synthesis of methyl salicylate acid

Question 1

discovery:

what plant did methyl salicylate isolate from?

Answer 1

gaultheria procumbens

Question 2

who isolated methyl salicylate and what year?

Answer 2

Auguste Andre Thomas Cahours - 1843

Question 3

the process of the isolation or biosynthesis of Auguste on the methyl salicylate

Answer 3

Hydroxylation of benzoic acid via cytochrome p450 and then methylation by methylase enzyme

Question 4

METHYL SALICYLATE

CHEMICAL PROPERTIES:

Answer 4

Soluble in many organic solvents ether , alcohol
● IUPAC name: Methyl-2-hydroxybenzoate
● Molecular formula : C8H8O3
● Melting point :8.6 degrees Celsius
● Boiling point : 222 degrees Celsius
● Density : 1.17g/ml

Question 5

METHYL SALICYLATE

PHYSICAL PROPERTIES:

Answer 5

● Oily liquid having the smell odor of wintergreen
● *methyl salicylate –benzoate ester /methyl ester of salicylic acid
● *forms colorless viscous liquid to yellow or reddish liquid and exhibits a characteristic odor and taste of wintergreen

Question 6

METHYL SALICYLATE

USES:

Answer 6

● Rubefacient, analgesic (high concentration) in deep heating liniment Bengay
● Flavouring agent (low conc)like mints and gums
● Antiseptic
● elastomeric properties of old rubber rollers especially in printers or as a
transfer agent in order to produced a manual copy of an image on a surface
● odor-masking agent for some organophosphate pesticides (ex malathion
insecticides)

Question 7

TOXICITY

Methyl salicylate is potentially deadly, especially for

Answer 7

young children.

Question 8

Toxic ingestions of salicylates typically occur with doses of approximately

Answer 8

150 mg/kg body weight

Question 9

how is the toxic ingestions 150 mg/kg body weight achieved

Answer 9

This can be achieved with 1 ml of oil of wintergreen, which equates to 140 mg/kg of salicylates for a 10 kg child (22 lbs)

Question 10

lowest published lethal dose of methyl salicyate is

Answer 10

101 mg/kg body weight in adult humans, (or 7.07 grams for a 70 kg adult).

Question 11

It has proven fatal to small children in doses as small as

Answer 11

4 ml

Question 12

SOURCES

methyl salicylate is produced by?

Answer 12

produced by esterifying salicylic acid with methanol.

Question 13

what are the twigs where in the past methyl salicylate is distilled from

Answer 13

distilled from the twigs of Betula lenta (sweet birch) and 
Gaultheria procumbens (eastern teaberry or wintergreen)

Question 14

OTHER NAMES of methyl salicylate

Answer 14

● Salicylic acid methyl ester
● Oil of wintergreen
● Betula oil
● Methyl 2-hydroxybenzoate

Question 15

chemical reaction involved in the synthesis of methyl salicylate

Answer 15

salicylic acid + methanol = methyl salicylate (oil of wintergreen)

Question 16

methyl salicylate + ferric chloride

Answer 16

violet discoloration

Question 17

single teaspoon (5 ml) of methyl salicylate contains approximately ___ Salicylic acid

Answer 17

6 g

Question 18

EQUIVALENCE OF METHYL SALICYLATE TO ASPIRIN

Answer 18

1 tsp = 5 ml MA = 6 g SA = 300 g aspirin = 5.87