264279-20-1

Basic information

• Product Name: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile
• Synonyms: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile
• CAS NO: 264279-20-1
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Mol File: 264279-20-1.mol

Chemical Properties

• Boiling Point: 249.2±23.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Dichloromethane, Diethyl Ether, Ethyl Acetate
• CAS DataBase Reference: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile(264279-20-1)
• EPA Substance Registry System: 1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile(264279-20-1)

Safety Data

• Hazardous Substances Data: 264279-20-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3,3-TriMethyl-7-oxabicyclo[4.1.0]heptane-2-carbonitrile is used as a key intermediate in the synthesis of Retinoic acid derivatives, which are vital for the development of pharmaceuticals targeting various health conditions. Its unique chemical structure allows for the creation of Retinoic acid analogs with potential therapeutic applications.

Upstream product

• 57524-13-7 2,6,6-trimethyl-2-cyclohexenecarbonitrile 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 5146-66-7 geranonitrile 
• 23089-87-4 5-methyl-4-hexenenitrile 
• 5585-39-7 (E)-3,7-dimethylocta-2,6-dienenitrile 

Downstream Products

• 145106-79-2 3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 
• 116-26-7 safranal 
• 72152-84-2 2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile 
• 42926-75-0 2,6,6-trimethyl-4-hydroxy-1-cyclohexene-1-carboxaldehyde 
• 60078-92-4 2,4,4-trimethyl-3-formyl-2-cyclohexen-1-ol 
• 7542-45-2 3,3'-dihydroxy-β,β-carotene-4,4'-dione 
• 29538-78-1 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol 
• 56830-39-8 2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile 
• 94669-81-5 (E)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on 
• 80736-89-6 (2E,4E)-1-bromo-3-methyl-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadiene 
• 6890-91-1 (3RS,all-E)-hydroxyretinal 

Relevant articles and documents

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.

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.

Synthesis and characterization of all-E-(4,4'-13C2)-astaxanthin strategies for labelling the C15-end groups of carotenoids

The all-E isomer of (4,4'-13C2)astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% 13C enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C15 + C10 + C15 strategy was used. The central C10-synthon, 2,7-dimethylocta-2,4,6-triene- 1,8-dial (3), was coupled with 13C-enriched C15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C15-phosphonium salt.