CAS: 6093-68-1; 6-Hydroxy-2H-Chromen-2-One

该化合物是各种植物中天然存在的化合物,其特点是苯丙丙胺结构,其特点是一个有引信的苯苯和丙环,其特点是六点位置的氢氧基环,该化合物以其甜美,令人愉快的味道闻名,经常用于香味和调味工业.Coumarin展示了一系列生物活动,包括抗coaguant,抗气炎和抗氧化剂特性,使其在药理研究中引起兴趣.该物质在有机溶剂中可溶解,但水溶性有限.此外,coumarin可发生多种化学反应,例如氧化和酯化,这可以改变其特性和应用.但必须指出,Comarin及其衍生物在高浓度下可能有毒性,监管机构已对其在食品中的用途设定了限制.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

2-formyl-1,4-phenylene diacetate ethyl diphenylphosphonoacetate coumarin 6-methoxycoumarin cis-cinnamic acid2,5-dimethoxy-cis-cinnamic acid H-chromeno[5,6-e][1,3]oxazin-8-one2-phenyl-2,3-dihydro-1H-chromeno[5,6-e][1,3]oxazin-8-one H-chromeno[5,6-e][1,3]oxazin-8-one2-benzyl-2,3-dihydro-1H-chromeno[5,6-e][1,3]oxazin-8-one

合成工艺路线路线简述

    香豆素置于硫酸,硝酸,氯化铵,锌,Sodium Nitrite体系中,用 四氢呋喃,甲醇,水 作为反应溶剂,化学反应 20.5H,反应生成 6-羟基香豆素
    参考文献:Transtaganolides / Basiliolides的生物发生中建议的氧化裂解的研究:Pyran-2-One芳香介导的区域选择性控制和生物遗传学意义.
    标题:Transtaganolides / Basiliolides的生物发生中建议的氧化裂解的研究:Pyran-2-One芳香介导的区域选择性控制和生物遗传学意义.
    摘要:研究了在transtaganolides / Basiliolides的生物发生中提出的氧化裂解的合成可行性.吡喃-2-一环芳香族化合物在香豆素测定中控制氧化裂解向不希望的位置进行.使用咖啡因模型克服了这个问题,并允许在生物发生过程中合成吡喃-2-一键的类似物.
    DOI:10.1002/ejoc.201901894

    海关参考信息

    专利信息


    专利号:US-2003182068-A1
    优先权日:2001-10-30
    标 题 :Device and methods for directed synthesis of chemical libraries
    发明人:BATTERSBY BRONWYN J; MILLER CHRISTOPHER R; TRAU MATHIAS; WAY JEFFERY C; JOHNSTON ANGUS
    摘要:The invention features a sort computer which interfaces with a sorting device in order to control the sorting of beads on a bead by bead basis. The invention further features novel methods for the directed synthesis of encoded libraries of oligomers, e.g., oligonucleotides, on beads. These methods allow the synthesis of libraries that are sufficiently large to permit complex genomic analyses to be carried out. New methods of using the encoded libraries also are described.

    专利号:US-6998484-B2
    优先权日:2000-10-04
    标 题:Synthesis of purine locked nucleic acid analogues
    发明人:KOCH TROELS; JENSEN FLEMMING REISSIG
    权利人:SANTARIS PHARMA AS
    摘要:The present invention relates to a new method for the synthesis of purine LNA (Locked Nucleic Acid) analogues which provides a higher overall yield. The method comprising a regioselective 9-N purine glycosylation reaction followed by a one-pot nucleophilic aromatic substitution reaction of the 6-substituent in the purine ring and simultaneous nucleophile-induced intramolecular ring closure of the C-branched carbohydrate to form novel purine LNA analogues. The novel strategy is illustrated by the synthesis of the novel compound (1S,3R,4R,7S)-7-benzyloxy-1-methanesulfonylmethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane which is easily converted into (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-((2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane after isobutyryl protection of the 2-amino purine group and subsequent substitution of 1-methanesulfonyl with benzoate, debenzoylation and debenzylation.

