3-hydroxy-3-methyl-2,4-nonanedione | 544409-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-3-methyl-2,4-nonanedione
• 英文别名: 3-hydroxy-3-methylnonane-2,4-dione
• CAS: 544409-58-7
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: LWAGDIOTWITDPB-UHFFFAOYSA-N

物化性质

• 沸点：
  275.8±20.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)
• LogP：
  3.25
• 保留指数：
  1202

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-methyl-2,4-nonanedione 在 sodium hypochlorite 、 formate dehydrogenase 、 2,2,6,6-四甲基哌啶氧化物 、 乙二胺四乙酸 、 β-烟酰胺腺嘌呤二核苷酸 、 sodium formate 、 碳酸氢钠 、 2-巯基乙醇 、 potassium bromide 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 水 为溶剂， 反应 0.83h， 生成 (3R)-3-hydroxy-3-methylnonane-2,4-dione
  参考文献：
  名称：

  An enzymatic approach to the synthesis of optically pure (3R)- and (3S)-enantiomers of green tea flavor compound 3-hydroxy-3-methylnonane-2,4-dione

  摘要：

  Both (3R)- and (3S)-enantiomers of the chiral green tea flavor compound 3-hydroxy-3-methylnonane-2,4-dione were synthesized by the combined use of acetylacetoin synthase and acetylacetoin reductase from Bacillus licheniformis. The first enzyme was utilized to catalyze the homo-coupling of 2,3-octanedione and obtain the enantioenriched (3R)-3-hydroxy-3-methylnonane-2,4-dione (ee 44%). The NADH-dependent acetylacetoin reductase was then employed for the diastereoselective (de > 95%) C2 carbonyl reduction of the sole (3R)-enantiomer of the above 2,4-dione, thus affording the syn diol (2S,3R)-2,3-dihydroxy-3-methylnonan-4-one in enantiomerically pure form. While this step allowed for the recovery of unreacted, optically pure (3S)-3-hydroxy-3-methylnonae-2,4-dione, the corresponding (3R)-enantiomer was obtained by subsequent TEMPO-mediated oxidation of the syn dial intermediate. Moreover, using the title compounds as analytical standards, predominance of the (3R) enantiomer in the natural flavor compound was finally demonstrated by chiral GC-MS analysis. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.08.015
• 作为产物：
  描述：

  (+/-)-1-acetyl-1-methyl-2-oxoheptyl dimethyl phosphate 在 水 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以1.97 g的产率得到3-hydroxy-3-methyl-2,4-nonanedione
  参考文献：
  名称：

  绿茶中鉴定出的与3-甲基-2,4-壬二酮有关的新成分。

  摘要：

  研究了两种精美的绿茶品种（日本的清泽茶和中国的龙井茶）的挥发性成分，以鉴定出引起绿茶冲泡特有风味的新化合物。提取物是使用Oasis-HLB-弹药筒通过固相提取制备的。除了常见的绿茶化学化合物外，已经描述的化合物3-甲基-2,4-壬二酮（1）和3-羟基-3-甲基-2,4-壬二酮（2）是呋喃脂肪酸降解的产物。 ，以及与化合物1有关的三个新化合物。它们是1-甲基-2-氧代丙基己酸酯（3），1-甲基-2-氧代庚基乙酸酯（4）和2-丁基-4,5-二甲基-3（2H）-呋喃酮（5）。报告了它们的合成和光谱数据。化合物2增加了甜味，

  DOI：

  10.1021/jf061738o

文献信息

• FLAVORING INGREDIENTS
  申请人：Naef Regula

  公开号：US20070259088A1

  公开（公告）日：2007-11-08

  The present invention relates to a compound of formula wherein R 1 is a C 2-7 linear alkyl group. This compound can be used as flavoring ingredient, for instance to impart flavor notes of the green tea and creamy/fatty type as well as to impart a desirable mouthfeel effect.

  本发明涉及一种化合物，其化学式为其中R1是一种C2-7的直链烷基。该化合物可用作调味成分，例如赋予绿茶和奶油/脂肪类型的风味注释，以及赋予理想的口感效果。
• Aroma Compounds Formed from 3-Methyl-2,4-nonanedione under Photooxidative Conditions
  作者：Isabelle A. Sigrist、Giuseppe G. G. Manzardo、Renato Amadò

  DOI：10.1021/jf021110n

  日期：2003.5.1

  The behavior of the prominent aroma compound 3-methyl-2,4-nonanedione under photooxidative conditions was investigated in a model experiment. The four well-known aroma compounds 2,3-butanedione, 2,3-octanedione, acetic acid, and caproic acid were identified. The main oxidation product was 3-hydroxy-3-methyl-2,4-nonanedione, an aroma compound with the odor description of rubbery, earthy, and plasticlike (GC-O). Its structure has been tentatively assigned based on mass (GC-MS) and vapor phase infrared spectra (GC-IR). The formal formation pathways are discussed for these compounds, and other origins described in the literature are presented.
• Chemosensory Receptor Ligand-Based Therapies
  申请人：Brown Martin R.

  公开号：US20130303466A1

  公开（公告）日：2013-11-14

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administering a composition comprising a chemosensory receptor ligand. Also provided herein are chemosensory receptor ligand compositions and methods for the preparation thereof for use in the methods of the present invention.
• US7794767B2
  申请人：——

  公开号：US7794767B2

  公开（公告）日：2010-09-14
• [EN] FLAVORING INGREDIENTS<br/>[FR] PRODUITS AROMATIQUES
  申请人：FIRMENICH & CIE

  公开号：WO2006092749A1

  公开（公告）日：2006-09-08

  [EN] The present invention relates to a compound of formula (I) wherein R¹ is a C _2-7 linear alkyl group; which can be used as flavouring ingredient, for instance to impart flavour notes of the green tea and creamy /fatty type as well as a mouthfeel effect.
  [FR] La présente invention concerne un composé selon une formule dans laquelle R¹ est un groupe alkyle linéaire C _2-7 ; qui peut être utilisé comme produit aromatique, par exemple pour donner des notes aromatiques de thé vert et de type crémeux/gras de même qu'un effet de bouche.