[2H2]-3-sulfanylhexan-1-ol | 309250-81-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: [2H2]-3-sulfanylhexan-1-ol
• 英文别名: 3-mercapto-[1-(2)H2]hexan-1-ol；[1,1-(2)H2]-3-sulfanyl-1-hexanol
• CAS: 309250-81-5
• 化学式: C₆H₁₄OS
• 分子量: 136.227
• InChiKey: TYZFMFVWHZKYSE-BFWBPSQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  8.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 [2H2]-3-sulfanylhexan-1-ol 以 二氯甲烷 为溶剂， 反应 18.0h， 以71%的产率得到3-mercapto-[1-(2)H2]hexyl acetate
  参考文献：
  名称：

  Synthesis of isotopically labelled thiol volatiles and cysteine conjugates for quantification of Sauvignon Blanc wine

  摘要：

  贡献于长相思以及其他葡萄酒香气特征的硫醇类物质，包括4-巯基-4-甲基戊烷-2-醇（4MMPOH）、3-巯基己烷-1-醇（3MH）和3-巯基己基乙酸酯（3MHA），已通过氘标记合成的技术手段制得。同时，存在于葡萄汁中的半胱氨酸硫醇前体，即4-(4-甲基戊烷-2-酮)-L-半胱氨酸（4MMP-cys）与4-(4-甲基戊烷-2-醇)-L-半胱氨酸（4MMPOH-cys），也实现了氘标记合成。这些氘化化合物为利用LCMS（液相色谱-质谱联用）技术定量分析葡萄酒中上述硫醇提供了有效的内部参考标准。版权所有 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1262
• 作为产物：
  描述：

  反式-2-己烯酸乙酯 在 lithium aluminum deutheride 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 [2H2]-3-sulfanylhexan-1-ol
  参考文献：
  名称：

  Synthesis of isotopically labelled thiol volatiles and cysteine conjugates for quantification of Sauvignon Blanc wine

  摘要：

  贡献于长相思以及其他葡萄酒香气特征的硫醇类物质，包括4-巯基-4-甲基戊烷-2-醇（4MMPOH）、3-巯基己烷-1-醇（3MH）和3-巯基己基乙酸酯（3MHA），已通过氘标记合成的技术手段制得。同时，存在于葡萄汁中的半胱氨酸硫醇前体，即4-(4-甲基戊烷-2-酮)-L-半胱氨酸（4MMP-cys）与4-(4-甲基戊烷-2-醇)-L-半胱氨酸（4MMPOH-cys），也实现了氘标记合成。这些氘化化合物为利用LCMS（液相色谱-质谱联用）技术定量分析葡萄酒中上述硫醇提供了有效的内部参考标准。版权所有 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1262

文献信息

• Characterization of the Key Aroma Compounds in Pink Guava (Psidium guajava L.) by Means of Aroma Re-engineering Experiments and Omission Tests
  作者：Martin Steinhaus、Diana Sinuco、Johannes Polster、Coralia Osorio、Peter Schieberle

  DOI：10.1021/jf803728n

  日期：2009.4.8

  Seventeen aroma-active volatiles, previously identified with high flavor dilution factors in fresh, pink Colombian guavas (Psidium guajava L.), were quantified by stable isotope dilution assays. On the basis of the quantitative data and odor thresholds in water, odor activity values (OAV; ratio of concentration to odor threshold) were calculated. High OAVs were determined for the green, grassy smelling (Z)-3-hexenal and the grapefruit-like smelling 3-sulfanyl-1-hexanol followed by 3-sulfanylhexyl acetate (black currant-like), hexanal (green, grassy), ethyl butanoate (fruity), acetaldehyde (fresh, pungent), trans-4,5-epoxy-(E)-2-decenal (metallic), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel, sweet), cinnamyl alcohol (floral), methyl (2S,3S)-2-hydroxy-3-methylpentanoate (fruity), cinnamyl acetate (floral), methional (cooked potato-like), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like). Studies on the time course of odorant formation in guava puree or cubes, respectively, showed that (2)-3-hexenal was hardly present in the intact fruits, but was formed very quickly during crushing. The aroma of fresh guava fruit cubes, which showed a very balanced aroma profile, was successfully mimicked in a reconstitute consisting of 13 odorants in their naturally occurring concentrations. Omission tests, in which single odorants were omitted from the entire aroma reconstitute, revealed (2)-3-hexenal, 3-sulfanyl-1-hexanol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, hexanal, ethyl butanoate, cinnamyl acetate, and methional as the key aroma compounds of pink guavas.
• Quantitative Determination of Sulfur Containing Wine Odorants at Sub-ppb Levels. 1. Synthesis of the Deuterated Analogues
  作者：Yorgos Kotseridis、Jean-Loïc Ray、Christian Augier、Raymond Baumes

  DOI：10.1021/jf0004715

  日期：2000.12.1

  [H-2(10)]-4-Sulfanyl-4-methylpentan-2-one (d(10)-SMP), [H-2(2)]-3-sulfanylhexan-1-ol (d(2)-3SH), and [H-2(5)]-3-sulfanylhexyl acetate (d(5)-3SHAc), the -labeled analogues of impact odorants of wines and other foods, were synthesized to be used for the quantitative determination of the natural compounds in white and red wines by stable isotope dilution assay. The sulfidation was achieved by Michael addition, on mesityl oxide or ethyl hex-2-enoate, respectively, of the sulfhydryl anion generated in situ from triphenylsilanethiol and potassium fluoride under phase transfer conditions. The labeling of 4-sulfanyl-4-methylpentan-2-one (SMP) was obtained from the commercial starting material, [H-2(6)]-acetone, so that this method could be used to synthesize C-13-labeled SMP from 13C-labeled acetone. The labeling of 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHAc) was obtained from reduction with lithium aluminum deuteride of the Michael adduct ethyl 5-sulfanylhexanoate and [H-2(3)]-acetylation. During the synthesis, 3SH and 3SHAc were partially oxidized to their disulfide, which were reduced back to the thiols by an additional reduction step; the tertiary thiol SMP was less sensitive to this oxidation..