奥克立林

奥克立林
	IUPAC名; 2-氰基-3,3-二苯基丙-2-烯酸（2-乙基）己酯; 2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
别名	Uvinul N-539
识别
CAS号	6197-30-4
PubChem	22571
ChemSpider	21165
SMILES	N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2;
InChI	1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3;
InChIKey	FMJSMJQBSVNSBF-UHFFFAOYAD
性质
化学式	C24H27NO2
摩尔质量	361.48 g/mol g·mol⁻¹
密度	1.05 g/cm3
熔点	14 °C（287 K）
沸点	218 °C（491 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

奥克立林（英语：Octocrylene），别名氰双苯丙烯酸辛酯，是一种有机化合物，化学式：C₂₄H₂₇NO₂，为透明粘稠油状液体。常作为化学防晒剂在防晒霜等化妆品中使用。由氰乙酸异辛酯与二苯酮发生克脑文盖尔缩合反应得到。

其结构中酯基、氰基、偏二苯乙烯基构成的大共轭体系可以吸收A波段长波紫外线（UVA，波长280 - 320 nm）^[1]，以此来到达防紫外线的效果，其烷基部分则提供油溶性和增稠性。

安全性[编辑]

奥克立林可以渗透到皮肤内，并起到光敏剂的作用，在受光激发产生自由^[2]。透过皮肤后可能会进入血液循环，然后其代谢产物经尿液排出^[3]^[4]。奥克立林可以经逆羟醛缩合产生二苯酮^[5]。该反应随着时间的推移缓慢发生，在所有含有奥克立林的市售化妆品中二苯甲酮的浓度都很高。

在珊瑚中，奥克立林已被证明会以脂肪酸结合物的形式积聚，并引发线粒体功能障碍^[6]。

各地规定[编辑]

被禁止[编辑]

帕劳

2018年通过《负责任旅游教育法案》，禁止在当地销售和使用包括奥克立林在内的三种对珊瑚礁有毒的防晒霜，成为首个对危害珊瑚礁和其他海洋生物的防晒霜实施禁令的国家^[7]。2020年1月1日起，将范围扩大都到含有二苯丙酮、桂皮酸盐等常见成分的防晒霜，有十种化学品被列入禁令^[8]

美属维尔京群岛

在2019年通过法案禁止携带包括奥克立林在内的羟苯甲酮和桂皮酸盐的防晒霜使用，自2019年9月30日起，禁止进口含有该化学品的防晒霜；仅可使用非纳米矿物型防晒剂（氧化锌、二氧化钛）^[9]。2020年3月30日起，禁止其分销、销售、持有和使用。^[10]

美国（夏威夷）

夏威夷群岛自2018年5月起禁止包括奥克立林等二苯丙酮类防晒剂销售^[11]。

博奈尔

2021年5月起，禁止使用包括奥克立林等二苯丙酮类防晒剂^[8]。

限量[编辑]

欧洲联盟、美国、大韩民国、日本、中华人民共和国

化妆品中奥克立林最大含量规定为 100 g/kg（按酸计）^[12]。

参考文献[编辑]

^ Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent. www.smartskincare.com.
^ Hanson Kerry M.; Gratton Enrico; Bardeen Christopher J. Sunscreen enhancement of UV-induced reactive oxygen species in the skin. Free Radical Biology and Medicine. 2006, 41 (8): 1205–1212. PMID 17015167. S2CID 13999532. doi:10.1016/j.freeradbiomed.2006.06.011.
^ Bury, Daniel; Belov, Vladimir N.; Qi, Yulin; Hayen, Heiko; Volmer, Dietrich A.; Brüning, Thomas; Koch, Holger M. Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS. Analytical Chemistry. 2018, 90 (1): 944–951. PMID 29188988. doi:10.1021/acs.analchem.7b03996. hdl:21.11116/0000-0000-3212-3 .
^ Bury, Daniel; Modick-Biermann, Hendrik; Leibold, Edgar; Brüning, Thomas; Koch, Holger M. Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure. Archives of Toxicology. 2019, 93 (5): 1227–1238. PMID 30739143. S2CID 59622082. doi:10.1007/s00204-019-02408-7.
^ Downs, C. A.; DiNardo, Joseph C.; Stien, Didier; Rodrigues, Alice M. S.; Lebaron, Philippe. Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products. Chemical Research in Toxicology. 7 March 2021, 34 (4): 1046–1054. PMID 33682414. doi:10.1021/acs.chemrestox.0c00461 .
^ Stien, Didier; Clergeaud, Fanny; Rodrigues, Alice M.S.; Lebaron, Karine; Pillot, Rémi; Romans, Pascal; Fagervold, Sonja; Lebaron, Philippe. Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction (PDF). Analytical Chemistry. 2019, 91 (1): 990–995. PMID 30516955. S2CID 54567139. doi:10.1021/acs.analchem.8b04187.
^ Republic of Palau. RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw. PalauGov.pw Your guide to finding and using Palau National Government services. [16 October 2019].
^ ^8.0 ^8.1 BBC. 防晒霜危害珊瑚帕劳成全球首个禁用禁售的国家. BBC中文. [2024-07-05].
^ Sustainable Travel in USVI. United States Virgin Islands. [17 February 2024]. （原始内容存档于14 January 2024）（英语）. Avoid sunscreens that contain the “Toxic 3 Os” of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States Virgin Islands. Wear rashguards, hats and use only non-nano mineral sunscreen containing zinc oxide and titanium dioxide, the only sunscreen ingredients deemed safe and effective by the FDA.
^ 防晒霜祸害珊瑚礁！美属维尔京群岛下禁令，市场期待生态友好型护肤品. 文汇网. [2024-07-05].
^ 环球网. 为保护珊瑚礁，一些防晒霜可能会在夏威夷被禁！.
^ 张伟清、罗飞亚、李彬、刘慧锦、侯俐南、乔亚森、王海燕、孙磊. 防晒类化妆品中奥克立林等4种化学防晒剂检测结果分析及各国标准比对. 香料香精化妆品. 2020, (02): 40–44.

[1] Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent. www.smartskincare.com.

[Hanson-2] Hanson Kerry M.; Gratton Enrico; Bardeen Christopher J. Sunscreen enhancement of UV-induced reactive oxygen species in the skin. Free Radical Biology and Medicine. 2006, 41 (8): 1205–1212. PMID 17015167. S2CID 13999532. doi:10.1016/j.freeradbiomed.2006.06.011.

[3] Bury, Daniel; Belov, Vladimir N.; Qi, Yulin; Hayen, Heiko; Volmer, Dietrich A.; Brüning, Thomas; Koch, Holger M. Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS. Analytical Chemistry. 2018, 90 (1): 944–951. PMID 29188988. doi:10.1021/acs.analchem.7b03996. hdl:21.11116/0000-0000-3212-3 .

[4] Bury, Daniel; Modick-Biermann, Hendrik; Leibold, Edgar; Brüning, Thomas; Koch, Holger M. Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure. Archives of Toxicology. 2019, 93 (5): 1227–1238. PMID 30739143. S2CID 59622082. doi:10.1007/s00204-019-02408-7.

[5] Downs, C. A.; DiNardo, Joseph C.; Stien, Didier; Rodrigues, Alice M. S.; Lebaron, Philippe. Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products. Chemical Research in Toxicology. 7 March 2021, 34 (4): 1046–1054. PMID 33682414. doi:10.1021/acs.chemrestox.0c00461 .

[6] Stien, Didier; Clergeaud, Fanny; Rodrigues, Alice M.S.; Lebaron, Karine; Pillot, Rémi; Romans, Pascal; Fagervold, Sonja; Lebaron, Philippe. Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction (PDF). Analytical Chemistry. 2019, 91 (1): 990–995. PMID 30516955. S2CID 54567139. doi:10.1021/acs.analchem.8b04187.

[7] Republic of Palau. RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw. PalauGov.pw Your guide to finding and using Palau National Government services. [16 October 2019].

[bbc-8] 8.0 ^8.1 BBC. 防晒霜危害珊瑚帕劳成全球首个禁用禁售的国家. BBC中文. [2024-07-05].

[9] Sustainable Travel in USVI. United States Virgin Islands. [17 February 2024]. （原始内容存档于14 January 2024）（英语）. Avoid sunscreens that contain the “Toxic 3 Os” of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States Virgin Islands. Wear rashguards, hats and use only non-nano mineral sunscreen containing zinc oxide and titanium dioxide, the only sunscreen ingredients deemed safe and effective by the FDA.

[10] 防晒霜祸害珊瑚礁！美属维尔京群岛下禁令，市场期待生态友好型护肤品. 文汇网. [2024-07-05].

[11] 环球网. 为保护珊瑚礁，一些防晒霜可能会在夏威夷被禁！.

[12] 张伟清、罗飞亚、李彬、刘慧锦、侯俐南、乔亚森、王海燕、孙磊. 防晒类化妆品中奥克立林等4种化学防晒剂检测结果分析及各国标准比对. 香料香精化妆品. 2020, (02): 40–44.

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