(1'R,S)-1'-hydroxychavicol | 53580-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (1'R,S)-1'-hydroxychavicol
• 英文别名: (+/-)-1'-hydroxychavicol；(±)-1'-hydroxychavicol；4-(1-hydroxy-2-propenyl)phenol；4-(1-hydroxyallyl)-phenol；(R)-4-(1-Hydroxyallyl)phenol；4-(1-hydroxyprop-2-enyl)phenol
• CAS: 53580-61-3
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: UGNPXYBKDPBTAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.1±25.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'R,S)-1'-hydroxychavicol 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以2.4 g (83% by weight)的产率得到(rac)-isobutyric acid 1-(4-isobutyryloxy-phenyl)-allyl ester
  参考文献：
  名称：

  Flavorant compositions

  摘要：

  这项发明涉及一种含有1'-乙酰氧基茴香酚醋酸酯和1'-乙酰氧基丁香酚醋酸酯衍生物的香精组合物，以及一种适用的香精载体。该香精组合物可用于调味食品、饮料或保健产品，具有与高良姜相关的温热、辛辣和辛辣感。

  公开号：

  US06476252B1
• 作为产物：
  描述：

  1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (1'R,S)-1'-hydroxychavicol
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070

文献信息

• Palladium-Catalyzed Aerobic Oxidative Coupling of <i>ortho</i>-(Alkynyl)styrenes with Allylic Alcohols via 6-<i>endo-dig</i> Cyclization: Regioselective Construction of Polysubstituted Naphthalenes
  作者：Perla Ramesh、Gedu Satyanarayana

  DOI：10.1021/acs.joc.9b01240

  日期：2019.10.18

  An efficient protocol is described for the regioselective construction of polysubstituted functionalized naphthalenes from easily accessible ortho-(alkynyl)styrenes under mild reaction conditions. The reaction proceeds via cycloaromatization and intermolecular coupling of ortho-(alkynyl)styrenes with allylic alcohols catalyzed by PdCl2. Notably, the reaction is successful under open air as the green

  描述了一种有效的方案，用于在温和的反应条件下从容易获得的邻（炔基）苯乙烯区域选择性构建多取代的官能化萘。该反应通过环芳构化和邻-（炔基）苯乙烯与PdCl 2催化的烯丙基醇的分子间偶联而进行。值得注意的是，该反应在露天作为绿色氧化剂源时是成功的。发现包括保护游离的OH基在内的一系列官能团（F，Cl，Br，NO 2和酯）是相容的。
• Melanogenesis inhibitory activity of a 7-O-9′-linked neolignan from Alpinia galanga fruit
  作者：Yoshiaki Manse、Kiyofumi Ninomiya、Ryosuke Nishi、Iyori Kamei、Yushi Katsuyama、Takahito Imagawa、Saowanee Chaipech、Osamu Muraoka、Toshio Morikawa

  DOI：10.1016/j.bmc.2016.10.001

  日期：2016.12

  exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy

  从高良姜（Zingiberaceae）果实中提取的丙酮水溶液对茶碱刺激的鼠B16黑色素瘤4A5细胞（IC50 =7.3μg/ mL）的黑色素生成具有抑制作用。通过生物测定指导的提取物分离，分离出一种新的7-O-9'-连接的新木脂素，称为高良醇D二乙酸酯（1），以及16种已知化合物，其中包括14种苯基丙烷（2-15）。通过广泛的NMR分析和全合成，阐明了1的结构，包括其在C-7位置的绝对立体化学。在分离物中，1（IC50 =2.5μM），1'S-1'-乙酰氧基丁香酚乙酸酯（2，5.0μM）和1'S-1'-乙酰氧基丁香酚乙酸酯（3，5.6μM）表现出相对强的抑制作用，在有效浓度。提出以下结构要求以增强苯基丙烷对黑素生成的抑制活性：（i）具有4-乙酰氧基的化合物比具有4-羟基的化合物具有更高的活性；（ii）3-甲氧基不影响活性；（iii）1'-羟基部分的乙酰化增强了活性；（iv）具有7-O-9′
• [EN] SUBSTITUTED PHENOLS HAVING ANTICONVULSANT PROPERTIES<br/>[FR] PHÉNOLS SUBSTITUÉS PRÉSENTANT DES PROPRIÉTÉS ANTICONVULSIVANTES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2013188716A1

  公开（公告）日：2013-12-19

  Substituted phenol compounds and methods of using the compounds, e.g., for anesthetizing a subject, are disclosed.

