CAS: 5289-74-7; (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-En-6-One

该化合物是自然形成的植物类动物,其结构类似于昆虫缠绕激素,广泛研究其在内分泌学,发育生物学和代谢研究中的潜在应用.Crustecdysone具有很高的生物利用率和稳定性,使它成为调查节肢动物生长调节和应激反应的宝贵化合物.它在调制细胞类受体途径中的作用也引起了药理学研究的兴趣.该化合物通常与植物来源隔离,确保实验用途的纯度和一致性.研究人员对Crustecdysonesone在模型生物中诱发摩托和变形的能力给予了价值,为激素信号机制提供了见解.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

20-hydroxyecdysone-2,3,22-triacetate 22-Dehydro-20-hydroxyecdysone (20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one (20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-onePoststerone 20-Hydroxyecdysone-2-acetate 20-Hydroxyecdysone-22-acetate 20-hydroxyecdysone 2,3-diacetate

合成工艺路线路线简述

  • 合成目标产物 Hydroxyecdysone 主要起始原料 Turkesterone
  • (文献来源)合成步骤主要原料 Turkesterone
蜕皮激素置于ecdysone 20-Monooxygenase,氧气,还原型辅酶ii(Nadph)四钠盐体系中,化学反应生成 蜕皮激素
参考文献:蜕皮激素 20-单加氧酶,一种来自菠菜,菠菜的细胞色素 P450 酶
标题:蜕皮激素 20-单加氧酶,一种来自菠菜,菠菜的细胞色素 P450 酶
摘要:从 25 天龄菠菜的第一片叶子中分离出的微粒体制剂催化蜕皮激素的羟基化,产生昆虫蜕皮激素 20-羟基蜕皮激素.羟基化依赖于 Nadph 和分子氧,并被一氧化碳抑制.一氧化碳抑制是部分可逆的白光.菊芋 Nadph-细胞色素 P450 还原酶的多克隆抗体抑制羟基化反应以及菠菜微粒体 Nadph 细胞色素 C 还原酶.这些结果共同确定了作为菠菜中细胞色素 P450 依赖性反应的蜕皮激素羟基化,已知菠菜可合成大量植物蜕皮激素.
DOI:10.1016/0031-9422(96)00094-5

海关参考信息

专利信息


专利号:WO-2025056767-A1
优先权日:2023-09-15
标题 :Process for the preparation of enantiomerically enriched aliphatic amines
发明人:BOU HAMDAN FARHAN; GODINEAU EDOUARD; SMEJKAL TOMAS; DUMEUNIER RAPHAEL; BOUSSEMGHOUNE MOHAMED ABDELOUAHAB; BLUM MATHIAS
权利人:SYNGENTA CROP PROTECTION AG
摘要:The present invention relates to a process for the preparation of enantiomerically enriched cyclobutylamines of formula (I) from α-tertiary cyclobutanones and reacting said enantiomerically enriched cyclobutylamines to enantiomerically enriched cyclobutylamides. Such compounds are useful intermediates in the synthesis of microbiocidal thiazole compounds.

专利号:US-8293797-B2
优先权日:2004-02-19
标题:Use of molt-accelerating compounds, ecdysteroids, analogs thereof, and chitin synthesis inhibitors for controlling termites
发明人:SU NAN-YAO; KING JAMES EDWARD; NEESE PAUL ALLEN
权利人:SU NAN-YAO; KING JAMES EDWARD; NEESE PAUL ALLEN; UNIV FLORIDA
摘要:The subject invention relates in part to the oral administration of ecdysteroids for controlling subterranean termites. Preferred ecdysteroids for use according to the subject invention are ecdysone, certain ecdysone analogs, and 20-hydroxyecdysone, for example. In some preferred embodiments, one or more of these compounds is used in a termite bait in combination with one or more chitin synthesis inhibitors. Thus, the subject invention also relates in part to controlling termites by the use of a chitin synthesis inhibitor (CSI), such as hexaflumuron and/or noviflumuron, together with an ecdysteroid (and analogs thereof) or molt-accelerating compound (MAC), such as halofenozide. The subject invention also relates to mixtures comprising these two active ingredients. The MAC/ecdysteroid analog induces a preliminary molting event in termite workers (they could not complete the molting), which then allows the CSI to further disrupt the molt and cause mortality. The combination of these active ingredients, causing accelerated molting together with inhibition of chitin synthesis, is surprisingly shown herein to enhance activity against termites, as compared to either group of compounds alone.

专利号:US-5747538-A
优先权日:1994-03-18
标 题 :Use of ginsenoside R0 or a plant extract containing same to promote collagen synthesis
发明人:MEYBECK ALAIN; BONTE FREDERIC; DUMAS MARC; CHAUDAGNE CATHERINE
权利人:LVMH RECH
摘要:PCT No. PCT/FR95/00326 Sec. 371 Date Sep. 18, 1996 Sec. 102(e) Date Sep. 18, 1996 PCT Filed Mar. 17, 1995 PCT Pub. No. WO95/25524 PCT Pub. Date Sep. 28, 1995The use of ginsenoside R0 or a plant extract containing same to prepare a cosmetic or pharmaceutical composition, particularly a skin care composition, for promoting collagen synthesis, particularly collagen I and/or collagen III synthesis. Said cosmetic or pharmaceutical composition is administered to a mammal, particularly a human being, in order to promote collagen synthesis. A method for promoting collagen synthesis in fibroblast growth media is also disclosed.

