14393-37-4

Basic information

• Product Name: 2H-Pyran-2-one, 5,6-dihydro-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-
• CAS NO: 14393-37-4
• Molecular Formula: C15H22O2
• Molecular Weight: 234.338
• Mol File: 14393-37-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, 5,6-dihydro-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, 5,6-dihydro-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-(14393-37-4)
• EPA Substance Registry System: 2H-Pyran-2-one, 5,6-dihydro-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-(14393-37-4)

Safety Data

• Hazardous Substances Data: 14393-37-4(Hazardous Substances Data)

Upstream product

• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 79863-93-7 γ-bromosenecioate de trimethylsilyl 
• 88239-43-4 C₈H₁₅BrO₂Si 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 924-50-5 Methyl 3,3-dimethylacrylate 

Downstream Products

• 14398-44-8 (2Z,4E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-2,4-pentadienoic acid 
• 855461-42-6 5-Hydroxy-3-methyl-5-<2.2.6-trimethyl-2.3.4.5-tetrahydrophenyl>-penten-(2)-saeure-(1) 
• 57023-47-9 3-methyl-5-(2,2,6-trimethyl-cyclohexyl)-valeric acid 
• 20110-08-1 methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 
• 161676-56-8 C₁₅H₂₄O₂ 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 68-26-8 9-cis-retinol 
• 13312-52-2 9-cis-β-carotene 

Relevant articles and documents

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.

A General Synthesis of 5,6-Dihydro-α-pyrones

Crotonate esters substituted at C-3 by alkyl, alkoxy, or dialkylamino groups are deprotonated and the resulting dienolates added to aldehydes and ketones.Kinetic reaction is at C-2 of the ester, leading to the isolation of 2-alkyl-3-hydroxy esters such as 3 and 4 if the reaction mixture is quenched at -70 deg C.However, retroaldolization occurs readily.If the initial reaction mixtures are allowed to warm to 15 deg C before workup, the isolated products are 5,6-dihydro-α-pyrones (such as 5), accompanied in some cases by the (E)-4-substituted crotonate (such as 6).The method has been applied to the synthesis of a series of retinoid lactones (5f,18,21a-c) which are of interest as potential antineoplastic agents.