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    Chemistry

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    Also known as: 21245-02-3, Padimate o, 2-ethylhexyl 4-dimethylaminobenzoate, Padimate-o, Escalol 507, Octyl dimethyl paba
    Molecular Formula
    C17H27NO2
    Molecular Weight
    277.4  g/mol
    InChI Key
    WYWZRNAHINYAEF-UHFFFAOYSA-N
    FDA UNII
    Z11006CMUZ
    2-Ethylhexyl 4-(Dimethylamino)Benzoate
    Padimate O is an active sunscreen agent in cosmetics and over-the-counter sunscreen drug products in concentrations up to 8%, as regulated by the FDA. It is a structurally-related compound to [DB02362] that absorbs UV-B rays to prevent photodamage. It penetrates human skin, and is shown to induce non-ligatable strand breaks on DNA in vitro and mutagenic effects on yeast in vivo.
    1 2D Structure

    2-Ethylhexyl 4-(Dimethylamino)Benzoate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-ethylhexyl 4-(dimethylamino)benzoate
    2.1.2 InChI
    InChI=1S/C17H27NO2/c1-5-7-8-14(6-2)13-20-17(19)15-9-11-16(12-10-15)18(3)4/h9-12,14H,5-8,13H2,1-4H3
    2.1.3 InChI Key
    WYWZRNAHINYAEF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCC(CC)COC(=O)C1=CC=C(C=C1)N(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    Z11006CMUZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-ethylhexyl-p-dimethylaminobenzoate

    2. 4-n,n'-dimethylamino-benzoic Acid, 2-ethylhexyl Ester

    3. Arlatone 507

    4. Climacel

    5. Escalol 507

    6. Padimate O

    7. Padimate-o

    2.3.2 Depositor-Supplied Synonyms

    1. 21245-02-3

    2. Padimate O

    3. 2-ethylhexyl 4-dimethylaminobenzoate

    4. Padimate-o

    5. Escalol 507

    6. Octyl Dimethyl Paba

    7. Eusolex 6007

    8. Arlatone Uvb

    9. 2-ethylhexyl P-dimethylaminobenzoate

    10. Benzoic Acid, 4-(dimethylamino)-, 2-ethylhexyl Ester

    11. 2-ethylhexyl-p-dimethyl-aminobenzoate

    12. Uvasorb Dmo

    13. 2-ethylhexyl-4-dimethylaminobenzoate

    14. 2-ethylhexyl P-(dimethylamino)benzoate

    15. 4-(dimethylamino)benzoic Acid 2-ethylhexyl Ester

    16. Ethylhexyl Dimethyl Paba

    17. Z11006cmuz

    18. Ncgc00090764-02

    19. Dsstox_cid_9320

    20. Dsstox_rid_78762

    21. Dsstox_gsid_29320

    22. Radiacare Lip Balm

    23. Cas-21245-02-3

    24. Octyl Dimethyl P-aminobenzoate

    25. Caraloe Snow & Sun Lip Balm

    26. Pamimate O

    27. Hsdb 7169

    28. Einecs 244-289-3

    29. Mfcd00017526

    30. Padimate O (usp)

    31. Arlatone Uvb (tn)

    32. Photoplex (salt/mix)

    33. Padimate O [usan:usp]

    34. Presun 23 (salt/mix)

    35. Padimate O [hsdb]

    36. Padimate O [usan]

    37. Padimate O [vandf]

    38. Padimate-o [vandf]

    39. Pamimate O [vandf]

    40. Unii-z11006cmuz

    41. Padimate O [mart.]

    42. Schembl15432

    43. Padimate O [usp-rs]

    44. Padimate O [who-dd]

    45. 4-(dimethylamino)benzoic Acid, 2-ethylhexyl Ester

    46. Mls001055379

    47. (+/-)-padimate O

    48. Benzoic Acid, P-(dimethylamino)-, 2-ethylhexyl Ester

    49. Padimate O, Analytical Standard

    50. Radiacare Lip Balm (salt/mix)

    51. Chembl1323699

    52. Dtxsid7029320

    53. Chebi:135932

    54. Padimate O, (+/-)-

    55. Hms3039f10

    56. Padimate O [usp Monograph]

    57. Octyl Dimethyl Paba [vandf]

    58. Tox21_111013

    59. Tox21_202421

    60. Tox21_303574

    61. Akos015890282

    62. Tox21_111013_1

    63. 2-ethylhexyl-4'-dimethylamino-benzoate

    64. Am84740

    65. Db11570

    66. Ethylhexyl Dimethyl Paba [inci]

    67. Padimate O 100 Microg/ml In Methanol

    68. Ncgc00090764-01

    69. Ncgc00090764-03

    70. Ncgc00090764-04

    71. Ncgc00257250-01

    72. Ncgc00259970-01

    73. 2-ethylhexyl N,n-dimethyl-p-aminobenzoate

    74. Ac-13165

    75. As-75461

    76. Smr000677935

    77. Caraloe Snow & Sun Lip Balm (salt/mix)

    78. Db-021046

    79. 2-ethyl-hexyl 4-dimethylaminobenzoate

    80. D1871

    81. Ft-0616757

    82. 2-ethylhexyl 4-(dimethylamino)benzoate, 98%

    83. 2-ethylhexyl 4-(dimetylamino)benzoate

    84. P-dimethylaminobenzoic Acid 2-ethylhexyl Ester

    85. D05335

    86. F71555

    87. A815219

    88. Sr-01000864568

    89. Q6628390

    90. Sr-01000864568-2

    91. 4-(dimethylamino)benzoic Acid 2-ethylhexyl Ester [mi]

