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芸苔素内酯

芸苔素内酯

CAS号：72962-43-7
英文名：brassinolide
分子式
C28H48O6
熔点
200-204ºC
密度
1.141 g/cm3
分子量
480.677
沸点
633.7ºC at 760 mmHg
溶解度
信号词
危险品标志
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化合物简介
Brassinolide is a plant hormone. The first isolated brassinosteroid, it was discovered when it was shown that pollen from rapeseed (Brassica napus) could promote stem elongation and cell division. The biologically active component was isolated and named brassinolide.
基本信息
中文名称
芸苔素内酯
英文名称
brassinolide
中文别名
油菜素内酯、2α,3α,22R-四羟基-24-S-构型甲基-β-高-7-氧杂-5α胆淄烷-6酮
英文别名
cis,cis-1,6-Dioxa-3,8-cyclodecadien、Brassinolide、(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one、1,6-Dioxacyclodeca-3,8-dien、brassinosteroid、1,6-dioxa-cyclodeca-3,8-diene、(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-3H-benzo[c]indeno[5,4-e]oxepin-3-one
CAS号
72962-43-7
分子式
C28H48O6
分子量
480.677
精确质量
480.345
PSA
107.22
LOGP
3.39
编号系统
UNII
Y9IQ1L53OX
物化性质
密度
1.141 g/cm3
沸点
633.7ºC at 760 mmHg
熔点
200-204ºC
储存条件
-20ºC
安全信息
WGK Germany
3
生产方法及用途
生产方法
1.本品最初是从油菜花粉中提取精制出来的。自美国农业部犕犻狋犮犺犲犾犾的研究小组确定其结构后，1985年开始进行合成。云苔素内酯由麦角甾醇通过甲磺酰化反应制得麦角甾醇甲磺化物，水解得异麦角甾醇，氧化反应制得相应的烯酮，还原制得酮，开环得二烯酮，羟基化得四羟基酮，扩环制得云苔素内酯，反应过程：
用途
芸苔素内酯为甾醇类植物激素。20世纪80年代初期，首先从油菜花粉中提取精制出来。由于它在很低浓度下，能明显地增加植物的营养体生长和促进受精作用，因而受到广泛注意。迄今为止，人们已从几十种植物体中分离鉴定出这类化合物。植物的各个阶段的生长发育是受自身的激素控制和调节的。鉴于目前的五大类植物内源激素不足以解释植物生长发育的全部过程，因此，人们普遍认为芸苔素是新的一类植物激素。加之芸苔素内酯的化学结构与动物性激素极其近似，因此，它在植物生殖生理中的作用引起人们越来越多的兴趣。在上述工作的基础上，人们发现24-表芸苔素内酯使作物增产作用较其他天然芸苔素内酯更高。目前在农业生产上使用的便是24－表芸苔素内酯的化学复制品。油菜素内酯(Brassinolide，简称BR)是一个具有高生理活性促进植物生长作用的甾体化合物。油菜素内酯的发现和极高的生理活性可以说是植物生长调节物质研究的一个新的里程碑。经过多年研究，科学家们发现油菜素内酯类化合物是广泛存在于许多植物体中的一类天然甾体化合物。植物的各种器官如花(花粉)、种子、根茎和叶中均曾发现油莱素内酯类化合物。目前该类化合物已发现18个。油菜素内酯的处理浓度极低，一般10-1～10-5(mg/L)就显示强大的生理活性。其主要特点：促进作物生长，增加营养体收获量；提高坐果率，促进果实肥大；提高结实率，增加千粒重；提高作物的耐冷性，减轻药害，增加抗病性。
合成路线
(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-2,3-dihydroxy-10,13-dimethylhexadecahydro-6H-cyclopenta[a]phenanthren-6-one
83066-72-2
(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-2,3-dihydroxy-10,13-dimethylhexadecahydro-6H-cyclopenta[a]phenanthren-6-one
芸苔素内酯
72962-43-7
芸苔素内酯
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
146205-07-4
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
上游原料
共找到37个上游原料 >
(3S,5S,6S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-6-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzenesulfonate
75608-29-6
(3S,5S,6S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-6-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzenesulfonate
(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol
103881-47-6
(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol
(22R,23R,24S)-22,23-isopropylidenedioxy-24-methyl-5α-cholest-2-en-6-one
83066-71-1
(22R,23R,24S)-22,23-isopropylidenedioxy-24-methyl-5α-cholest-2-en-6-one
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1R,2S)-1-hydroxy-1-((R)-3-isopropyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl)-8,8,10a,12a-tetramethylhexadecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one
174656-34-9
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1R,2S)-1-hydroxy-1-((R)-3-isopropyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl)-8,8,10a,12a-tetramethylhexadecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one
(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol
148705-11-7
(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol
1-溴-3-甲基-2-丁酮
19967-55-6
1-溴-3-甲基-2-丁酮
上游原料
(3S,5S,6S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-6-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzenesulfonate (22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol (22R,23R,24S)-22,23-isopropylidenedioxy-24-methyl-5α-cholest-2-en-6-one (1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1R,2S)-1-hydroxy-1-((R)-3-isopropyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl)-8,8,10a,12a-tetramethylhexadecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one (2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol 1-溴-3-甲基-2-丁酮 4-(1-methylethyl)furan-2(5H)-one (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-2,3-dihydroxy-10,13-dimethylhexadecahydro-6H-cyclopenta[a]phenanthren-6-one 3-甲基-2-丁酮 (2R,3S,24S)-2,3-isopropylidenedioxy-24-ethyl-6,6-ethylenedioxy-5α-cholestan-22(E)-ene (2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol (22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide (3S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (2S,3R,4R,5S)-2-((3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-5,6-dihydroxy-7a,9a-dimethyl-3-oxohexadecahydro-1H-benzo[c]indeno[5,4-e]oxepin-10-yl)-5,6-dimethylheptane-3,4-diyl diacetate (20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde (2R,3S,5α,22R)-23,24-epoxy-6,6-(ethylenedioxy)-2,3-(isopropylidenedioxy)-26,27-dinorcholestan-22-ol 1-(acetyloxy)-3-methyl-2-butanone (2R,3S,22S)-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholest-23-yne (20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde (S)-3-((4R,5R)-2,2-dimethyl-5-((S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxohexadecahydro-1H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-1-yl)ethyl)-1,3-dioxolan-4-yl)-4-methylpentanal (22R,23R,24S)-22,23-diacetoxy-2β,3β-isopropylidenedioxy-5α-ergostan-6-one (1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((2R,3S)-3-isopropyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one (1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((2S,3S,4S,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl)-8,8,10a,12a-tetramethylhexadecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one (22E)-3α,5-cyclo-5α-24-ethylcholest-22-en-6-one (22R,23R,24S)-3β-bromo-22,23-diacetoxy-5α-ergostan-6-one (3S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzenesulfonate (22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one (22E,24S)-5α-stigmasta-2,22-dien-6-one (2R,3S,22R)-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholest-23-yne (22R,23R,24S)-22,23-diacetoxy-24-methyl-5α-cholest-2-en-6-one (2R,3S,22R,23S,24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane (22R,23R,24S)-22,23-dihydroxy-24-methyl-5α-cholestan-3,6-dione (1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((S)-1-((4R,5R)-2,2-dimethyl-5-((S)-3-methylbutan-2-yl)-1,3-dioxolan-4-yl)ethyl)-8,8,10a,12a-tetramethylhexadecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one (2R,3S,22R,23Z)-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholest-23-ene 油菜素甾酮 2,3,22,23-tetra-O-acetylcastasterone 2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
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