异柏烯酸 | 1909-91-7

• 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
• 中文名称: 异柏烯酸
• 英文名称: isocupressic acid
• 英文别名: (1S,4aR,5S,8aR)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 1909-91-7
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: DOYKMKZYLAAOGH-DOEMEAPXSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  454.2±38.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• LogP：
  4.867 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异柏烯酸 在 sodium chlorite 、 potassium dihydrogenphosphate 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 16.5h， 生成 玛瑙酸
  参考文献：
  名称：

  Preparation of Tetrahydroagathic Acid:  A Serum Metabolite of Isocupressic Acid, a Cattle Abortifacient in Ponderosa Pine

  摘要：

  Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.

  DOI：

  10.1021/jf011501m
• 作为产物：
  描述：

  cryptomeridiol-4-yl-19-acetoxylabda-8(17),13E-dien-19-oate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以4 mg的产率得到cryptomeridiol
  参考文献：
  名称：

  Labdanes from Cryptomeria japonica

  摘要：

  DOI：

  10.1016/s0031-9422(00)89538-2

文献信息

• Microbial Transformations of Isocupressic Acid
  作者：Shwu-Jiuan Lin、John P. N. Rosazza

  DOI：10.1021/np980064b

  日期：1998.7.1

  Microbial transformations of the labdane-diterpene isocupressic acid (1) with different microorganisms yielded several oxygenated metabolites that were isolated and characterized by MS and NMR spectroscopic analyses. Nocardia aurantia (ATCC 12674) catalyzed the cleavage of the 13,14-double bond to yield a new nor-labdane metabolite, 2. Cunninghamella elegans (-) (NRRL 1393) gave 7beta-hydroxyisocupressic

  用不同微生物对拉丹烷-二萜异癸酸（1）进行微生物转化，产生了几种氧化代谢产物，这些代谢产物已通过MS和NMR光谱分析进行了分离和表征。诺卡氏菌（ATCC 12674）催化了13,14-双键的裂解，产生了一个新的正二十烷酸代谢产物2。秀丽线虫（-）（NRRL 1393）得到了7β-羟基异柏油酸（3）和labda-7， 13（E）-二烯-6beta，15、17-三醇-19-油酸（4）和Mucor Mucedo（ATCC 20094）得到2α-羟基异cucudocicic酸（5）和labda-8（17），14-二烯- 2α，13-二醇-19-油酸（6）。
• A Concise Route to the Strongylophorines
  作者：Wanwan Yu、Per Hjerrild、Jacob Overgaard、Thomas B. Poulsen

  DOI：10.1002/anie.201602476

  日期：2016.7.11

  into this class of natural products and provides access to six additional family members. A novel iron(III)‐mediated rearrangement–cyclization cascade and a directed photochemical sp3 C−H δ‐lactonization are the key transformations that enable concise assembly of these bioactive polycyclic meroterpenoids.

  据报道，可以从丰富的构建基异癸酸中高效地进行八步法强力比目鱼碱2的合成。这条路线是此类天然产品的第一个人工合成入口，并为其他六个家庭成员提供了通行途径。一种新颖的铁（III）介导的重排-环化级联和定向光化学SP 3 C-H δ -lactonization是关键变换，使简明装配这些生物活性的多环meroterpenoids的。
• Potential Antitumor Promoting Diterpenoids from the Stem Bark of <i>Thuja standishii</i>
  作者：Manabu Iwamoto、Toshifumi Minami、Harukuni Tokuda、Hironori Ohtsu、Reiko Tanaka

  DOI：10.1055/s-2003-37037

  日期：——

  Six diterpenes, including one new natural product, were isolated from a CHCl 3 extract of the stem bark of Thuja standishii. The new compound has been characterized as 15-oxolabda-8(17),13 Z-dien-19-oic acid. The known compounds were identified as ferruginol (2), sugiol (3), isocupressic acid (4), sandaracopimaric acid (5) and 15-oxolabda-8(17),13 E-dien-19-oic acid (6). Compounds 2-5 and the derivatives

  从侧柏茎皮的 CHCl 3 提取物中分离出六种二萜，包括一种新的天然产物。新化合物已被表征为 15-oxolabda-8(17),13 Z-dien-19-oic 酸。已知的化合物被鉴定为ferruginol (2)、sugiol (3)、isocupressic acid (4)、sandaracopimaric acid (5) 和 15-oxolabda-8(17), 13 E-dien-19-oic acid (6)。测试了化合物 2-5 以及衍生物 4a 和 4b 对 12-O-十四烷酰佛波醇 13-乙酸酯 (TPA) 诱导的 Epstein-Barr 病毒早期抗原 (EBV-EA) 激活的抑制作用。化合物 2、3、4 和 5 对 EBV-EA 诱导显示出强抑制作用（在 1000 摩尔比/TPA 下抑制 100%）。
• Caputo,R. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 639 - 642
  作者：Caputo,R. et al.

  DOI：——

  日期：——
• Cambie, Richard C.; Grigor, Bruce A.; Mee-Ing, Tiong, Australian Journal of Chemistry, 1981, vol. 34, # 5, p. 1073 - 1078
  作者：Cambie, Richard C.、Grigor, Bruce A.、Mee-Ing, Tiong

  DOI：——

  日期：——