224631-90-7

Basic information

• Product Name: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one
• Synonyms: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one
• CAS NO: 224631-90-7
• Molecular Weight: 206.285
• Mol File: 224631-90-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one(224631-90-7)
• EPA Substance Registry System: 4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one(224631-90-7)

Safety Data

• Hazardous Substances Data: 224631-90-7(Hazardous Substances Data)

Upstream product

• 120330-44-1 citroside A <(5-dehydroxygrasshopper ketone-5-yl) 5-β-D-glucopyranoside> 
• 76530-42-2 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-enyl acetate 
• 322474-86-2 1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane 
• 118829-40-6 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol 
• 322474-87-3 4-({(4R)-4-[(1,1-dimethylethyl)dimethylsilyl]oxy}-2,6,6-trimethylcyclohex-1-enyl)but-3-yn-2-one 

Downstream Products

• 322474-89-5 Acetic acid (R)-4-((S)-3-hydroxy-but-1-ynyl)-3,5,5-trimethyl-cyclohex-3-enyl ester 
• 322474-90-8 Acetic acid (R)-4-((R)-3-hydroxy-but-1-ynyl)-3,5,5-trimethyl-cyclohex-3-enyl ester 
• 162601-88-9 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol 
• 162601-89-0 (3R,9R)-3-hydroxy-7,8-dehydro-ionol-9-O-β-D-glucopyranoside 
• 521291-39-4 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(R)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 521291-38-3 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(S)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 35734-61-3 3-hydroxymegastigma-5,8-dien-7-one 
• 23726-93-4 Damascenon 
• 322474-88-4 4-[(4R)-4-acetyloxy-2,6,6-trimethylcyclohex-1-enyl]but-3-yn-2-one 

Relevant articles and documents

C13-norisoprenoid glucoconjugates from lulo (Solanum quitoense L.) leaves

With the aid of multilayer coil countercurrent chromatography, subsequent acetylation, and liquid chromatographic purification of a glycosidic mixture obtained from lulo (Solanum quitoense L.) leaves, three C13-norisoprenoid glucoconjugates were isolated in pure form. Their structures were elucidated by NMR, MS, and CD analyses to be the novel (6R,9R)-13-hydroxy-3-oxo-α-ionol 9-O-β-D-glucopyranoside (4a), the uncommon (3S,5R,8R)-3,5-dihydroxy-6,7-megastigmadien-9-one 5-O-β-D-glucopyranoside (citroside A) (5a), and the known (6S,9R)-vomifoliol 9-O-β-D-glucopyranoside (6a). Enzymatic treatment of compound 5a showed the formation of 3-hydroxy- 7,8-didehydro-β-ionone (7), an important lulo peeling volatile, which in its turn after chemical reduction and heated acid catalyzed rearrangement generates β-damascenone (9) and 3-hydroxy-β-damascone (10).

Stereocontrolled synthesis of optically active β-D-glucopyranosides of 3-hydroxy-7,8-didehydro-β-ionol

A stereocontrolled synthesis of optically active β-D-glucopyranosides 1-4 of 3-hydroxy-7,8-didehydro-β-ionol utilizing an asymmetric transfer hydrogenation to α,β-acetylenic ketones catalyzed by chiral ruthenium complexes as the key step is described.