    92. Padimate O, United States Pharmacopeia (usp) Reference Standard

    93. Padimate O, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 277.4 g/mol
    Molecular Formula C17H27NO2
    XLogP35
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count9
    Exact Mass277.204179104 g/mol
    Monoisotopic Mass277.204179104 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity270
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    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.

    4.2 Drug Warning

    PABA derivatives reportedly have weak sensitization potential, but the incidence of allergic and photoallergic contact dermatitis associated with their use is increasing. Contamination of PABA derivatives with benzocaine which may cause allergic reactions has been reported. In patients allergic to compounds that are structurally similar to PABA (e.g., ester-type anesthetics, aniline dyes, thiazides, sulfonylurea and paraphenylenediamine drugs), cross-sensitivity to PABA derivatives has been reported occasionally; therefore, sunscreens containing PABA derivatives may be contraindicated in patients with a history of hypersensitivity to these chemicals.

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

    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

    For more Drug Warnings (Complete) data for PADIMATE O (12 total), please visit the HSDB record page.

    4.3 Drug Indication

    Indicated as an active UV-B filter to prevent photodamage.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Padimate O absorbs UV-B rays, which can in turn induce DNA damage in human keratinocytes. While treatment of padimate O suppresses the formation of UV-endonuclease-sensitive sites, there is also an increase in direct strand breaks of DNA in cells.

    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 Absorption, Distribution and Excretion

    Absorption

    Padimate O is capable of human skin penetration.

    Route of Elimination

    No pharmacokinetic data available.

    Volume of Distribution

    No pharmacokinetic data available.

    Clearance

    No pharmacokinetic data available.

    ... None of the subjects tested showed any sign of skin irritation at the application site. ... In four postmenopausal women (age 54-63 years, weight 67-93 kg) the mean estradiol level 24 hr postapplication over the 9 day study period was 53 pg/mL. This result was significantly greater (p < 0.001) than the baseline value of 13 pg/mL. The mean estradiol/estrone ratio also rose significantly (p < 0.04) from a baseline value of 0.2 up to 0.8.

    PMID:9758681 Morgan TM et al; J Pharm Sci 87(10): 1226-8 (1998)

    It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. /Sunscreens/

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

    Sunscreen skin penetration and safety assessment should be considered together in order to ensure that in vitro cytotoxicity studies examine relevant doses of these organic chemical UV filters to which viable epidermal cells are realistically exposed. In this study, /investigators/ sought to determine whether sufficient topically applied sunscreens penetrated into human viable epidermis to put the local keratinocyte cell populations at risk of toxicity. The penetration and retention of five commonly used sunscreen agents (avobenzone, octinoxate, octocrylene, oxybenzone and padimate O) in human skin was evaluated after application in mineral oil to isolated human epidermal membranes. Sunscreen concentration-human keratinocyte culture response curves were then defined using changes in cell morphology and proliferation (DNA synthesis using radiolabelled thymidine uptake studies) as evidence of sunscreens causing toxicity. Following 24 hr of human epidermal exposure to sunscreens, detectable amounts of all sunscreens were present in the stratum corneum and viable epidermis, with epidermal penetration most evident with oxybenzone. The concentrations of each sunscreen found in human viable epidermis after topical application, adjusting for skin partitioning and binding effects, were at least 5-fold lower, based on levels detected in viable epidermal cells, than those appearing to cause toxicity in cultured human keratinocytes. It is concluded that the human viable epidermal levels of sunscreens are too low to cause any significant toxicity to the underlying human keratinocytes.

    PMID:15908756 Hayden CG et al; Skin Pharmacol Physiol. 18 (4): 170-4 (2005)

    Researchers in Europe analyzed samples of human milk for the presence of sunscreens and other chemicals with possible endocrine activity. Mothers were asked about their use of sunscreens and cosmetics that contained sunscreen ingredients (benzophenone 2, benzophenone 3, 3-benzylidene camphor, 4-MBC, OMC, homosalate, octocrylene, and octyl-dimethyl PABA). Responding to questionnaires, 78.8% of the women reported using products that contained sunscreens; 76.5% of human milk samples contained these chemicals. There was a high correlation reported between mothers' use of these chemicals and their concentrations in human milk. The authors concluded that except for lipsticks (the ingestion of which is probably important), their results agree with studies in animals and humans showing dermal absorption of sunscreens. Given that some of these chemicals have endocrine activity in animals, the authors suggested that exposure could be lessened if mothers abstained from using these products during their children's sensitive life stages.

