546-49-6

Basic information

• Product Name: 3,3,6-TRIMETHYL-1,5-HEPTADIEN-4-ONE
• Synonyms: ARTEMISIA KETONE;3,3,6-TRIMETHYL-1,5-HEPTADIEN-4-ONE;1,5-Heptadien-4-one, 3,3,6-trimethyl-;2,5,5-Trimethyl-2,6-heptadien-4-one;Artemesia;Hepta-1,5-dien-4-one, 3,3,6-trimethyl;Isoartemisia ketone;3,3,6-trimethylhepta-1,5-dien-4-one
• CAS NO: 546-49-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 208-903-3
• Mol File: 546-49-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 199.6°Cat760mmHg
• Flash Point: 57 °C
• Appearance: /
• Density: 0.869 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.339mmHg at 25°C
• Refractive Index: n20/D 1.466
• CAS DataBase Reference: 3,3,6-TRIMETHYL-1,5-HEPTADIEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,6-TRIMETHYL-1,5-HEPTADIEN-4-ONE(546-49-6)
• EPA Substance Registry System: 3,3,6-TRIMETHYL-1,5-HEPTADIEN-4-ONE(546-49-6)

Safety Data

• Safety Statements: 23-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 546-49-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O/c1-6-10(4,5)9(11)7-8(2)3/h6-7H,1H2,2-5H3

Upstream product

• 512-37-8 2,5,5-trimethyl-hepta-1,6-dien-4-one 
• 52528-20-8 3,3,6-trimethyl-4-methylsulfanyl-hepta-1,4,5-triene 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 29887-38-5 (-)-artemisia alcohol 
• 85433-81-4 6-(1-Ethoxy-ethoxy)-4-ethylsulfanyl-3,3,6-trimethyl-4-methylsulfanyl-hept-1-ene 
• 85433-79-0 6-(1-Ethoxy-ethoxy)-3,3,6-trimethyl-4,4-bis-methylsulfanyl-hept-1-ene 
• 113793-73-0 6-hydroxy-2,5,5-trimethyl-1-hepten-4-one 
• 70030-51-2 S-phenyl 3,3-dimethylthioacrylate 
• 541-47-9 3-Methylbutenoic acid 
• 121726-27-0 methyl-3 N-phenyl butene-3 imidothioate de methyle 
• 121726-29-2 methyl-3 N-phenyl butene-2 imidothioate de methyle 
• 89487-33-2 prenylmagnesium bromide 
• 870-63-3 prenyl bromide 

Downstream Products

• 27644-04-8 (+-)-artemisia alcohol 

Relevant articles and documents

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A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia × intermedia secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes.

Synthesis and Acylation of Allylic Mercuric Iodides: A Convenient Synthesis of Allylic Ketones

Allylic mercuric iodides are readily prepared by the reaction of mercury(0) and allylic iodides.They undergo efficient acylation with allylic rearrangement upon reaction with acyl chlorides and aluminium chloride to provide a convenient synthesis of allylic ketones.Artemisia ketone is prepared in two steps by this approach.

Reaction of Ester Enolates with Nucleophiles. Stereocontrolled Formation of Ketone and Aldehyde Enolates

Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively.This reaction is applied to the synthesis of γ-damascone, α-damascone, β-safranal, and artemisia ketone.