(S)-(+)-3-mercaptohexyl acetate | 145937-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(+)-3-mercaptohexyl acetate
• 英文别名: (3S)-3-sulfanylhexyl acetate；(S)-3-Mercaptohexylacetat；[(3S)-3-sulfanylhexyl] acetate
• CAS: 145937-72-0
• 化学式: C₈H₁₆O₂S
• 分子量: 176.28
• InChiKey: JUCARGIKESIVLB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-phenylpropionyl chloride 、 (S)-(+)-3-mercaptohexyl acetate 反应 96.0h， 生成 Acetic acid (S)-3-((S)-2-phenyl-propionylsulfanyl)-hexyl ester
  参考文献：
  名称：

  手性，schwefelhaltige香气和百香果（西番莲），对映体和绝对构象

  摘要：

  将黄色百香果的3-甲基硫代己烷-1-醇和2-甲基-4-丙基-1,3-氧杂蒽，手性含S的香气物质拆分为对映异构体，并阐明了其绝对构型。

  DOI：

  10.1016/s0040-4039(00)99923-4
• 作为产物：
  描述：

  2,2-dimethyl-propionic acid 3-formyloxy-hexyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 (S)-(+)-3-mercaptohexyl acetate
  参考文献：
  名称：

  Stereoisomeric Distribution of 3-Mercaptohexan-1-ol and 3-Mercaptohexyl Acetate in Dry and Sweet White Wines Made from Vitis vinifera (Var. Sauvignon Blanc and Semillon)

  摘要：

  The enantiomeric distribution of 3-mercaptohexan-1-ol (3MH) and 3-mercaptohexyl acetate (3MHA) in Vitis vinifera wines was determined by combining two techniques: specific purification of volatile thiols from the wines using p-hydroxymercuribenzoate and separation of the chiral molecules by gas-phase chromatography on a cyclodextrin capillary column. The R and S enantiomer ratios of these two thiols in dry white Sauvignon blanc and Semillon wines are approximately 30: 70 for A3MH and 50: 50 for 3MH. However, in sweet white wines made from grapes affected by "noble rot" due to the development of Botrytis cinerea on ripe grapes, the proportion of the R and S forms of 3MH is in the vicinity of 30:70. During alcoholic fermentation, a change in the ratio of the two enantiomers of 3MH in dry white wines was observed. At the beginning of fermentation (around density 1.08), the S form represented over 60%; then, at lower density, as fermentation proceeded, the enatiomeric ratio approached 50:50. The ratio of the two 3MHA enantiomers remained constant throughout fermentation. On the contrary, the distribution of the two 3MH enantiomers changed very little during fermentation of the botrytized sweet wines. The perception thresholds for the R and S forms of 3MH in hydroalcoholic model solution are similar (50 and 60 ng/L). These two enantiomers have quite different aromas: The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit. The perception thresholds of the R and S enantiomers of 3MHA are slightly different (9 and 2.5 ng/L). The less odoriferous R form is reminiscent of passion fruit, while the S form has a more herbaceous odor of boxwood.

  DOI：

  10.1021/jf061566v

文献信息

• THIOLS AS FLAVORING INGREDIENT
  申请人：ESCHER Dorothea Sina

  公开号：US20080020116A1

  公开（公告）日：2008-01-24

  The present invention relates to the use of a 3-mercaptoheptyl carboxylate, in the form of any one of its stereoisomers or mixture thereof, as flavoring ingredient, in particular to impart fruity, teas and citrus aftertaste. The compounds provide long-lastingness to the flavors composition in which they are added.

  本发明涉及使用3-巯基庚酸酯作为调味成分，其形式可以是其任何立体异构体或其混合物，特别是用于赋予水果、茶和柑橘的余味。这些化合物为它们所添加的口味组合提供持久性。
• Increased stability of flavor compounds
  申请人：Kraft Foods R & D, Inc.

  公开号：EP2145547A1

  公开（公告）日：2010-01-20

  The present invention is directed to the treatment of reactive thiol groups (-SH) found in thiol-containing flavor compounds by a highly selective enzymatic conversion into aroma-active disulides compounds using sulfhydryl oxidase.

  本发明的目的是利用巯基氧化酶将含巯基香精化合物中的活性巯基（-SH）高选择性地酶促转化为具有香气活性的二巯基化合物。
• Characterization of the Aroma-Active Compounds in Pink Guava (<i>Psidium guajava</i>, L.) by Application of the Aroma Extract Dilution Analysis
  作者：Martin Steinhaus、Diana Sinuco、Johannes Polster、Coralia Osorio、Peter Schieberle

  DOI：10.1021/jf8005245

  日期：2008.6.1

  The volatiles present in fresh, pink-fleshed Colombian guavas (Psidium guajava, L.), variety regional rojo, were carefully isolated by solvent extraction followed by solvent-assisted flavor evaporation, and the aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis. The results of the identification experiments in combination with the FD factors revealed 4-methoxy-2,5-dimethyl-3(2H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, and 3-sulfanyl-1-hexanol followed by 3-hydroxy-4,5-dimethyl-2(5H)-furanone, (2)-3-hexenal, trans-4,5,-epoxy-(E)-2-decenal, cinnamyl alcohol, ethyl butanoate, hexanal, methional, and cinnamyl acetate as important aroma contributors. Enantioselective gas chromatography revealed an enantiomeric distribution close to the racemate in 3-sulfanylhexyl acetate as well as in 3-sulfanyl-1 -hexanol. In addition, two fruity smelling diastereomeric methyl 2-hydroxy-3-methylpentanoates were identified as the (R,S)- and the (S,S)-isomers, whereas the (S,R)- and (R,R)-isomers were absent. Seven odorants were identified for the first time in guavas, among them 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, trans-4,5-epoxy-(E)-2-decenal, and methional were the most odor-active.
• Increased Stability Of Flavor Compounds
  申请人：SilanesKenny Francisco Javier

  公开号：US20100015276A1

  公开（公告）日：2010-01-21

  The present invention is directed to the treatment of reactive thiol groups (—SH) found in thiol-containing flavor compounds by a highly selective enzymatic conversion into aroma-active disulides compounds using sulfhydryl oxidase.
• [EN] THIOLS AS FLAVORING INGREDIENT<br/>[FR] THIOLS EN TANT QU'INGREDIENT AROMATIQUE
  申请人：FIRMENICH & CIE

  公开号：WO2006120625A1

  公开（公告）日：2006-11-16

  [EN] The present invention concerns the use of a 3-mercaptoheptyl carboxylate, in the form of any one of its stereoisomers or mixture thereof, as flavoring ingredient, in particular to impart fruity, teas and citrus aftertaste. Said compounds provide long- lastingness to the flavors composition in which they are added.
  [FR] L'invention concerne l'utilisation d'un 3-mercaptoheptyle carboxylate, sous forme de l'un ou l'autre de ses stéréoisomères ou leurs mélanges, en tant qu'ingrédient aromatique, en particulier, afin de donner un arrière goût fruité et citronné au thé. Ces composés rendent très durables la composition aromatique à laquelle on les ajoute.