3β-Acetoxyolean-12-en-30-oate | 53402-18-9

• 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: 3β-Acetoxyolean-12-en-30-oate
• 英文别名: betuloleanoic acid acetate；3β-acetoxy-11-dioxyglycyrrhetic acid；3-acetyl-11-deoxyglycyrrhetic acid；11-desoxoglycyrrhetic acid 3-O-acetate；3-O-Acetyl-11-desoxo-18β-glycyrrhetinsaeure；3β-acetoxy-oleanen-(12)-oic acid-(30)；olean-12-en-3β-ylacetate-29-oic acid；3β-Acetoxy-oleanen-(12)-saeure-(30)；3β-O-acetoxyolean-12-en-30-oic acid；(2S,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-acetyloxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
• CAS: 53402-18-9
• 化学式: C₃₂H₅₀O₄
• 分子量: 498.747
• InChiKey: WVHHZBXERBMTER-OJTFNSJNSA-N

物化性质

• 熔点：
  280-281 °C(Solv: ethanol (64-17-5))
• 沸点：
  563.6±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-Acetoxyolean-12-en-30-oate 在 氯化亚砜 作用下， 生成 3-acetyl-11-deoxyglycyrrhetic acid chloride
  参考文献：
  名称：

  Folate Deficiency In Vitro Induces Uracil Misincorporation and DNA Hypomethylation and Inhibits DNA Excision Repair in Immortalized Normal Human Colon Epithelial Cells

  摘要：

  Epidemiological studies have indicated that folic acid protects against a variety of cancers, particularly cancer of the colorectum. Folate is essential for efficient DNA synthesis and repair. Moreover folate can affect cellular S-adenosylmethionine levels, which regulate DNA methylation and control gene expression. We have investigated the mechanisms through which folate affects DNA stability in immortalized normal human colonocytes (HCEC). DNA strand breakage, uracil misincorporation, and DNA repair, in response to oxidative and alkylation damage, were determined in folate-sufficient and folate-deficient colonocytes by single cell gel electrophoresis. In addition, methyl incorporation into genomic DNA was measured using the bacterial enzyme Sss1 methylase. Cultured human colonocyte DNA contained endogenous strand breaks and uracil. Folate deficiency significantly increased strand breakage and uracil misincorporation in these cells. This negative effect on DNA stability was concentration dependent at levels usually found in human plasma (1-10 ng/ml). DNA methylation was decreased in HCEC grown in the absence of folate. Conversely, hypomethylation was nor concentration dependent. Folate deficiency impaired the ability of HCEC to repair oxidative and alkylation damage. These results demonstrate that folic acid modulates DNA repair DNA strand breakage, and uracil misincorporation in immortalized human colonocytes and that folate deficiency substantially decreases DNA stability in these cells.

  DOI：

  10.1207/s15327914nc372_18
• 作为产物：
  描述：

  甘草次酸 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 potassium permanganate 、 sodium dihydrogenphosphate 、 四丁基氟化铵 、 氢气 、 红铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3β-Acetoxyolean-12-en-30-oate
  参考文献：
  名称：

  Synthesis of new glycyrrhetinic acid (GA) derivatives and their effects on tyrosinase activity

  摘要：

  To synthesize glycyrrhetinic acid (GA) derivatives (3, 4, 5, 10, 13, 14, 15, and 16), we first removed the ketonic group in the C-11 position, and the carboxylic function at the C-30 position was kept intact, reduced to an alcohol, or transformed to an aldehyde corresponding derivatives 10 and 13. Glycyrrhetinic acid (GA) derivatives (3, 4, 5, 15, and 16) were coupled with 4-amino piperpyridine derivatives (12 and 14) and 4-fluorobenzyl bromide at C-30 carboxylic acid position of glycyrrhetinic acid. In subsequent tyrosinase assays, we found that GA derivatives 4, 5, and 16 were not active at early time points, but strongly inhibited tyrosinase activity at late time points. Of the GA derivatives examined, derivative 5 was most active, with an IC50 value of 50 muM after 2 h reaction. IC50 values of derivatives 4 and 16 were 120 and 170 muM respectively. Further kinetic data indicated that these derivatives are slow-binding inhibitors of tyrosinase. The time-dependent inhibition was reversed when vitamin C or kojic acid was used, that is, both compounds showed active inhibition at early time points. These results suggest that GA derivatives are much more stable than vitamin C or kojic acid, although their intrinsic inhibitory potentials are relatively low. Higher stability and activity suggest that GA derivative 5 might be a useful candidate for skin whitening. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2003.09.046

