BioXtra, ≥99.0%
Synonym: 2-Hydroxybenzoic acid
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Linear
Formula 2-(HO)C6H4CO2H
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Molecular
Weight 138.12
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Beilstein
Registry Number 774890
Properties
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Related Categories
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More...
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vapor density
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4.8 (vs air)
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vapor pressure
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1 mmHg ( 114 °C)
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InChI Key
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YGSDEFSMJLZEOE-UHFFFAOYSA-N
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product line
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BioXtra
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assay
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≥99.0%
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impurities
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≤0.015% Phosphorus (P)
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≤0.1% Insoluble matter
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Salicylic acid (from Latin salix, willow tree) is a monohydroxybenzoic
acid, a type of phenolic acid, and a beta hydroxy
acid (BHA). It has the formula C7H6O3.
This colorless crystalline organic acid is widely used in organic
synthesis and functions as a plant hormone.
Detailed description
It is derived from the metabolism of salicin.
In addition to serving as an important active metabolite of aspirin (acetylsalicylic
acid), which acts in part as a prodrug to salicylic acid, it is probably best
known for its use as a key ingredient in topical anti-acne products. The salts
and esters of salicylic acid
are known as salicylates. The medicinal part of the plant is the inner bark.
It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.
Uses
Medicine
Salicylic acid as a medication is used most commonly
to help remove the outer layer of the skin.[10] As such it is used
to treat warts, psoriasis, dandruff, acne, ringworm, and ichthyosis.[10][11]
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.[12]
Manufacturing
Salicylic acid is used in the production of other
pharmaceuticals, including 4-aminosalicylic acid sandulpiride landetimide
(via Salethamide).
Salicylic acid was one of the original starting
materials for making acetylsalicylic acid (aspirin) in 1897.[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]
Other derivatives include methyl salicylate used as a liniment to soothe joint and
muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers.
Chemistry
Salicylic acid has the formula C6H4(OH)COOH,
where the OH group is ortho to the carboxyl group. It is also known
as 2-hydroxybenzoic acid. It is poorly soluble in water (2 g/L at 20 °C).[15] Aspirin (acetylsalicylic
acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid
with the acetyl group from acetic anhydride or acetyl chloride. Salicylic acid can
also be prepared using the Kolbe-Schmitt reaction.
Other uses
Sodium salicylate is a useful phosphor in the vacuum ultraviolet,
with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.[17] It fluoresces in the
blue at 420 nm. It is easily prepared on a clean surface by spraying a
saturated solution of the salt in methanol followed by
evaporation.
Safety
Burns
As a topical agent and as a beta-hydroxy acid (and
unlike alpha-hydroxy acids), salicylic acid is capable of penetrating and
breaking down fats and lipids, causing moderate chemical burns of the skin at
very high concentrations. It may damage the lining of pores if the solvent is
alcohol, acetone or an oil. Over-the-counter limits are set at 2% for topical
preparations expected to be left on the face and 3% for those expected to be
washed off, such as acne cleansers or
shampoo. 17% and 27% salicylic acid, which is sold for wart removal, should not
be applied to the face and should not be used for acne treatment. Even for wart
removal, such a solution should be applied once or twice a day – more frequent
use may lead to an increase in side-effects without an increase in efficacy.[18]
Hearing
When ingested, salicylic acid has a possible ototoxic effect
by inhibiting prestin.[19] It can induce
transient hearing loss in zinc-deficient rats. An injection of salicylic acid induced hearing
loss, while an injection of zinc reversed the hearing loss. An injection of magnesium in the
zinc-deficient rats did not reverse the induced hearing loss.
