64809-50-3

Basic information

• Product Name: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (S)-
• CAS NO: 64809-50-3
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Mol File: 64809-50-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (S)-(64809-50-3)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 4-hydroxy-2,6,6-trimethyl-, (S)-(64809-50-3)

Safety Data

• Hazardous Substances Data: 64809-50-3(Hazardous Substances Data)

Upstream product

• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 169124-54-3 (S)-4-tert-butyldimethylsilyloxy-2,6,6-trimethyl-2-cyclohexenone 
• 199921-92-1 (2R,4S)-4-acetoxy-2-bromo-2,6,6-trimethylcyclohexanone 
• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 
• 254963-54-7 (+/-)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 19620-37-2 (+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone 
• 254963-53-6 (S)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 64839-19-6 4(S)-2,6,6-trimethyl-4-acetoxy-cyclohex-2-en-1-one 
• 20107-09-9 (2S,4S)-4-acetoxy-2-bromo-2,6,6-trimethylcyclohexanone 

Downstream Products

• 64809-51-4 4(S)-2,6,6-trimethyl-4-[(trimethylsilyl)oxy]-cyclohex-2-en-1-one 
• 80736-90-9 (2S,3R,4S)-2,3-Dibrom-4-hydroxy-2,6,6-trimethylcyclohexanon 
• 1064557-76-1 (4S)-2,6,6-trimethyl-4-O-(2',3',4',6'-tetrapivaloyl-β-D-glucopyranosyl)-cyclohex-2-en-1-one 
• 69350-37-4 (1S,4S)-1-((Z)-5-Hydroxy-3-methyl-pent-3-en-1-ynyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol 
• 69350-38-5 (1R,4S)-1-((Z)-5-Hydroxy-3-methyl-pent-3-en-1-ynyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol 
• 64839-28-7 (2E,4E)-5-[(4S)-4-Hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-enyl]-3-methylpenta-2,4-dienal 
• 64809-43-4 (2Z,4E)-5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal 
• 69350-54-5 Phenoxy-acetic acid (S)-4-((1Z,3E)-5-hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl ester 
• 69297-10-5 Phenoxy-acetic acid (S)-4-((1Z,3E)-5-bromo-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl ester 
• 64809-44-5 Phenoxy-acetic acid (S)-3,5,5-trimethyl-4-((1E,3Z)-3-methyl-5-oxo-penta-1,3-dienyl)-2-oxo-cyclohex-3-enyl ester 
• 64809-42-3 (Z)-5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-3-methyl-pent-2-en-4-ynal 
• 76686-12-9 (1R,4R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-2-enecarbaldehyde 
• 76686-10-7 (R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-2-enone 
• 76739-79-2 Acetic acid (R)-3,5,5-trimethyl-4-oxo-cyclohex-2-enyl ester 

Relevant articles and documents

An engineered old yellow enzyme that enables efficient synthesis of (4R,6R)-actinol in a one-pot reduction system

(4R,6R)-Actinol can be stereo-selectively synthesized from ketoisophorone by a two-step conversion using a mixture of two enzymes: Candida macedoniensis old yellow enzyme (CmOYE) and Corynebacterium aquaticum (6R)-levodione reductase. However, (4S)-phorenol, an intermediate, accumulates because of the limited substrate range of CmOYE. To address this issue, we solved crystal structures of CmOYE in the presence and absence of a substrate analogue p-HBA, and introduced point mutations into the substrate-recognition loop. The most effective mutant (P295G) showed two- and 12-fold higher catalytic activities toward ketoisophorone and (4S)-phorenol, respectively, than the wild-type, and improved the yield of the two-step conversion from 67.2 to 90.1%. Our results demonstrate that the substrate range of an enzyme can be changed by introducing mutation(s) into a substrate-recognition loop. This method can be applied to the development of other favorable OYEs with different substrate preferences.

β-hydroxysulfoxides as chiral cyclic ketone equivalents: Enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

The β-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.

Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6- trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2- cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroaceta