(+/-)-endo-2-hydroxy-1,8-cineol | 60761-00-4

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (+/-)-endo-2-hydroxy-1,8-cineol
• 英文别名: 2-endo-hydroxy-1,8-cineole；2α-hydroxycineole；2-hydroxy-1,8-cineole；(+/-)-2-exo-Hydroxycineole；2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol)；(1RS,2RS)-1,8-epoxy-p-menthan-2-ol；(1SR,2SR,4RS)-1,8-epoxy-p-menthan-2-ol；(+/-)-α2-hydroxy-1,8-cineole；6-hydroxycineole；(1s,4r,6s)-1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-ol
• CAS: 60761-00-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: YVCUGZBVCHODNB-WEDXCCLWSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  储存温度应控制在2-8℃，需保持干燥并密封保存。

制备方法与用途

2α-羟基-1,8-桉叶素是1,8-桉叶醇（HY-N0066）的代谢产物。

反应信息

• 作为反应物：
  描述：

  (+/-)-endo-2-hydroxy-1,8-cineol 在 caesium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 29.75h， 生成 cesium 2-oxo-2-(((1S,4R,6S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-yl)oxy)acetate
  参考文献：
  名称：

  草酸铯的自由基脱氧氯化法合成烷基氯化物

  摘要：

  草酸铯的自由基脱氧氯化已被开发用于制备受阻的仲和叔烷基氯。该反应可耐受许多官能团，包括酮，醇和酰胺，并为通过杂化机理进行的标准脱氧氯化反应提供互补的反应性。初步研究表明，开发的条件也可用于脱氧溴化和脱氧氟化反应。

  DOI：

  10.1021/acs.orglett.8b02045
• 作为产物：
  描述：

  (1S,4R,6S)-2-hydroxy-1,8-cineole (S)-O-methylmandelate ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+/-)-endo-2-hydroxy-1,8-cineol
  参考文献：
  名称：

  Enantiomeric Purity and Odor Characteristics of 2- and 3-Acetoxy-1,8-cineoles in the Rhizomes of Alpinia galanga Willd.

  摘要：

  (S)-(+)-O-methylmandelate esters of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-ols (2- and 3-hydroxy-1,8-cineoles) were prepared, and eight diastereomers were separated. The absolute configuration of the asymmetric carbons of the cineole moiety of each diastereomer was determined by H-1 NMR data according to the Mosher theory. Each mandelate was reduced with LiAlHe4 to obtain optically pure hydroxy-1,8-cineoles, this being followed by acetylation to afford optically pure acetoxy-1,8-cineoles. These acetates were subjected to chiral GC, using a cyclodextrin column, and the enantiomeric purity of trans- and cis-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5- and 6-yl acetates in the aroma concentrate from the rhizomes of Alpinia galanga was determined as 93.9 (5S), 19.4 (5R), 63.5 (6R), and 100 (6R) % cc, respectively. The aroma character of each enantiomer was also evaluated by GC-sniffing.

  DOI：

  10.1021/jf9807465

文献信息

• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• The 3-Hydroxycineoles
  作者：Raymond M. Carman、Ward T. Robinson、Craig J. Wallis

  DOI：10.1071/ch05144

  日期：——

  Data concerning the 3-hydroxycineoles 1 and 2 are provided to enable the ready identification of these metabolites and to determine their enantiomeric excess in mixtures. An unusual SN2-type inversion at a tertiary center is observed during one synthetic approach.

  本研究提供了有关 3-hydroxycineoles 1 和 2 的数据，以便随时识别这些代谢物，并确定它们在混合物中的对映体过量。在一种合成方法中，在一个三级中心观察到了不寻常的 SN2 型反转。
• Cloning, Expression and Purification of Cindoxin, an Unusual Fmn-Containing Cytochrome P450 Redox Partner
  作者：David B. Hawkes、Kate E. Slessor、Paul V. Bernhardt、James J. De Voss

  DOI：10.1002/cbic.201000119

  日期：——

  Living in cin: Cindoxin is an FMN‐containing cytochrome P450 redox partner that mediates the transfer of electrons derived ultimately from NADPH to P450cin, which then catalyses the enantiospecific hydroxylation of cineole. The P450cin/cindoxin system is unique and represents a new cytochrome P450/redox partner class.

