Ethylhexyl methoxycrylene

Identification

Name
Ethylhexyl methoxycrylene
Accession Number
DB11226
Description

Ethylhexyl methoxycrylene is a photostabilizer that preserves the effectiveness of UV filters by interacting with both the singlet and triplet states 6. It returns UV filters to their ground states without absorbing sunlight 6. It is used as a solvent for crystalline UV filters and is easily emulsified and suitable for use in various lotions, creams, sprays, sticks, and gel formulations 6. It currently enjoys regional approvals in Canada, the EU, and the US 3.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 391.511
Monoisotopic: 391.214743798
Chemical Formula
C25H29NO3
Synonyms
Not Available
External IDs
  • RX-14180

Pharmacology

Indication

Ethylhexyl methoxycrylene is employed as a photostabilizing agent in various sunscreen products 3.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

As an active ingredient in topical sunscreen products, ethylhexyl methoxycrylene is applied directly onto human skin where it acts as a critical component for conferring photostability to the product's other constituent ingredients, protecting the product as a whole from deterioration in the sunlight 3. Additionally, considering the high log Pow value (6.05-6.32) and low water solubility, dermal absorption of ethylhexyl methoxycrylene is expected to be low. This is supported by a dermal absorption of less than 5% observed for an acceptable analogue of the notified chemical 4. Consequently, little systemic exposure and pharmacokinetics are expected and users can freely wash off and re-apply ethylhexyl methoxycrylene containing compounds as necessary.

Mechanism of action

Ethylhexyl methoxycrylene is a photostabilizer with exceptionally low singlet (S1) and triplet (T1) energy states 1. Given these properties, ethylhexyl methoxycrylene is capable of draining the singlet excited state reservoir of UV radiation excited molecules of various sunscreen agents 5. This action used to be considered impossible because molecules stay in the singlet excited state for a very short period of time - often as short as 13 one-thousandths of a billionth of a second 5. Ethylhexyl methoxycrylene, however, is a singlet quencher that dramatically reduces the flow of energy to the triplet escited state reservoir 5. As it quenches the singlet excited state, molecules do not have the chance to get to the triplet excited state reservoir and largely return to the ground state where they can continue functioning 5. In fact, this mechanism of action of ethylhexyl methoxycrylene is considered as being able to return UV filters to their ground states without absorbing sunlight 6.

Ultimately, because ethylhexyl methoxycrylene can work so quickly, it allows manufacturers to formulate products with combinations of sunscreen ingredients that used to be considered too photo-unstable to be effective 5. Moreover, ethylhexyl methoxycrylene is easily emulsified, and is suitable for use in lotions, creams, sprays, sticks, and gel formulations 6.

Absorption

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. At this time, however, studies demonstrate that the components of most commonly used sunscreens are likely absorbed into the skin at least to some extent - although penetration to deeper tissues and the cutaneous circulation remains limited 2. Despite the extensive use of sunscreen products around the world, there have been few reports of adverse effects related to their use 2.

Volume of distribution

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Protein binding

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Metabolism

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Route of elimination

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Half-life

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Clearance

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal.

Adverse Effects
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Toxicity

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin 4. The systemic presence of the compound is consequently expected to be minimal. Additionally, no ocular irritation, phototoxicity, dermal irritation, or allergic contact sensitization has been reported to any significant degree 3.

Affected organisms
  • Humans and other mammals
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

International/Other Brands
Solastay S1
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Almost Makeup SPF 15Ethylhexyl methoxycrylene (2 g/100g) + Titanium dioxide (13 g/100g)PowderTopicalAsanuma Corporation2007-11-092017-10-12US flag
Almost Makeup SPF 18Ethylhexyl methoxycrylene (2 g/100g) + Titanium dioxide (1.23 g/100g)PowderTopicalAsanuma Corporation2018-03-01Not applicableUS flag
Sunscreen SPF30Ethylhexyl methoxycrylene (1.25 g/100g) + Avobenzone (0.75 g/100g) + Benzophenone (0.5 g/100g) + Peg-100 stearate (2.5 g/100g) + Titanium dioxide (4 g/100g)LiquidTopicalNINGBO JIANGBEI OCEAN STAR TRADING CO.,LTD2015-02-20Not applicableUS flag

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Cinnamic acid esters / Phenoxy compounds / Methoxybenzenes / Anisoles / Fatty acid esters / Alkyl aryl ethers / Enoate esters / Nitriles / Monocarboxylic acids and derivatives / Organopnictogen compounds
show 3 more
Substituents
Alkyl aryl ether / Alpha,beta-unsaturated carboxylic ester / Anisole / Aromatic homomonocyclic compound / Carbonitrile / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cinnamic acid ester / Cinnamic acid or derivatives
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
S3KFG6Q5X8
CAS number
947753-66-4
InChI Key
WAJCJDLRJVDSSD-UHFFFAOYSA-N
InChI
InChI=1S/C25H29NO3/c1-4-6-10-19(5-2)18-29-25(27)23(17-26)24(20-11-8-7-9-12-20)21-13-15-22(28-3)16-14-21/h7-9,11-16,19H,4-6,10,18H2,1-3H3
IUPAC Name
2-ethylhexyl 2-cyano-3-(4-methoxyphenyl)-3-phenylprop-2-enoate
SMILES
CCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=C(OC)C=C1

References

General References
  1. Kikuchi A, Hata Y, Kumasaka R, Nanbu Y, Yagi M: Photoexcited singlet and triplet states of a UV absorber ethylhexyl methoxycrylene. Photochem Photobiol. 2013 May-Jun;89(3):523-8. doi: 10.1111/php.12017. Epub 2012 Dec 17. [PubMed:23136952]
  2. Benson HA: Assessment and clinical implications of absorption of sunscreens across skin. Am J Clin Dermatol. 2000 Jul-Aug;1(4):217-24. [PubMed:11702366]
  3. Hallstar: SolaStay S1 Product Profile [Link]
  4. NATIONAL INDUSTRIAL CHEMICALS NOTIFICATION AND ASSESSMENT SCHEME (NICNAS) Public Report On: Ethylhexyl Methoxycrylene [File]
  5. Sunscreen Photostability 101 [File]
  6. Hallstar Sun Care Advanced Formulated Solutions Brochure [File]
ChemSpider
52085894
RxNav
1311616
MSDS
Download (40.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderTopical
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00109 mg/mLALOGPS
logP6.19ALOGPS
logP6.63ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.05 m3·mol-1ChemAxon
Polarizability44.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created on December 03, 2015 09:51 / Updated on October 06, 2020 11:43

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