Pregnancy
No studies examine topical salicylic acid in
pregnancy. Oral salicylic acid is not associated with an increase in
malformations if used during the first trimester, but in late pregnancy has
been associated with bleeding, especially intracranial bleeding.[20] The risks of aspirin
late in pregnancy are probably not relevant for a topical exposure to salicylic
acid, even late in the pregnancy, because of its low systemic levels. Topical
salicylic acid is common in many over-the-counter dermatological agents and the
lack of adverse reports suggests a low teratogenic potential.[21]
Overdose
Salicylic acid overdose can lead to salicylate intoxication, which often presents
clinically in a state of metabolic acidosis with compensatory respiratory alkalosis. In patients presenting with an acute overdose, a 16% morbidity
rate and a 1% mortality rate are observed.[22]
Allergy
Sun exposure
The United States Food and Drug
Administration (FDA) recommends the
use of sun protection when using skincare products containing salicylic acid
(or any other BHA) on sun-exposed skin areas.[23]
Reye's syndrome
Data support an association between exposure to
salicylic acid and Reye's Syndrome. The National
Reye's Syndrome Foundation cautions against the use of these and other
substances similar to aspirin on children and adolescents. Epidemiological
research associated the development of Reye's Syndrome and the use of aspirin
for treating the symptoms of influenza-like illnesses, chicken pox, colds, etc.
The U.S. Surgeon General, the FDA, the Centers for Disease
Control and Prevention and the American Academy of
Pediatrics recommend that aspirin and combination products containing
aspirin not be given to children under 19 years of age during episodes of
fever-causing illnesses.[24]
Mechanism of action
Salicylic acid works through several different
pathways. It produces its anti-inflammatory effects via suppressing the
activity of cyclooxygenase (COX), an enzyme that is responsible
for the production of pro-inflammatory mediators such as the prostaglandins. It does this not
by direct inhibition of COX like most
other non-steroidal
anti-inflammatory drugs (NSAIDs) but instead
by suppression of the expression of the enzyme
through a mechanism not yet understood.[25]
Salicylic acid activates adenosine monophosphate-activated protein kinase (AMPK) and this
action may play a role in the anticancer effects of the
compound and its prodrugs aspirin and salsalate. The antidiabetic effects
of salicylic acid are likely mediated by AMPK activation primarily through
allosteric conformational change that increases levels of phosphorylation.[26]
Salicylic acid also uncouples oxidative
phosphorylation, which leads to increased ADP:ATP and AMP:ATP ratios in the
cell. As a consequence, salicylic acid may alter AMPK activity and work as an
anti-diabetic by altering the energy status of the cell. AMPK knockout mice
display an anti-diabetic effect, demonstrating at least one additional, yet
unidentified action.[27]
Salicylic acid regulates c-Myc level at both
transcriptional and post-transcription levels. Inhibition of c-Myc may be an
important pathway by which aspirin exerts an anti-cancer effect, decreasing the
occurrence of cancer in epithelial tissues.[28]
Plant hormone
Salicylic acid (SA) is a phenolic phytohormone and
is found in plants with roles in plant growth and development, photosynthesis, transpiration, ion uptake and
transport. SA also induces specific changes in leaf anatomy and chloroplast structure.[which?] SA is involved in endogenous signaling, mediating
in plant defense against pathogens.[29] It plays a role in
the resistance to pathogens by inducing the production of pathogenesis-related
proteins.[30] It is involved in
the systemic acquired
resistance (SAR) in which a pathogenic attack on one part of the plant
induces resistance in other parts. The signal can also move to nearby plants by
salicylic acid being converted to the volatile ester, methyl salicylate.[31]
Production
Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana it can be
synthesized via a phenylalanine-independent pathway.
Sodium salicylate is commercially
prepared by treating sodium phenolate (the sodium salt of phenol) with carbon dioxide at high pressure
(100 atm) and high temperature (390 K) – a method known as the Kolbe-Schmitt reaction. Acidification of the product with sulfuric acid gives salicylic
acid:
It can also be prepared by the hydrolysis of aspirin (acetylsalicylic
acid)[32] or methyl salicylate (oil of wintergreen) with a strong acid
or base.
Packaging
100, 500 g in poly bottle
PRICE
$1554.24/KG OR $706.47/IB
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