  生活在cin中：Cindoxin是一种含FMN的细胞色素P450氧化还原伙伴，它介导最终将NADPH衍生的电子转移至P450 cin，然后催化桉树脑的对映体特异性羟基化。P450 cin / cindoxin系统是独特的，代表了新的细胞色素P450 /氧化还原伴侣类别。
• Syntheses of Chiral 1,8-Cineole Metabolites and Determination of Their Enantiomeric Composition in Human Urine After Ingestion of 1,8-Cineole-Containing Capsules
  作者：Monika Schaffarczyk、Teodor Silviu Balaban、Michael Rychlik、Andrea Buettner

  DOI：10.1002/cplu.201200253

  日期：2013.1

  The chiral metabolites in human urine were investigated after ingestion of a 1,8‐cineole (eucalyptol)‐containing entero‐coated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (−/+)‐α2‐hydroxy‐1,8‐cineole, (−/+)‐β2‐hydroxy‐1,8‐cineole, (−/+)‐9‐hydroxy‐1,8‐cineole, and (−/+)‐2‐oxo‐1,8‐cineole were prepared. To achieve this aim, after acetylation of the synthesized

  摄入含1,8-桉树脑（桉树脑）的肠溶胶囊（Soledum）后，研究了人类尿液中的手性代谢物。为了鉴定各种对映异构体，对映体纯的（-/ +）-α2-羟基-1,8-桉树脑，（-/ +）-β2-羟基-1,8-桉树脑，（-/ +）-9-羟基制备了-1,8-桉树脑和（-/ +）-2-氧代-1,8-桉树脑。为实现这一目标，在合成的外消旋2-羟基和9-羟基-1,8-桉树脑被乙酰化后，猪肝酯酶或酵母介导的水解作用为（-）-醇及其对映异构体的对映体（+）-乙酸酯提供了对映体超过33–100％。通过拆分乙酸盐的水解获得的Dess-Martin高碘烷对醇（+）-α2-羟基-1,8-桉树脑的氧化，提供了相应的（+）-2-氧代-1,8-桉树脑，同时进行了氧化（-）-α2-羟基-1,8-桉树脑的化合物得到（-）-2-2-氧-1,8-桉树脑。使用这些标准品的七个代谢物（+/-）-α2-羟基-1,8-桉树脑，（+/-）-β2-羟基-1
• Biotransformation of 1,8-cineole by cultured cells of Eucalyptus perriniana
  作者：Yutaka Orihara、Tsutomu Furuya

  DOI：10.1016/s0031-9422(00)90578-8

  日期：1994.2

  Abstract Four new biotransformation products, (1 R , 2 R , 4 S )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranoside, (1 S , 3 R , 4 R )- and (1 R , 3 S , 4 S )-1,8-epoxy- p -menthan-3-yl O -β- d -glucopyranosides, and (1 S , 2 S , 4 R )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranosyl-(1→6)-β- d -glucopyranoside, together with a known (1 S , 2 S , 4 R )-1,8-epoxy- p -menthan-2-yl O -β- d -glucopyranoside

  摘要 四种新的生物转化产物, (1 R , 2 R , 4 S )-1,8-epoxy-p -menthan-2-yl O -β-d -glucopyranoside, (1 S , 3 R , 4 R )-和(1 R , 3 S , 4 S )-1,8-环氧-p -薄荷醇-3-基 O -β-d -吡喃葡萄糖苷，和 (1 S , 2 S , 4 R )-1,8-环氧- p-薄荷醇-2-基O-β-d-吡喃葡萄糖基-(1→6)-β-d-吡喃葡萄糖苷，连同已知的(1 S , 2 S , 4 R )-1,8-环氧- p -在施用 1,8-桉树脑后，从 Eucalyptus perriniana 的细胞悬浮培养物中分离出薄荷-2-基 O-β-d-吡喃葡萄糖苷。