CAS: 2052-63-3; (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-Trimethylcyclohex-1-En-1-yl)Nona-2,4,6,8-Tetraen-1-Ol

该化合物是维生素A的衍生物,在视觉和生物过程方面起着关键作用,其特点是分子结构,包括一个混合的双联体系统,有助于其光吸收特性;该化合物是全转异异醇的立体异构体,其结构在第13个碳位置的双联体上有所不同.13-cis-Retinol通常是一种黄色至橙晶状固体,在有机溶剂中可溶解,但在水中则不那么明显.它对光和氧很敏感,这可能导致降解,使其在暗的,空气密的条件下储存起来非常重要.在生物系统中,13-cis-retinol可转换为11-cis-retinal,这是视觉循环中的一个关键组成部分,有助于将光转换成视像信号.此外,还研究了其在皮肤学和肿瘤学中的潜在治疗应用,特别是其对于细胞分化和扩散的影响.

英文名称(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-Trimethylcyclohex-1-En-1-yl)Nona-2,4,6,8-Tetraen-1-Ol
中文名称13-顺式视黄醇
IUPAC名称(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
其它别名(13Z)-Retinol; 13-cis-Retinol; 13-cis-Vitamin A; Neovitamin A; Neovitamin A1; neo-Retinol
CAS编号2052-63-3
MFCD编号:MFCD00079548
EINECS号:633-789-0
FDA UNII编号:J72YRO1DWF
分子式:C20H30O分子量:286.46
产品CID: 1040200
产品分类有机原料 → 脂质和类脂质分子 → 异戊烯醇脂质

相似结构搜索
InChIKey: FPIPGXGPPPQFEQ-HWCYFHEPSA-N
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
计算化学: 氢键受体数1.0氢键供体数1.0可旋转键数5.0

物理性质

熔点58-60°
沸点421.2 °C at 760 mmHg
闪点147.3 °C
密度0.954 g/cm 3
pKa:14.09±0.10(预测)
PSA:20.23
LogP:5.5103
折射率1.549
蒸汽压0mmHg at 25°C
溶解性Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
外观形态淡黄色至黄色固体
储存条件-20°C

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别皮肤腐蚀/刺激类别2
警示词Warning(警告)
危险描述H315 |造成皮肤刺激.
防范说明P264-P280-P302+P352-P321-P332+P313-P362
危险品标志Xi
安全声明22-36/37
危险类别码38

欧盟法规

C&L通报

上下游产品

合成工艺路线路线简述

📜维生素a置于wilkinson'S Catalyst,三乙胺体系中,用正己烷用作溶剂,化学反应 20.0H,以10%的收率获得13-顺式视黄醇
参考文献:9-顺式-类维生素a的催化合成:机理见解.
标题:9-顺式-类维生素a的催化合成:机理见解.
摘要:热力学稳定的全反式类维生素a的区域选择性z异构化仍然具有挑战性,并最终限制了治疗人类疾病急需的疗法的可用性.我们在这里提出了一种使用传统热处理或微波辐射催化类视黄醇 Z 异构化的新颖,简单的方法.通过筛选 20 种过渡金属催化剂,确定了区域选择性生产 Z-类维生素a 的最佳方法.最有效的催化系统由具有不稳定配体的钯配合物组成.多项机理研究,包括同位素 H/d 交换和使用耦合簇方法的最先进的量子化学计算表明,异构化是由催化剂二聚引发的,随后形成环状六元氯钯酸催化剂-底物加合物,最终打开生成所需的 Z 异构体.这里描述的合成开发,结合对基础化学的彻底机械分析,强调了以简单的形式使用现成的过渡金属催化剂来进行克级药物合成.
Doi:10.1039/c9Dt02189B

海关参考信息

2901210000-乙烯
2901220000-丙烯
2901241000-1,3-丁二烯
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-2025296906-A1
优先权日:2022-08-24
标题 :Method for preparing 4-hydroxy-2-methylene-butanal, 4-hydroxy-2-methyl-but-2-enal and esters thereof
发明人：SCHAEFER BERND; SIEGEL WOLFGANG
权利人:BASF SE
摘要:The present invention relates to a method for preparing 4-hydroxy-2-methylene-butanal, 4-hydroxy-2-methyl-but-2-enal and esters thereof of the formula (I.a) and (I.b) where R1 is as defined in the claims and the description, by subjecting isoprenol or an ester thereof to a photooxidation in the presence of a photosensitizer and an acylating agent. The invention relates moreover to certain hydroperoxides of the compounds (I.a) or (I.b), and to the use thereof as intermediates in the synthesis of compounds (I.a) and (I.b) or in the synthesis of retinol, stereoisomers and derivatives thereof.

专利号:US-2576103-A
优先权日:1946-12-24
标题:Synthesis of vitamin a active compounds containing repeated isoprene units
发明人：CAWLEY JOHN D; ROBESON CHARLES D; SHANTZ EDGAR M; BAXTER JAMES G
权利人:EASTMAN KODAK CO

专利号:US-5605929-A
优先权日:1992-05-27
标题:Methods and compositions for inhibiting 5Î±-reductase activity
发明人：LIAO SHUTSUNG; LIANG TEHMING
权利人:ARCH DEV CORP
摘要:Disclosed are a novel class of antiandrogenic compounds including saturated and unsaturated fatty acids, catechin gallates, their derivatives, and synthetic analogs, their method of synthesis, and their use in treating disorders associated with androgenic activities. Also disclosed is the use of known compounds not previously known for their antiandrogenic activity in treating disorders related to androgenic activities and cancers.