CAS: 11103-57-4; All-Trans-Retinol

该化合物是各种生物功能,包括视觉,免疫功能和皮肤健康所必需的脂肪溶解维生素A,其特点是它具有疏水性,允许将其储存在肝脏和脂肪组织中.维他命A的分子结构具有β离子环和长碳氢化合物尾,有助于其生物活动.作为强效抗氧化剂,它有助于中和自由基,从而保护细胞免受氧化性损害.维他命A对于合成红黄素至关重要,因为红黄素是视网膜中的色素,能够产生低光视力.维生素A的缺乏可能导致严重的健康问题,包括夜间失明和感染的易感性增加.它存在于各种饮食来源,包括肝脏,鱼类,奶制品和某些水果和蔬菜,特别是富含卡罗尼基素的水果和蔬菜,该体可以转化成活性维生素A.由于其在人类健康中的重要性,维生素A经常被纳入饮食补充品和强化食品.

结构式图片

物理性质

欧盟法规

欧盟化妆品法规附录三-限用物质清单ECHA物质ECHA物质C&L通报REACH预注册

合成工艺路线路线简述

    海关参考信息

    专利信息


    专利号:US-9040742-B2
    优先权日:2011-12-27
    标题:Catalytic synthesis of vitamin A intermediate
    发明人:BONRATH WERNER; WUESTENBERG BETTINA; NETSCHER THOMAS; SCHUETZ JAN
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to a process of production of a compound, which is useful as an intermediate (building block) in organic synthesis, especially in the synthesis of vitamin A or β-carotene and derivatives thereof, e.g. canthaxanthin, astaxanthin or zeaxanthin.

    专利号:US-2005027142-A1
    优先权日:2003-08-01
    标题 :Method for synthesis of 2,2,6-trimethylcyclohexan-1-one
    发明人:KLEINFELD SUSANNE; FISCHER ACHIM; WILZ FRANK; WECKBECKER CHRISTOPH; HUTHMACHER KLAUS
    权利人:DEGUSSA
    摘要:The present invention relates to a method for synthesis of 2,2,6-trimethylcyclohexan-1-one (TMCH) by partial reduction of 2,6,6-trimethyl-2-cyclohexen-1,4-dione (ketoisophorone, KIP), the reaction being carried out in the gas phase in the presence of oxide catalysts.

    专利号:US-5191110-A
    优先权日:1987-05-21
    标题 :Process for the synthesis of vitamin A and certain ones of derivatives
    发明人:SOLLADIE GUY; FORESTIER SERGE; LANG GERARD
    权利人:OREAL
    摘要:According to this process, one effects a stereospecific reduction of the two hydroxyl groups of an ether-diol by a mixture (titanium trichloride, lithium aluminum hydride) at a temperature between 5° C. and about 40° C. and that optionally, one converts the resulting ether into vitamin A, retinol or retinoic acid. n Application to the synthesis of all-trans compounds selected from the group consisting of vitamin A and its ethers, retinol and retinoic acid, and their 13-cis isomers.

    专利号:US-4035425-A
    优先权日:1973-04-23
    标 题 :Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A
    发明人:OROSHNIK WILLIAM
    权利人:SCM CORP
    摘要:A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.

    专利号:US-4092366-A
    优先权日:1975-04-10
    标题:Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A
    发明人:OROSHNIK WILLIAM
    权利人:SCM CORP
    摘要:A synthesis of novel Vitamin A intermediates from betaionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.

    专利号:US-3949006-A
    优先权日:1972-04-24
    标题:Synthesis of vitamin A, intermediates and conversion thereof to vitamin A
    发明人:OROSHNIK WILLIAM
    权利人:SCM CORP
    摘要:A synthesis of novel Vitamin A intermediates from betaionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
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    合成参考文献


    参考文献:10.1007/s11596-010-0121-5
    摘要:Fang J, Zheng C, Tao H, Zhao H, Ren J, Feng G. Therapeutic effects of all trans-retinoic acid combined with transarterial chemoembolization on Walker-256 hepatoma in rats. J Huazhong Univ Sci Technolog Med Sci. 2010 Feb;30(1):113–8. doi: 10.1007/s11596-010-0121-5.
    参考文献:10.1186/1741-7015-8-13
    摘要:Ritchie SA, Ahiahonu PW, Jayasinghe D, Heath D, Liu J, Lu Y, Jin W, Kavianpour A, Yamazaki Y, Khan AM, Hossain M, Su-Myat KK, Wood PL, Krenitsky K, Takemasa I, Miyake M, Sekimoto M, Monden M, Matsubara H, Nomura F, Goodenowe DB. Reduced levels of hydroxylated, polyunsaturated ultra long-chain fatty acids in the serum of colorectal cancer patients: implications for early screening and detection. BMC Medicine. 2010 Feb 15;8(1):13. doi: 10.1186/1741-7015-8-13.
    参考文献:10.1007/s12245-009-0105-z
    摘要:Phua DH, Zosel A, Heard K. Dietary supplements and herbal medicine toxicities—when to anticipate them and how to manage them. International Journal of Emergency Medicine. 2009 Jun 10;2(2):69–76. doi: 10.1007/s12245-009-0105-z.
    参考文献:10.1007/s00105-011-2137-6
    摘要:Kerscher M, Buntrock H. [Anti-aging creams. What really helps ]. Hautarzt. 2011 Aug;62(8):607–13. doi: 10.1007/s00105-011-2137-6.
    参考文献:10.1007/s10552-011-9811-y
    摘要:Fulan H, Changxing J, Baina WY, Wencui Z, Chunqing L, Fan W, Dandan L, Dianjun S, Tong W, Da P, Yashuang Z. Retinol, vitamins A, C, and E and breast cancer risk: a meta-analysis and meta-regression. Cancer Causes Control. 2011 Oct;22(10):1383–96. doi: 10.1007/s10552-011-9811-y.
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