Homosalate

Identification

Name
Homosalate
Accession Number
DB11064
Description

Homosalate is an organic compound that belongs to salicylates. It is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. Salicylates prevent direct skin exposure to the sun’s harmful rays by absorbing ultraviolet (UV) light. Homosalate specifically absorbs short-wave UVB rays, which are associated with DNA damage and increased risk of skin cancer.

It is a common ingredient in many commercially available sunscreens. There are no reported adverse effects from homosalate.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 262.349
Monoisotopic: 262.156894568
Chemical Formula
C16H22O3
Synonyms
  • 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate
  • Homosalate
  • Homosalato
  • Homosalatum
External IDs
  • Caswell No. 482B

Pharmacology

Indication

As ingredient in many sunscreen for protection against sunburn, skin aging and skin cancer.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Acts as UV filters.

Mechanism of action

Homosalate has the ability to convert incident ultraviolet radiation into less damaging infrared radiation (heat).

TargetActionsOrganism
UProgesterone receptor
antagonist
Humans
UAndrogen receptor
antagonist
Humans
UEstrogen receptor alphaNot AvailableHumans
Absorption

For local use only, no systemic absorption.

Volume of distribution

For local use only, no systemic absorption.

Protein binding

For local use only, no systemic absorption.

Metabolism

For local use only, no systemic absorption.

Route of elimination

For local use only, no systemic absorption.

Half-life

For local use only, no systemic absorption.

Clearance

For local use only, no systemic absorption.

