(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione

• ChemBase编号: 72956
• 分子式: C26H30O8
• 平均质量: 470.5116
• 单一同位素质量: 470.19406792
• SMILES: C1(=O)O[C@H]([C@]2([C@]3([C@@H]1O3)[C@]1([C@H](CC2)[C@]23[C@@H](CC1=O)C(O[C@H]2CC(=O)OC3)(C)C)C)C)c1cocc1
• Canonical SMILES: O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C
• InChI: InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
• InChIKey: KBDSLGBFQAGHBE-MSGMIQHVSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione; (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^2,^7.0^2,^1^0.0^1^4,^1^6.0^1^4,^2^0]docosane-5,12,17-trione; (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0?,?.0?,??.0??,??.0??,??]docosane-5,12,17-trione
• IUPAC传统名: limonin
• 别名: Limonin; Limonin; limonoate D-ring-lactone; limonoic acid di-delta-lactone; Limonoic acid 3,19:16,17 dilactone

登记号

• CAS号: 1180-71-8
• MDL号: MFCD00075922
• PubChem SID: 162037876; 24896458
• PubChem CID: 179651
• CHEBI ID: 16226
• Chemspider ID: 156367
• 维基百科标题: Limonin

理论计算性质

• Acid pKa: 17.60684
• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): 2.4571912
• LogD (pH = 7.4): 2.4571912
• Log P: 2.4571912
• 摩尔折射率: 114.7192 cm^3
• 极化性: 46.453953 Å^3
• 极化表面积: 104.57 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Powder
• 熔点: 298-300°C

安全信息

• 保存条件: -20°C; 2-8°C
• 德国WGK号: 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: >90% (HPLC)
• 成盐信息: Free Base
• 生物来源: from citrus seeds

详细说明

MP Biomedicals - 02193765

From Citrus Seeds
A natural compound found in grapefruit and other citrus seeds. It has been shown to inhibit chemically induced carcinogenesis and demonstrates anti-feedant properties.

Selleck Chemicals - S2319

Research Area: Inflammation
Biological Activity:
Limonin is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones. [1]

Sigma Aldrich - L9647

Biochem/physiol Actions
Limonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. It has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. It also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.
General description
Limonin may be used in assays to quantify limonin in citrus products. It may also be used in other assays as a control, standard, or competitor or in studies on the physiology, metabolism, and biosynthesis of limonin.

参考文献

• Altieri, M.A., et al., Protect. Ecol. , 6 : 91, (1984).
• http://en.wikipedia.org/wiki/Limonin