CAS: 14101-61-2; (R)-2,7,8-Trimethyl-2-((3E,7E)-4,8,12-Trimethyltrideca-3,7,11-Trien-1-yl)Chroman-6-Ol

该化合物是托科狄纳醇家族的成员,是一种具有独特化学结构的维他命E形式,包括一个铬环和三联双环的副链,该化合物以其抗氧化特性而著称,它有助于通过消除自由基质来保护细胞免受氧化性压力. -托科狄纳醇主要存在于某些植物油,谷物和坚果中,它因其潜在的健康惠益而得到承认,包括抗炎效应和对心血管健康的支持. 它的亲脂性质使它得以融入细胞膜,影响细胞功能和信号路径.此外,对托科特宁醇在癌症预防和...

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2'-phenylsulfonyl-γ-t°Cotrienyl benzyl ether methyl 2,7,8-trimethyl-6-benzoyloxychroman-2-carboxylate 2,7,8-trimethyl-6-hydroxychroman-2-methanol (R)-6-(3,5-dimethoxybenzyl)oxy-2,7,8-trimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman (R)-2,7,8-trimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl tosylcarbamate (R)-2,7,8-trimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl phenylcarbamate (R)-2,7,8-trimethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl 4-chlorophenylsulfonylcarbamate

合成工艺路线路线简述

    📜2'-Phenylsulfonyl-γ-Tocotrienyl Benzyl Ether置于lithium,甲胺体系中,用 乙醚 用作溶剂,化学反应 0.75H,以73%的收率获得b-生育三烯醇
    参考文献:短而便捷的化学路线,即可制得光学纯的2-甲基氯代甲醇.β-,γ-和δ-生育三烯酚的总不对称合成
    标题:短而便捷的化学路线,即可制得光学纯的2-甲基氯代甲醇.β-,γ-和δ-生育三烯酚的总不对称合成
    摘要:使用廉价的可商购的原料,已经以高收率制备了天然β-,γ-和δ-生育三烯酚的苯甲醇甲醇前体.酶促拆分得到高对映体过量的手性苯并二甲醇.法呢基侧链的后续附接是高产率的,因此允许在最后的步骤中制备不对称的β-,γ-和δ-生育三烯酚,其中同时发生苯酚的脱保护和砜基的去除.该化学方法提供了天然系列β-生育三烯酚的首次合成.
    Doi:10.1021/jo0705418

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    专利信息


    专利号:US-2008221377-A1
    优先权日:2006-06-16
    标题 :Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
    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; BRAUN CRISTI L
    权利人:LOCKWOOD SAMUEL F; TANG PENG CHO; NADOLSKI GEOFF; JACKSON HENRY L; FANG ZHIQIANG; DU YISHU; YANG MIN; GEISS WILLIAM; WILLIAMS RICHARD; BURDICK DAVID; BRAUN CRISTI L
    摘要:A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

    专利号:US-9981935-B2
    优先权日:2013-07-05
    标 题:Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids
    发明人:MEDLOCK JONATHAN ALAN; LETINOIS ULLA; NETSCHER THOMAS; BONRATH WERNER
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to a synthesis of chromanones or chromanes in a stereospecific matter in view of the 2-position in the chromanone or chromane ring. It has been found that this synthesis is particularly possible in the presence of a chiral compound of a specific type and of at least one Bransted acid or in the presence a specific chiral compound having a Bransted acid functional group in the molecule.

    专利号:US-9815809-B2
    优先权日:2013-07-05
    标题:Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of phenols or thiophenols
    发明人:LETINOIS ULLA; NETSCHER THOMAS
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to a synthesis of chromanones or chromanes in a stereospecific matter in view of the 2-position in the chromanone or chromane ring. It has been found that this synthesis is particularly possible in the presence of a chiral compound of formula of a specific type and of at least one phenol or thiophenol.

