CAS: 144-68-3; (1R,1'R)-4,4'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-Nonaene-1,18-Diyl)Bis(3,5,5-Trimethylcyclohex-3-Enol)

该化合物是一种有力的抗氧化剂,在保护生物系统免受光和自由基引起的氧化压力方面发挥着关键作用. 在结构上,它与Lutein相似,Zeaxanthin是人体眼部肌肉色素的一个关键组成部分,它通过过滤高能蓝光和减轻光损害,有助于视觉健康.它的亲血性能可以有效地融入细胞膜.工业性,亚xanthin由于稳定性和生物活性特性,被用于营养树脂,食品添加剂和化妆品.合成和自然提取方法确保研究和商业应用的高纯度.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

ethanol all-trans lutein sodium ethanolate benzenetrans-Zeaxanthin-dimethylether O-acetyl-β-citraurin trans-β-apo-8'-carotenal 3,3'-dihydroxy-β,β-carotene-4,4'-dione

合成工艺路线路线简述

    叶黄素置于四氢呋喃,甲醇,Sodium Tetrahydroborate,硫酸,Potassium Hydroxide,碘甲烷体系中,用 四氢呋喃,丙醇,水 用作溶剂,化学反应 72.0H,反应生成玉米黄质
    参考文献:(3R,3'R,6'R)-叶黄素通过(3R)-3',4'-脱水叶黄素合成(3R,3'R)-玉米黄质及其内消旋立体异构体
    标题:(3R,3'R,6'R)-叶黄素通过(3R)-3',4'-脱水叶黄素合成(3R,3'R)-玉米黄质及其内消旋立体异构体
    摘要:的方法,已经开发了的部分合成(3-[r,3'-[r)-Zeaxanthin和(3-[r,3'小号;内消旋)从可商购的(3-Zeaxanthin-[r,3'-[r,6'-[r)-Lutein .这涉及叶黄素脱水产物(即(3 R)-3',4'-二氢-β,β-胡萝卜素-3-醇[(3 R)-3',4'-脱水叶黄素]的区域选择性氢硼化,得到(3的混合物[r,3'-[r)-Zeaxanthin和(3-[r,3'小号;内消旋玉米黄质,然后通过酶介导的酰化作用分离这些类胡萝卜素.(3-[r,3'-[r,6'-[r)-Lutein,(3-[r,3'-[r)-Zeaxanthin及其内消旋异构体累加在人体眼组织和预防年龄相关性黄斑变性的有牵连(amd ). 光学活性羟基类胡萝卜素-部分合成-手性拆分-区域选择性硼氢化-高共轭多烯
    Doi:10.1055/s-0031-1289662

    海关参考信息

    专利信息


    专利号:US-7247752-B2
    优先权日:2004-10-01
    标 题 :Methods for the synthesis of astaxanthin
    发明人:LOCKWOOD SAMUEL F; TANG PENG CHO; NADOLSKI GEOFF; JACKSON HENRY L; FANG ZHIQIANG; DU YISHU; YANG MIN; GEISS WILLIAM; WILLIAMS RICHARD; BURDICK DAVID
    权利人:CARDAX PHARMACEUTICALS INC
    摘要:A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids. Synthesis of optically active carotenoids, in one embodiment, may be accomplished by forming an optically active dihydroxy intermediate from ketoisopherone. The optically active dihydroxy intermediate may be converted into optically active astaxanthin derivatives.

    专利号:US-8222458-B2
    优先权日:2008-06-13
    标题 :Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
    发明人:KHACHIK FREDERICK; CHANG AN-NI
    权利人:KHACHIK FREDERICK; CHANG AN-NI; UNIV MARYLAND
    摘要:Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C 15 -Wittig salt] and its (3S)-enantiomer [(3S)-C 15 -Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C 15 -Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.

