76985-03-0

Basic information

• Product Name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile
• Synonyms: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile
• CAS NO: 76985-03-0
• Molecular Weight: 281.441
• Mol File: 76985-03-0.mol

Chemical Properties

• CAS DataBase Reference: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile(76985-03-0)
• EPA Substance Registry System: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile(76985-03-0)

Safety Data

• Hazardous Substances Data: 76985-03-0(Hazardous Substances Data)

Upstream product

• 1856-64-0 2-Cyan-Vitamin-A-saeure 
• 1220-77-5 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 1856-64-0 C₂₁H₂₇NO₂ 
• 20638-88-4 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 76929-15-2 (5Z,7E)-6-Methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-5,7-dien-3-yn-2-ol 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 110875-15-5 (4E,6E,8E)-3,7-dimethyl-3-hydroxy-9-(2,6,6-trimethyl-1-cyclohexenyl)-4,6,8-nonatrienenitrile 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 21658-95-7 diisopropyl (cyanomethyl)phosphonate 
• 5560-99-6 (2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal 
• 82648-70-2 diethyl (3-cyano-2-methyl-2-trans-propenyl)phosphonate 

Downstream Products

• 1436-55-1 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal 
• 116-31-4 all-trans-Retinal 
• 87391-97-7 <15-13C>13-cis-retinal 
• 78508-47-1 C₁₉⁽¹³⁾CH₂₈O 
• 472-86-6 13-cis-vitamin A aldehyde 
• 99302-31-5 retinal 
• 99302-30-4 retinal 
• 7235-40-7 beta-carotene 
• 564-87-4 (11Z)-retinal 

Relevant articles and documents

A Highly Stereoselective Synthesis of 11Z-Retinal Using Tricarbonyliron Complex

A stereoselective synthesis of 11Z-retinal 2, which is the chromophore of visual pigment (rhodopsin), was accomplished from the β-ionylideneacetaldehyde-tricarbonyliron complex 3. The Peterson reaction of 3 using ethyl trimethylsilylacetate smoothly proce

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

Synthesis of (12,13-(13)C2)retinal and (13,14-(13)C2)retinal: a strategy to prepare multiple-(13)C-labeled conjugated systems

(12,13-(13)C2)Retinal, (13,14-(13)C2)retinal, (19-(13)C)retinal and (20-(13)C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy.The key step is the reaction of a N-methoxy-N-methylamide with an alkyllithium or a Grignard reagent.The preparation of the required N-methoxy-N-methylamide is discussed.In this scheme, only three commercially available (13)C-labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of (13)C labeling in the conjugated tail end.This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.

Preparation of (9Z, 11Z) - Vitamin A

Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z, 11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a

SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. L. SYNTHESIS OF THE NITRILES AND HYDROXYNITRILES OF RETINOIC ACID

Glycidonitrile was synthesized from 9-methyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-9,11-octadien-13-one and chloroacetonitrile by a modified Darzens reaction.Opening of the epoxide ring in the glycidonitrile gave 9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile with a yield of 70percent calculated on the ketone.Partial dehydration of the latter gave 14-hydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,10,12-nonatriene-15-nitrile - the key compound in the synthesis of the biologically active analog of the vitamin Ametabolite.The total dehydration of the dihydroxynitrile led to retinonitrile.

Synthesis of 8-, 9-, 12-, and 13-mono-13C-retinal

The 8-, 9-, 12-, and 13-mono-13C-retinals were synthesized with >98percent chemical purity and 93percent 13C incorporation from 13C-labelled acetonitrile.Their 13C-13C and 13C-1H nmr coupling constants were determined.

SOLVENT DEPENDENT PHOTOISOMERIZATION OF POLYENE NITRILES

The initial product ratio of several polyene nitriles, wich do not have low lying n,?* states, are reported.The solvent dependent chemistry has been discussed in conjunction with the well known retinal chemistry.

A SHORT PATH SYNTHESIS OF RETINALS. SYNTHESIS OF 13C- OR 2H-LABELED RETINALS

Trimethylsilylated acetaldehyde t-butylimine 4 was found to be an effective two carbon-homologenation reagent in the synthesis of retinals and its congeners.A short path synthesis of retinals (1 and 2) by using 4 and its application to the synthesis of 13C-labeled retinal 12 and octadeuterium retinal 27 is described.KEYWORDS - retinal; retinoid; vitamin A aldehyde; visual pigment; α,β-unsaturated aldehyde synthesis; silylated imine