Octinoxate

Identification

Name
Octinoxate
Accession Number
DB09496
Type
Small Molecule
Groups
Approved
Description

Octinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. It is often combined with nanoparticles or other water-resistant liposomes in formulations to increase the localization at the epidermis and decrease the risk of percutaneous absorption. Its use in pharmaceutical and cosmetic formulations is approved by FDA.

Structure
Thumb
Synonyms
  • ethylhexyl methoxycinnamate
  • ethylhexyl p-methoxycinnamate
  • octyl methoxycinnamate
  • parsol
External IDs
Eusolex 2292 / Uvinul MC80
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fresh Umbrain Clay Freshface Foundation SPF 20 CroisetteEmulsion3 g/100gTopicalGuerlain2009-04-012015-12-29Us
No7 Protect and Perfect Foundation Sunscreen Broad Spectrum SPF 15 CalicoEmulsion1.5 g/30gTopicalBoots Retail Usa Inc2012-10-26Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
125 Fl Moisture Whip Lipstick-stk Top 50mg/gStick50 mgTopicalMaybelline Canada1996-12-311998-07-11Canada
25 Creme 410Cream7.5 %TopicalMultaler & Cie2004-06-012008-03-28Canada
275lw Long Wearing Lipstick 50mg/gStick50 mgTopicalMaybelline Canada1996-12-311998-07-11Canada
4-IN-1 Liquid 14-hour Wear Foundation SPF 15Emulsion5 %TopicalPurminerals2013-02-202017-03-28Canada
6 Creme 410Cream5 %TopicalMultaler & Cie2004-12-012008-06-25Canada
6 Creme 410 TeinteeCream5 g/100gTopicalMultaler & Cie2011-02-152017-05-13Us
6 Creme 410 TeinteeCream5 %TopicalMultaler & Cie2004-12-032013-07-31Canada
6 Lait SolaireLotion5 %TopicalMultaler & Cie2004-12-012013-07-31Canada
675rl Revitalizing Lip Indulgence - Stk 7.5%Stick7.5 %TopicalMaybelline Canada1996-12-311999-07-30Canada
Absolue MakeupCream7.5 %TopicalLancome Canada2005-01-152014-02-10Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dr. IasoCream7.5 mL/100mLTopicalIaso Inc2012-06-17Not applicableUs
Dr.eslee Sun MatteLiquid7.5 g/100gTopicalAjou Medics Co., Ltd2011-08-10Not applicableUs
Dr.eslee Sun ProtectionCream7 g/100gTopicalAjou Medics Co., Ltd2011-08-10Not applicableUs
UV Shield SPF 42Liquid.075 mL/mLTopicalIaso Inc2011-01-09Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
01 Balancing Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Octisalate (2.5 mg/.5mL) + Titanium dioxide (1.45 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-062017-10-17Us
01 Moisture Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Zinc oxide (3.9 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-06Not applicableUs
02 Balancing Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Octisalate (2.5 mg/.5mL) + Titanium dioxide (1.45 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-062017-10-17Us
02 Moisture Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Zinc oxide (3.9 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-06Not applicableUs
03 Balancing Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Octisalate (2.5 mg/.5mL) + Titanium dioxide (1.45 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-062017-10-17Us
03 Moisture Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Zinc oxide (3.9 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-06Not applicableUs
04 Balancing Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Octisalate (2.5 mg/.5mL) + Titanium dioxide (1.45 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-062017-10-17Us
04 Moisture Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Zinc oxide (3.9 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-06Not applicableUs
05 Balancing Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Octisalate (2.5 mg/.5mL) + Titanium dioxide (1.45 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-062017-10-17Us
05 Moisture Foundation SPF 15Octinoxate (3.75 mg/.5mL) + Zinc oxide (3.9 mg/.5mL)EmulsionTopicalThe Body Shop, Wake Forest2009-09-06Not applicableUs
Categories
UNII
4Y5P7MUD51
CAS number
5466-77-3
Weight
Average: 290.3972
Monoisotopic: 290.188194698
Chemical Formula
C18H26O3
InChI Key
YBGZDTIWKVFICR-JLHYYAGUSA-N
InChI
InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+
IUPAC Name
2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate
SMILES
[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC

Pharmacology

Indication

As an active ingredient in sunscreens and lip balms. Used for protection against damaging effects of sun rays.