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

LD50: Not available.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Active Moieties
NameKindUNIICASInChI Key
Salicylic acidunknownO414PZ4LPZ69-72-7YGSDEFSMJLZEOE-UHFFFAOYSA-N
International/Other Brands
Eusolex
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sei Bella Age Defying Foundation AlmondLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation BeigeLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation CashmereLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation ChestnutLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation Classic BeigeLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation EspressoLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation FawnLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation GoldenLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation IvoryLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Sei Bella Age Defying Foundation NaturalLiquid2.9313 g/30mLTopicalMelaleuca, Inc.2011-05-022013-02-01Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
100 SPF CreamHomosalate (15 %) + Avobenzone (3 %) + Octisalate (5 %) + Octocrylene (10 %) + Oxybenzone (6 %)CreamTopicalVital Science A Div. Of/Une Div. De Valeant Canada Ltd/Ltee2010-06-032014-08-27Canada
14-day Skin Rescue SPF 30Homosalate (4 %) + Avobenzone (3 %) + Octisalate (5 %) + Octocrylene (2.35 %) + Oxybenzone (6 %)CreamTopicalJohnson & Johnson2009-02-162013-07-31Canada
15 Tanning CVSHomosalate (10 g/100mL) + Avobenzone (2 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (5 g/100mL)LotionTopicalProduct Quest Mff, Llc2014-11-062016-04-20Us
2 in 1 Sunscreen and Gradual Self-TannerHomosalate (15 g/100mL) + Avobenzone (3 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (8 g/100mL)Aerosol, sprayTopicalSunless, Inc2018-09-07Not applicableUs
21STAY A Thera Sun BlockHomosalate (20 mg/1mL) + Octinoxate (60 mg/1mL) + Octisalate (40 mg/1mL) + Titanium dioxide (54.6 mg/1mL) + Zinc oxide (58.2 mg/1mL)CreamTopicalOracle Cosmetic Co., Ltd.2017-11-21Not applicableUs
24K Bio-Brightening Skin Tone Moisturizer SPF 30Homosalate (6.2 g/100g) + Avobenzone (1.5 g/100g) + Octinoxate (7.4 g/100g) + Octisalate (5 g/100g) + Oxybenzone (3.1 g/100g)CreamTopicalVivo Per-lei, Inc.2014-10-032019-12-31Us
24K Skin Tone Moisturizer SPF 30Homosalate (6.2 g/100g) + Avobenzone (1.5 g/100g) + Octinoxate (7.4 g/100g) + Octisalate (5.0 g/100g) + Oxybenzone (3.1 g/100g)CreamTopicalVivo Per-lei, Inc.2019-07-29Not applicableUs
29 by LYDIA MONDAVI Napa Valley BROAD SPECTRUM SPF 30 D VINE DAYHomosalate (100 mg/1mL) + Avobenzone (30 mg/1mL) + Octisalate (50 mg/1mL) + Octocrylene (20 mg/1mL) + Oxybenzone (25 mg/1mL)CreamTopical29 Luxury Goods, Inc.2013-10-162019-01-31Us
2X Sunblock SPF 50Homosalate (15 mL/100mL) + Avobenzone (3 mL/100mL) + Octocrylene (6 mL/100mL) + Oxybenzone (6 mL/100mL)LiquidTopicalNupur Formulations Inc2011-04-22Not applicableUs
3-in-1 Face Moisturizer Broad Spectrum SPF 20Homosalate (10 g/100mL) + Avobenzone (3 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (10 g/100mL)JellyTopicalJafra cosmetics International2019-03-27Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4362 First Aid KitHomosalate (5 g/100mL) + Ammonia (0.045 g/0.3mL) + Avobenzone (1 g/100mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Octinoxate (7.5 g/100mL) + Octisalate (5 g/100mL) + Oxybenzone (6 g/100mL) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)Ophthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
BEYOND THE SHAVE For MenHomosalate (2.5 g/100mL) + Allantoin (0.5 g/100mL) + Avobenzone (3.0 g/100mL) + Dimethicone (2.9 g/100mL) + Octasulfur (3.0 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (2.7 g/100mL)KitTopicalRodan & Fields2017-06-01Not applicableUs
CoreTex Professional Outdoor Skin Protection WalletHomosalate (5 g/100mL) + Homosalate (5 g/100g) + Homosalate (7.5 g/100mL) + Avobenzone (1 g/100mL) + Avobenzone (1 g/100g) + Avobenzone (3 g/100mL) + Benzocaine (6 g/100mL) + Diphenhydramine hydrochloride (2 g/100mL) + Ethanol (62.5 mL/100mL) + Octinoxate (7.5 g/100mL) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100mL) + Octisalate (5 g/100g) + Octisalate (5 g/100mL) + Octocrylene (2.5 g/100mL) + Oxybenzone (6 g/100mL) + Oxybenzone (6 g/100g) + Oxybenzone (6 g/100mL) + Synthetic camphor (0.1 g/100mL) + Zinc acetate dihydrate (1 g/100mL)TopicalCoreTex Products2019-11-27Not applicableUs
CoreTex Professional Outdoor Skin Protection WalletHomosalate (5 g/100mL) + Homosalate (5 g/100g) + Homosalate (7.5 g/100mL) + Avobenzone (1 g/100mL) + Avobenzone (1 g/100g) + Avobenzone (3 g/100mL) + Benzocaine (6 g/100mL) + Diphenhydramine hydrochloride (2 g/100mL) + Ethanol (62.5 mL/100mL) + Octinoxate (7.5 g/100mL) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100mL) + Octisalate (5 g/100g) + Octisalate (5 g/100mL) + Octocrylene (2.5 g/100mL) + Oxybenzone (6 g/100mL) + Oxybenzone (6 g/100g) + Oxybenzone (6 g/100mL) + Synthetic camphor (0.1 g/100mL) + Zinc acetate dihydrate (1 g/100mL)TopicalCoreTex Products2019-11-27Not applicableUs
CoreTex Professional Outdoor Skin Protection WalletHomosalate (5 g/100mL) + Homosalate (5 g/100g) + Homosalate (7.5 g/100mL) + Avobenzone (1 g/100mL) + Avobenzone (1 g/100g) + Avobenzone (3 g/100mL) + Benzocaine (6 g/100mL) + Diphenhydramine hydrochloride (2 g/100mL) + Ethanol (62.5 mL/100mL) + Octinoxate (7.5 g/100mL) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100mL) + Octisalate (5 g/100g) + Octisalate (5 g/100mL) + Octocrylene (2.5 g/100mL) + Oxybenzone (6 g/100mL) + Oxybenzone (6 g/100g) + Oxybenzone (6 g/100mL) + Synthetic camphor (0.1 g/100mL) + Zinc acetate dihydrate (1 g/100mL)TopicalCoreTex Products2019-11-27Not applicableUs
Epionce Active Shield SPF 30Homosalate (0.1 mL/1mL) + Octisalate (0.05 mL/1mL) + Zinc oxide (0.92 mL/1mL)LotionTopicalEpisciences, Inc.2005-03-242005-03-24Us
Nu-derm System Normal-dry Skin TransformationHomosalate (100 mg/1g) + Hydroquinone (40 mg/1g) + Hydroquinone (40 mg/1g) + Octisalate (50 mg/1g) + Zinc oxide (165 mg/1g)TopicalOBAGI COSMECEUTICAL LLC2019-12-02Not applicableUs
Obagi Nu-Derm FX System Normal - Dry Skin Transformation Complexion Brightening SystemHomosalate (100 mg/1g) + Octisalate (50 mg/1g) + Zinc oxide (165 mg/1g)TopicalObagi Cosmeceuticals LLC2019-12-02Not applicableUs
Obagi Nu-Derm FX System Normal - Oily Skin Transformation Complexion Brightening SystemHomosalate (100 mg/1g) + Octisalate (50 mg/1g) + Zinc oxide (165 mg/1g)TopicalObagi Cosmeceuticals LLC2019-12-02Not applicableUs
Obagi-C Fx System Normal-Dry Skin Brightening System With ArbutinHomosalate (100 mg/1g) + Octisalate (50 mg/1g) + Zinc oxide (165 mg/1g)TopicalObagi Cosmeceuticals LLC2019-12-02Not applicableUs