    Balk SJ et al; PEDIATRICS 127 (3): e791-e817 (2011)

    Information on the cutaneous absorption, distribution, and elimination of most topically applied sunscreen agents is limited. Solvents used in sunscreen products affect the stability and binding of the drug to the skin; in general, alcoholic solvents allow for the most rapid and deepest epidermal penetration of sunscreens. It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. PABA reportedly diffuses into the stratum corneum, reaching maximum concentrations there 2 hours following application, but apparently does not penetrate deeper layers of the skin to a substantial extent. Homosalate's penetration also appears to be limited to the stratum corneum. One study in animals indicated that PABA may penetrate the skin to a greater extent than does padimate A. Although some studies have shown that substantive concentrations of PABA remain on the skin after washing, other studies have failed to confirm this. One study showed that PABA esters were removed from the skin less readily than was PABA or other chemical sunscreens. /PABA/

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

    5.4 Metabolism/Metabolites

    No pharmacokinetic data available.

    5.5 Biological Half-Life

    No pharmacokinetic data available.

    5.6 Mechanism of Action

    It is proposed that simultaneous contact of padimate O with keratinocytes can stimulate the diffusion through human epidermis. Upon photoexcitation, padimate O generates singlet oxygen and forms carbon-centred free radicals. While padimate O attenuates simple and repairable, UV-induced cellular damage, it may also increase complex chemical damage that is more difficult to repair by normal cells.

    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

    ... The photomutagenic sunscreen Padimate-O attacks DNA on illumination with simulated sunlight, producing strand breaks and lesions that are labile to N,N'-dimethylethylenediamine but few, if any, cyclobutane dimers or other direct photoproducts. The damage can be completely suppressed by the free radical quenchers Tris, ethanol, mannitol and dimethylsulfoxide, which is commonly used as a solvent in conventional photomutagenicity assays.

    McHugh PJ, Knowland J; Photochem Photobiol 66(2): 279-81 (1997)

    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.

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    ABOUT THIS PAGE

    Looking for 21245-02-3 / 2-Ethylhexyl 4-(Dimethylamino)Benzoate API manufacturers, exporters & distributors?

    2-Ethylhexyl 4-(Dimethylamino)Benzoate manufacturers, exporters & distributors 1

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    API | Excipient name

    2-Ethylhexyl 4-(Dimethylamino)Benzoate

    Synonyms

    21245-02-3, Padimate o, 2-ethylhexyl 4-dimethylaminobenzoate, Padimate-o, Escalol 507, Octyl dimethyl paba

    Cas Number

    21245-02-3

    Unique Ingredient Identifier (UNII)

    Z11006CMUZ

    About 2-Ethylhexyl 4-(Dimethylamino)Benzoate

    Padimate O is an active sunscreen agent in cosmetics and over-the-counter sunscreen drug products in concentrations up to 8%, as regulated by the FDA. It is a structurally-related compound to [DB02362] that absorbs UV-B rays to prevent photodamage. It penetrates human skin, and is shown to induce non-ligatable strand breaks on DNA in vitro and mutagenic effects on yeast in vivo.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate Manufacturers

    A 2-Ethylhexyl 4-(Dimethylamino)Benzoate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of 2-Ethylhexyl 4-(Dimethylamino)Benzoate, including repackagers and relabelers. The FDA regulates 2-Ethylhexyl 4-(Dimethylamino)Benzoate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. 2-Ethylhexyl 4-(Dimethylamino)Benzoate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate Suppliers

    A 2-Ethylhexyl 4-(Dimethylamino)Benzoate supplier is an individual or a company that provides 2-Ethylhexyl 4-(Dimethylamino)Benzoate active pharmaceutical ingredient (API) or 2-Ethylhexyl 4-(Dimethylamino)Benzoate finished formulations upon request. The 2-Ethylhexyl 4-(Dimethylamino)Benzoate suppliers may include 2-Ethylhexyl 4-(Dimethylamino)Benzoate API manufacturers, exporters, distributors and traders.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate GMP

    2-Ethylhexyl 4-(Dimethylamino)Benzoate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of 2-Ethylhexyl 4-(Dimethylamino)Benzoate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right 2-Ethylhexyl 4-(Dimethylamino)Benzoate GMP manufacturer or 2-Ethylhexyl 4-(Dimethylamino)Benzoate GMP API supplier for your needs.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate CoA

    A 2-Ethylhexyl 4-(Dimethylamino)Benzoate CoA (Certificate of Analysis) is a formal document that attests to 2-Ethylhexyl 4-(Dimethylamino)Benzoate's compliance with 2-Ethylhexyl 4-(Dimethylamino)Benzoate specifications and serves as a tool for batch-level quality control.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate CoA mostly includes findings from lab analyses of a specific batch. For each 2-Ethylhexyl 4-(Dimethylamino)Benzoate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    2-Ethylhexyl 4-(Dimethylamino)Benzoate may be tested according to a variety of international standards, such as European Pharmacopoeia (2-Ethylhexyl 4-(Dimethylamino)Benzoate EP), 2-Ethylhexyl 4-(Dimethylamino)Benzoate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (2-Ethylhexyl 4-(Dimethylamino)Benzoate USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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