24-hydroxychol-4-en-3-one | 17597-30-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 24-hydroxychol-4-en-3-one
• 英文别名: 3-oxochol-4-en-24-ol；24hydroxychol-4-en-3-one；24-Hydroxychola-4-ene-3-one；(8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 17597-30-7
• 化学式: C₂₄H₃₈O₂
• 分子量: 358.565
• InChiKey: QJKBUSGUNXZSRG-SVYVOUITSA-N

物化性质

• 沸点：
  488.3±14.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24-hydroxychol-4-en-3-one 在 咪唑 、 lithium amide 、 叔丁醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 24-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4α-(2-propenyl)-5α-cholan-3-one
  参考文献：
  名称：

  Synthesis and in vitro biological activity of 4α-(2-propenyl)-5α-cholest-24-en-3α-ol: A 24,25-dehydro analog of the hypocholesterolemic agent 4α-(2-propenyl)-5α-cholestan-3α-ol

  摘要：

  4 alpha-(2-Propenyl)-5 alpha-cholestan-3 alpha-ol (LY295427) was previously identified from a Chinese hamster ovary (CHO) cell-based low density lipoprotein receptor/luciferase (LDLR/Luc) assay to be a potent transcriptional activator of the LDL receptor promoter in the presence of 25-hydroxycholesterol. To investigate the effect of the 24,25-unsaturation in the D-ring side chain (desmosterol D-ring side chain) on antagonizing the repressing effect of 25-hydroxycholesterol, 4 alpha-(2-propenyl)-5 alpha-cholest-24-en-3 alpha-ol (17), a 24,25-dehydro analog of LY295427, was thus synthesized from lithocholic acid via the formation of 3 alpha-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-4 alpha-(2-propenyl)-5 alpha-cholan-24-al (15). Test results showed that 17 had an EC30 value of 2.6 mu M, comparable to 2.9 mu m of LY295427, in the CHO cell-based LDLR/Luc assay in the presence of 25-hydroxycholesterol. Apparently, the built-in 24,25-unsaturation in the D-ring side chain of 17 had added little effect to antagonizing the repressing effect of 25-hydroxycholesterol. In the [1-C-14-acetate]cholesterol biosynthesis inhibition assay, 17 at 10 mu g/ml (23 mu M) has been shown to inhibit the cholesterol biosynthesis in CHO cells by 38% relative to the vehicle control; whereas LY295427 showed no inhibition in the same assay in our previous studies. In contrast to LY295427, the built-in 24,25-unsaturation in the D-ring side chain of 17 has conferred an inhibitory effect on cholesterol biosynthesis in CHO cells. In summary, the observed LDL receptor promoter activity of 17 is related to its ability to prevent 25-hydroxycholesterol from exerting the repressing effect via an undetermined mechanism and, in part, to inhibit the cholesterol biosynthesis. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(98)00083-x
• 作为产物：
  描述：

  石胆酸 在 盐酸 、 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 、 lithium chloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成 24-hydroxychol-4-en-3-one
  参考文献：
  名称：

  Synthesis and in vitro biological activity of 4α-(2-propenyl)-5α-cholest-24-en-3α-ol: A 24,25-dehydro analog of the hypocholesterolemic agent 4α-(2-propenyl)-5α-cholestan-3α-ol

  摘要：

  4 alpha-(2-Propenyl)-5 alpha-cholestan-3 alpha-ol (LY295427) was previously identified from a Chinese hamster ovary (CHO) cell-based low density lipoprotein receptor/luciferase (LDLR/Luc) assay to be a potent transcriptional activator of the LDL receptor promoter in the presence of 25-hydroxycholesterol. To investigate the effect of the 24,25-unsaturation in the D-ring side chain (desmosterol D-ring side chain) on antagonizing the repressing effect of 25-hydroxycholesterol, 4 alpha-(2-propenyl)-5 alpha-cholest-24-en-3 alpha-ol (17), a 24,25-dehydro analog of LY295427, was thus synthesized from lithocholic acid via the formation of 3 alpha-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-4 alpha-(2-propenyl)-5 alpha-cholan-24-al (15). Test results showed that 17 had an EC30 value of 2.6 mu M, comparable to 2.9 mu m of LY295427, in the CHO cell-based LDLR/Luc assay in the presence of 25-hydroxycholesterol. Apparently, the built-in 24,25-unsaturation in the D-ring side chain of 17 had added little effect to antagonizing the repressing effect of 25-hydroxycholesterol. In the [1-C-14-acetate]cholesterol biosynthesis inhibition assay, 17 at 10 mu g/ml (23 mu M) has been shown to inhibit the cholesterol biosynthesis in CHO cells by 38% relative to the vehicle control; whereas LY295427 showed no inhibition in the same assay in our previous studies. In contrast to LY295427, the built-in 24,25-unsaturation in the D-ring side chain of 17 has conferred an inhibitory effect on cholesterol biosynthesis in CHO cells. In summary, the observed LDL receptor promoter activity of 17 is related to its ability to prevent 25-hydroxycholesterol from exerting the repressing effect via an undetermined mechanism and, in part, to inhibit the cholesterol biosynthesis. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(98)00083-x

文献信息

• Skin anti-ageing composition
  申请人：Conopco, Inc.

  公开号：US10406091B2

  公开（公告）日：2019-09-10

  The invention relates to a skin anti-ageing composition. In particular a skin anti-ageing composition comprising myricetin or glycoside thereof, and at least one LXR alpha agonist. By skin ageing is meant the appearance or manifestation of any one or more of wrinkles or sagging, poor skin barrier such as dryness, scalp itch, or uneven skin tone such as age spots.

  本发明涉及一种皮肤抗衰老组合物。特别是一种皮肤抗衰老组合物，它包含有杨梅素或其苷，以及至少一种 LXR alpha 激动剂。皮肤老化是指皱纹或松弛、皮肤屏障不良（如干燥）、头皮瘙痒或肤色不均（如老年斑）等任何一种或多种现象的出现或表现。
• Hair composition
  申请人：Conopco, Inc.

  公开号：US10456344B2

  公开（公告）日：2019-10-29

  Disclosed is an oral or topical composition comprising a nuclear factor erythroid-2 related factor 2 agonist and a liver X receptor agonist, wherein the amounts of each of the nuclear factor erythroid-2 related factor 2 agonist and the liver X receptor agonist produce a synergistic benefit of hair fiber growth, wherein the oral or topical composition comprises ≤9, preferably ≤8% w/w β-sitosterol, wherein when the oral or topical composition comprises a catechin, the oral or topical composition comprises 0.001 to 90, preferably 0.005 to 70, most preferably 0.01 to 50% w/w catechins, wherein the oral or topical composition excludes pregnenolone, 4, 5-dihydrofuranodiene-6-one, epoxy santamarin, hydroquinone, longistyline, monacolin K, protoanemonin, N-(2,2,2-tri-fluoro-ethyl)-N-[4-(2,2,2-tri-fluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-benzenesulfonamide, dihydronepetalactone, iridomyrmecin, and dihydroactinidiolide, wherein when the oral or topical composition comprises guggelsterone and epigallocatechin gallate, the oral or topical composition excludes a guggelsterone to epigallocatechin gallate weight ratio of 1 to 28, and wherein when the oral or topical composition comprises sodium dilauramide glutamide lysine, the oral or topical composition excludes 0.3% w/w sodium dilauramide glutamide lysine.

  公开了一种口服或外用组合物，该组合物包含核因子红细胞生成素-2 相关因子 2 激动剂和肝 X 受体激动剂，其中核因子红细胞生成素-2 相关因子 2 激动剂和肝 X 受体激动剂各自的用量对毛发纤维生长产生协同益处，其中口服或外用组合物包含 ≤9% w/w，优选 ≤8% w/w β-谷甾醇，其中当口服或外用组合物包含儿茶素时，口服或外用组合物包含 0.001至90，优选0.005至70，最优选0.其中口服或外用组合物不包括孕烯醇酮、4, 5-二氢呋喃二烯-6-酮、环氧山奈酚、对苯二酚、龙胆紫、莫那可林 K、原橙皮甙、N-(2,2,2-三氟-乙基)-N-[4-(2,2,2-三氟-1-羟基-1-三氟甲基乙基)-苯基]-苯磺酰胺、二氢吡咯内酯、鸢尾霉素和二氢吡咯内酯、其中，当口服或外用组合物包含钩藤甾酮和表没食子儿茶素没食子酸酯时，口服或外用组合物排除钩藤甾酮与表没食子儿茶素没食子酸酯的重量比为1比28，并且其中，当口服或外用组合物包含二月桂酰胺谷酰胺赖氨酸钠时，口服或外用组合物排除0.3% w/w 的二月桂酰胺谷酰胺赖氨酸钠。
• Enhancing epidermal barrier development in skin
  申请人：Unilever Home & Personal Care USA, Division of Conopco, Inc

  公开号：US20030124159A1

  公开（公告）日：2003-07-03

  The invention relates to the field of skin compsitions and to the identification of novel effects of molecules when incorporated into a skin composition. More particularly the invention relates to systemic or topical compositions and their use in providing a variety of skin care benefits by enhancing the development of a healthy epidermal barrier layer in the skin through the activation of the nuclear receptor LXR&agr;.

  本发明涉及皮肤组合物领域，以及鉴定分子加入皮肤组合物后的新作用。更具体地说，本发明涉及全身或局部组合物及其用途，通过激活核受体 LXR&agr;，促进皮肤表皮屏障层的健康发展，从而提供各种皮肤护理功效。
• ENHANCING EPIDERMAL BARRIER DEVELOPMENT IN SKIN
  申请人：UNILEVER PLC

  公开号：EP1432399A1

  公开（公告）日：2004-06-30
• SKIN TREATMENTS
  申请人：UNILEVER PLC

  公开号：EP1624853A2

  公开（公告）日：2006-02-15