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(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 | 1477-44-7

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

(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯

中文别名

——

英文名称

methyl glycyrrhetinate

英文别名

glycyrrhetinic acid methyl ester；glycyrrhetic acid methyl ester；18β-glycyrrhetinic acid methyl ester；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate

(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯化学式

CAS

1477-44-7

化学式

C₃₁H₄₈O₄

mdl

——

分子量

484.72

InChiKey

RMIVRCBSQPCSCQ-BDANYOJNSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

253～255℃
沸点：

170-190 °C(Press: 0.001 Torr)
密度：

1.11±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

6.7
重原子数：

35
可旋转键数：

2
环数：

5.0
sp3杂化的碳原子比例：

0.87
拓扑面积：

63.6
氢给体数：

1
氢受体数：

4

SDS

SDS：bdc8895b1acc008b53e3df334d1f482c

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上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
甘草次酸	enoxolone	471-53-4	C₃₀H₄₆O₄	470.693
——	3β-acetoxy-11-oxo-olean-12-en-30-oic acid methyl ester	10301-74-3	C₃₃H₅₀O₅	526.757
——	glycyrrhetol	14226-18-7	C₃₀H₄₈O₃	456.709
乙酰甘草亭酸铝	acetoxolone	6277-14-1	C₃₂H₄₈O₅	512.73
——	methyl 3β-hydroxy-18β-olean-12-en-30-oate	10527-59-0	C₃₁H₅₀O₃	470.736
——	araboglycyrrhizin	121687-83-0	C₄₁H₆₂O₁₄	778.935
(3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸	glycyrrizhin	103000-77-7	C₄₂H₆₂O₁₆	822.945
甘草酸	glycyrrhizin	1405-86-3	C₄₂H₆₂O₁₆	822.945
——	apioglycyrrhizin	121709-66-8	C₄₁H₆₂O₁₄	778.935

