2-Ethylhexyl salicylate (CHEM017599)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:29:24 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017599
Identification
Common Name2-Ethylhexyl salicylate
ClassSmall Molecule
DescriptionEthylhexyl salicylate, or octyl salicylate, is an organic compound used as an ingredient in sunscreens and cosmetics to absorb UVB (ultraviolet) rays from the sun. It is an ester formed by the condensation of a salicylic acid with 2-ethylhexanol. It is a colorless oily liquid with a slight floral odor.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Octyl salicylateKegg
UvinulKegg
Octyl salicylic acidGenerator
Ethylhexyl salicylic acidGenerator
OCTISALic acidHMDB
Ethyl hexyl salicylateHMDB
OctylsalicylateHMDB
Salicylic acid 2-ethylhexyl esterHMDB
trans-2-Hexenyl salicylateHMDB
OctisalateMeSH
2-Ethylhexyl 2-hydroxybenzoic acidGenerator
Chemical FormulaC15H22O3
Average Molecular Mass250.333 g/mol
Monoisotopic Mass250.157 g/mol
CAS Registry Number118-60-5
IUPAC Name2-ethylhexyl 2-hydroxybenzoate
Traditional Nameoctisalate
SMILESCCCCC(CC)COC(=O)C1=CC=CC=C1O
InChI IdentifierInChI=1S/C15H22O3/c1-3-5-8-12(4-2)11-18-15(17)13-9-6-7-10-14(13)16/h6-7,9-10,12,16H,3-5,8,11H2,1-2H3
InChI KeyFMRHJJZUHUTGKE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parento-Hydroxybenzoic acid esters
Alternative Parents
Substituents
  • O-hydroxybenzoic acid ester
  • Salicylic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP4.79ALOGPS
logP5.35ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.21 m³·mol⁻¹ChemAxon
Polarizability29.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-e6bf91bd63e14169eb92Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-e6bf91bd63e14169eb92Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6910000000-0846696bc11027535246Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-5911000000-4e9e3df7eea4e7398171Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-2960000000-63063e687c4f0a8a3102Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-6910000000-69e92883b4ccaac7336fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kfx-9100000000-add879fc2c2e2c83ce6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2490000000-76cec8f8c72dad507a4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000g-6930000000-1bd98f5314ffed506fc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-6e0906ad02af5116c830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0490000000-02d7f6aaed2cc27aac00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-885ced603138644e1152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9100000000-313f672c7fc52f7c8948Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1980000000-3a31c02a91c43cbf6c21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9310000000-9576266ee493b89c1d9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7fc6b22785a698eafb23Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061839
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID8364
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Authors unspecified: Safety assessment of Salicylic Acid, Butyloctyl Salicylate, Calcium Salicylate, C12-15 Alkyl Salicylate, Capryloyl Salicylic Acid, Hexyldodecyl Salicylate, Isocetyl Salicylate, Isodecyl Salicylate, Magnesium Salicylate, MEA-Salicylate, Ethylhexyl Salicylate, Potassium Salicylate, Methyl Salicylate, Myristyl Salicylate, Sodium Salicylate, TEA-Salicylate, and Tridecyl Salicylate. Int J Toxicol. 2003;22 Suppl 3:1-108.
2. Shaw DW: Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. 2006 Sep;17(3):152-5.
3. Masse MO, Herpol-Borremans M: Dosage de l'octyl dimethyl PABA, de l'homosalate et de l'octyl salicylate dans les produits de protection solaire. Int J Cosmet Sci. 2001 Dec;23(6):325-31.
4. Nambiar DC, Gaudh JS, Shinde VM: Tris(2-ethylhexyl)phosphate as an extractant for trivalent gallium, indium and thallium. Talanta. 1994 Nov;41(11):1951-5.
5. Chhatre MH, Shinde VM: Separation of scandium(III) and yttrium(III) by tris(2-ethylhexyl)phosphate (TEHP). Talanta. 1998 Oct;47(2):413-9.
6. Mortz CG, Thormann H, Goossens A, Andersen KE: Allergic contact dermatitis from ethylhexyl salicylate and other salicylates. Dermatitis. 2010 Mar-Apr;21(2):E7-10.
7. Wikipedia: http://en.wikipedia.org/wiki/Octyl_salicylate
8. Rene Rivero, Frank Lucia, Vinod Topiwala, 'Ultra-violet inhibition system.' U.S. Patent US20060057080, issued March 16, 2006.: http://www.google.ca/patents/US20060057080
9. Roland Langner, 'MIXTURES OF ETHYLHEXYL P-METHOXYCINNAMATE AND ETHYLHEXYL SALICYLATE.' U.S. Patent US20090053154, issued February 26, 2009.: http://www.google.ca/patents/US20090053154
10. Isabelle Hansenne, Victoria Van Leeuwen, 'Photoprotective/cosmetic compositions comprising 2,4,6-tris[p-((2'-ethylhexyl)oxycarbonyl)anilino]-1,3,5-triazine and salicylate solvents therefor.' U.S. Patent US6096294, issued November, 1994.: http://www.google.ca/patents/US6096294