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247588

Sigma-Aldrich

Salicylic acid

ACS reagent, ≥99.0%

Synonym(s):

2-Hydroxybenzoic acid

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About This Item

Linear Formula:
2-(HO)C6H4CO2H
CAS Number:
69-72-7
Molecular Weight:
138.12
Beilstein/REAXYS Number:
774890
EC Number:
200-712-3
MDL number:
MFCD00002439
UNSPSC Code:
12352100
PubChem Substance ID:
24854876

grade

ACS reagent

Quality Level

200

vapor density

4.8 (vs air)

vapor pressure

1 mmHg ( 114 °C)

assay

≥99.0%

impurities

H2SO4, passes test (darkened)

ign. residue

≤0.01%

bp

211 °C (lit.)

mp

158-161 °C (lit.)

anion traces

chloride (Cl-): ≤0.001%
sulfate (SO42-): ≤0.003%

cation traces

Fe: ≤2 ppm
heavy metals (as Pb): ≤5 ppm

SMILES string

OC(=O)c1ccccc1O

InChI

1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

InChI key

YGSDEFSMJLZEOE-UHFFFAOYSA-N

Gene Information

human ... ALB(213) , PTPN1(5770)

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General description

Salicylic acid is mainly used as the precursor to synthesize aspirin, a commonly used analgesic and antipyretic. Due to its keratolytic action, it is also used in topical ointments.

Application

Salicylic acid has been used:
  • as one of the chemical compound in exposure-based validation of in vitro gastrulation model employed in developmental toxicity screening assays
  • as a reference standard in salicylate quantification by reverse-phase high-performance liquid chromatography (RP-HPLC)

Biochem/physiol Actions

Salicylic acid (SA) delivers local and systemic acquired resistance (LAR and SAR) against various diseases in plants. It acts as a secondary metabolite and regulate various physiological processes such as respiration, stomatal closure and senescence-associated gene expression. In addition, SA also controls abiotic stress, basal thermotolerance, nodulation in legumes and fruit yield. It plays a vital role in modulation of flowering and thermogenesis (heat production) in plants. SA together with reactive oxygen species (ROS) and nitric oxide (NO) triggers cell death in plants.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

314.6 °F - closed cup

flash_point_c

157 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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SAFC

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Salicylic acid

A central role of salicylic acid in plant disease resistance
Delaney TP, et al.
Science, 266(5188), 1247-1250 (1994)
Efficacy of salicylic acid to reduce Penicillium expansum inoculum and preserve apple fruits
da Rocha Neto AC, et al.
International Journal of Food Microbiology, 221, 54-60 (2016)
Influence of cyclooxygenase-1 genotype on ex vivo aspirin response in patients at risk for stroke
Momary KM, et al.
Cerebrovascular Diseases (Basel, Switzerland), 27(6), 585-593 (2009)
Xanthone
AF Holleman
Organic Syntheses, 1, 552-552 (1941)
Isochorismate synthase is required to synthesize salicylic acid for plant defence
Wildermuth MC, et al.
Nature, 414(6863), 562-562 (2001)
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