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(3α,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid methyl ester	21857-94-3	C₃₁H₄₈O₄	484.72
——	3-methoxy-18β-glycyrrhetinic acid	460721-67-9	C₃₁H₄₈O₄	484.72
——	3α-hydroxyglycyrrhetic acid	90365-60-9	C₃₀H₄₆O₄	470.693
——	3,4-seco-30-methyloxicarbonyl-11-oxo-olean-4(23),12-dien-3-oic acid	1158817-90-3	C₃₁H₄₆O₅	498.703
——	3β-acetoxy-11-oxo-olean-12-en-30-oic acid methyl ester	10301-74-3	C₃₃H₅₀O₅	526.757
——	(2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR)-2,4a,6a,6b,9,9,12a-Heptamethyl-10,13-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid methyl ester	5195-71-1	C₃₁H₄₆O₄	482.704
——	3-Isopropyliden-11-oxo-4.23.24-trisnor-18αH-Δ¹²-oleanen-30-saeure-methylester	6471-55-2	C₃₁H₄₆O₃	466.704
——	methyl glycyrrhetate hemisuccinate	17956-20-6	C₃₅H₅₂O₇	584.794
——	methyl 3β-(chloroacetyloxy)-11-oxo-olean-12-en-30-oate	1261081-68-8	C₃₃H₄₉ClO₅	561.202
——	methyl 3β-hydroxy-18β-olean-12-en-30-oate	10527-59-0	C₃₁H₅₀O₃	470.736
——	apo-allo-18β-glycyrrhetinic-30-methyl ester	5092-06-8	C₃₁H₄₆O₃	466.704
——	methyl 3,11-dioxo-4-oxa-A-homo-olean-12-en-30-oate	1158817-88-9	C₃₁H₄₆O₅	498.703
——	methyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-10-(sulfamoyloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate	——	C₃₁H₄₉NO₆S	563.799
——	(3β,18β)-methyl 3-amino-11-oxoolean-12-en-30-oate	39775-94-5	C₃₁H₄₉NO₃	483.735
——	(3α,18β)-methyl 3-amino-11-oxoolean-12-en-30oate	759407-80-2	C₃₁H₄₉NO₃	483.735
——	methyl 3-oxo-18βH-olean-12(13)-en-30-oate	39704-69-3	C₃₁H₄₈O₃	468.72
——	methyl (3β)-3-(O-methyl-L-glutamyl)-11-oxo-olean-12-en-30-oate	1332480-71-3	C₃₇H₅₇NO₇	627.862
——	methyl (3β)-3-(O-methyl-L-asparagyl)-11-oxo-olean-12-en-30-oate	1332480-70-2	C₃₆H₅₅NO₇	613.835
——	methyl 2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oate	944832-18-2	C₃₂H₄₃NO₄	505.698
——	dimethyl (3β,3'β)-3,3'-(dithiobis([(2S)-2-amino-1-oxoethane-2,1-diyl]oxy)) bis(11-oxoolean-12-en-30-oate)	1345513-25-8	C₆₈H₁₀₄N₂O₁₀S₂	1173.71
——	methyl 3β-O-[4-(1-piperazinyl)-4-oxobutyryl]-11-oxoolean-12-ene-30-oate	——	C₃₉H₆₀N₂O₆	652.915
——	(2S,4aS,6aR,6bS,8aR,12aS,14aR,14bS)-methyl 11-cyano-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,14,14a,14b-octadecahydropicene-2-carboxylate	1198578-12-9	C₃₂H₄₅NO₄	507.714
——	2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oic acid	944832-16-0	C₃₁H₄₁NO₄	491.671
——	methyl glycyrrhetate α-D-arabinoside	148556-64-3	C₃₆H₅₆O₈	616.836
——	methyl glycyrrhetate α-L-arabinoside	——	C₃₆H₅₆O₈	616.836
——	methyl glycyrrhetate β-D-xyloside	——	C₃₆H₅₆O₈	616.836
——	soloxolone methyl	1032131-00-2	C₃₂H₄₃NO₄	505.698
——	methyl 3β-([S-benzyl-L-cysteinyl]oxy)-11-oxo-olean-12-en-30-oate	1345513-27-0	C₄₁H₅₉NO₅S	677.989
——	methyl (3β)-3-(O-benzyl-L-glutamyl)-11-oxo-olean-12-en-30-oate	1332480-63-3	C₄₃H₆₁NO₇	703.96
——	methyl glycyrrhetinate α-L-rhamnoside	——	C₃₇H₅₈O₈	630.863
——	methyl (3β)-3-(L-alanylamino)-11-oxo-olean-12-en-30-oate	1345513-20-3	C₃₄H₅₄N₂O₄	554.814
——	methyl glycyrrhetate β-D-galactoside	——	C₃₇H₅₈O₉	646.862
——	methyl 3β-(α-D-mannopyranosyloxy)-11-oxo-olean-12-en-30-oate	1547223-30-2	C₃₇H₅₈O₉	646.862
——	methyl (3β)-3-(O-benzyl-L-asparagyl)-11-oxo-olean-12-en-30-oate	1332480-62-2	C₄₂H₅₉NO₇	689.933
——	3β-Acetoxy-11-oxo-Δ^12,18-oleanadien-30-saeure-methylester	17991-71-8	C₃₃H₄₈O₅	524.741
——	glycyrrhetic acid 3-O-β-D-glucopyranoside	——	C₃₆H₅₆O₉	632.835
——	methyl 3β-O-[4-(4-tert-butoxycarbonyl-1-piperazinyl)-4-oxobutyryl]-11-oxoolean-12-ene-30-oate	——	C₄₄H₆₈N₂O₈	753.033
——	3O-Tosyl-18β-glycyrrhetinsaeuremethylester	5999-11-1	C₃₈H₅₄O₆S	638.909
(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-羧基-4,4,6a,6b,8a,11,14b-七甲基-14-氧代-2,3,4a,5,6,7,8,9,10,12,12a,14a-十二氢-1H-苉-3-基]氧基]-3,4,5-三羟基四氢吡喃-2-羧酸	glycyrrhetic acid mono-glucuronide	34096-83-8	C₃₆H₅₄O₁₀	646.819
——	methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate	1345513-15-6	C₄₅H₇₅NO₈Si	786.178
——	methyl 3β-([S-benzyl-N-boc-L-cysteinyl]oxy)-11-oxo-olean-12-en-30-oate	1345513-26-9	C₄₆H₆₇NO₇S	778.106
——	methyl (3β)-3-(([(2L)-(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)thio]acetyl)oxy)-11-oxoolean-12-en-30-oate	1345513-24-7	C₄₄H₆₉NO₉S	788.099

反应信息

作为反应物：

描述：

(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯在 Jones reagent 作用下，以丙酮为溶剂，反应 1.0h，以79%的产率得到(2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR)-2,4a,6a,6b,9,9,12a-Heptamethyl-10,13-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid methyl ester