    专利号:US-7858828-B2
    优先权日:2008-03-26
    标 题 :Process for synthesis of (3R,3'R,6'R)-lutein and its stereoisomers
    发明人:KHACHIK FREDERICK; CHANG AN-NI
    权利人:UNIV MARYLAND
    摘要:(3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C 15 +C 10 +C 15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

    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-9943544-B2
    优先权日:2015-03-18
    标 题:Process for bio synthesis of nano arsenic trioxide and its use in treatment of diseases including cancer
    发明人:BENDALE YOGESH NARAYAN; BENDALE VINEETA YOGESH
    权利人:BENDALE YOGESH NARAYAN; BENDALE VINEETA YOGESH
    摘要:The present invention is a process for bio synthesis of nano arsenic trioxide defined by its low toxicity, higher bio availability and nano particle size with the aid of buttermilk, goat urine, dolichos biflorous and other plant materials such as ginger, momordica charantia and musa paradisiaca . The invention is carried out in different steps involving purification of crude form of arsenic trioxide by boiling it with buttermilk, goat urine and extract of dolichos biflorous in subsequent steps, followed by the trituration of the bio purified arsenic trioxide with extracts of ginger and momordica charantia in subsequent steps and heating of the dry product obtained after trituration with musa paradisiaca resulting in the production of novel nano arsenic trioxide. The product is effective in the treatment of various diseases including different types of cancer in animals and humans. The product obtained through the process is less toxic with higher bio availability.

    专利号:US-6150130-A
    优先权日:1993-12-27
    标题 :DNA strands useful for the synthesis of xanthophylls and the process for producing the xanthophylls
    发明人:MISAWA NORIHIKO; KONDO KEIJI; KAJIWARA SUSUMU; YOKOYAMA AKIHIRO
    权利人:KIRIN BREWERY; MARINE BIOTECH INST CO LTD
    摘要:Disclosed are the following DNA strands relating to the synthesis of keto group-containing xanthophylls such as astaxanthin and the like, and the techniques relating to the production of xanthophylls by genetic engineering: A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of a beta -ionone ring into a keto group. A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for converting a methylene group at the 4-position of a 3-hydroxy- beta -ionone ring into a keto group. A DNA strand having a nucleotide sequence which encodes a polypeptide having an enzyme activity for adding a hydroxyl group to the 3-carbon of a 4-keto- beta -ionone ring. It is possible to produce a variety of xanthophylls such as canthaxanthin, astaxanthin and the like by introducing the DNA strands into an appropriate microorganism such as Escherichia coli and the like.
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    主要参考文献


    1: Kumar P, Banik SP, Ohia SE, Moriyama H, Chakraborty S, Wang CK, Song YS, Goel A, Bagchi M, Bagchi D. Current Insights on the Photoprotective Mechanism of the Macular Carotenoids, Lutein and Zeaxanthin: Safety, Efficacy and Bio-Delivery. J Am Nutr Assoc. 2024 Feb
    23:1-14. doi: 10.1080/27697061.2024.2319090. Epub ahead of print.
    171:112013. doi: 10.1016/j.exger.2022.112013. Epub 2022 Nov 3. 81(6):670-683. doi: 10.1093/nutrit/nuac076. 87(3):1079-1087. doi: 10.3233/JAD-215736. 14(4):827. doi: 10.3390/nu14040827.

    合成参考文献


    摘要:Koo, S., Science of Synthesis, (2010) 45, 1382.
    摘要:Koo, S., Science of Synthesis, (2010) 45, 1396.
    参考文献:10.1007/s11130-020-00842-y
    摘要:Panfili G, Niro S, Bufano A, D'Agostino A, Fratianni A, Paura B, Falasca L, Cinquanta L. Bioactive Compounds in Wild Asteraceae Edible Plants Consumed in the Mediterranean Diet. Plant Foods Hum Nutr. 2020 Dec;75(4):540–6. doi: 10.1007/s11130-020-00842-y.
    参考文献:10.1021/jf990096k
    摘要:Hadden WL, Watkins RH, Levy LW, Regalado E, Rivadeneira DM, van Breemen RB, Schwartz SJ. Carotenoid composition of marigold (Tagetes erecta) flower extract used as nutritional supplement. J Agric Food Chem. 1999 Oct;47(10):4189–94. doi: 10.1021/jf990096k.
    参考文献:10.1079/phn2005892
    摘要:Englberger L, Aalbersberg W, Dolodolotawake U, Schierle J, Humphries J, Iuta T, Marks GC, Fitzgerald MH, Rimon B, Kaiririete M. Carotenoid content of pandanus fruit cultivars and other foods of the Republic of Kiribati. Public Health Nutr. 2006 Aug;9(5):631–43. doi: 10.1079/phn2005892.
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