rac-L-因子 | 82309-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: rac-L-因子
• 英文名称: erithro 5-hydroxy-4-decanolide
• 英文别名: (5S)-5-[(1R)-1-hydroxyhexyl]oxolan-2-one
• CAS: 82309-35-1；87877-77-8；92470-98-9；95586-41-7；98974-75-5；98974-76-6；124439-59-4；82309-34-0
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WPWMAIDTZPLUGB-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-谷氨酸 在 Pd-BaSO₄ 盐酸 、 氯化亚砜 、 氢气 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 26.0h， 生成 rac-L-因子
  参考文献：
  名称：

  Microbial transformation of (−)-Vernolic acid into (4r,5r).5.Hydroxy-γ-decalactone

  摘要：

  （-） Wojlgpert酸从喜马拉雅大戟（Euphorbia lagascae）的种子中分离并纯化后，给予Sporobolomyces odorus的培养物。主要产物为（4R,5R)-5-羟基-γ-癸内酯1。通过合成所有四种立体异构体，并对比光谱和色谱数据，确定了产物的构型。

  DOI：

  10.1016/s0957-4166(00)80249-9

文献信息

• Taste modifiers
  申请人：Givaudan S.A.

  公开号：US09480280B2

  公开（公告）日：2016-11-01

  A method of modifying the taste of a consumable, comprising adding to a consumable base at least one compound of the formula I in which (a) A is selected from the moieties (b) n is from 0-7, such that X is absent or a linear alkylene group in which n is from 1-7; and (c) Z is absent and Y is a moiety selected from the groups —CHO, or —CH2OH; or (d) Z is present and is a C1-7 linear alkane, and Y is selected from —CHOH, —CO, or —COC(CH3)O. The result is a consumable with enhanced mouthfeel and/or creaminess.

  一种修改可食用物品口味的方法，包括向可食用基料中添加至少一种符合以下式I的化合物：(a) A从基团中选择；(b) n取值范围为0-7，使得X不存在或为n取值范围为1-7的线性烷基基团；以及(c) Z不存在且Y为从基团—CHO或—CH2OH中选择的一种；或(d) Z存在且为C1-7线性烷烃，Y从—CHOH，—CO或—COC(CH3)O中选择。结果是一种口感和/或奶香更佳的可食用物品。
• Chemoenzymatic synthesis of (4S,5R)-5-hydroxy-γ-decalactone
  作者：N.W Fadnavis、S.Kumara Vadivel、Mohd Sharfuddin

  DOI：10.1016/s0957-4166(99)00411-5

  日期：1999.9

  2-hydroxy-3-oxooctanoate with immobilised baker's yeast at pH 4.0 yields anti-2R,3R-dihydroxy ester with high diastereoselectivity and enantioselectivity (de 70%, ee 80%) which is conveniently converted to (4S,5R)-5-hydroxy-γ-decalactone.

  用固定化的贝克酵母在pH 4.0下还原2-羟基-3-氧辛酸乙酯可产生具有高非对映选择性和对映选择性（de 70％，ee 80％）的抗-2 R，3 R-二羟基酯，可方便地转化为（4 S，5 R）-5-羟基-γ-癸内酯。
• Synthesis of (4s,5r)-(+)-factor, a proposed autoregulator of anthracycline biosynthesis
  作者：Leonidas Stamatatos、Pierre Sinay、Jean-René Pougny

  DOI：10.1016/s0040-4020(01)91120-2

  日期：1984.1

  A 12 steps synthesis of the 6-C-(n-butyl)-2,3,6-trideoxy-D-erythro-1, 4-lactone 14 from commercial 2,3,6-tri-O-acetyl-D-glucal is described.

  由商业2,3,6-三-O-乙酰基-D-进行12步合成6-C-（正丁基）-2,3,6-三苯氧基-D-赤藓醇-1，4-内酯14描述了葡萄糖。
• Diastereoselectivity in the directed aldol condensation of 2-trimethylsiloxyfuran with aldehydes. A stereodivergent route to threo and erythro δ-hydroxy-γ-lactones
  作者：Charles W. Jefford、Danielle Jaggi、John Boukouvalas

  DOI：10.1016/s0040-4039(01)83855-7

  日期：1987.1

  Threo and erythro-δ-hydroxy-α,β-unsaturated γ-lactones are obtained with useful diastereoselection by condensing 2-trimethylsiloxyfuran and aldehydes by varying the reaction reaction conditions. A stereomechanistic rationale is presented together with a practical two-step synthesis of the threo and erythro 5-hydroxy-4-decanolides (L factors).

  通过改变反应反应条件，使2-三甲基甲硅烷氧基呋喃和醛缩合，可以得到有用的非对映体选择，得到苏-和赤--δ-羟基-α，β-不饱和γ-内酯。提出了立体力学原理，并结合了实用的两步合成苏式和赤式5-羟基-4-癸醇化物（L因子）的方法。
• (±)-<i>erythro</i>-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes
  作者：Michael Plewe、Richard R. Schmidt

  DOI：10.1055/s-1989-27308

  日期：——

  Reaction of β-ethylthio-β-lithioacrylate 1A with α-chloroaldehydes furnished predominantly the erythro products 3, which were isolated as γ-lactones 4. At room temperature intermediates 3 are transformed into the (±)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones 8. Raney nickel treatment provided interesting natural γ-lactone derivatives; thus, from erythro-8c the socalled L-factor erythro-9c was obtained. Similarly, from β-methoxy β-lithioacrylate 10A the (±)-erythro-γ,δ-dihydroxycarboxylic acid δ-lactone erythro-11 was gained.

  β-乙硫基-β-锂丙烯酸酯1A与α-氯醛的反应主要生成红Arrow产物3，这些产物被分离为γ-内酯4。在室温下，中间体3转化为(±)-红Arrow-γ,δ-二羟基羧酸γ-内酯8。Raney镍处理提供了有趣的天然γ-内酯衍生物；因此，从红Arrow-8c获得了所谓的L因子红Arrow-9c。同样，从β-甲氧基β-锂丙烯酸酯10A获得了(±)-红Arrow-γ,δ-二羟基羧酸δ-内酯红Arrow-11。