参考文献：

名称：

Synthesis of methyl 2-cyano-3,12-dioxo-18β-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

摘要：

合成了14种具有不同C环结构的2-氰基-3,12-二氧-18β-油烯-1,9(11)-二烯-30-酸甲酯(CDODO-Me-12，10d)类似物，以确定抑制人白血病HL-60细胞增殖和诱导凋亡的活性基团。C环中需要一个不饱和基团来维持抑制细胞增殖和诱导凋亡的能力。C环中具有9(11),12-二烯的化合物10e显示出了与10d相当的诱导凋亡能力，这与其降低了c-FLIP而非Mcl-1和XIAP的水平有关。与化合物10d相比，化合物10e的耗竭谷胱甘肽能力降低。化合物10e是一种通过不同于化合物10d的作用机制发挥活性的新型活性化合物。

DOI：

10.1039/c4ob00703d
作为产物：

描述：

glycyrrhizic acid 30-O-methyl ester 在硫酸作用下，以 1,4-二氧六环为溶剂，反应 2.0h，以6 mg的产率得到(3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯

参考文献：

名称：

Kitagawa, Isao; Kamigauchi, Toshiyuki; Ohmori, Hidenobu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3078 - 3086

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

作者：Jingjing Wu、Robin M. Bär、Lin Guo、Adam Noble、Varinder K. Aggarwal

DOI：10.1002/anie.201910051

日期：2019.12.19

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton-McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted

描述了一种将脂肪醇转化为硼酸酯的光化学方法。将醇预活化为 2-碘苯基硫代碳酸酯，可实现新型 Barton-McCombie 型自由基脱氧，该自由基脱氧可在可见光照射下有效进行，且无需光催化剂、自由基引发剂或锡或氢化硅。生成的烷基被双（儿茶酚）二硼拦截，从各种结构复杂的醇中提供硼酸酯。
Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives

作者：Gayathri Chadalapaka、Indira Jutooru、Alan McAlees、Tom Stefanac、Stephen Safe

DOI：10.1016/j.bmcl.2008.03.031

日期：2008.4

Derivatives of oleanolic acid, ursolic acid and glycyrrhetinic acid substituted with electron-withdrawing groups at the 2-position in the A-ring which also contains a 1-en-3-one structure are potent inhibitors of cancer cell growth. In this study, we have compared the effects of several 2-substituted analogs of triterpenoid acid methyl esters derived from ursolic and glycyrrhetinic acid on proliferation

齐墩果酸、熊果酸和甘草次酸的衍生物在 A 环的 2 位被吸电子基团取代，其中也包含 1-en-3-one 结构，是癌细胞生长的有效抑制剂。在这项研究中，我们比较了几种衍生自熊果酸和甘草次酸的三萜酸甲酯的 2-取代类似物对 KU7 和 253JB-V 膀胱以及 Panc-1 和 Panc-28 胰腺癌细胞增殖的影响。结果表明，2-氰基和2-三氟甲基衍生物是活性最强的化合物。具有包含 9(11)-en-12-one 结构的重排 C 环的甘草次酸衍生物通常比相应的 12-en-11-one 异构体更具活性。然而，
Scalable and sustainable electrochemical allylic C–H oxidation

作者：Evan J. Horn、Brandon R. Rosen、Yong Chen、Jiaze Tang、Ke Chen、Martin D. Eastgate、Phil S. Baran

DOI：10.1038/nature17431

日期：2016.5.5

transformation, the majority of conditions still use highly toxic reagents (based around toxic elements such as chromium or selenium) or expensive catalysts (such as palladium or rhodium). These requirements are problematic in industrial settings; currently, no scalable and sustainable solution to allylic oxidation exists. This oxidation strategy is therefore rarely used for large-scale synthetic applications

