(S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid | 5027-76-9

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid
• 英文别名: (-)-(S)-oleuropeic acid；(-)-oleuropeic acid；oleuropeic acid；(S)-8-hydroxy-p-menth-1-en-7-oic acid；(S)-8-Hydroxy-p-menth-1-en-7-saeure；(S)-Oleuropeinsaeure；(4S)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carboxylic acid
• CAS: 5027-76-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BFYWJELXORKNFO-MRVPVSSYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  319.6±25.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid 、 三甲基硅烷化重氮甲烷 在 甲醇 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.17h， 生成 (-)-methyl 4-(1-hydroxy-1-methylethyl)cyclohex-1-ene-carboxylate
  参考文献：
  名称：

  Non-volatile components of the essential oil secretory cavities of Eucalyptus leaves: Discovery of two glucose monoterpene esters, cuniloside B and froggattiside A

  摘要：

  The essential oils extracted from the embedded foliar secretory cavities of many Eucalyptus species are of economic value as pharmaceuticals and fragrance additives. Recent studies have indicated that Eucalyptus secretory cavities may not be exclusively involved in the biosynthesis and storage of essential oils. Therefore, we selected three species upon which to perform an examination of the contents of foliar secretory cavities: Eucalyptus froggattii, E. polybractea and E. globulus. This paper describes the isolation and structural characterization of two non-volatile glucose monoterpene esters, which we have named cuniloside B and froggattiside A, from within the secretory cavities of these species, and shows the presence of these compounds in solvent extracts of the leaves from two other species of Eucalyptus. Both compounds were found in high proportions relative to the essential oils extracted from the leaves. We propose that many other carbohydrate monoterpene esters previously isolated from bulk leaf extracts of various Eucalyptus species may also be localized within the non-volatile fraction of foliar secretory cavities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.06.004
• 作为产物：
  描述：

  beta-pinene 在 过氧乙酸 、 sodium chlorite 、 potassium dihydrogenphosphate 、 碳酸 、 sodium acetate 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 叔丁醇 、 环己烯 为溶剂， 反应 6.0h， 生成 (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Pellegata, R.; Ventura, P.; Villa, M., Synthetic Communications, 1985, vol. 15, # 2, p. 165 - 170

  摘要：

  DOI：

文献信息

• A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa
  作者：Tsutomu Nakanishi、Naoki Iida、Yuka Inatomi、Hiroko Murata、Akira Inada、Jin Murata、Frank A. Lang、Munekazu Iinuma、Toshiyuki Tanaka、Yoshikazu Sakagami

  DOI：10.1248/cpb.53.783

  日期：——

  A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2—4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.

  从美国俄勒冈州采集的桧柏（Cupressaceae）的枝叶中分离出一种新的单萜葡萄糖苷（1）和三种新的天然大戟烷苷（2-4）以及一种已知的大戟烷葡萄糖苷（5），并根据光谱和化学证据确定了它们的结构。此外，还研究了分离出的成分对幽门螺杆菌的抗菌活性。
• Farges,G.; Kergomard,A., Bulletin de la Societe Chimique de France, 1975, p. 315 - 318
  作者：Farges,G.、Kergomard,A.

  DOI：——

  日期：——
• Non-volatile components of the essential oil secretory cavities of Eucalyptus leaves: Discovery of two glucose monoterpene esters, cuniloside B and froggattiside A
  作者：Jason Q.D. Goodger、Benjamin Cao、Inneke Jayadi、Spencer J. Williams、Ian E. Woodrow

  DOI：10.1016/j.phytochem.2009.06.004

  日期：2009.6

  The essential oils extracted from the embedded foliar secretory cavities of many Eucalyptus species are of economic value as pharmaceuticals and fragrance additives. Recent studies have indicated that Eucalyptus secretory cavities may not be exclusively involved in the biosynthesis and storage of essential oils. Therefore, we selected three species upon which to perform an examination of the contents of foliar secretory cavities: Eucalyptus froggattii, E. polybractea and E. globulus. This paper describes the isolation and structural characterization of two non-volatile glucose monoterpene esters, which we have named cuniloside B and froggattiside A, from within the secretory cavities of these species, and shows the presence of these compounds in solvent extracts of the leaves from two other species of Eucalyptus. Both compounds were found in high proportions relative to the essential oils extracted from the leaves. We propose that many other carbohydrate monoterpene esters previously isolated from bulk leaf extracts of various Eucalyptus species may also be localized within the non-volatile fraction of foliar secretory cavities. (C) 2009 Elsevier Ltd. All rights reserved.
• Pellegata, R.; Ventura, P.; Villa, M., Synthetic Communications, 1985, vol. 15, # 2, p. 165 - 170
  作者：Pellegata, R.、Ventura, P.、Villa, M.、Palmisano, G.、Lesma, G.

  DOI：——

  日期：——