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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:37 UTC
Update Date2021-09-14 15:45:49 UTC
HMDB IDHMDB0061839
Secondary Accession Numbers
  • HMDB61839
Metabolite Identification
Common NameEthylhexyl salicylate
DescriptionEthylhexyl salicylate, also known as uvinul or octyl salicylic acid, 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. Ethylhexyl salicylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethylhexyl 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.
Structure
Data?1563866237
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 Weight250.3334
Monoisotopic Molecular Weight250.15689457
IUPAC Name2-ethylhexyl 2-hydroxybenzoate
Traditional Nameoctisalate
CAS Registry NumberNot Available
SMILES
CCCCC(CC)COC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-e6bf91bd63e14169eb922017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-e6bf91bd63e14169eb922018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6910000000-0846696bc110275352462017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-5911000000-4e9e3df7eea4e73981712017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-6910000000-0846696bc110275352462021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-2960000000-63063e687c4f0a8a31022016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-6910000000-69e92883b4ccaac7336f2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kfx-9100000000-add879fc2c2e2c83ce6a2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2490000000-76cec8f8c72dad507a4e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000g-6930000000-1bd98f5314ffed506fc52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-6e0906ad02af5116c8302016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0490000000-02d7f6aaed2cc27aac002021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-885ced603138644e11522021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9100000000-313f672c7fc52f7c89482021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1980000000-3a31c02a91c43cbf6c212021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9310000000-9576266ee493b89c1d9c2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7fc6b22785a698eafb232021-09-07View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8364
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:14617432 ]
  2. Shaw DW: Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. 2006 Sep;17(3):152-5. [PubMed:16956469 ]
  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. [PubMed:18498482 ]
  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. [PubMed:18966155 ]
  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. [PubMed:18967342 ]
  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. [PubMed:20233542 ]
  7. Wikipedia [Link]
  8. Rene Rivero, Frank Lucia, Vinod Topiwala, 'Ultra-violet inhibition system.' U.S. Patent US20060057080, issued March 16, 2006. [Link]
  9. Roland Langner, 'MIXTURES OF ETHYLHEXYL P-METHOXYCINNAMATE AND ETHYLHEXYL SALICYLATE.' U.S. Patent US20090053154, issued February 26, 2009. [Link]
  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. [Link]