demethoxy-feruloylacetone | 1032967-50-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: demethoxy-feruloylacetone
• 英文别名: 6-(m,p-dihydroxyphenyl)-5-hexene-2,4-dione；hispolon；6-(3,4-Dihydroxyphenyl)hex-5-ene-2,4-dione
• CAS: 1032967-50-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: SEOGGTOIKLUNNM-UHFFFAOYSA-N

物化性质

• 沸点：
  434.2±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  demethoxy-feruloylacetone 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以90%的产率得到(E)-4-(2-(3-methyl-1H-pyrazol-5-yl)vinyl)benzene-1,2-diol
  参考文献：
  名称：

  含氮杂环基取代的烯类化合物的用途

  摘要：

  本发明涉及一系列含氮杂环基取代的烯类化合物的新用途，更具体地涉及由通式a表示的化合物或其盐用于生物成像、pH值检测、生物大分子检测或细胞微环境检测的用途，其中Z、S1、S2和R1如本文中所定义。通过利用该类化合物作为生物成像的荧光染料、检测pH值的荧光pH探针和/或用作肿瘤细胞检测的诊断剂，本发明的成像效果优异并表现出单组分多色的性质，可用于单组分多色成像或常规成像等，在生物成像和肿瘤检测中具有巨大应用前景。

  公开号：

  CN107118586A
• 作为产物：
  描述：

  feruloylacetone 在 吡啶 、 aluminum (III) chloride 、 盐酸 作用下， 以 乙酸乙酯 、 水 为溶剂， 反应 7.25h， 以51%的产率得到demethoxy-feruloylacetone
  参考文献：
  名称：

  Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, anti-proliferative and anti-inflammatory activities in vitro

  摘要：

  Curcumin, a component of turmeric (Curcuma longa), exhibits anti-inflammatory and anti-proliferative activities through the generation of reactive oxygen species (ROS). Curcumin (diferuloylmethane) contains two hydroxyl, two methoxy and two phenyl groups but how these groups contribute to its activity is poorly understood. We synthesized analogues that varied in inclusion of these groups and compared their activity. We found that bisdemethylcurcumin (BDC) was more potent than curcumin as an anti-inflammatory agent as indicated by suppression of TNF-induced NF-kappa B activation, more potent as an anti-proliferative agent, and more potent in inducing ROS. Hispolon, which lacks one aromatic unit in relation to curcumin, also exhibited enhanced anti-inflammatory and anti-proliferative activities. When synthetic curcumin (Cur-S) was compared with bisdemethylcurcumin (BDC), hispolon, hispolon methyl ether (HME), dehydroxy hispolon (DH), hydroxy hispolon (HH), methoxy hispolon methyl ether (MHME), and methoxy hispolon (MH), we found that following order of anti-inflammatory activity: BDC = Hispolon > HME > HH > Cur-S> MHME > MH > DH; for anti-proliferative: Hispolon > BDC > MHME > Cur-S > MR > HME = HH > DH; and for prooxidant: BDC > CurS = MHME > FIR > MR + HME > DH (254-1414 mean fluorescence intensity). Thus, dehydroxy hispolon was least potent for all three activities. Overall the results indicate that the substitution of a hydroxyl group for a methoxy group at the meta positions of the phenyl rings in curcumin significantly enhanced the anti-inflammatory activity, and the removal of phenyl ring at the 7(th) position of the heptadiene back bone and addition of hydroxyl group significantly increased the anti-proliferative activity of curcumin. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2010.01.033

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。
• Feruloylacetone as the model compound of half-curcumin: Synthesis and antioxidant properties
  作者：Jian-Ying Feng、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2011.01.039

  日期：2011.4

  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.
• Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1
  作者：Hiroyuki Konno、Hitoshi Endo、Satomi Ise、Keiki Miyazaki、Hideo Aoki、Akira Sanjoh、Kazuya Kobayashi、Yasunao Hattori、Kenichi Akaji

  DOI：10.1016/j.bmcl.2013.11.039

  日期：2014.1

  To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp(2) carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation. (C) 2013 Elsevier Ltd. All rights reserved.
• 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
• [EN] HYDROXYPHENYLALKADIONES AND THEIR USE FOR MASKING BITTER TASTE AND/OR FOR INTENSIFYING SWEET TASTE<br/>[FR] HYDROXYPHÉNYLALCADIONES ET LEUR UTILISATION POUR MASQUER UN GOÛT AMER ET/OU POUR INTENSIFIER UN GOÛT SUCRÉ
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2007003527A1