Structured Indications
Pharmacodynamics

Acts as a photoprotective agent that protects the skin by preventing and minimizing the damaging effects of ultraviolet (UV) rays of natural light. The cellular effects of UV irradiation include DNA damage, cell cycle arrest, immunological depression, apoptosis, and transcriptional changes [7].

Mechanism of action

Absorbs UV-B (predominantly) and UV-A rays while accumulating in the outermost layer of the epidermis. Like any other photoprotective agents, octinoxate prevents the damage to cells and deoxyribonucleic acid (DNA) by reducing the p53 protein expression following UV exposure [7] and also increases the skin's tolerability to UV rays [6].

Absorption

Can be systemically absorbed after skin application, being found in the deeper layers of the stratum corneum as well as urine, plasma, and breast milk [2]. The mean maximum plasma concentration detected after application of 2mg/cm2 sunscreen was 7ng/mL in women and 16ng/mL in men [6].

Volume of distribution
Not Available
Protein binding

None

Metabolism

Can undergo hepatic metabolism when systematically absorbed. Can be enzymatically degraded by lipases in the stratum corneum where esters undergo hydrolysis [2]. Degrade into photoproducts when exposed to sunlight, which leads to a decrease in UV absorption efficiency [6].

Route of elimination

Can be detected in urine in unchanged form [4].

Half life
Not Available
Clearance
Not Available
Toxicity

Slightly hazardous in case of skin contact, eye contact, ingestion and inhalation. Octinoxate may form reactive singlet oxygen species and induce anti-estrogenic effects [8]. UV-induced molecular breakdown of octinoxate may interfere with cellular processes or induce oxidative damage in human skin [6]. The NOAEL (no observed adverse effect level) is 450 mg/kg bw/day for fertility and reproductive performance, for systemic parental and developmental toxicity in Wistar rats [3].

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

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Monteiro MS, Ozzetti RA, Vergnanini AL, de Brito-Gitirana L, Volpato NM, de Freitas ZM, Ricci-Junior E, dos Santos EP: Evaluation of octyl p-methoxycinnamate included in liposomes and cyclodextrins in anti-solar preparations: preparations, characterizations and in vitro penetration studies. Int J Nanomedicine. 2012;7:3045-58. doi: 10.2147/IJN.S28550. Epub 2012 Jun 20. [PubMed:22787399]
  2. Mota Ade C, de Freitas ZM, Ricci Junior E, Dellamora-Ortiz GM, Santos-Oliveira R, Ozzetti RA, Vergnanini AL, Ribeiro VL, Silva RS, dos Santos EP: In vivo and in vitro evaluation of octyl methoxycinnamate liposomes. Int J Nanomedicine. 2013;8:4689-701. doi: 10.2147/IJN.S51383. Epub 2013 Dec 10. [PubMed:24376350]
  3. Schneider S, Deckardt K, Hellwig J, Kuttler K, Mellert W, Schulte S, van Ravenzwaay B: Octyl methoxycinnamate: two generation reproduction toxicity in Wistar rats by dietary administration. Food Chem Toxicol. 2005 Jul;43(7):1083-92. [PubMed:15833384]
  4. Janjua NR, Mogensen B, Andersson AM, Petersen JH, Henriksen M, Skakkebaek NE, Wulf HC: Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans. J Invest Dermatol. 2004 Jul;123(1):57-61. [PubMed:15191542]
  5. Hayden CG, Cross SE, Anderson C, Saunders NA, Roberts MS: Sunscreen penetration of human skin and related keratinocyte toxicity after topical application. Skin Pharmacol Physiol. 2005 Jul-Aug;18(4):170-4. Epub 2005 May 20. [PubMed:15908756]
  6. Latha MS, Martis J, Shobha V, Sham Shinde R, Bangera S, Krishnankutty B, Bellary S, Varughese S, Rao P, Naveen Kumar BR: Sunscreening agents: a review. J Clin Aesthet Dermatol. 2013 Jan;6(1):16-26. [PubMed:23320122]
  7. Duale N, Olsen AK, Christensen T, Butt ST, Brunborg G: Octyl methoxycinnamate modulates gene expression and prevents cyclobutane pyrimidine dimer formation but not oxidative DNA damage in UV-exposed human cell lines. Toxicol Sci. 2010 Apr;114(2):272-84. doi: 10.1093/toxsci/kfq005. Epub 2010 Jan 13. [PubMed:20071424]
  8. Maipas S, Nicolopoulou-Stamati P: Sun lotion chemicals as endocrine disruptors. Hormones (Athens). 2015 Jan-Mar;14(1):32-46. [PubMed:25885102]
  9. The Dermatology Review: Octinoxate [Link]
External Links
Human Metabolome Database
HMDB61861
KEGG Drug
D05225
ChemSpider
4511170
ChEBI
88667
ChEMBL
CHEMBL1200608
Wikipedia
Octyl_methoxycinnamate
ATC Codes
D02BA02 — Octinoxate
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingSupportive CareDermatologic Complications / Neoplasms, Malignant1
3CompletedSupportive CareDermatologic Complications / Unspecified Adult Solid Tumor, Protocol Specific1
3RecruitingTreatmentAdult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Childhood Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Myeloid Neoplasm1
3RecruitingTreatmentFollicular Lymphoma (FL)1
4CompletedTreatmentMelasma1
Not AvailableCompletedNot AvailableLaryngospasm1
Not AvailableCompletedPreventionPigmentation From Visible Light1
Not AvailableCompletedTreatmentFoot Dryness in Patients With NIDDM / Foot Transepidermal Water Loss in Patients in NIDDM1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
StickTopical50 mg
CreamTopical5 g/100g
CreamTopical.9 g/30mL
GelCutaneous
KitTopical
StickTopical7 %
PowderTopical2.0 %
SprayCutaneous
LotionTopical.975 g/15g
EmulsionTopical75 mg/mL
CreamTopical3 g
SalveTopical
LotionTopical4.5 %
LotionTopical30 mg
GelTopical25 mg/g
OintmentTopical5.5 %
CreamTopical5550 mg/75g
CreamTopical.6 g/12g
StickTopical7.5 %
LipstickTopical75 mg/g
LotionTopical3 %
CreamTopical3 %
PasteTopical
Ointment; stickTopical
GelTopical
StickTopical3.50 %
EmulsionTopical2.23 %
Cloth; creamTopical
LotionTopical4 %
CreamTopical70 mg/mL
LiquidTopical6.0 %
LiquidTopical3.00 %
LiquidTopical
PowderTopical6 %
LotionTopical3.5 %
CreamTopical3 g/50g
CreamTopical6 %
StickOral
StickTopical306 mg/9g
EmulsionTopical1690 mg/34.48g
CreamTopical1690 mg/34.48g
StickTopical3.4 %
CreamTopical5 %
OilTopical
PowderTopical.05 g/g
LiquidTopical6 g/100mL
PowderTopical5.0 %
PowderTopical5 g/100g
EmulsionTopical74.9 mg/mL
LotionTopical74.9 mg/mL
EmulsionTopical7.0 %
CreamTopical3.75 mg/50mL
LiquidTopical7.5 g/100g
CreamTopical7 g/100g
LipstickTopical.072 g/g
LiquidTopical5.0 %
EmulsionTopical4 %
Kit
LipstickTopical.068 g/g
PowderTopical.06 g/g
LipstickTopical.07 g/g
LipstickTopical.075 g/g
OintmentTopical6.5 %
LiquidTopical2.2 %
CreamTopical5.6 %
StickTopical6.5 %
CreamTopical.6 g/15mL
CreamTopical2 g/50mL
CreamTopical7 %
CreamTopical2 g/40mL
LiquidTopical4 g
LotionTopical6.5 %
PowderTopical7.5 g
PowderTopical4 %
PowderTopical7.5 %
EmulsionTopical18.75 mL/250mL
LotionTopical1.1988 mL/30mL
CreamTopical50 mg/mL
LipstickTopical69 mg/g
StickTopical68 mg/g
LipstickTopical68 mg/g
CreamTopical10 mg/mL
PowderTopical50 mg/g
AerosolTopical50 mg/mL
EmulsionTopical3 g/100g
Liquid; lotionTopical
Kit
LiquidTopical2.2 mL/100mL
StickTopical2 %
LiquidTopical2.23 %
CreamTopical3 mL/75mL
LotionTopical20 mg/mL
CreamTopical50 mg/g
LotionTopical.9 mL/30mL
LotionTopical67 mg/mL
CreamTopical2 %
StickCutaneous
CreamTopical2.5 %
SprayTopical3 %
LipstickTopical225 mg/3g
SprayTopical9.75 mL/130mL
LiquidTopical5 %
LiquidTopical2 %
LiquidTopical4 %
CreamTopical2.25 mL/30mL
CreamTopical4 %
CreamTopical15 mL/200mL
CreamTopical3.75 mL/50mL
LotionTopical2.0 %
CreamTopical1.5 g/30g
CreamTopical1.5 mL/30mL
LotionTopical2275 mg/35mL
Cream, augmentedTopical
SoapTopical
CreamTopical75 mg/mL
LotionTopical50 mg/mL
PowderTopical.975 g/13g
LiquidTopical.72 mL/24mL
LiquidTopical.9 mL/30mL
PowderTopical.75 g/10g
StickTopical.12 g/4g
CreamTopical35 mg/mL
CreamTopical3.5 g/100g
LotionTopical35 mg/mL
LotionTopical3.5 g/100mL
LotionTopical2.1 g/30mL
LiquidTopical.07 g/mL
LiquidTopical.045 g/g
CreamTopical1.35 g/30g
Lotion / shampooTopical
OintmentTopical1.0 %
LipstickTopical3.5 g/100g
JellyTopical
CreamTopical7.5 g
CreamTopical6 mL/30mL
CreamTopical1.8 g/30mL
LiquidTopical30 mg/mL
LiquidTopical70 mg/mL
CreamTopical49 mg/g
LiquidTopical60 mg/mL
CreamTopical60 mg/mL
CreamTopical6 mL/100mL
EmulsionTopical5.0 %
LiquidTopical3.5 %
LiquidTopical7 %
LiquidTopical7 mL/100mL
LiquidTopical7.5 %
SolutionTopical
CreamTopical2.25 g/30mL
LotionTopical7.5 %
CreamTopical7.5 %
LotionTopical3 g/30g
Aerosol, foamTopical
LotionTopical30 mg/mL
LiquidTopical2.1 mL/30mL
LotionTopical75 mg/mL
LiquidTopical1.5 mL/20mL
LotionTopical45 mg/mL
PowderTopical40 mg/g
OintmentTopical5 %
PowderTopical.42 g/14g
CreamTopical10 g/100g
LiquidTopical7.5 mL/100mL
CreamCutaneous
LipstickTopical2.2 mL/100mL
LiquidTopical3 %
SuspensionTopical
StickTopical30 mg/g
LotionTopical2 mL/100mL
EmulsionTopical2.25 g/30g
EmulsionTopical
EmulsionTopical1.5 g/30g
CreamTopical7.5 g/30g
Kit; lotionTopical
LotionTopical.05 g/mL
LotionTopical7 %
CreamTopical3.5 g/50mL
OilTopical16.8 mg/mL
OilTopical19.3 mg/mL
SprayTopical19.8 mg/mL
OilTopical2 g/100g
Aerosol, sprayTopical
CreamTopical11.25 mL/150mL
LotionTopical5.0 %
CreamTopical3.75 g/50mL
LotionTopical6 %
LotionCutaneous
StickTopical4.9 %
LiquidTopical50 mg/mL
Cream; kitTopical
PowderCutaneous
CreamTopical7.5 mL/100mL
StickTopical5 %
PowderTopical2 %
CreamTopical1.3 g/30mL
PasteTopical7.5 g/100g
LipstickTopical7.5 g/100g
LipstickTopical.28 g/4g
CreamTopical7.0 %
ClothTopical
LotionTopical2.25 g/30mL
SuspensionTopical7.5 %
SuspensionTopical4 %
CreamTopical6.0 %
StickTopical
EmulsionTopical7.5 %
LotionTopical7.4 %
CreamTopical7.4 %
CreamTopical2036 mg/30mL
CreamTopical1832 mg/30mL
StickTopical196 mg/4g
EmulsionTopical4.5 %
LipstickTopical196 mg/4g
StickTopical4.996 %
StickTopical4 %
LotionTopical1.125 mL/15mL
LotionTopical2.25 mL/30mL
LiquidTopical6 %
LotionTopical60 mg/mL
AerosolTopical
SprayTopical
CreamTopical
StickTopical7.0 %
CreamTopical4.5 %
OintmentTopical
Spray, suspensionTopical
LotionTopical2 %
SprayOral
EmulsionTopical2 %
LiquidTopical2.5 %
GelTopical3.5 mL/100mL
PasteTopical67.4 mg/g
LiquidTopical1.95 g/30mL
LotionTopical1.95 g/30mL
SpongeTopical
StickTopical3.5 %
LotionTopical2.5 %
LotionTopical5.5 %
Liquid; sprayTopical
LiquidTopical1 %
SprayTopical16.7 mg/mL
GelTopical.075 g/g
LipstickTopical122.5 mg/3.5g
StickTopical3 %
Lotion; sprayTopical
EmulsionTopical3 %
EmulsionTopical5 %
CreamTopical3.0 %
LotionTopical7.50 %
PowderTopical25 mg/mL
CreamTopical3 g/100mL
CreamTopical.36 g/7.2g
PowderTopical5 %
PowderTopical5.2 %
CreamTopical2 mL/100mL
LipstickTopical7 g/100g
LiquidTopical5 g
LipstickTopical210 mg/3g
LipstickTopical
LipstickTopical.225 g/3g
LotionTopical4.995 %
CreamTopical4.995 %
LiquidTopical.075 mL/mL
LotionTopical1.25 %
Cream; liquidTopical
LiquidTopical5.4 mL/100mL
LotionTopical6.0 %
CreamTopical4.0 %
LotionTopical5 %
EmulsionTopical50 mg/mL
EmulsionTopical1.5 mL/30mL
LotionTopical
SprayTopical3 g/100g
PowderTopical
LotionTopical3 g/100g
LotionTopical65 mg/mL
LotionTopical70 mg/mL
LotionTopical2.1 mL/30mL
LipstickTopical.076 g/3.8g
PowderTopical.6 g/10g
CreamTopical74.9 mg/mL
LotionTopical68 mg/mL
LotionTopical40 mg/mL
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-25°CMSDS
boiling point (°C)185-195°C at 1mbarMSDS
water solubility<0.1 g/100 mL at 27°CA19210
logP5.8MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.000452 mg/mLALOGPS
logP5.62ALOGPS
logP5.38ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.44 m3·mol-1ChemAxon
Polarizability34.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Cinnamic acid esters
Direct Parent
Cinnamic acid esters
Alternative Parents
Styrenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Fatty acid esters / Alkyl aryl ethers / Enoate esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Cinnamic acid ester / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / Styrene / Alkyl aryl ether / Fatty acid ester / Monocyclic benzene moiety / Fatty acyl
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on November 30, 2015 12:10 / Updated on October 02, 2017 06:16