Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H6O3 |
Molecular Weight | 138.121 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(c(c1)C(=O)O)O
InChI
InChIKey=YGSDEFSMJLZEOE-UHFFFAOYSA-N
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
Molecular Formula | C7H6O3 |
Molecular Weight | 138.121 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdfhttp://www.drugbank.ca/drugs/DB00936Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdfhttp://www.drugbank.ca/drugs/DB00936
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html
Salicylic acid is obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. Salicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution 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. Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined the two key ingredients help control diarrhea, nausea, heartburn, and even gas. It is also very mildly anti-biotic. Salicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.
Originator
Sources: https://books.google.ru/books?id=iUpwBAAAQBAJ&pg=PT83&lpg=PT83&dq=Methyl+salicylate+Auguste+Andr%C3%A9+Thomas+Cahours&source=bl&ots=nFDf2n2bpT&sig=wAKTDamdc7xWWgRxOrTeokeji8g&hl=ru&sa=X&ved=0ahUKEwj-q8769PzTAhVFfhoKHYEqDgkQ6AEIODAD#v=onepage&q=Methyl%20salicylate%20Auguste%20Andr%C3%A9%20Thomas%20Cahours&f=falsehttp://www.casinapioiv.va/content/dam/accademia/pdf/acta18/acta18-szczeklik.pdf
Curator's Comment:: In 1859 Friedrich Kolbe identified the structure of salicylic acid as an o-hydroxybenzoic acid, managed to obtain it synthetically and introduced it to therapy.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936 |
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Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936 |
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Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955 |
1.48 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date1.20346562E12 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date1.20346562E12 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date1.20346562E12 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date1.20346562E12 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date1.35501119E12 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date1.35501119E12 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date1.35501119E12 |
Doses
Dose | Population | Adverse events |
---|---|---|
30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: |
Other AEs: Redness, Scales... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Redness | 30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: |
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Scales | 30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
major | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions]. | 1999 |
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Salicylate attenuates gentamicin-induced ototoxicity. | 1999 Jul |
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Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE). | 1999 May |
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Effects of salicylates on evoked otoacoustic emissions and remote masking in humans. | 1999 May-Jun |
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False-high blood salicylate levels in neonates with hyperbilirubinemia. | 2000 Dec |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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Sodium salicylate increases CYP2E1 levels and enhances arachidonic acid toxicity in HepG2 cells and cultured rat hepatocytes. | 2001 Apr |
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Ascorbic acid prevents 3,4-methylenedioxymethamphetamine (MDMA)-induced hydroxyl radical formation and the behavioral and neurochemical consequences of the depletion of brain 5-HT. | 2001 Apr |
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Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo). | 2001 Apr 13 |
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Effect of fluvastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase, on nitric oxide-induced hydroxyl radical generation in the rat heart. | 2001 Apr 30 |
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[Tolerability of a selective cyclooxygenase-2-inhibitor (rofecoxib) in patients with intolerance reactions to nonsteroidal anti-inflammatory agents]. | 2001 Apr 6 |
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Non-ionic micellar affinity capillary electrophoresis for analysis of interactions between micelles and drugs. | 2001 Feb |
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Increased leukotriene production by food additives in patients with atopic dermatitis and proven food intolerance. | 2001 Feb |
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A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics. | 2001 Feb |
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Characterization of PBZ1, a probenazole-inducible gene, in suspension-cultured rice cells. | 2001 Jan |
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Non-uniform mapping of stress-induced, motility-related charge movement in the outer hair cell plasma membrane. | 2001 Jan |
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Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action. | 2001 Jan |
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Microfabrication of individual 200 microm diameter transdermal microconduits using high voltage pulsing in salicylic acid and benzoic acid. | 2001 Jan |
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Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors. | 2001 Jan |
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Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis. | 2001 Jan 15 |
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Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism. | 2001 Jan 15 |
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Pathogen-induced expression of plant ATP: citrate lyase. | 2001 Jan 19 |
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Characterization of a rice (Oryza sativa L.) Bowman-Birk proteinase inhibitor: tightly light regulated induction in response to cut, jasmonic acid, ethylene and protein phosphatase 2A inhibitors. | 2001 Jan 24 |
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Quantitative analysis of hydroxyl radicals in the anterior optic nerve of the cat following transient ischemia. | 2001 Jan-Feb |
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A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus. | 2001 Jul 6 |
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A recessive mutation in the Arabidopsis SSI2 gene confers SA- and NPR1-independent expression of PR genes and resistance against bacterial and oomycete pathogens. | 2001 Mar |
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Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways. | 2001 Mar |
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Identification of free radicals produced during phacoemulsification. | 2001 Mar |
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In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis. | 2001 Mar 1 |