C-H 键直接功能化的新方法和策略开始重塑逆合成分析领域，影响天然产物、药物和材料的合成。由于烯酮和烯丙醇作为多功能中间体的实用性，以及它们在天然和非天然材料中的普遍性，烯丙基系统的氧化在这方面发挥了重要作用，可能是应用最广泛的 C-H 官能化。烯丙基氧化在数百种合成中具有特色，包括一些被视为“经典”的天然产物合成。尽管多次尝试提高这种转换的效率和实用性，大多数条件仍然使用剧毒试剂（基于有毒元素，如铬或硒）或昂贵的催化剂（如钯或铑）。这些要求在工业环境中是有问题的；目前，不存在可扩展和可持续的烯丙基氧化解决方案。因此，这种氧化策略很少用于大规模合成应用，限制了工业科学家采用这种逆合成策略。在这里，我们描述了一种电化学 C-H 氧化策略，它具有广泛的底物范围、操作简单性和高化学选择性。它使用廉价且容易获得的材料，并代表可扩展的烯丙基 C-H 氧化（以 100 克为单位证明），
Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents

作者：Chun-hui Zhao、Cui-li Zhang、Jin-jie Shi、Xi-yan Hou、Bin Feng、Long-xuan Zhao

DOI：10.1016/j.bmcl.2015.08.076

日期：2015.10

A series of pentacyclic triterpenoids derivatives bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety has been synthesized and investigated for their potential antiproliferative activities. Pentacyclic triterpenoids derivative compounds were synthesized by a four or six step synthetic procedure. The activity studies were evaluated using Cell Counting Kit-8 method, and Western blotting analysis on A549

合成了一系列带有O- [4-（1-哌嗪基）-4-氧代-丁酰基部分的五环三萜衍生物，并研究了它们潜在的抗增殖活性。五环三萜类化合物的衍生物是通过四步或六步合成程序合成的。使用Cell Counting Kit-8方法评估活性研究，并对A549细胞，MCF-7细胞和Hela细胞进行Western印迹分析。化合物3-O- [4-（1-哌嗪基）-4-氧代-丁酰基] olean-12-ene-28-oate（OA-4）和化合物2-O- [4-（1-哌嗪基）-发现4-氧代-丁酰基] -3，23-二羟基urs-12-烯-28-油酸酯（AA-5）是有前途的抗增殖剂。这些化合物显示出进一步优化作为抗肿瘤药物的潜力。
Synthesis, Characterization and In Vitro Evaluation of Self-Assembled poly(ethylene glycol)-glycyrrhetinic Acid Conjugates

作者：Gu He、Zhiyao He、Xi Zheng、Junmin Li、Chi Liu、Xiangrong Song、Liang Ouyang、Fengbo Wu

DOI：10.2174/157017812800167448

日期：2012.3.1

Glycyrrhetinic acid (GA) is a commonly used drug for the chemotherapy of Chronic Hepatitis B, allergic dermatitis, inflammation, etc. But some problems such as poor water-solubility, low bioavailability and short plasma halflife, have limited its use. In the present study, PEGylation derivatives of GA derivatives were synthesized and characterized by FTIR, NMR, transmission electron microscopy, particle size analysis, etc. The PEG-GA conjugates having a critical micelle concentration of 0.081-0.73 mg/mL were used to form nano-sized micelles, with mean diameters of 120.86 ± 31.74 nm. The physico-chemical properties of the PEG – GA conjugate were evaluated including stability, cellular toxicity, and drug release profile. All the conjugates synthesized showed good stabilities in acidic and neutral solutions, while the stability in alkaline solution and the enzymatic hydrolysis rate, were significantly affected by the linkage between the GA and PEG chain. The results demonstrate that, by PEGylation of GA derivatives, the greatly increased water solubility and desirable self-assembly abilities of PEG-GA were obtained. The novel conjugates have potential medical applications for intravenously delivery of insoluble drug delivery.

甘草次酸(GA)是一种常用于慢性乙型肝炎、过敏性皮炎、炎症等化疗的药物。然而，其水溶性差、生物利用度低和血浆半衰期短等问题限制了其应用。在本研究中，GA的PEG化衍生物通过FTIR、NMR、透射电子显微镜、粒径分析等方法进行了合成和表征。PEG-GA共轭物具有0.081-0.73 mg/mL的临界胶束浓度，用于形成纳米尺寸的胶束，平均直径为120.86 ± 31.74 nm。评估了PEG-GA共轭物的物理化学性质，包括稳定性、细胞毒性和药物释放曲线。所有合成的共轭物在酸性和中性溶液中均显示出良好的稳定性，而在碱性溶液中的稳定性和酶解速率则显著受到GA与PEG链之间连接的影响。结果表明，通过PEG化GA衍生物，获得了显著增加的水溶性和理想的自我组装能力。这种新型共轭物具有通过静脉输注不可溶药物的潜在医疗应用。