24672-83-1

Basic information

• Product Name: 1-[2-HYDROXY-4-(3-METHYL-BUT-2-ENYLOXY)-PHENYL]-ETHANONE
• Synonyms: 1-[2-HYDROXY-4-(3-METHYL-BUT-2-ENYLOXY)-PHENYL]-ETHANONE
• CAS NO: 24672-83-1
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26434
• Mol File: 24672-83-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 47 °C
• Boiling Point: 365.8±27.0 °C(Predicted)
• Appearance: /
• Density: 1.085±0.06 g/cm3(Predicted)
• PKA: 9.79±0.10(Predicted)
• CAS DataBase Reference: 1-[2-HYDROXY-4-(3-METHYL-BUT-2-ENYLOXY)-PHENYL]-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-HYDROXY-4-(3-METHYL-BUT-2-ENYLOXY)-PHENYL]-ETHANONE(24672-83-1)
• EPA Substance Registry System: 1-[2-HYDROXY-4-(3-METHYL-BUT-2-ENYLOXY)-PHENYL]-ETHANONE(24672-83-1)

Safety Data

• Hazardous Substances Data: 24672-83-1(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of prenyl bromide on resacetophenonebr/in the presence of potassium carbonate in refluxing acetone in the presence of potassium hydroxide in methanol, at 0° (14%) or at r.t. (4%) by photochemical method in the presence of benzoyl peroxide in dry benzene for 8 h (10%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 870-63-3 prenyl bromide 

Downstream Products

• 93176-13-7 4'-(3,3-dimethylallyloxy)-3-benzyloxy-2'-hydroxy-4-methoxychalcone 
• 1776-30-3 (E)-2',4'-dihydroxychalcone 
• 82416-22-6 2',4'-dihydroxy-5'-(α,α-dimethylallyl)chalkone 
• 219119-52-5 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3(pyridine-4-yl)-propen-1-one 
• 156698-77-0 C₂₇H₂₆O₄ 
• 443684-33-1 C₂₁H₂₂O₃ 
• 1252677-49-8 C₂₀H₁₉ClO₃ 
• 51619-65-9 cordoin 
• 162138-76-3 4-methoxyderricidine 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Relevant articles and documents

Antibacterial and anti-inflammatory activities of 4-Hydroxycordoin: Potential therapeutic benefits

4-Hydroxycordoin (1), a natural isopentenyloxychalcone, is a plant secondary metabolite that is relatively rare. Since there are very few reports about the biological activities of 1, its potential benefits for periodontal disease were investigated. A mar

Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate

An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Synthesis of isobavachalcone and some organometallic derivatives

Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.