BSP3D

Members:
Ramos, Dwight
Brito, Stacey
Narvaez, Alyanna
Odra, Anne Karolyn
To synthesize eugenol-5-
aldehyde from eugenol in
glacial acetic acid and
hexamine.

4 Allyl-2-methoxyphenol
Obtained primarily from clove oil
Slightly soluble in water but it is miscible with alcohol and other
organic solvents
The para-allyl and ortho-methoxy groups contribute to the
antiseptic and anesthetic activity of the phenolic group that is
used for toothaches and for its antiseptic activity in mouthwashes
Classification: Analgesic, Anti-infective, Insect attractant,
Repellent


Molecular Formula: C
10
H
12
O
2 +
CHO

Molecular weight: 193.2g/mol
Density: 1.06 g/cm3
Physical state: clear to pale yellow oily liquid
Melting point:-9C
Boiling point: 254C
Solubility in water : < 1mg/mL (68 F)


Eugenol
Glacial acetic
acid
Concentrated HCl


Ether
Purified Water
20% NaOH


Strong Aqueous
Sodium Bisulfite
Diluted Sulfuric
Acid
Ferric Chloride T.S.
ROLE OF
REAGENTS
Conc. HCl acidifying agent
Ether extraction solvent
20 % NaOH alkalinizing agent
Strong aqueous sodium bisulfate
decolorizing agent
Ferric Chloride T.S detect presence of
phenols

A solution of eugenol (10ml) in glacial acetic acid (75ml) was
treated with hexamine (40g).
Heat the mixture with shaking over wire gauze to get a clear solution
(pale brown) and was kept in a boiling water bath for six hours.
The dark brown-red solution was treated while hot with a boiling mixture of
concentrated hydrochloric acid (50ml) and water (100ml).
Heating on the water bath was continued for another five
minutes and the mixture slowly cooled.
Extract twice ether and the ether extract washed with water.
Lower aqueous layer must be colorless showing that only
acetic acid had been extracted

Shake, to separate the lower layer with 10% alkali to
complete the sodium salt of 5-eugenol-aldehyde
Filter, Wash with 10% alkali and ether. Dissolve the
precipitate in excess of water and filter and acidify the
clear filtrate

Leave it overnight, and filter the pale cream colored
solid that separated out, wash well with water and dry
Wash the ether extract with water, concentrate to a
small bulk and shake thoroughly with strong aqueous
sodium bisulfite

Filter the crystalline bisulfate, heat and wash with ether
Dilute with sulfuric acid and place the mixture in a
boiling water bath until the solid giving oil drops

Cooling the reaction mixture and filter the aldehyde that
crystallized out
Melting point determination
Collect the crystals. Calculate the percentage yield

CHEMICAL REACTION

Physical Test
COLOR:
ODOR:
SPECIFIC GRAVITY:
MELTING POINT:
Colorless or pale yellow
Spicy, clove-like aroma
Clear to pale yellow oily liquid
-9C

Chemical Test: Solubility
WATER
ALCOHOL
ETHER
ACETONE
SOLUBLE
SOLUBLE
SOLUBLE
SOLUBLE

In 10% sodium hydroxide it readily
dissolved and the solution soon
deposited yellow crystals of the sodium
salt
Chemical Test: Reaction with 10%
Sodium Hydroxide

With a drop of ferric chloride in
alcoholic solution it gave a deep blue
color which did not change on
further addition
Chemical Test: Reaction with Ferric
Chloride

CHEMICAL DENSITY MOLECULAR
WEIGHT
Glacial acetic
acid
1.05 g/mL 60.05 g/mol
Hexamine
1.33 g/mL 140. 19g/mol
Eugenol
1. 0652 g/mL 164. 20g/mol
Aldehyde
0.785 g/mL 29 g/mol

Glacial Acetic Acid (excess) Hexamine (rate limiting)
(1.05g/cm3)(75mL)=78.75g 40g/140.19g/mol=0.2853

No. of moles of limiting reactant= weight of the reactant/ MW of the
reactant
= 78.75g/60.05g/mol
= 1.3114

Theoretical yield= (no. of moles of LR) X (MW of the product)
= (0.2853) X (164+29)
= (0.2853)(193.2)
= 55.12


It occurs naturally in cloves, cinnamon,
nutmeg and bay. It is extracted by
Steam Distillation.
1. What are the natural sources of eugenol? What
is the method of extraction?
Phenols and their derivatives
2. What class of local anti-infective does eugenol
belongs?
3. What are the uses of eugenol-5-aldehyde? Give the limitation of its
use?
Uses :
Eugenol is used in perfumeries, flavorings, essential oils and in
medicine as a local antiseptic and anesthetic
Eugenol can be combined with zinc oxide to form a material -
known as zinc oxide eugenol - which
has restorative and prosthodontic applications in dentistry.
They are used in formulating insect attractants and UV
absorbers, analgesics, biocides, and antiseptics.
Limitations:
Eugenol is hepatotoxic, meaning it may cause damage to
the liver.
Overdose is possible, causing a wide range of symptoms
from blood in the patient's urine,
to convulsions, diarrhea, nausea, unconsciousness, dizziness
, or rapid heartbeat.
Eugenol can cause an allergic reaction in humans including
rash, itching or shortness of breath.
Eugenol can cause immunotoxicity
When used in undiluted form causes burning, nerve or
tissue damage
Clove Oil Clove oil has a local anaesthetic effect and temporarily
numbs and relieves the pain
Zinc-oxide eugenol used in dentistry
Eugenol Oil Insecticide insecticide
4. What are the different preparations in the market
containing eugenol? Give the use/s of the products?
60 to 90% of eugenol, which is the source of its
antifungal, anesthetic and antiseptic properties.
5. What is the concentration and the effect of eugenol found
in the toothache drop preparation?