42926-75-0

Usage

Explanation

The compound's name describes its structure, which includes a cyclohexene ring, a carboxaldehyde group, a hydroxy group, and three methyl groups.

Explanation

The molecular formula represents the number of carbon (C), hydrogen (H), and oxygen (O) atoms in the compound, which are 10, 16, and 3, respectively.

Explanation

The compound consists of a six-membered carbon ring (cyclohexene) with a double bond, a carbonyl group (carboxaldehyde), a hydroxy group (OH), and three methyl groups (CH3) attached to specific carbon atoms.

Explanation

The stereochemistry (4R) indicates the orientation of the substituents on the chiral center at the 4th carbon atom in the cyclohexene ring.

Explanation

The compound contains an aldehyde group (R-CHO), a hydroxy group (R-OH), and three methyl groups (R-CH3) as its main functional groups.

Explanation

Due to its unique structure, the compound may be used in various applications, such as the synthesis of complex organic molecules, development of pharmaceutical compounds, or other industries that require specific molecular structures.

Explanation

The compound's properties, reactivity, and potential applications can be influenced by the method of synthesis and the level of purity achieved during its production.

Explanation

The compound is likely to be soluble in organic solvents, such as ethanol, methanol, or acetone, due to its nonpolar nature and the presence of hydrocarbon groups.

Explanation

The compound, containing an aldehyde and a hydroxy group, may be sensitive to oxidation, light, and heat, which could lead to degradation or alteration of its structure.

Explanation

As a chemical compound, it may pose health risks, such as being an irritant, toxic if ingested, or harmful if inhaled, and should be handled with care and proper safety measures.

Structure

Cyclohexene ring with a carboxaldehyde group, a hydroxy group, and three methyl groups.

Stereochemistry

(4R)

Functional Groups

Aldehyde, Hydroxy, and Methyl groups.

Applications

Organic synthesis, pharmaceuticals, and other industries requiring specific molecular structures.

Synthesis and Purity

Properties and potential uses depend on the exact synthesis and purity of the compound.

Solubility

Soluble in organic solvents.

Stability

May be sensitive to oxidation, light, and heat.

Hazards

Potential irritant, toxic by ingestion, and harmful if inhaled.

Upstream product

• 76686-20-9 (4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexene-1-methanol 
• 121401-82-9 (R)-4-(1-Methoxy-1-methyl-ethoxymethyl)-3,5,5-trimethyl-cyclohex-3-enol 
• 76686-26-5 [(R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol 
• 76686-19-6 1-(1-Methoxy-1-methyl-ethoxymethyl)-2,6,6-trimethyl-cyclohexa-1,3-diene 
• 4436-51-5 1-hydroxymethyl-2,6,6-trimethylcyclohexa-1,3-diene 
• 116-26-7 safranal 
• 5146-66-7 geranonitrile 
• 5585-39-7 (E)-3,7-dimethylocta-2,6-dienenitrile 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 1373498-20-4 C₁₁H₁₈O 
• 1373498-18-0 C₁₁H₁₈O 
• 264279-20-1 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile 
• 145106-79-2 3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 
• 57524-13-7 2,6,6-trimethyl-2-cyclohexenecarbonitrile 

Downstream Products

• 116-26-7 safranal 
• 6890-91-1 (3RS,all-E)-hydroxyretinal 
• 7584-74-9 C₂₀H₂₈O₂ 
• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 121401-89-6 (2E,4E,6E,8E)-9-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenenitrile 
• 121401-90-9 (2E,4E,6E,8E)-9-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenenitrile 
• 60046-53-9 (-)-(R)-all-trans-3-hydroxyretinal 
• 121468-88-0 (-)-(2E,4E)-5-[(R)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3-methylpenta-2,4-dienal 
• 121401-88-5 (2E,4E)-5-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-3-methyl-penta-2,4-dienenitrile 

Relevant academic research and scientific papers

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.

Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.

Total synthesis of (±)-3-hydroxy-β-ionone through a ring-closing enyne metathesis

The total synthesis of (±)-3-hydroxy - ionone, a bisnor-sesquiterpene having allelopathic activity, has been accomplished employing an enyne metathesis for the construction of the C1-C8 segment and two-carbon elongation via a nitrile oxide-alkene [3+2] cycloaddition as the key steps. Georg Thieme Verlag Stuttgart · New York.

Synthetic scheme for the preparation of 13C-labeled 3,4-didehydro-retinal, 3-hydroxyretinal, and 4-hydroxyretinal up to uniform 13C-enrichment

A modular synthetic scheme has been developed for the synthesis of 13C-labeled naturally occurring visual pigment chromophores; 3,4-didehydroretinal, 3-hydroxyretinal, and 4-hydroxyretinal. These compounds can now be made with > 99% 13C enrichment at any position or combination of positions. We used the common C10+C5+C5 scheme for the synthesis of retinals, and by making variations in the C10 part we can now prepare the desired retinal derivatives with selective or uniform 13C enrichment. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Measurement of xanthoxin in higher plant tissues using 13c labelled internal standards

A new procedure for the reliable measurement of xanthoxin from plant tissues has been developed. This accounts for both its breakdown and its isomerization to 2-trans-xanthoxin, and relies on the use of 12C-labelled internal standards, HPLC pur

SYNTHESIS OF OPTICALLY ACTIVE 3-DIAZOACETYLRETINALS WITH TRIISOPROPYLPHENYLSULFONYLHYDRAZONE

An improved synthesis of photoaffinity labeled, optically active retinal derivatives is presented.A stable, easy to handle, glyoxalic acid 2,4,6-triisopropylphenylsulfonylhydrazone (TIPPS) reacts with 3-hydroxyretinal to give the diazoacetylretinal analog in satisfactory yield.

154. Synthese von optisch aktiven, natuerlichen Carotinoiden und strukturell verwandten Naturprodukten. V. Synthese von (3R,3'R)-, (3S,3'S)- und (3R,3'S; meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu optisch aktiven Carotinoidba

The synthesis of (3R,3'R)-, (3S,3'S)- and (3R,3'S; meso)-zeaxanthin (1), (19) and (21) is reported utilizing asymmetric hydroboration as the key reaction.Thus, safranol isopropenylmethylether (4) is hydroborated with (+)- and (-)-(IPC)2BH to give the opti