  公开（公告）日：2007-01-11

  [EN] The use of a hydroxyphenylalkadione derivative of the formula (I) wherein, for X, a and Y: X is a -CH₂-, -NH- or -O- group, Y is a -CH₂- 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 R¹ , R² and R³ R¹ denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a -O-R⁵, -S-R⁵ or -NR⁵R⁶ group and R² and R³ 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 R⁷-O- groups or R¹ and R² 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 R¹ and R² is optionally substituted by one or more oxo groups and/or R⁷-O- groups and/or aliphatic radicals having 1 to 4 C atoms and R³ 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 R⁷-O- groups or R² and R³ 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 R² and R3 is optionally substituted by one or more oxo groups and/or R⁷-O- groups and/or aliphatic radicals having 1 to 4 C atoms and R¹ denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a -O-R⁵, -S-R⁵ or -NR⁵R⁶ group, wherein, for R⁴ and R: R⁴ and R independently of one another denote hydrogen, methyl or ethyl and wherein, for R⁵, R⁶ and R⁷: R⁵ R⁶ and R⁷ 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 hydroxy- phenylalkadiones of the formula (I), wherein X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ 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, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ 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, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ 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, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ 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.
  [FR] La présente invention concerne l'utilisation d'un dérivé hydroxyphénylalcadione répondant à la formule (I) dans laquelle, en ce qui concerne X, a et Y : X représente un groupe -CH₂-, -NH- ou -O-, Y représente un groupe -CH₂- et a représente une liaison simple ou X et Y représentent dans chaque cas un groupe -CH- et a représente une liaison double en configuration Z ou E, où, en ce qui concerne R¹, R² et R³, R¹ représente un atome d'hydrogène, un radical aliphatique ayant 1 à 4 atomes de carbone ou un groupe -O-R⁵, -S-R⁵ ou -NR⁵R⁶ et R² et R³ représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe alkyle ayant 1, 2, 3, 4 ou 5 atomes de carbone qui est éventuellement substitué par un ou plusieurs groupes oxo ou groupes R⁷-O- ou R¹ et R² forment ensemble un cycle aliphatique qui contient un total de 4 à 10 atomes de carbone et 0 ou 1 atome d'oxygène, où le constituant du cycle représenté par R¹ et R² est éventuellement substitué par un ou plusieurs groupes oxo et/ou groupes R⁷-O- et/ou radicaux aliphatiques ayant 1 à 4 atomes de carbone et R³ représente un atome d'hydrogène ou un groupe alkyle ayant 1, 2, 3, 4 ou 5 atomes de carbone qui est éventuellement substitué par un ou plusieurs groupes oxo ou groupes R⁷-O- ou R² et R³ forment ensemble un cycle aliphatique qui contient un total de 4 à 10 atomes de carbone et 0 ou 1 atome d'oxygène, où le constituant du cycle représenté par R² et R³ est éventuellement substitué par un ou plusieurs groupes oxo et/ou groupes R⁷-O- et/ou radicaux aliphatiques ayant 1 à 4 atomes de carbone et R¹ représente un atome d'hydrogène, un radical aliphatique ayant 1 à 4 atomes de carbone ou un groupe -O-R⁵, -S-R⁵ ou -NR⁵R⁶, où, en ce qui concerne R⁴ et R : R⁴ et R représentent indépendamment l'un de l'autre un atome d'hydrogène, un groupe méthyle ou éthyle et où, en ce qui concerne R⁵, R⁶ et R⁷ : R⁵, R⁶ et R⁷ représentent indépendamment les uns des autres un atome d'hydrogène ou un radical aliphatique ayant 1 à 4 atomes de carbone, un sel d'une telle hydroxyphénylalcadione répondant à la formule (I), un mélange comprenant ou se composant de deux ou plusieurs hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, ou un mélange comprenant ou se composant d'une hydroxyphénylalcadione répondant à la formule (I) ou de deux ou plusieurs hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, et un sel d'une hydroxyphénylalcadione répondant à la formule (I) ou deux ou plusieurs sels d'hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, pour modifier, masquer ou réduire l'impression de saveur désagréable d'une substance ayant un goût désagréable et/ou pour intensifier le goût sucré d'une substance sucrée et/ou l'impression d'odeur sucrée d'une substance aromatique ce qui entraîne une impression d'odeur sucrée, ainsi que des formulations et des procédés comprenant une hydroxyphénylalcadione répondant à la formule (I).