(1R,2R,5R,8S)-4,4,8-三甲基三环[6.3.1.02,5]十二烷-1-醇 | 58404-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R,5R,8S)-4,4,8-三甲基三环[6.3.1.02,5]十二烷-1-醇
• 英文名称: β-caryolanol
• 英文别名: β-caryophyllene alcohol；caryophyllene alcohol；(-)-caryolan-1-ol；(1R)-caryolanol；caryolan-1-ol；(-)-β-caryophyllene alcohol；Tricyclo(6.3.1.02,5)dodecan-1-ol, 4,4,8-trimethyl-, (1R,2S,5R,8S)-；(1R,2S,5R,8S)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol
• CAS: 58404-89-0；472-97-9；56747-96-7
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: FUQAYSQLAOJBBC-PAPYEOQZSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  295.0±8.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)
• LogP：
  4.81
• 物理描述：
  White crystalline solid; Warm moss-like, spicy aroma
• 溶解度：
  Practically insoluble or insoluble in water
• 折光率：
  1.498-1.503

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R,8S)-4,4,8-三甲基三环[6.3.1.02,5]十二烷-1-醇 在 五氯化磷 作用下， 生成 caryolane chloride
  参考文献：
  名称：

  A serological re-evaluation of acute non-A non-B hepatitis from the early 1970s

  摘要：

  Abstract: Background: The epidemiology and natural history of recently discovered viruses, which may be responsible for cases of seronegative infectious hepatitis, are currently being investigated. Retrospective studies of stored sera can provide a historical perspective of these infections. Aims: To re‐evaluate the serological, demographic and clinical characteristics of patients hospitalised in the early 1970s with acute hepatitis. Methods: The stored sera of 57 patients hospitalised between 1971 and 1974 with acute hepatitis, designated at that time as non‐A non‐B (NANB) hepatitis, were re‐tested using commercially available enzyme‐linked immunosorbent assays (ELISAs) for the presence of anti‐hepatitis A virus (HAV) IgM, hepatitis B surface antigen (HBsAg), anti‐hepatitis C virus (HCV) IgG, and anti‐hepatitis E virus (HEV) IgG. Stored sera from a group of 57 patients concurrently hospitalised for other conditions were also tested. Detailed records of the original epidemiological interviews were examined to compare patient demographics, risk factors for infectious hepatitis and clinical data for the NANB hepatitis group and an original control group of 604 hospitalised patients. Results: Serum from 15 of the 57 (26%) previously designated NANB hepatitis cases had elevated anti‐HAV IgM and are likely to represent missed cases of hepatitis A. Thirteen (23%) of cases previously designated as NANB hepatitis had positive hepatitis C antibody tests. These patients were younger and significantly more likely to have used intravenous drugs than control patients. Three NANB hepatitis and two hospital control patients were anti‐HEV IgG antibody positive. All of these individuals were born in, or had travelled to, developing countries. Serum from 27 (47%) of the NANB hepatitis patients were negative on all tests. These hepatitis non‐A‐E cases included children and elderly adults, but as a group were significantly more likely to have used intravenous drugs than hospitalised control patients.

  DOI：

  10.1111/j.1445-5994.2000.tb04361.x
• 作为产物：
  描述：

  farnesyl pyrophosphate 在 DL-dithiothreitol 、 caryolan-1-ol-synthase from Streptomyces griseus 、 pyrophosphatase from S_. cerevisiae 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 17.0h， 以16%的产率得到(1R,2R,5R,8S)-4,4,8-三甲基三环[6.3.1.02,5]十二烷-1-醇
  参考文献：
  名称：

  利用倍半萜环化酶的合成潜力来产生非天然萜类化合物。

  摘要：

  使用六种新的杂原子修饰的法呢基焦磷酸酯评估了八种纯化的倍半萜环化酶的底物柔性，并描述了六种新的杂原子修饰的大环和三环倍半萜的形成。GC‐O分析表明，三环四氢呋喃具有醚味，胡椒味和樟脑味的嗅觉气味。

  DOI：

  10.1002/anie.201805526

文献信息

• Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid
  作者：E. P. Romanenko、A. V. Tkachev

  DOI：10.1007/s11172-018-2179-3

  日期：2018.6

  The conversion of caryophyllene upon contact with Al2O3 and SiO2 impregnated with sulfuric acid was carried out, and the components of the resulting mixtures were identified. Having in hands such “standard” mixtures greatly facilitates identification of components of sesquiterpene fractions of essential oils and other mixtures of natural origin. The catalytic activity of silica gel impregnated with

  在与硫酸浸渍的 Al2O3 和 SiO2 接触时进行石竹烯的转化，并确定所得混合物的组分。掌握这样的“标准”混合物极大地促进了精油和其他天然来源混合物的倍半萜成分成分的鉴定。用硫酸(H+-SiO2)浸渍的硅胶对石竹烯酸催化异构化的催化活性明显高于H+-Al2O3，与浓硫酸的活性相当。
• Etudes sur les matières végétales volatiles LX. Présence d'époxydihydrocaryophyllène (Caryophyllenoxyd de<i>Treibs</i>) dans l'extrait benzénique de bourgeons floraux du giroflier
  作者：Yves-René Naves