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Microdialysis of salicylic acid from viscous emulsion samples prior to high-performance liquid chromatographic determination. | 2001 Mar 30 |
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Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection. | 2001 Mar 5 |
Sample Use Guides
adults 18 years and older:
apply one patch to affected area and leave in place for up to 8-12 hours; if pain lasts lasts after using the first patch, a second patch may be applied for up to another 8 to 12 hours; use only one patch at a time; do not use more than 2 patches per day; do not use for more 3 days in a row
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17497409
In vitro tests with fresh dermatomed (0.3 to 0.4 mm thick) female breast skin and one leg skin specimen were conducted in Bronaugh flow-through Teflon diffusion cells with three chemicals used to simulate chemical warfare agents: 14C-radiolabeled methyl salicylate (MES), ethyl parathion (PT), and malathion (MT), at three dose levels (2, 20, and 200 mM). Tests were conducted at a skin temperature of 29 degrees C using a brief 30-min exposure to the chemical and a 6.5-h receivor collection period. Rapid absorption of all three chemicals was observed, with MES absorbed about 10-fold faster than PT and MT. For MES, PT, and MT, respectively, there was 32%, 7%, and 12% absorption into the receivor solution at the low dose (2 mM), 17%, 2%, and 3% at the medium dose (20 mM), and 11%, 1%, and 1% at the high dose (200 mM) levels. Including the skin depot for MES, PT, and MT, respectively, there was 40%, 41%, and 21% (low dose), 26%, 16%, and 8% (medium dose), and 13%, 19%, and 10% (high does) absorption.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:14:17 UTC 2021
by
admin
on
Fri Jun 25 21:14:17 UTC 2021
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Record UNII |
O414PZ4LPZ
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 358.710
Created by
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CFR |
21 CFR 333.310
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NCI_THESAURUS |
C257
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NCI_THESAURUS |
C52588
Created by
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CFR |
21 CFR 358.510
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WHO-VATC |
QD01AE12
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CFR |
21 CFR 862.3830
Created by
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EPA PESTICIDE CODE |
76602
Created by
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CFR |
21 CFR 358.720
Created by
admin on Fri Jun 25 21:14:18 UTC 2021 , Edited by admin on Fri Jun 25 21:14:18 UTC 2021
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WHO-VATC |
QS01BC08
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WHO-ATC |
S01BC08
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CFR |
21 CFR 358.110
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FDA ORPHAN DRUG |
359211
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WHO-VATC |
QM02AC99
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JECFA EVALUATION |
2-HYDROXYBENZOIC ACID
Created by
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WHO-ATC |
D01AE12
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WHO-ESSENTIAL MEDICINES LIST |
13.4
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Code System | Code | Type | Description | ||
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9525
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PRIMARY | |||
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672
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PRIMARY | |||
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O414PZ4LPZ
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PRIMARY | |||
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338
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PRIMARY | |||
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9522
Created by
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ALTERNATIVE | |||
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Salicylic Acid
Created by
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PRIMARY | |||
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SUB15180MIG
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PRIMARY | |||
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SALICYLIC ACID
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PRIMARY | |||
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69-72-7
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PRIMARY | |||
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1609002
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PRIMARY | USP-RS | ||
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200-712-3
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PRIMARY | |||
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D020156
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4306
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PRIMARY | |||
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2416
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PRIMARY | |||
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M9739
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PRIMARY | Merck Index | ||
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C61934
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PRIMARY | |||
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SALICYLIC ACID
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PRIMARY | Description: Colourless crystals, usually needle-like, or a white, crystalline powder; odourless. Solubility: Slightly soluble in water; soluble in 4 parts of ethanol (~750 g/l) TS and in 3 parts of ether R. Category: Keratolytic. Storage: Salicylic acid should be kept in a well-closed container. Definition: Salicylic acid contains not less than 99.0% and not more than 101.0% of C7H6O3, calculated with reference to the dried substance. | ||
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CHEMBL424
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PRIMARY | |||
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DB00936
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PRIMARY | |||
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69-72-7
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PRIMARY |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Salicylic acid content for water extract of plant callus was 3.22+/-0.06 as expressed as mg/100 g of dry base of extract.
For the analysis of phenolic acids, a Nova pack C18 UG120 equipped with a Guard column, a JASCO HPLC system consisting of a column oven, a UV-Vis diode array detector set at 280 nm, a Liquid chromatography pump and a ChromNAV software program were used.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
MINOR
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
IDENTIFIED AS IMPURITY C
Limits: impurity C: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (a) (0.15 per cent)
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IMPURITY -> PARENT |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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PARENT -> IMPURITY |
Correction factors: for the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |