3
52
# **SALICYLIC ACID | PRODUCT** PHYSICAL DESCRIPTION
odorless white crystalline powder
53
# **SALICYLIC ACID | PRODUCT** MOLECULAR WEIGHT
138.12 g/mol
54
# **SALICYLIC ACID | PRODUCT** BOILING POINT
211 C
55
# **SALICYLIC ACID | PRODUCT** MELTING POINT
158 C
56
# **SALICYLIC ACID | PRODUCT** SOLUBILITY
2.24 g per 1L water at 25C
57
# **SALICYLIC ACID | PRODUCT** DENSITY
1.443 g/cm3
58
# **SALICYLIC ACID | PRODUCT** CHEMICAL SAFETY
corrosive irritant health hazard
59
# **SALICYLIC ACID | PRODUCT** STABILITY
gradullat **discolors** in sunlight
60
# **SALICYLIC ACID | PRODUCT** STRUCTURE
phenol with an attached carboxyl group on **ortho** position
61
# **SALICYLIC ACID | SAR** **essential** for its activity
ortho-position of the -OH group
62
# **SALICYLIC ACID | SAR** if the position of the **-OH** group is **changed** to **meta-** or **para-** positions with respect to **-COOH**, the activity is ____
abolished
63
# **SALICYLIC ACID | SAR** **REMOVING** the **-OH** group ____ its activity
reduces
64
# **SALICYLIC ACID | SAR** ____ of **salicylic acid** will give **aspirin**, a potent analgesic
ACETYLATION
65
# **SALICYLIC ACID | SAR** **GIT side effects** are associated with ____ group
-COOH carboxyl group
66
# **SALICYLIC ACID | SAR** **substitutions** on the ____ will **DECREASE** its activity
aromatic ring
67
# **SALICYLIC ACID | SAR** **substitutions** of ____ on ____ **INCREASES** **potency** and **toxicity**
HALOGEN ATOMS on AROMATIC RING

PMOC LAB (11 decks)

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