二甲氨苯酸辛酯

二甲氨苯酸辛酯
	IUPAC名; 2-ethylhexyl 4-(dimethylamino)benzoate
別名	帕地馬酯O; Escalol 507; Sundown; OD-PABA(octyldimethyl PABA)
識別
CAS號	21245-02-3
PubChem	30541
ChemSpider	28343
SMILES	O=C(OCC(CC)CCCC)c1ccc(N(C)C)cc1;
InChI	1/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;
InChIKey	WYWZRNAHINYAEF-UHFFFAOYAL
KEGG	D05335
性質
化學式	C17H27NO2
摩爾質量	277.4 g·mol−1
密度	0.99 g/cm3
熔點	<25 °C
沸點	362 °C（635 K）
危險性
NFPA 704	1 1 0
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二甲氨苯酸辛酯，俗稱帕地馬酯O（英語：Padimate O）是一種有機化合物，為對氨基苯甲酸（PABA）衍生物，可吸收紫外線，常用於防曬劑中。為淡黃色油狀液體，不溶於水，由2-乙基己醇與二甲氨基苯甲酸發生酯化反應得到。

光生物學

二甲氨苯酸辛酯可以吸收中波紫外光（UVB，波長315–280 nm），防止紫外線對DNA造成直接損傷。但吸收紫外光後產生的激發態二甲氨苯酸辛酯會與DNA反應造成間接損傷，產生電離輻射類似的傷害效果。1993年一項針對酵母的體外研究證實二甲氨苯酸辛酯會產生光誘導的致突變性^[1]。作為米氏酮衍生物，二甲氨苯酸辛酯同樣被認為和米氏酮一樣對小鼠產生光致癌性^[2]。

然而，在眾多在無毛小鼠上展開的局部活體實驗證實二甲氨苯酸辛酯沒有致癌性，而且二甲氨苯酸辛酯可以減少和延緩紫外線誘發的皮膚腫瘤的出現^[3]^[4]^[5]^[6]。

參考文獻

^ Knowland, John; McKenzie, Edward A; McHugh, Peter J; Cridland, Nigel A. Sunlight-induced mutagenicity of a common sunscreen ingredient. FEBS Letters. 1993, 324 (3): 309–13. PMID 8405372. S2CID 23853321. doi:10.1016/0014-5793(93)80141-G.
^ Gulston, Melanie; Knowland, John. Illumination of human keratinocytes in the presence of the sunscreen ingredient Padimate-O and through an SPF-15 sunscreen reduces direct photodamage to DNA but increases strand breaks. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 1999, 444 (1): 49–60. PMID 10477339. doi:10.1016/S1383-5718(99)00091-1.
^ Kligman, Lorraine H.; Akin, Frank J.; Kligman, Albert M. Sunscreens prevent ultraviolet photocarcinogenesis. Journal of the American Academy of Dermatology. 1980, 3 (1): 30–5. PMID 6967495. doi:10.1016/S0190-9622(80)80221-0.
^ Bissett, Donald L.; McBride, James F.; Hannon, Daniel P.; Patrick, Larry F. Time-dependent decrease in sunscreen protection against chronic photodamage in UVB-irradiated hairless mouse skin. Journal of Photochemistry and Photobiology B: Biology. 1991, 9 (3–4): 323–334. PMID 1919875. doi:10.1016/1011-1344(91)80169-I.
^ Bissett, Donald L; McBride, James F. Synergistic topical photoprotection by a combination of the iron chelator 2-furildioxime and sunscreen. Journal of the American Academy of Dermatology. 1996, 35 (4): 546–9. PMID 8859281. doi:10.1016/S0190-9622(96)90677-5.
^ Kerr, Caroline. The effects of two UVB radiation-absorbing sunscreens on UV radiation-induced carcinogenesis, suppression of the contact hypersensitivity response and histological changes in the hairless mouse. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 1998, 422 (1): 161–4. PMID 9920441. doi:10.1016/S0027-5107(98)00188-2.

[Knowland1993-1] Knowland, John; McKenzie, Edward A; McHugh, Peter J; Cridland, Nigel A. Sunlight-induced mutagenicity of a common sunscreen ingredient. FEBS Letters. 1993, 324 (3): 309–13. PMID 8405372. S2CID 23853321. doi:10.1016/0014-5793(93)80141-G.

[Sensitization-2] Gulston, Melanie; Knowland, John. Illumination of human keratinocytes in the presence of the sunscreen ingredient Padimate-O and through an SPF-15 sunscreen reduces direct photodamage to DNA but increases strand breaks. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 1999, 444 (1): 49–60. PMID 10477339. doi:10.1016/S1383-5718(99)00091-1.

[3] Kligman, Lorraine H.; Akin, Frank J.; Kligman, Albert M. Sunscreens prevent ultraviolet photocarcinogenesis. Journal of the American Academy of Dermatology. 1980, 3 (1): 30–5. PMID 6967495. doi:10.1016/S0190-9622(80)80221-0.

[4] Bissett, Donald L.; McBride, James F.; Hannon, Daniel P.; Patrick, Larry F. Time-dependent decrease in sunscreen protection against chronic photodamage in UVB-irradiated hairless mouse skin. Journal of Photochemistry and Photobiology B: Biology. 1991, 9 (3–4): 323–334. PMID 1919875. doi:10.1016/1011-1344(91)80169-I.

[5] Bissett, Donald L; McBride, James F. Synergistic topical photoprotection by a combination of the iron chelator 2-furildioxime and sunscreen. Journal of the American Academy of Dermatology. 1996, 35 (4): 546–9. PMID 8859281. doi:10.1016/S0190-9622(96)90677-5.

[6] Kerr, Caroline. The effects of two UVB radiation-absorbing sunscreens on UV radiation-induced carcinogenesis, suppression of the contact hypersensitivity response and histological changes in the hairless mouse. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 1998, 422 (1): 161–4. PMID 9920441. doi:10.1016/S0027-5107(98)00188-2.

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光生物學

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參考文獻