    专利号:US-9440940-B2
    优先权日:2014-03-18
    标 题:Methods for synthesis of psoralen derivatives
    发明人:REFOUVELET BERNARD
    权利人:MACOPHARMA S A S
    摘要:Methods for the synthesis of psoralen derivatives are provided. In one embodiment, the method may include acetylating a compound of formula (II) to form a compound of formula (III), subjecting the compound of formula (III) to a Fries rearrangement to form a compound of formula (IV), and subjecting the compound of formula (IV) to cyclization, reduction and aromatization, to form a compound having the following formula (I):

    专利号:US-5247099-A
    优先权日:1989-08-17
    标题:Process for synthesis of 7-hydroxy coumarins having substitutions in the 4-position
    发明人:CELEBUSKI JOSEPH E
    权利人:ABBOTT LAB
    摘要:A process for synthesis of a compound of the formula: said process comprising the steps of (a) reacting 4-bromomethyl-7-methoxy coumarin with a malonic ester under conditions sufficient to achieve condensation of the ester to give the monoalkylated (2-bis(carbalkoxy)-2-R1-1-ethyl) derivative; (b) removing one of the carbalkoxy groups from the product of step (a); (c) demethylation of the product of step (b) to give the 7-hydroxycoumarin compound; and (d) chemically modifying the remaining ester to yield a desired R2.

    专利号:US-7598291-B2
    优先权日:2004-09-02
    标题 :Methods and compositions for enhancing collagen and proteoglycan synthesis in the skin
    发明人:NIMNI MARCEL; HAN BO
    权利人:NIMNI MARCEL; HAN BO
    摘要:A composition for application to the skin can stimulate the in vivo synthesis of collagen and proteoglycans and improve the appearance of the skin, increasing its elasticity and fullness. In general, a composition according to the present invention comprises: (1) an antioxidant compound in a quantity sufficient to enhance collagen synthesis in the skin; (2) an organic penetrant in which the antioxidant compound is soluble in a sufficient quantity that a concentration of the antioxidant compound sufficient to enhance collagen synthesis can be applied topically and penetrate the skin; (3) a mixture of essential amino acids; (4) a supplemental source of sulfur; and (5) a topical pharmaceutically acceptable carrier. The antioxidant compound can be lipoic acid, a lipoic acid analogue or derivative, a bioflavonoid, a constituent of ginkgo, or an isoflavone. The organic penetrant is preferably benzyl alcohol. Other ingredients, such as esters of tocopherol and ascorbic acid, can be included.

    专利号:US-5679773-A
    优先权日:1995-01-17
    标题 :Reagants and methods for immobilized polymer synthesis and display
    发明人:HOLMES CHRISTOPHER P
    权利人:AFFYMAX TECH NV
    摘要:Compounds and methods for solid phase synthesis of organic molecules including peptides, oligonucleotides, benzodiazepines, beta -turn mimetics, and prostaglandins. The present invention provides new reagents in the form of linking groups and resins and substrates having attached linking groups which are useful in solid phase synthesis of high density arrays of organic molecules. The invention also provides methods which increase yields of various organic synthesis strategies.
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    主要参考文献

    [参考文献]: Farooq S, Et Al. Isolation, Cytotoxicity Evaluation And Hplc-Quantification Of The Chemical Constituents From Prangos Pabularia. Plos One. 2014 Oct 14;9(10):E108713.

    合成参考文献


    参考文献:10.1107/s1600536810029430
    摘要:Adfa M, Koketsu M, Ebihara M. 6-Benzyl-oxycoumarin. Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 31;66(Pt 8):o2190.
    参考文献:10.1007/s10886-011-9968-6
    摘要:Adfa M, Hattori Y, Yoshimura T, Komura K, Koketsu M. Antifeedant and Termiticidal Activities of 6-Alkoxycoumarins and Related Analogs Against Coptotermes formosanus Shiraki. Journal of Chemical Ecology. 2011 May 20;37(6):598–606. doi: 10.1007/s10886-011-9968-6.
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