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247588

Sigma-Aldrich

Salicylic acid

ACS reagent, ≥99.0%

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Synonym(s):
2-Hydroxybenzoic acid
Linear Formula:
2-(HO)C6H4CO2H
CAS Number:
69-72-7
Molecular Weight:
138.12
Beilstein:
774890
EC Number:
200-712-3
MDL number:
MFCD00002439
UNSPSC Code:
12352100
PubChem Substance ID:
24854876
NACRES:
NA.21

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.

Signal Word

Danger

Hazard Statements

H302,H318,H361d

Hazard Classifications

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

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
A central role of salicylic acid in plant disease resistance
Delaney TP, et al.
Science, 266(5188), 1247-1250 (1994)
Thomas, M. R
Kirk-Othmer Encyclopedia of Chemical Technology (2006)
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)
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