3572-06-3

Basic information

• Product Name: 4-(4-Acetoxyphenyl)-2-butanone
• Synonyms: 2-Butanone, 4-(p-hydroxyphenyl)-, acetate;2-Butanone, 4-[4-(acetyloxy)phenyl]-;4-(p-hydroxyphenyl)-2-butanonacetate;4-[4-(acetyloxy)phenyl]-2-butanon;Acetate of 4-(hydroxyphenyl)-2-butanone;4-(4-Acetoxphenyl)butan-2-one;Cur-lure;Pherocon
• CAS NO: 3572-06-3
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• EINECS: 222-682-0
• Product Categories: A-B;Alphabetical Listings;Flavors and Fragrances;insect pheromone;Pesticide & intermediate
• Mol File: 3572-06-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 123-124 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.099 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Merck: 14,2616
• BRN: 1961620
• CAS DataBase Reference: 4-(4-Acetoxyphenyl)-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Acetoxyphenyl)-2-butanone(3572-06-3)
• EPA Substance Registry System: 4-(4-Acetoxyphenyl)-2-butanone(3572-06-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: EL8950000
• Hazardous Substances Data: 3572-06-3(Hazardous Substances Data)

Usage

Identification

▼▲ CAS.No.:? 3572-06-3 FL.No.:? 09.288 FEMA.No.:? 3652 NAS.No.:? 3652 CoE.No.:? n/a? EINECS.No.:? 222-682-0? JECFA.No.:? 731

Description

A yellow liquid with sweet, raspberry, fruity odor.

Regulatory Status

CoE: n/a FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2000).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Chewing.gum? 5 10 Confectionary,.frosting? 0.5 1 Fruit.ices? 0.5 1 Gelatins,.puddings? 1 2 Hard.candy? 1 2 Imitation.dairy? 0.2 1 Jams,.jellies? 0.2 1 Nonalcoholic.beverages? 0.2 0.5 Soft.candy? 0.5 2

Natural occurrence

Not reported found in nature.

Chemical Properties

A yellow liquid with sweet, raspberry, fruity odor

Uses

Different sources of media describe the Uses of 3572-06-3 differently. You can refer to the following data:
1. 4-(3-Oxobutyl)phenyl Acetate is a sexual attractant. Pheromone.
2. 4-(3-Oxobutyl)phenyl acetate was used as attractant for detection programs aimed at melon fly and other cuelure-responding Bactrocera fruit flies.
3. As attractant in melon fly traps.

General Description

4-(3-Oxobutyl)phenyl acetate (4-(4-acetoxyphenyl) -2-butanone) is a standard melon fly attractant.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits acrid smoke andirritating fumes.

InChI:InChI=1/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3

Synthetic route

acetic anhydride (108-24-7) + 4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) → 4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3)

Conditions	Yield
With pyridine at 0 - 20℃;	80%

acetyl chloride (75-36-5) + 4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) → 4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) + thiosemicarbazide (79-19-6) → 4-(4-acetoxyphenyl)butan-2-ylidenethiosemicarbazide

Conditions	Yield
With acetic acid In ethanol at 50 - 80℃; for 3h;	93%

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate (129752-69-8)

Conditions	Yield
With PS-TN lipase; hydrogen; (c-C5Ph4O)2H[Ru(CO)2]2H In toluene at 70℃; under 760.051 Torr; for 72h; Enzymatic reaction;	92%

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) + [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone (121512-93-4) → (2S,4S,5R,6R)-4-Acetoxy-2-[3-(4-acetoxy-phenyl)-1-hydroxy-1-methyl-propyl]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃;	82%

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) + methylmagnesium bromide (75-16-1) → 4-(3-hydroxy-3-methylbutyl)phenyl acetate

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	68%

(E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde (103909-81-5) + 4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → (4E,6E)-1,7-bis (4-hydroxyphenyl)hepta-4,6-dien-3-one

Conditions	Yield
Stage #1: 4-(p-hydroxyphenyl)-2-butanone acetate With pyrrolidine; acetic acid In diethyl ether at 0℃; for 0.5h; Stage #2: (E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde In diethyl ether at 20℃; for 12h; Claisen Schmidt condensation; Further stages;	59%

2-methyl-1,3-dithian (6007-26-7) + 4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → 4-(3-hydroxy-3-(2-methyl-1,3-dithian-2-yl)butyl)phenyl acetate

Conditions	Yield
With 3,5-difluoro-2,4,6-tris(N-phenylanilino)benzonitrile; triisopropylsilanethiol; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In N,N-dimethyl-formamide at 0℃; for 19h; Corey-Seebach Umpolung; Molecular sieve; Irradiation; Sealed tube; Inert atmosphere;	38%

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → (2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-[1-hydroxy-3-(4-hydroxy-phenyl)-1-methyl-propyl]-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid (525558-18-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / SmI2 / tetrahydrofuran / 20 °C 2.1: NaOMe / methanol / 8 h 2.2: KOH / H2O View Scheme

(E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde (103909-81-5) + 4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → C21H20O4 + C24H26O4 + C26H28O5

Conditions	Yield
Stage #1: 4-(p-hydroxyphenyl)-2-butanone acetate With pyrrolidine; acetic acid In diethyl ether at 0℃; for 0.5h; Stage #2: (E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde In diethyl ether at 20℃; for 12h; Claisen Schmidt condensation; Stage #3: With hydrogenchloride; water In diethyl ether

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) → ethyl 6-(4-acetoxyphenyl)-4,4-dimethylhexanoate

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: cyclopentadienyl titanium(IV) trichloride; zinc; triethylsilyl chloride / tetrahydrofuran / 12 h / 60 °C / Molecular sieve; Sealed tube; Inert atmosphere View Scheme

4-(p-hydroxyphenyl)-2-butanone acetate (3572-06-3) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → C14H18O3 + C14H18O3

Conditions	Yield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at 0 - 10℃; for 1h; Stage #2: 4-(p-hydroxyphenyl)-2-butanone acetate In tetrahydrofuran for 4h; Overall yield = 73 percent; Overall yield = 3.42 g;

Upstream product

• 108-24-7 acetic anhydride 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 75-36-5 acetyl chloride 

Downstream Products

• 525558-18-3 (2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-[1-hydroxy-3-(4-hydroxy-phenyl)-1-methyl-propyl]-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 129752-69-8 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 

Relevant articles and documents

Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction

A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.

Rational design, synthesis and structure-activity relationships of 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues as novel tyrosinase inhibitors

In continuing our program aimed to search for potent compounds as highly efficient tyrosinase inhibitors, here a series of novel 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues were designed, synthesized and their biological activities on mushroom tyrosinase were evaluated. Notably, most of compounds displayed remarkable tyrosinase inhibitory activities with IC50 value of lower than 1.0 μM. Furthermore, the structure-activity relationships (SARs) were discussed and the inhibition mechanism and the inhibitory kinetics of selected compounds 7k and 8d were also investigated. Taken together, these results suggested that such compounds could serve as the promising candidates for the treatment of tyrosinase-related disorders and further development of such compounds might be of great interest.