SALICYLIC

HYDROCARBON
ROSE ANNE V. DELA VEGA
X-KELVIN
 SALYCYLIC ACID

Salicylic acid(fromLatinsalix,willow tree, from the bark of

which the substance used to be obtained) is a
monohydroxybenzoic acid, a type of phenolic acid and abeta
hydroxy acid. It has the formula C7H6O3. This colorless crystalline
organicacidis widely used inorganic synthesisand functions as a
plant hormone. It is derived from the metabolism ofsalicin. In
addition to being an importantactive metaboliteofaspirin
(acetylsalicylic acid), which acts in part as aprodrugto salicylic
acid, it is probably best known for its use as a key ingredient in
topical anti-acne products. The salts andestersof salicylic acid are
known assalicylates.
 SALICYLIC ACID
CAS Number 69-72-7
ChEBI CHEBI:16914
ChEMBL ChEMBL424
ChemSpider 331
DrugBank DB00936
EC Number 200-712-3
IUPHAR/BPS 4306
Jmolinteractive 3D Image
KEGG D00097
PubChem 338
RTECS number VO0525000
UNII O414PZ4LPZ
InChI[show]
SMILES[show]
 Properties
Chemical formula C7H6O3
Molar mass 138.12gmol1
Appearance colorless to white crystals
Odor odorless
Density 1.443 g/cm3(20 C)[1]
Melting point 158.6C (317.5F; 431.8K)
Boiling point 200C (392F; 473K)
decomposes[2]
211C (412F; 484K)
at 20 mmHg[1]
Sublimation conditions sublimes at 76 C[3]
Solubility in water 1.24 g/L (0 C)
2.48 g/L (25 C)
4.14 g/L (40 C)
17.41 g/L (75 C)[2]
77.79 g/L (100 C)[4]
Solubility soluble inether,CCl4,benzene,propanol,
acetone,ethanol,oil of turpentine,toluene
PRODUCTION
Salicylic acid isbiosynthesizedfrom the amino acidphenylalanine. In
Arabidopsis thalianait can also be synthesized via a phenylalanine-
independent pathway.
Sodium salicylateis commercially prepared by treatingsodium phenolate(the
sodium salt ofphenol) withcarbon dioxideat high pressure (100 atm) and
high temperature (390K) -a method known as theKolbe-Schmitt reaction.
Acidification of the product withsulfuric acidgives salicylic acid:

It can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid)[19] or methyl salicylate (oil of wintergreen)
with a strong acid or base.
PRODUCTION
Salicylic acid is known for its ability to ease aches and pains and reduce fevers.[9] These medicinal properties,
particularly fever relief, have been known since ancient times, and it is used as an anti-inflammatory drug.[9]
In modern medicine, salicylic acid and its derivatives are used as constituents of some rubefacient products. For
example, methyl salicylate is used as a liniment to soothe joint and muscle pain, and choline salicylate is used
topically to relieve the pain of mouth ulcers.

Cotton pads soaked in salicylic acid can be used to chemically exfoliate skin
As with other hydroxy acids, salicylic acid is a key ingredient in many skin-care products for the treatment of
seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans,ichthyosis, and warts.
[9]
The standard treatment for calluses is a 6% aspirin suspension in petroleum jelly, applied on the callus for one
hour and then removed with washing.[citation needed] Salicylic acid works as akeratolytic, comedolytic, and bacteriostatic
agent, causing the cells of the epidermis to shed more readily, opening clogged pores and neutralizing bacteria
within, preventing pores from clogging up again by constricting pore diameter, and allowing room for new cell growth.
[9][10][11]
Because of its effect on skin cells, salicylic acid is used in several shampoos to treat dandruff. Use of
concentrated solutions of salicylic acid may cause hyperpigmentation on unpretreated skin for those with darker skin
types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock.[12][13]
Bismuth subsalicylate, a salt of bismuth and salicylic acid, is the active ingredient in stomach relief aids such as
Pepto-Bismol, is the main ingredient of Kaopectate, and "displays anti-inflammatory action (due to salicylic acid) and
also acts as an antacid and mild antibiotic".[14]
Salicylic acid is used in the production of other pharmaceuticals including 4-aminosalicylic acid and sulpiride.
PHYSICAL PROPERTIES

Colour

Colourless or white

State/form

Solid-crystals

Description

Colourless acicular crystals or a white crystalline powder. The synthetic form is white but if prepared
from natural methyl salicylate, it may have a slightly yellow or pink tint.

Salicylic acid is a white crystalline powder with a sweetish acrid taste. If prepared from natural methyl
salicylate, it may have a faint mint like odour. It is available in forms of ointments, cream, gel, transdermal patches,
liquids and plaster.
Salicylic acid is soluble 1 in 460 to 550 of water, 1in 15 of boiling water, 1 in 3 to 4 in alcohol, 1 in 3
in ether and 1 in 45 in chloroform (Reynolds, 1996).
OTHER CHARACTERISTICS

Shelf-life of the substance

Shelf-life is dependent on the manner of storage. It should be

stored in well closed containers and protected from light (Reynolds,
1996).

Storage conditions

Store in well closed containers and protect from light (Reynolds,

1996).