文献信息

• Oxidation of Licorice-Root Triterpene-Acid Derivatives by m-Chloroperbenzoic Acid
  作者：L. R. Mikhailova、A. S. Budaev、L. V. Spirikhin、L. A. Baltina

  DOI：10.1007/s10600-019-02619-5

  日期：2019.1

  12(13)-dien-30-oic, and 3β-O-acetoxy-18βH-olean-12-en-30-oic acids were oxidized by meta-chloroperbenzoic acid (m-CPBA) to produce methyl esters of 3β-O-acetoxy-12α,13α-epoxy-18β-oleanan-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in addition to 3β-hydroxy-12-oxo-18βH-olean-9(11)-en-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in 70–75% yields. The structures of the synthesized compounds

  3β-O-乙酰氧基-18βH-olean-12-en-30-oic、3β-羟基-9(11​​)、12(13)-dien-30-oic和3β-O-乙酰氧基-18βH-的甲酯olean-12-en-30-oic 酸被间氯过苯甲酸 (m-CPBA) 氧化生成 3β-O-acetoxy-12α,13α-epoxy-18β-oleanan-30-oic 和 3β-O 的甲酯-acetoxy-18β-oleanan-12-on-30-oic 酸以及 3β-hydroxy-12-oxo-18βH-olean-9(11​​)-en-30-oic 和 3β-O-acetoxy-18β-oleanan -12-on-30-油酸的产率为 70-75%。合成化合物的结构经PMR和13C NMR谱确证。
• Ozonolysis of 11-desoxoglycyrrhetic acid and its derivatives
  作者：L. R. Mikhailova、M. V. Khudobko、L. A. Baltina、O. S. Kukovinets、V. K. Mavrodiev、F. Z. Galin

  DOI：10.1007/s10600-007-0195-x

  日期：2007.9

  12-Oxo derivatives of 11-desoxolycyrrhetic acid and its derivatives were produced by oxidative transformation using ozone. Olean-3,12-dion-30-oic acid was produced for the first time by exhaustive ozonolysis of 11-desoxoglycyrrhetic acid at −60°C.

  通过臭氧氧化转化，制备了11-去氧甘草次酸及其衍生物的12-氧化衍生物。首次通过在-60°C下对11-去氧甘草次酸进行彻底的臭氧化分解，得到了油酸-3,12-二酮-30-羧酸。
• Cattel, Luigi; Delprino, Laura; Biglino, Giuseppe, Journal of Chemical Research, Miniprint, 1980, # 2, p. 731 - 751
  作者：Cattel, Luigi、Delprino, Laura、Biglino, Giuseppe

  DOI：——

  日期：——
• Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability
  作者：Kun Li、Tianyi Ma、Jingjing Cai、Min Huang、Hongye Guo、Di Zhou、Shenglin Luan、Jinyu Yang、Dan Liu、Yongkui Jing、Linxiang Zhao

  DOI：10.1016/j.bmc.2017.08.002

  日期：2017.10

  Twenty-six conjugates of 18 beta-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d] imidazol-2-yl) propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI(50) values of 7.80 mu M and 3.52 mu M, respectively. The enzyme inhibition ratio of nine compounds at 10 mu M was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition. (C) 2017 Published by Elsevier Ltd.
• A NEW REDUCTION OF THE ENONE SYSTEM OF 18B-GLYCYRRHETIC ACID
  作者：R. Pellegatat、M. Pinza、G. Pifferi、C. Farina

  DOI：10.1080/00304949909355708

  日期：1999.4