1-(4-hydroxy-3-methoxyphenyl)hexa-3,5-dione | 113465-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)hexa-3,5-dione
• 英文别名: 6-(p-hydroxy-m-methoxyphenyl)hexane-2,4-dione；1-(4'-hydroxy-3'-methoxyphenyl)-3,5-hexanedione；[2]-Gingerdione；6-(4-hydroxy-3-methoxyphenyl)hexane-2,4-dione
• CAS: 113465-66-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ASOVUCJFCHQGTH-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  387.5±32.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  feruloylacetone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以89%的产率得到1-(4-hydroxy-3-methoxyphenyl)hexa-3,5-dione
  参考文献：
  名称：

  Feruloylacetone as the model compound of half-curcumin: Synthesis and antioxidant properties

  摘要：

  In order to clarify the contribution of phenolic and enolic hydroxyl group to the antioxidant capacity of feruloylacetone, a model compound of half-curcumin, 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-dione (FT), 6-(p-benzyloxy-m-methoxyphenyl)-5-hexene-2,4-dione (BMFT), 6-(m,p-dihydroxyphenyl)-5-hexene-2,4-dione (DDFT), 6-(p-hydroxy-m-methoxyphenyl)hexane-2,4-dione (DHFT), 6-(p-hydroxy-m-methoxyphenyl)-5-hexene-2,4-diol (THFT), and ethyl 2-(p-hydroxy-m-methoxybenzylidene)-3-oxobutanoate (EOFT) were synthesized. The radical-scavenging abilities of these compounds were tested by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl (DPPH), and galvinoxyl radicals. The reductive capacities were screened by quenching singlet oxygen and by inhibiting the oxidation of linoleic acid. They were also employed to inhibit the oxidation of DNA mediated by hydroxyl radical and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). In addition, they were applied to protect erythrocytes against AAPH- and hemin-induced hemolysis. The obtained results revealed that the antioxidant capacity of half-curcumin was derived from the phenolic-OH and the conjugated linkage between phenolic and enolic-OH. The enolic-OH itself cannot trap radicals. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.039

文献信息

• Hydroxyphenylalkadiones and Their Use for Masking Bitter Taste and/or for Intensifying Sweet Taste
  申请人：Ley Jakob

  公开号：US20080227866A1

  公开（公告）日：2008-09-18

  The use of a hydroxyphenylalkadione derivative of the formula (I) wherein, for X, a and Y: X is a —CH 2 —, —NH— or —O— group, Y is a —CH 2 — group and a is a single bond or X and Y are in each case a —CH— group and a is a double bond in the Z or E configuration, wherein, for R 1 , R 2 and R 3 R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group and R 2 and R 3 independently of one another denote hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 1 and R 2 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 1 and R 2 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 3 denotes hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 2 and R 3 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 2 and R 3 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group, wherein, for R 4 and R: R 4 and R independently of one another denote hydrogen, methyl or ethyl and wherein, for R 5 , R 6 and R 7 : R 5 , R 6 and R 7 independently of one another denote hydrogen or an aliphatic radical having 1 to 4 C atoms, a salt of such a hydroxyphenylalkadione of the formula (I), a mixture comprising or consisting of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, a mixture comprising or consisting of salts of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, or a mixture comprising or consisting of a hydroxyphenylalkadione of the formula (I) or two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, and a salt of a hydroxyphenylalkadione of the formula (I) or two or more salts of different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, for modifying, masking or reducing the unpleasant flavour impression of an unpleasantly tasting substance and/or for intensifying the sweet taste of a sweet-tasting substance and/or the sweet odour impression of an aroma substance which causes a sweet odour impression, as well as formulations and processes including a hydroxyphenylalkadione of the formula (I), are described.

  本文描述了使用公式（I）的羟基苯基丙酮衍生物的用途，其中，对于X、a和Y： X是一个-CH2-，-NH-或-O-基团， Y是一个-CH2-基团， a是一个单键； 或者X和Y在每种情况下都是一个-CH-基团，并且在Z或E构型中有一个双键； 对于R1、R2和R3，它们分别表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； R2和R3独立地表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R1和R2共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R1和R2表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代，而R3表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R2和R3共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R2和R3表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代； R1表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； 对于R4和R： R4和R分别独立地表示氢、甲基或乙基； 对于R5、R6和R7： R5、R6和R7分别独立地表示氢或具有1至4个C原子的脂肪基； 本文还描述了使用公式（I）的羟基苯基丙酮衍生物的盐，包括或仅包括两种或两种以上不同的公式（I）的羟基苯基丙酮衍生物的混合物，其中X、a、Y、R、R1、R2、R3、R4、R5、R6和R7在每种情况下具有上述给定的含义，以及包括公式（I）的羟基苯基丙酮衍生物的制剂和过程，用于修改、掩盖或减少令人不愉快的味道物质的不愉快的口感印象，以及用于增强甜味物质的甜味和/或引起甜味印象的香气物质的甜味气味印象。
• Verwendung von Propenylphenylglycosiden zur Verstärkung süßer sensorischer Eindrücke
  申请人：Symrise GmbH & Co. KG

  公开号：EP1955601A1

  公开（公告）日：2008-08-13

  Die Erfindung betrifft die Verwendung - eines Propenylphenylglycosids der Formel (I) wobei R entweder (1 E)-Prop-1-enyl-, (1 Z)-Prop-1 -enyl- oder Prop-2-enyl- darstellt und Glc ein α- oder β-glycosidisch gebundenes Mono- oder Oligosaccharid sein kann zur Verstärkung des süßen Geschmacks eines süß schmeckenden Stoffes oder des süßen Geruchseindrucks eines Aromastoffes, der einen süßen Geruchseindruck verursacht.

  本发明涉及使用 - 式 (I) 的丙烯基苯基糖苷的用途 式中 R 代表(1 E)-丙-1-烯基、(1 Z)-丙-1-烯基或丙-2-烯基 和 Glc 可以是α-或β-糖苷键合的单糖或寡糖 用于增强甜味物质的甜味，或增强能产生甜味的调味物质的甜味。
• Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxy-genase inhibitors and pharmaceutical compositions containing them
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0245825B1

  公开（公告）日：1991-03-13
• HYDROXYPHENYLALKADIONES AND THEIR USE FOR MASKING BITTER TASTE AND/OR FOR INTENSIFYING SWEET TASTE
  申请人：Symrise GmbH & Co. KG

  公开号：EP1901618A1

  公开（公告）日：2008-03-26
• USE OF HESPERETIN FOR ENHANCING THE SWEET TASTE
  申请人：Symrise AG

  公开号：EP1909599B1

  公开（公告）日：2014-04-23