专利号:US-9468207-B2
优先权日:2012-04-12
标 题 :Insecticide and acaricide paints that inhibit chitin synthesis, regulate insect juvenile hormone and repel arthropods, for controlling endemic diseases, pests and allergens
发明人:MATEO HERRERO MARIA PILAR
权利人:MATEO HERRERO MARIA PILAR
摘要:The present invention relates to insecticide and acaricide paints that inhibit chitin synthesis, regulate insect juvenile hormone and repel arthropods, for controlling endemic diseases, pests and allergens. The paints comprise at least the following compounds (in any combination): 1%-100% water, 0.0001%-20% insecticides, 0.0001%-20% chitin inhibitor, 0.0001%-20% juvenile hormone regulator, 1%-50% polymers, 0%-40% pigments, 0%-60% fillers, 0%-60% natural repellents, and 0.01%-20% stabilizers. The composition of the paints allows the active ingredients to be encapsulated in an aqueous polymer with or without the incorporation of fillers and pigments, and therefore the range of use thereof is increased.

专利号:US-2014274978-A1
优先权日:2013-03-15
标题 :Phytosterol spirostane and spirostene derivatives having a wide variety of utilities in humans and other animals
发明人:FASCIOLA ANDRE ARMEL
权利人:FASCIOLA ANDRE ARMEL
摘要:The present invention utilizes phytosterol, phytoecdysteroid, sapogenin, triterpene, terpene, spirostane, spirostene and androstene derivative compounds to provide a wide variety of utilities to humans and other animals. The compounds and methods provide numerous and wide-ranging benefits including biochemical and constructive metabolic benefits including increases in protein synthesis and synthesis efficiency, ergogenic, adaptogenic, cosmetic and medicinal skin agents and veterinary utilities. The compounds provide agents that increase physical endurance and work output, act as a general tonic for increasing health and vigor, increase sleep time and sleep efficiency and act as rejuvenating agents to reverse the effects of fatigue and stress. Novel utilities for pet, farm, zoo and companion animals are also provided.

专利号:WO-2021074309-A1
优先权日:2019-10-16
标 题:1-(3-quinolyl)-3,4-dihydroisoquinoline derivatives as fungicides for combating specific phytopathogens
发明人:WEISS MATTHIAS; QUARANTA LAURA; BOU HAMDAN FARHAN; MAHAJAN ATUL; WILLIAMS SIMON; KILARU JAGADEESH; SEN INDIRA; BIERI STEPHANE; DIGGELMANN MARTIN
权利人:SYNGENTA CROP PROTECTION AG
摘要:1-(3-quinolyl)-3,4-dihydroisoquinoline derivatives of formula (I) as well as a method of combating, preventing or controlling the phytopathogens Mycosphaerella graminicola (Septoria tritici), Fusarium culmorum, Gibberella zeae (Fusarium graminearum) and Monographella nivalis (Microdochium nivale), which comprises applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to propagation material thereof, a fungicidally effective amount of a 1-(3-quinolyl)-3,4-dihydroisoquinoline derivative of formula (I). The present description discloses the synthesis of exemplary compounds, formulation examples, relevant biological data (antifungal activity against Mycosphaerella graminicola (Septoria tritici), Fusarium culmorum, Gibberella zeae (Fusarium graminearum) and Monographella nivalis (Microdochium nivale) when spayed on plants), as well as comparative data against three prior art compounds (e.g. pages 52 to 85; formulation examples; examples A1 to A3; table E; compounds E.01 to E.187; biological examples). Exemplary compounds are e.g.: 5-bromo-1-(8-fluoro-3-quinolyl)spiro[4H-isoquinoline-3,1'- cyclopropane] (example A1) 5-bromo-1-(8-fluoro-3-quinolyl)-3,3-dimethyl-4H-isoquinoline (example A2) 1-(8-fluoro-3-quinolyl)-3,3-dimethyl-4H-isoquinoline-5-carbonitrile (example A3)
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主要参考文献


1: CahlÃková L, Macáková K, Chlebek J, Host'álková A, Kulhánková A, Opletal L. Ecdysterone and its activity on some degenerative diseases. Nat Prod Commun. 2011 May;6(5):707-18. Review.

合成参考文献


参考文献:10.1186/1472-6793-11-11
摘要:DePina AS, Iser WB, Park SS, Maudsley S, Wilson MA, Wolkow CA. Regulation of Caenorhabditis elegans vitellogenesis by DAF-2/IIS through separable transcriptional and posttranscriptional mechanisms. BMC Physiol. 2011 Jul 12;11():11.
参考文献:10.1016/j.abb.2011.06.011
摘要:Kayser H, Eilinger P, Piechon P, Wagner T. C-26 vs. C-27 Hydroxylation of insect steroid hormones: Regioselectivity of a microsomal cytochrome P450 from a hormone-resistant cell line. Archives of Biochemistry and Biophysics. 2011 Sep;513(1):27–35. doi: 10.1016/j.abb.2011.06.011.
参考文献:10.1007/s00359-011-0667-0
摘要:Penick CA, Liebig J, Brent CS. Reproduction, dominance, and caste: endocrine profiles of queens and workers of the ant Harpegnathos saltator. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2011 Nov;197(11):1063–71. doi: 10.1007/s00359-011-0667-0.
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