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    Chemistry

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    Also known as: 5466-77-3, 83834-59-7, 2-ethylhexyl 4-methoxycinnamate, Parsol mcx, Parsol mox, Parsol
    Molecular Formula
    C18H26O3
    Molecular Weight
    290.4  g/mol
    InChI Key
    YBGZDTIWKVFICR-JLHYYAGUSA-N
    FDA UNII
    4Y5P7MUD51
    Octylmethoxycinnamate
    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.
    1 2D Structure

    Octylmethoxycinnamate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate
    2.1.2 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+
    2.1.3 InChI Key
    YBGZDTIWKVFICR-JLHYYAGUSA-N
    2.1.4 Canonical SMILES
    CCCCC(CC)COC(=O)C=CC1=CC=C(C=C1)OC
    2.1.5 Isomeric SMILES
    CCCCC(CC)COC(=O)/C=C/C1=CC=C(C=C1)OC
    2.2 Other Identifiers
    2.2.1 UNII
    4Y5P7MUD51
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-ethylhexyl-4-methoxycinnamate

    2. 2-ethylhexyl-p-methoxycinnamate

    3. Escalol 557

    4. Heliopan New

    5. Octyl-methoxycinnamate

    6. Octylmethoxycinnamate

    7. Omc Cinnamate

    8. Parsol Mcx

    2.3.2 Depositor-Supplied Synonyms

    1. 5466-77-3

    2. 83834-59-7

    3. 2-ethylhexyl 4-methoxycinnamate

    4. Parsol Mcx

    5. Parsol Mox

    6. Parsol

    7. 2-ethylhexyl P-methoxycinnamate

    8. 2-ethylhexyl-p-methoxycinnamate

    9. 4-methoxycinnamic Acid 2-ethylhexyl Ester

    10. 2-ethylhexyl Trans-4-methoxycinnamate

    11. Octyl Methoxycinnamate

    12. Escalol 557

    13. 2-ethylhexyl 3-(4-methoxyphenyl)acrylate

    14. Octyl-methoxycinnamate

    15. Ethylhexyl Methoxycinnamate

    16. (e)-2-ethylhexyl 3-(4-methoxyphenyl)acrylate

    17. Neo Heliopan Av

    18. 2-ethylhexyl (e)-3-(4-methoxyphenyl)prop-2-enoate

    19. 2-ethylhexyl-4-methoxycinnamate

    20. Sunscreen Av

    21. Uvinul Mc 80

    22. Octyl P-methoxycinnamate

    23. Ethylhexyl P-methoxycinnamate

    24. Octyl 4-methoxycinnamic Acid

    25. 2-ethylhexyl

    26. Trans

    27. -4-methoxycinnamate

    28. 4y5p7mud51

    29. Chebi:88667

    30. 2-propenoic Acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl Ester, (2e)-

    31. 2-ethylhexyl Methoxycinnamate

    32. Octylmethoxycinnamate

    33. Uvinul Mc80

    34. 2-propenoic Acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl Ester

    35. Nsc-26466

    36. Nsc 26466

    37. Ocinoxate

    38. Jeescreen Omc

    39. Octinoxate [usan]

    40. Solarom Omc

    41. Parsol Mcx-sa

    42. Escalol 557nb

    43. Uvinul Mc 80n

    44. Escalol 557t

    45. Heliopan New

    46. Uvinul Mc 90

    47. Eusolex Uv-pearls Omc

    48. Sun Caps 664

    49. Unii-4y5p7mud51

    50. Ncgc00160623-01

    51. Parsol (tn)

    52. Uvinult Mc 80 N

    53. 2-ethylhexyl 3-(4-methoxyphenyl)-2-propenoate

    54. Neo Heliopan, Type Av

    55. Octinoxate (usp/inn)

    56. Octinoxate [inn]

    57. Octinoxate [hsdb]

    58. Octinoxate [vandf]

    59. Ec 629-661-9

    60. Octinoxate [mart.]

    61. Dsstox_cid_28119

    62. Dsstox_rid_82199

    63. Octinoxate [usp-rs]

    64. Octinoxate [who-dd]

    65. Dsstox_gsid_47205

    66. Schembl15609

    67. Mls004773966

    68. Chembl1200608

    69. Dtxsid9047205

    70. Octinoxate [orange Book]

    71. 3-(4-methoxyphenyl)-2-propenoic Acid 2-ethylhexyl Ester

    72. Octinoxate [usp Monograph]

    73. 4-methoxycinnamic Acid Octyl Ester

    74. Octyl Methoxycinnamate [mi]

    75. Hy-b1234

    76. Nsc26466

    77. P-methoxyzimtsaure-2-ethylhexylester

    78. Tox21_302576

    79. Mfcd00072582

    80. S5320

    81. Octyl Methoxycinnamate [vandf]

    82. Akos015838519

    83. 2-ethylhexyl 4-methoxycinnamate, 98%

    84. Ccg-267384

    85. Cs-4732

    86. Db09496

    87. Ncgc00160623-02

    88. Ncgc00160623-03

    89. Ncgc00181309-01

    90. Ncgc00256897-01

    91. As-11708

    92. Ethylhexyl Methoxycinnamate [inci]

    93. Shade Uvaguard Component Octinoxate

    94. Smr001550370

    95. Cas-83834-59-7

    96. 2-ethylhexyl Trans-4-methoxycinnamate, 98%

    97. 4-methoxycinnamicacid2-ethylhexylester

    98. Ethylhexyl P-methoxycinnamate [vandf]

    99. M1082

    100. Octinoxate Component Of Shade Uvaguard

    101. (e)-2-ethylhexyl3-(4-methoxyphenyl)acrylate

    102. D05225

    103. D95744

    104. P-methoxycinnamic Acid 2-ethylhexyl Ester

    105. A840663

    106. Q739648

    107. Sr-01000883955

    108. 2-ethylhexyl 4-methoxycinnamate, Analytical Standard

    109. Sr-01000883955-1

    110. 3-(4-methoxy-phenyl)-acrylic Acid 2-ethyl-hexyl Ester

    111. C118580000

    112. Octinoxate, Pharmaceutical Secondary Standard; Traceable To Usp

    113. Octinoxate, United States Pharmacopeia (usp) Reference Standard

    114. 2-propenoic Acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl Ester, (e)-

    115. Octinoxate, Pharmaceutical Secondary Standard; Certified Reference Material

    116. 2-ethylhexyl Trans-4-methoxycinnamate, 98%, Contains 500-1000 Ppm Bht As Stabilizer

    117. Octyl Methoxycinnamate 7.5%, Octinoxate, Octyl Methoxycinnamate, Octyl Methoxycinnamate (2-ethylhexyl Trans-4-methoxycinnamate)

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 290.4 g/mol
    Molecular Formula C18H26O3
    XLogP35.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count10
    Exact Mass290.18819469 g/mol
    Monoisotopic Mass290.18819469 g/mol
    Topological Polar Surface Area35.5 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity304
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Ultraviolet /UVB/ screen

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1259

    /The authors/ tested the sun protection factor of a hydroquinone formulation (Lustra-Ultra, TaroPharma, Hawthorne, NY) containing avobenzone 3%, and octinoxate 7.5% according to the FDA Sunscreen Monograph on 20 volunteer subjects. We also determined the UVR absorbance spectrum of the preparation. ... The mean sun protection factor (SPF) of 21.7 satisfied labeling requirements for SPF 20. The formulation exhibited strongest photoprotection near the wavelengths of peak sun burning effectiveness in the UVB region and maintains significant UVR absorbance through the entire UVA region. Avobenzone 3% and octinoxate 7.5% provide broad spectrum UV protection. Incorporating these sunscreens into a hydroquinone preparation simplifies the treatment regimen while providing significant photoprotection for patients being treated for dyschromia.

    PMID:16673798 Stanfield JW et al; J Drugs Dermatol 5 (4): 321-4 (2006)

    Sunscreens capable of inhibiting erythema are assumed to protect against UV-induced carcinogenesis as well. However, the correlation between inflammation and carcinogenesis is uncertain, and the prevention of UV-induced erythema might in fact be biologically irrelevant as an indicator of protection against UV-induced skin cancer. Ultraviolet-B radiation promotes cutaneous immunosuppression by the release of immunoregulatory cytokines and by depletion of Langerhans cells. /The authors/ investigated the ability of two different sunscreens to inhibit UVB-induced expression of epidermal interleukin (IL)-10 and depletion of Langerhans cells. Chemical and physical sunscreens were applied to the forearms of volunteers 15 min prior to 4 minimal erythemal doses of UVB exposure. Suction blisters were induced 24 hr after irradiation, and RNA was extracted from the blister roofs. Reverse transcription polymerase chain reaction was performed using primers for IL-10 and CD1a. A chemical sunscreen containing octyl methoxycinnamate (12 sun protection factor (SPF)) and a physical sunscreen containing zinc oxide (16 SPF) were assayed: UVB-induced IL-10 mRNA expression was nearly totally inhibited by both sunscreens (median protection for chemical and physical sunscreens was 95% and 78%, respectively), whereas UVB-induced Langerhans cell depletion was partially prevented (47% and 50% for chemical and physical sunscreens, respectively). Langerhans cell protection by sunscreens was confirmed by estimation of cell density after ATPase staining. In contrast, both sunscreens effectively prevented the induction of UVB-induced erythema. /The authors/ believe this to be the first demonstration that sunscreens can prevent the induction of cutaneous mediators of immunosuppression, and that the results indicate that the immunoprotection offered by the sunscreens is significantly lower than their ability to prevent erythema.

    PMID:10568168 Hochberg M, Enk CD; Photochem Photobiol 70 (5): 766-72 (1999)

    Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.

    IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.

    Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    4.2 Drug Warning

    The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

    Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

    Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

    Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/

    IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.

    For more Drug Warnings (Complete) data for OCTINOXATE (11 total), please visit the HSDB record page.

    4.3 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Sunscreening Agents

    Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Cell-mediated Immunity [PE]; Glycerol [CS]; Increased Histamine Release [PE]; Increased IgG Production [PE]; Non-Standardized Chemical Allergen [EPC]; Allergens [CS]
    5.4 ATC Code

    D - Dermatologicals

    D02 - Emollients and protectives

    D02B - Protectives against uv-radiation

    D02BA - Protectives against uv-radiation for topical use

    D02BA02 - Octinoxate

    5.5 Absorption, Distribution and Excretion

    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. The mean maximum plasma concentration detected after application of 2mg/cm2 sunscreen was 7ng/mL in women and 16ng/mL in men.

    Route of Elimination

    Can be detected in urine in unchanged form.

    Naked rat skin. This was studied in a chamber experiment. Most of the material was found in the stripped skin; there was less in the stratum corneum, and least in the chamber. The approximate amounts found in the chamber were: after 6 hrs, 1.13 %; after 16 hrs, 11.4 %; and at 24 hrs 17,9 %. The figures for the horny layer and the strippings combined were, respectively, 31.4 %, 44.4 % and 45.7 % (percentages of applied doses). Solutions of 3% and 20 % of a.i. gave similar results.

    European Commission; Reports of the Scientific Committee on Cosmetology (Ninth Series): 2-Ethylhexyl-4-methoxycinnamate (5466-77-3) p. 70 (1999). Available from, as of September 10, 2013: https://ec.europa.eu/health/scientific_committees/consumer_safety/docs/scc_o_9.pdf

    Eight healthy volunteers had small amounts of radioactive a.i. applied to the interscapular region. One group of 4 had the material applied under a watch glass; the other 4 had it applied on gauze, with occlusion in one case. Tests for absorption of a.i. were negative except for about 0.2 % in urine. The concentrations used were not stated.

    European Commission; Reports of the Scientific Committee on Cosmetology (Ninth Series): 2-Ethylhexyl-4-methoxycinnamate (5466-77-3) p. 70 (1999). Available from, as of September 10, 2013: https://ec.europa.eu/health/scientific_committees/consumer_safety/docs/scc_o_9.pdf

    In a preliminary experiment, a capsule containing 100 mg of a.i. was taken orally. ... The cumulative excretion of 4methoxycinnamate in the urine over 24 hours was studied by GC/MS of the methyl ester derivative. (This method would also detect 4-hydroxycinnamic acid). Over 24 hours, 13.2 % of the amount ingested was recovered, equivalent to 21.5 % of the amount that would be expected if the a.i. were completely absorbed. In the main part of the experiment, an o/w cream containing 10 % a.i. was used. Applications of 2 grams of this material (= 200 mg a.i.) were made to the interscapular area of each of 5 male subjects, aged 29 to 46. The area of skin covered was 25x30 cm. After application, the area was covered with 3 layers of gauze, left in place for 12 hours. Blood was taken at times 0, 0.5, 1, 2, 3, 5, 7, and 24 hours. Urine was collected at 0, 1, 2, 3, 4, 5, 6, 7, 12, 24, 48, 72 and 96 hours. The control plasma samples showed a level equivalent to about 10 ng/ml before any application had been made. There was no evidence of any rise in plasma levels during the experiment. The urine showed a "physiological" level of 100 to 300 ng/ml. No significant increase in this amount was found in any sample. The authors conclude that very little, if any, of the compound was absorbed under the conditions of the experiment.