  揭示了替代酚化合物及使用这些化合物的方法，例如用于麻醉受试者。
• Identification of Dihydrogalangal Acetate in Galangal [<i>Alpinia galangal</i> (L.) Swartz] Extracts
  作者：Xiaogen Yang、Martin Rohr、Jason Jordan

  DOI：10.1021/jf803387z

  日期：2009.4.22

  dihydrogalangal acetate were separated and evaluated by sensory analysis. (R)-Galangal acetate has a very faint woody and sweet aroma, and (R)-dihydrogalangal acetate is almost odorless, while (S)-galangal acetate has strong and (S)-dihydrogalangal acetate has weak pungent and woody notes. Although the aroma characters of these optical isomers are different, taste sensations were found to have no significant

  高加仑根[ Alpinia galangal（L.）Swartz]中首次发现了乙酸二氢高良姜。该化合物的味觉类似于乙酸高良姜（高良姜的辛辣成分），但在食品和饮料应用中更稳定。因此，乙酸二氢高良姜酸酯作为用于增强醇和改变味道的风味成分提供了许多优点。乙酸二氢高良姜酮存在于约0.0005％的新鲜根中和约0.004％的干根中。（S）-二氢高良姜酸酯是高良姜根中的主要旋光异构体（98％），而其次要（R）-异构体的丰度较低（2％）。分离乙酸高良姜酸酯和乙酸二氢高良姜酸酯的对映异构体，并通过感官分析对其进行评估。（[R）-Galangal醋酸有一个非常微弱的木香和甜香气，以及（[R）-dihydrogalangal醋酸是几乎无臭，而（小号）-galangal酯具有和（强小号）乙-dihydrogalangal具有弱刺激性和木香调。尽管这些旋光异构体的香气特征是不同的，但是发现乙酸高良姜酸酯，乙酸二氢高
• Ppar delta activators
  申请人：——

  公开号：US20040097739A1

  公开（公告）日：2004-05-20

  Compounds of the general formula (I) or salts thereof and activators of PPAR&dgr; (peroxisome proliferator activated receptor &dgr;) containing the compounds or the salts as the active ingredient: wherein R 1 and R 2 each are hydrogen, C 1-8 alkyl, an aryl or heterocyclic group which may be substituted, or the like; A is oxygen, sulfur, or the like; X 1 and X 2 are each a free valency, oxygen, S(O) p (wherein p is an integer of 0 to 2), C(═O), C(═O)NH, NHC(═O), CH═CH, or the like; Y is optionally substituted C 1-8 alkylene; Z is oxygen or sulfur; R 3 and R 4 are each optionally substituted C 1-8 alkyl; and R 8 is hydrogen or C 1-8 alkyl, with the proviso that when X 1 is a free valency, X 2 is not O or S(O) p , while when X 1 is C(═O)NH, X 2 is not a free valency. 1

  通式（I）的化合物或其盐以及PPARδ（过氧化物酶体增殖物激活受体δ）激活剂，其中化合物或盐为活性成分：其中R1和R2分别为氢，C1-8烷基，取代的芳基或杂环基等；A为氧，硫等；X1和X2分别为自由价，氧，S（O）p（其中p为0至2的整数），C（═O），C（═O）NH，NHC（═O），CH═CH或类似物；Y为可选的取代的C1-8烷基；Z为氧或硫；R3和R4分别为可选的取代的C1-8烷基；而R8为氢或C1-8烷基，但当X1为自由价时，X2不为O或S（O）p，而当X1为C（═O）NH时，X2不为自由价。