Phenyl salicylate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Phenyl salicylate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Phenyl salicylate?

The molecule Phenyl salicylate presents a molecular formula of C13H10O3 and its IUPAC name is phenyl 2-hydroxybenzoate.

Phenyl salicylate (C6H5CO2C6H4OH) is a white, crystalline solid with a faint, characteristic odor. It is insoluble in water and has a melting point of 108-109°C. Phenyl salicylate is used as an aromatic in perfumes and as a rubefacient in liniments and ointments. It is also used as a photographic developer and as an insecticide..

Phenyl salicylate is prepared by the esterification of salicylic acid with phenol:.

C6H5OH + C6H4(OH)CO2H → C6H5CO2C6H4OH + H2O.

The reaction is usually conducted in the presence of a strong acid catalyst, such as sulfuric acid or p-toluenesulfonic acid..

Phenyl salicylate is a member of the class of salicylates, which are derivatives of salicylic acid. Salicylates are used as analgesics, anti-inflammatories, and antipyretics. They are also used as ingredients in topical preparations for the treatment of acne, dandruff, and other skin conditions..

Phenyl salicylate is readily hydrolyzed in the presence of water or moisture to yield phenol and salicylic acid:.

C6H5CO2C6H4OH + H2O → C6H5OH + C6H4(OH)CO2H.

Phenyl salicylate is a mild irritant to the skin and eyes. Ingestion of large amounts may cause nausea, vomiting, and diarrhea. Overdose may lead to salicylate poisoning, which is characterized by tinnitus, dizziness, headache, and hyperventilation. Treatment is symptomatic and supportive..

3D structure

Cartesian coordinates

Geometry of Phenyl salicylate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Phenyl salicylate ZQBAKBUEJOMQEX-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Phenyl salicylate

 

Molecule descriptors

 
IUPAC namephenyl 2-hydroxybenzoate
InChI codeInChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
InChI KeyZQBAKBUEJOMQEX-UHFFFAOYSA-N
SMILESO=C(Oc1ccccc1)c1ccccc1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 118-55-8
  • 2-Hydroxy-benzoic acid phenyl ester
  • 2-Hydroxybenzoic acid phenyl ester
  • 2-Hydroxybenzoic acid, phenyl ester
  • 2-Phenoxycarbonylphenol
  • 28A37T47QO
  • A804056
  • AB00443435-03
  • AC-11469
  • AI3-00195
  • BIDD:ER0018
  • BRN 0393969
  • Benzoic acid, 2-hydroxy-, phenyl ester
  • CCRIS 4859
  • DB-024372
  • DB11071
  • DSSTox_CID_1957
  • DSSTox_GSID_21957
  • DSSTox_RID_76426
  • FEMA NO. 3960
  • FT-0689174
  • Fenylester kyseliny salicylove
  • J-200110
  • MFCD00002213
  • Mettler-Toledo Calibration substance ME 30034252, Phenyl salicylate
  • Mettler-Toledo Calibration substance ME 30034252, Phenyl salicylate, traceable to primary standards
  • Musol
  • NCGC00090887-01
  • NCGC00090887-02
  • NCGC00090887-03
  • NCGC00090887-04
  • NCGC00090887-05
  • NCGC00091499-03
  • NCGC00256612-01
  • NCGC00259360-01
  • NSC 33406
  • NSC-33406
  • NSC33406
  • NSC33406NSC 33406
  • Oprea1_020651
  • Oprea1_771794
  • PHENYL 2-HYDROXYBENZOATE
  • PS-7960
  • Phenol salicylate
  • Phenyl Salicylate, Crystal, Purified
  • Phenyl salicylate
  • Phenyl salicylate melting point standard
  • Phenyl-2-hydroxybenzoate
  • Q421259
  • S0017
  • SR-01000883691
  • SR-01000883691-1
  • STK052177
  • STR06361
  • Salicylic Acid Phenyl Ester
  • Salicylic acid, phenyl ester
  • Salol
  • Salphenyl
  • Seesorb 201
  • Seesorb K 201
  • WLN: QR BVOR
  • Z57206005
  • phenyl-salicylate
  • phenylsalicylate
  • salicylic acid phenyl
  • salicylic phenyl ester

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC38545
  • CAS-118-55-8
  • UNII-28A37T47QO
  • AKOS000121203
  • DTXSID6021957
  • CHEMBL1339216
  • CHEBI:34918
  • Tox21_113459
  • Tox21_201811
  • Tox21_302949
  • Tox21_113459_1
  • EINECS 204-259-2
  • SCHEMBL24326

Physico-Chemical properties

IUPAC namephenyl 2-hydroxybenzoate
Molecular formulaC13H10O3
Molecular weight214.217
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity59.87
LogP2.6
Topological polar surface area46.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.