Phenyl Salicylate

• CAS: 118-55-8
• Catalog Number: ACM118558-2
• Category: Organic & Printed Electronics
• Molecular Weight: 214.217
• Molecular Formula: C13H10O3
• Description: Phenyl salicylate is the phenyl ester of salicylic acid, used pharmaceutically under the name "salol" as an internal preservative. Phenyl salicylate is a phenyl carboxylate known for its aroma and flavoring properties.
• Synonyms: Salol
• IUPAC Name: phenyl 2-hydroxybenzoate
• Canonical SMILES: C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2O
• InChI: InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
• InChI Key: ZQBAKBUEJOMQEX-UHFFFAOYSA-N
• Boiling Point: 306.6±0.0 °C at 760 mmHg
• Melting Point: 41-43 °C(lit.)
• Flash Point: 137.3±13.2 °C
• Density: 1.3±0.1 g/mL
• Solubility: water, 76.7 mg/L @ 25 °C (est)
• Appearance: White crystalline powder
• Application: It can be used in paints, waxes and varnishes as it absorbs UV radiation in the range 290-325 nm. It also appears in cosmetics and sunscreens as a UV filter.
• Storage: Store at 2-8 ℃
• Complexity: 233
• Covalently-Bonded Unit Count: 1
• EC Number: 204-259-2
• Exact Mass: 214.062988
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Heavy Atom Count: 16
• MDL Number: MFCD00002213
• Monoisotopic Mass: 214.062994g/mol
• NSC Number: 33406
• Packaging: 1 kg
• Physical State: Solid
• PSA: 46.53
• Refractive Index: 1.615
• Rotatable Bond Count: 3
• Stability: Light sensitive. Incompatible with strong oxidants. Flammable.
• UNII: 28A37T47QO
• Vapor Pressure: 0.0±0.6 mmHg at 25°C
• XLogP3: 3.8

Case Study

Photo-Fries Rearrangement of Phenyl Salicylate

Shinzawa H,et al. Vibrational Spectroscopy, 2015, 81: 131-135.

Phenyl salicylate is a commonly used UV filter. Changes in the spectral features were readily captured during the photo-induced chemical reaction of the phenyl salicylate by means of two-dimensional (2D) correlation spectroscopy. The photo-Fries rearrangement involves the transformation of molecules such as phenolic esters to hydroxy aryl ketones. This chemical reaction is important since the molecules generated by the rearrangement can be used as source for photoresist materials.
Reaction Mechanism
· When exposed to UV-irradiation, the majority of the phenyl salicylate predominantly undergoes photothermal degradation, generating oxides first.
· Further irradiation develops 2,20 -dihydroxybenzophenone followed by the production 2,40 -dihydroxybenzo-phenome.

Toxicity Assessment of Phenyl Salicylate as A Fragrance Ingredient

Lapczynski, A., et al. Food and chemical toxicology, 2007, 45(1), S472-S476.

Phenyl salicylate is a fragrance ingredient used in many fragrance compounds. It may be found in fragrances used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. A review summarizes the toxicology and dermatology of phenyl salicylate when used as a fragrance ingredient. Some important experimental results include:
· Acute toxicity: The acute oral LD50 of phenyl salicylate was evaluated in rats (10/dose). The acute LD50 was calculated to be 3.0 g/kg (95% CI 2.52-3.57 g/kg).
· Skin irritation: In a pre-test for a human maximization test, a 48 hour closed patch test was conducted on five healthy volunteers with 6% phenyl salicylate in petrolatum which were applied to the backs. No irritation was observed.
· Skin sensitization: A human maximization test was conducted with Phenyl salicylate. 6% phenyl salicylate in petrolatum under occlusion to the same site on the volar forearms of 25 healthy male and female volunteers for five alternate day 48-hour periods. No sensitization reactions were observed.

Custom Q&A

What is the molecular formula of Phenyl salicylate?

The molecular formula of Phenyl salicylate is C13H10O3.

What are some synonyms of Phenyl salicylate?

Some synonyms of Phenyl salicylate include Salol, Phenol salicylate, and Phenyl 2-Hydroxybenzoate.

What is the molecular weight of Phenyl salicylate?

The molecular weight of Phenyl salicylate is 214.22 g/mol.

How is Phenyl salicylate formed?

Phenyl salicylate can be formed by heating salicylic acid with phenol.

What role does Phenyl salicylate play in manufacturing?

Phenyl salicylate is used in the manufacture of some polymers, lacquers, adhesives, waxes, and polishes.

What is the chemical structure of Phenyl salicylate?

The chemical structure of Phenyl salicylate is C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2O.

What is the IUPAC name of Phenyl salicylate?

The IUPAC name of Phenyl salicylate is phenyl 2-hydroxybenzoate.

What are some other identifiers for Phenyl salicylate?

Some other identifiers for Phenyl salicylate include CAS number 118-55-8 and ChEBI ID CHEBI:34918.

What are some physical and chemical properties of Phenyl salicylate?

Some computed properties of Phenyl salicylate include a hydrogen bond donor count of 1, a hydrogen bond acceptor count of 3, and a topological polar surface area of 46.5Ų.

How is Phenyl salicylate used in pharmaceutical products?

Phenyl salicylate is used as a mild analgesic for pain relief in some pharmaceutical products by releasing salicylate.