玛瑙酸 | 640-28-8

• 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: 玛瑙酸
• 英文名称: agathic acid
• 英文别名: ent-linda-8(17),(13E)-dien-15,19-dioic acid；agathendioic acid；Agathendisaeure；(1S,4aR,5S,8aR)-5-[(E)-4-carboxy-3-methylbut-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 640-28-8
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: QYCOHMYDSOZCQD-GWEOMKHGSA-N

物化性质

• LogP：
  5.618 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  玛瑙酸 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (8S,13R,S)-labda-15,19-dioic acid
  参考文献：
  名称：

  橄榄油的结构和立体化学

  摘要：

  早在2a中就建立了橄榄的结构和立体化学，橄榄酸是Daniellia Oliveri树干树脂的主要成分。

  DOI：

  10.1016/s0040-4020(01)92925-4
• 作为产物：
  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

文献信息

• Chemistry of the natural order cupressales—41
  作者：V.P. Arya、H. Erdtman、T. Kubota

  DOI：10.1016/0040-4020(61)80076-8

  日期：1961.1

  A new diterpene acid, communic acid, has been isolated as its sodium salt from the bark of the common juniper, Juniperus communis L. The structure and configuration (1a) of this acid follows from direct correlations with torulosol and with agathene dicarboxylic acid as well as from the results of degradation experiments.

  从普通杜松（Juniperus communis L）的树皮中分离出一种新的二萜酸，其酸为钠盐。该酸的结构和构型（1a）来源于与甲苯酚和与邻苯二酚二羧酸的直接相关性。根据降解实验的结果。
• Mumic acids A–E: new diterpenoids from mumiyo
  作者：Yuko Kiren、Alfarius Eko Nugroho、Yusuke Hirasawa、Osamu Shirota、Myrzaim Bekenova、Narbekov Omorbay Narbekovich、Marina Shapilova、Hiromichi Maeno、Hiroshi Morita

  DOI：10.1007/s11418-013-0771-2

  日期：2014.1

  Five new diterpenoids belonging to labdane and isopimarane skeletons, mumic acids A–E (1–5), have been isolated from mumiyo. Their structures and absolute configurations were elucidated on the basis of spectroscopic data and chemical derivatization.

  五个属于半日花烷和异海松骨架，mumic酸A-E（新二萜类化合物1 - 5），已经从分离mumiyo。在光谱数据和化学衍生化的基础上阐明了它们的结构和绝对构型。
• The structure and stereochemistry of oliveric acid
  作者：J. Haeuser、S.F. Hall、A.C. Oehlschlager、G. Ourisson

  DOI：10.1016/s0040-4020(01)92925-4

  日期：1970.1

  The structure and stereochemistry of oliveric acid, a principal constituent of the trunk resin of Daniellia oliveri, have been established as in 2a.

  早在2a中就建立了橄榄的结构和立体化学，橄榄酸是Daniellia Oliveri树干树脂的主要成分。
• Caputo,R. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 639 - 642
  作者：Caputo,R. et al.

  DOI：——

  日期：——
• In Vitro Biotransformations of Isocupressic Acid by Cow Rumen Preparations:  Formation of Agathic and Dihydroagathic Acids
  作者：Shwu-Jiuan Lin、Robert E. Short、Stephen P. Ford、Elaine E. Grings、John P. N. Rosazza

  DOI：10.1021/np970372u

  日期：1998.1.1

  Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (I) was incubated under anaerobic conditions for 48 h in an in vitro luminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by H-1 and C-13 NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.