    专利号:US-9809565-B2
    优先权日:2013-07-05
    标 题 :Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of ureas or thioureas
    发明人:LETINOIS ULLA; NETSCHER THOMAS; ACKERMANN STEPHAN
    权利人:DSM IP ASSETS BV
    摘要:The present invention relates to a synthesis of chromanones or chromanes in a stereospecific matter in view of the 2-position in the chromanone or chromane ring. It has been found that this synthesis is particularly possible in the presence of a chiral compound of formula of a specific type and of at least one urea or thiourea.

    专利号:US-2003157592-A1
    优先权日:1999-12-16
    标题:Moss genes from physcomitrella patens encoding proteins involved in the synthesis of tocopherols and carotenoids
    发明人:LERCHL JENS; RENZ ANDREAS; EHRHARDT THOMAS; REINDL ANDREAS; CIRPUS PETRA; BISCHOFF FRIEDRICH; FRANK MARKUS; FREUND ANNETTE; DUWENIG ELKE; SCHMIDT RALF-MICHAEL; RESKI RALF; BADUR RALF
    摘要:Isolated nucleic acid molecules, designated TCMRP nucleic acid molecules, which encode novel TCMRPs from e.g. Phycomitrella patens are described. The invention also provides antisense nucleic acid molecules, recombinant expression vectors containing TCMRP nucleic acid molecules, and host cells into which the expression vectors have been introduced. The invention still further provides isolated TCMRPs, mutated TCMRPs, fusion proteins, antigenic peptides and methods for the improvement of production of a desired compound from transformed cells, organisms or plants based on genetic engineering of TCMRP genes in these organisms.

    专利号:US-11673874-B2
    优先权日:2018-08-17
    标 题 :Synthesis of chromanol derivatives
    发明人:WEINGARTEN MELANIE; SIEGEL WOLFGANG; PUHL MICHAEL
    权利人:BASF SE
    摘要:The present invention relates to a process for the production of chromanol derivatives, more specifically to a process for preparing a compound of the general formula I wherein R 1 , R 2 and R 3 independently of each other are selected from hydrogen and methyl, R 4 is selected from C- 1 -C 6 -alkyl, and X is selected from C 1 -C 20 -alkyl and C 2 -C 20 -alkenyl.

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    主要参考文献


    1: Hofer M, Hoferová Z, Falk M. Pharmacological Modulation of Radiation Damage. Does It Exist a Chance for Other Substances than Hematopoietic Growth Factors and Cytokines? Int J Mol Sci. 2017 Jun 28;18(7). pii: E1385. doi: 10.3390/ijms18071385. Review.
    2: Singh VK, Hauer-Jensen M. γ-Tocotrienol as a Promising Countermeasure for Acute Radiation Syndrome: Current Status. Int J Mol Sci. 2016 May 3;17(5). pii: E663. doi: 10.3390/ijms17050663. Review.
    3: Zhao L, Fang X, Marshall MR, Chung S. Regulation of Obesity and Metabolic Complications by Gamma and Delta Tocotrienols. Molecules. 2016 Mar 11;21(3):344. doi: 10.3390/molecules21030344. Review. doi: 10.3945/an.115.009456. Print 2015 Nov. Review.

    合成参考文献


    参考文献:10.1016/j.bmc.2009.11.054
    摘要:Elnagar AY, Wali VB, Sylvester PW, El Sayed KA. Design and preliminary structure-activity relationship of redox-silent semisynthetic tocotrienol analogues as inhibitors for breast cancer proliferation and invasion. Bioorg Med Chem. 2010 Jan 15;18(2):755–68. doi: 10.1016/j.bmc.2009.11.054.
    参考文献:10.1016/j.ejmech.2012.11.012
    摘要:Behery FA, Akl MR, Ananthula S, Parajuli P, Sylvester PW, El Sayed KA. Optimization of tocotrienols as antiproliferative and antimigratory leads. European Journal of Medicinal Chemistry. 2013 Jan;59():329–41. doi: 10.1016/j.ejmech.2012.11.012.
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