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Merck

247588

Salicylic acid

ACS reagent grade, ≥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
NACRES:
NA.21
PubChem Substance ID:
24854876
UNSPSC Code:
12352100
EC Number:
200-712-3
MDL number:
MFCD00002439
Beilstein/REAXYS Number:
774890

Product Name

Salicylic acid, ACS reagent, ≥99.0%

InChI key

YGSDEFSMJLZEOE-UHFFFAOYSA-N

InChI

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

SMILES string

OC(=O)c1ccccc1O

grade

ACS reagent

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

functional group

carboxylic acid

Quality Level

200

Gene Information

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

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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.

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.

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Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4119
MKCX4665
MKCV6094
MKCT5761
MKCR9026

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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)
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)
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