22737-96-8

Basic information

• Product Name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol
• Synonyms: 11-cis-VitaMin A Alcohol;(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol;11-cis-Retinol;11-cis Retinol Discontinued
• CAS NO: 22737-96-8
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.45
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Retinoids
• Mol File: 22737-96-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 421.2°C at 760 mmHg
• Flash Point: 147.3°C
• Appearance: /
• Density: 0.954g/cm³
• Vapor Pressure: 7.35E-09mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol(22737-96-8)
• EPA Substance Registry System: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol(22737-96-8)

Safety Data

• Hazardous Substances Data: 22737-96-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

A metabolite of Vitamin A (R252000(M)).

InChI:InChI=1/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-

Upstream product

• 2052-63-3 2-cis-Vitamin-A 
• 108-24-7 acetic anhydride 
• 204326-64-7 tert-Butyl-[(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-dimethyl-silane 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 74723-01-6 (Z)-4-bromo-3-methyl-3-buten-1-ol 
• 68-26-8 RETINOL 
• 564-87-4 (11Z)-retinal 
• 68-26-8 9-cis-retinol 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 37905-03-6 8-hydroxygeranyl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 204326-62-5 2-((1E,3E,5Z)-6-Bromo-3-methyl-hexa-1,3,5-trienyl)-1,3,3-trimethyl-cyclohexene 
• 29443-88-7 (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol 
• 103905-07-3 1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene 

Downstream Products

• 564-87-4 (11Z)-retinal 
• 472-86-6 13-cis-vitamin A aldehyde 
• 116-31-4 all-trans-Retinal 
• 556-82-1 3-methyl-2-buten-1-ol 
• 68-26-8 RETINOL 
• 68-26-8 9-cis-retinol 
• 2052-63-3 2-cis-Vitamin-A 
• 79-80-1 vitamin A₂ 
• 100-51-6 benzyl alcohol 
• 112-53-8 1-dodecyl alcohol 
• 143-08-8 nonyl alcohol 
• 624-15-7 geraniol 
• 96706-32-0 3,7-dimethyl-2,4,6-octatrien-1-ol 
• 111-27-3 hexan-1-ol 

Relevant articles and documents

Crystalline neoretinene b.

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Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.

METHOD FOR SYNTHESIS OF 9-CIS-BETA-CAROTENE AND FORMULATIONS THEREOF

The present invention relates to a method for total chemical synthesis of 9-cis-β-carotene (9CBC), and further provides stable formulations thereof.

Cross-coupling reactions of organosilicon compounds in the stereocontrolled synthesis of retinoids

This paper presents a full account of the use of Hiyama cross-coupling reactions in a highly convergent approach to retinoids in which the key step is construction of the central C10-C11 bond. Representatives of two families of oxygen-activated dienyl silanes (ethoxysilanes and silanols) and of all reported families of "safety-catch" silanols (siletanes, silyl hydrides, allyl-, benzyl-, aryl-, 2-pyridyl- and 2-thienylsilanes) were regio- and stereoselectively prepared and stereospecifically coupled to an appropriate electrophile by treatment with a palladium catalyst and a nucleophilic activator. Both all-trans and 11-cis-retinoids, and their chain-demethylated analogues, were obtained in good yields regardless of the geometry (E/Z) and of the steric congestion in each fragment. This comprehensive study conclusively establishes the Hiyama cross-coupling reaction, with its mild reaction conditions and stable, easily prepared, ecologically advantageous silicon-based coupling partners, as the most effective route to retinoids reported to date.