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
o-Hydroxybenzoic acid esters
Alternative Parents
Salicylic acid and derivatives / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / O-hydroxybenzoic acid ester / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
V06SV4M95S
CAS number
118-56-9
InChI Key
WSSJONWNBBTCMG-UHFFFAOYSA-N
InChI
InChI=1S/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3
IUPAC Name
3,3,5-trimethylcyclohexyl 2-hydroxybenzoate
SMILES
CC1CC(CC(C)(C)C1)OC(=O)C1=C(O)C=CC=C1

References

General References
  1. MSDS [Link]
  2. product info [Link]
PubChem Substance
347911103
ChemSpider
8059
RxNav
91326
ChEBI
91642
ChEMBL
CHEMBL1377575
Wikipedia
Homosalate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4TerminatedNot AvailableSkin Aging1
2Not Yet RecruitingSupportive CareCNS Tumor, Childhood / Pediatric Cancer / Skin Inflammation1
1CompletedOtherSystemic Exposure to Sunscreen Ingredients1
1CompletedTreatmentAtopic Dermatitis (AD)1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1
Not AvailableCompletedOtherSunscreening Agents3
Not AvailableCompletedPreventionSunscreening Agents1
Not AvailableCompletedTreatmentFoot Dryness in Patients With NIDDM / Foot Transepidermal Water Loss in Patients in NIDDM1
Not AvailableCompletedTreatmentSunscreening Agents1
Not AvailableTerminatedTreatmentDiaper Rash1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Lotion; sprayTopical
AerosolTopical
OilTopical
Cream, augmentedTopical
Spray, suspensionTopical
KitOral; Topical
StickTopical
JellyTopical
GelTopical
SalveTopical
Aerosol, foamTopical
LotionTopical
CreamTopical
LiquidTopical
Kit; stickTopical
PasteTopical
Kit
OintmentTopical
Lotion / shampooTopical
SolutionTopical
PowderTopical
SuspensionTopical
Kit; lotionTopical
Cream; kitTopical
LiquidTopical2.9313 g/30mL
SprayOral
EmulsionTopical
SprayTopical
LotionOral
ClothTopical
LipstickTopical
KitTopical
Aerosol, sprayTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0373 mg/mLALOGPS
logP4.05ALOGPS
logP5ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.65 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [PubMed:15537743]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [PubMed:15537743]
  2. Jimenez-Diaz I, Molina-Molina JM, Zafra-Gomez A, Ballesteros O, Navalon A, Real M, Saenz JM, Fernandez MF, Olea N: Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 1;936:80-7. doi: 10.1016/j.jchromb.2013.08.006. Epub 2013 Aug 8. [PubMed:24004914]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Jimenez-Diaz I, Molina-Molina JM, Zafra-Gomez A, Ballesteros O, Navalon A, Real M, Saenz JM, Fernandez MF, Olea N: Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 1;936:80-7. doi: 10.1016/j.jchromb.2013.08.006. Epub 2013 Aug 8. [PubMed:24004914]

Drug created on December 03, 2015 09:51 / Updated on June 12, 2020 10:53

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