    European Commission; Reports of the Scientific Committee on Cosmetology (Ninth Series): 2-Ethylhexyl-4-methoxycinnamate (5466-77-3) p. 70 (1999). Available from, as of September 10, 2013: https://ec.europa.eu/health/scientific_committees/consumer_safety/docs/scc_o_9.pdf

    The objective of this study was to determine the influence of vehicles on the penetration of octyl methoxycinnamate (OMC), as a UV absorber, to the stratum corneum by the stripping method. The experimental formulations consisted of a conventional o/w emulsion and multilamellar and small unilamellar liposomes (MLVs and SUVs) containing OMC. MLVs containing OMC were prepared by the fusion method and then converted to SUVs by probe sonication. Various formulations were then applied onto the midvolar forearms of six volunteers at a dose of 2 mg/sq cm. After determined timepoints, the stripping method was conducted whereby 22 tape strips were applied and subsequently divided into different stripping groups. The sunscreen agent was assessed by HPLC while the SPF (sun protection factor) of the formulations was determined in human volunteers in accordance with the Australian standard. Overall the results indicate that skin accumulation of OMC in MLVs was significantly greater than in the o/w emulsion and SUVs. Furthermore, SUV's penetration into the deeper skin layers was significantly greater than MLV's and that of a conventional o/w emulsion. Also, higher amounts of OMC were recovered from the upper layers of the stratum corneum than from the deeper layers in all the formulations tested. Finally, the SPF of the liposomes containing OMC was slightly greater than that of the control lotions at a similar concentration of OMC. In conclusion, the result of this study indicates that an MLV prepared by the fusion method could be a better vehicle for OMC as a sunscreen since it has a slightly better SPF compared to a conventional formulation and more remains in the stratum corneum, reducing its penetration to the deeper layers.

    PMID:18841304 Golmohammadzadeh S et al; J Cosmet Sci 59 (5): 385-98 (2008)

    For more Absorption, Distribution and Excretion (Complete) data for OCTINOXATE (19 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

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

    As a lipophilic substance, the a.i. is very likely to be metabolized; it is known in any case to be hydrolyzed by plasma esterases, although slowly.

    European Commission; Reports of the Scientific Committee on Cosmetology (Ninth Series): 2-Ethylhexyl-4-methoxycinnamate (5466-77-3) p. 70 (1999). Available from, as of September 10, 2013: https://ec.europa.eu/health/scientific_committees/consumer_safety/docs/scc_o_9.pdf

    5.7 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 and also increases the skin's tolerability to UV rays.

    Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    Radiation is absorbed by chemical sunscreens when the electron energy level of the drug is raised from its ground state to a higher energy level or excited state. Chromophore groups (C=C, C=O, O-N=O) with loosely held electrons are easily excited by radiation. Compounds which have several chromophore groups in optimal positions have high absorbance over a broad range of wavelengths. Chemical sunscreens are usually agents that absorb not less than 85% of UVB radiation (thus preventing burning) but may permit transmission of UVA radiation (thus allowing tanning). Some sunscreens may absorb wavelengths over a range that is slightly wider or narrower than that of UVB. All PABA derivatives absorb wavelengths of approximately 290-320 nm, benzophenone derivatives absorb wavelengths of approximately 250-360 nm, cinnamic acid derivatives absorb wavelengths of 280-320 nm, and salicylate derivatives and other miscellaneous chemical sunscreens absorb wavelengths of about 270-320 nm.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

    The wavelength to which the skin is maximally sensitive had been accepted for many years to be 296.7 nm; however, recent evidence suggests that the most erythemogenic UVB wavelength may be slightly lower (e.g., somewhere in the range of 292-295 nm). In addition, of the stronger burning wavelengths that reach the earth's surface, most are approximately 310 nm. Therefore, sunscreens that maximally absorb UVB radiation near either of these wavelengths are particularly effective at preventing sunburn. Maximum absorbance occurs at about 290 nm for PABA, at about 295 nm for glyceryl-p-aminobenzoate, and at about 310 nm for the remaining PABA derivatives. Maximum absorbance occurs at 280-290 nm for benzophenone derivatives, at 310 nm for cinnamic acid derivatives with the exception of diethanolamine-p-methoxycinnamate which has its maximum absorbance at 290 nm, and at 300-305 nm for salicylate derivatives and other miscellaneous sunscreens. /Sunscreens/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

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