  DOI：10.1002/hlca.19480310210

  日期：——

  L'extrait obtenu en traitant les bourgeons floraux du giroflier par le benzène ne renferme pas de caryophyllkne mais bien de l'époxy-dihydrocaryophyllèe(Caryophyllenoxyd de Treibs), tandis que le tourteau lime, sous l'action de l'eau bouillante, une huile essentielle constituée en majeure partie de caryophyllène. Ce dernier n'est donc pas un produit biologique.

  资产阶级化的资产阶级化石，苯并二苯丙酮酸化石（Caryophyllenoxyd de Treibs），tandis que le Tourteau青柠，酸奶酪必不可少的部分石竹叶素。Ce dernier n'est donc pas un produit biologique。
• Heteropoly acid catalysts in the valorization of the essential oils: Acetoxylation of β-caryophyllene
  作者：Kelly A. da Silva Rocha、Nathália V.S. Rodrigues、Ivan V. Kozhevnikov、Elena V. Gusevskaya

  DOI：10.1016/j.apcata.2009.11.032

  日期：2010.2

  efficient and clean method for the synthesis of 2, providing a mixture containing two stereoisomeric β-caryolanyl acetates 2a and 2b, 2a/2b = 80/20 mol/mol, with 100% GC yield, has been developed using PW as a homogeneous catalyst under mild reaction conditions. The reaction occurs at 25 °C with a catalyst turnover number of 2000. The catalyst can be recovered without neutralization and reused without loss

  H 3 PW 12 O 40（PW）是Keggin系列中最强的杂多酸，是一种活性且环境友好的催化剂，用于将β-石竹烯（1）液相转化为乙酸-β-戊烯基乙酸酯（2）异构系统。一种高效且清洁的合成2的方法，提供了包含两种立体异构体的β-羧甲基乙酸乙酸酯2a和2b，2a / 2b的混合物 在温和的反应条件下，使用PW作为均相催化剂已开发出= 80/20 mol / mol，GC产率为100％。该反应在25℃下进行，催化剂的周转数为2000。该催化剂无需中和就可以回收，并且可以在不损失活性和选择性的情况下重复使用。
• The oxymercuration-demercuration of caryophyllenes
  作者：A. V. Tkachev、Yu. V. Gatilov、I. K. Korobeinicheva、Zh. V. Dubovenko、V. A. Pentegova

  DOI：10.1007/bf00580549

  日期：——

  olefin to mercury salt of 1:2 has been performed. Using various chromatographic methods, the following substances have been isolated from the crude product: clovene (II), 1%; caryophyllane 4,8-α-oxide (III), 52%; 9-epicaryophyllane 4,8-β-oxide (IV), 11%; caryolan-l-ol (V), 5.3%; dihydrocaryophyllen-4α-ol (VI), 11%; caryophyllan-4-ol 5,8-oxide (VII), 6.5%; the symmetrical mercury derivative of the 9-epi-4

  已经在烯烃与汞盐的摩尔比为 1:2 的情况下进行了石竹烯 (I) 的氧汞化-脱汞。使用各种色谱方法，已从粗产物中分离出以下物质： 丁香烯 (II)，1%；石竹烷 4,8-α-氧化物 (III)，52%；9-epicaryophyllane 4,8-β-氧化物 (IV)，11%；山核桃-1-醇(V)，5.3%；dihydrocaryophyllen-4α-ol (VI), 11%; caryophyllan-4-ol 5,8-oxide (VII), 6.5%; 9-epi-4,8-​​β-氧化物(VIII)的对称汞衍生物，2.1%；和未知的碳氢化合物 A，1%。氧化物 (IV) 的结构已通过 X 射线结构分析确定。
• Microbial transformations. 14. Regioselective hydroxylation of(1R)-caryolanol by aspergillus niger. A reexamination of the 13C NMR spectrum of caryolanol
  作者：V. Lamare、A. Archelas、R. Faure、M. Cesario、C. Pascard、R. Furstoss

  DOI：10.1016/s0040-4020(01)89237-1

  日期：1989.1

  Oxidation of caryolan-1-ol by the fungus Aspergillus niger (MMP 521) led in fair yield (26%) to a single diol by regiospecific hydroxylation of the C(14) methyl group. 13C NMR analysis led to modification of the previous attributions to caryolan-1-ol ().

  黑曲霉（MMP 521）对Caryolan-1-ol的氧化作用导致C（14）甲基的区域特异性羟基化使单一二醇的收率合理（26％）。13 C NMR分析导致对caryolan-1-ol（）先前属性的修改。