1191-16-8

Basic information

• Product Name: Prenyl acetate
• Synonyms: 3,3-DIMETHYLALLYL ACETATE;ISOPENT-2-ENYL ACETATE;PRENYL ACETATE;VERTENOL-ACETATE;3-methyl, but-2-enyl acetate;3-methyl-2-buten-1-oacetate;3-methyl-2-butenyl;3-methyl-but-2-en-1-yl acetate
• CAS NO: 1191-16-8
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 214-730-4
• Mol File: 1191-16-8.mol
• Article Data: 57

Chemical Properties

• Melting Point: -62.68°C (estimate)
• Boiling Point: 151-152 °C752 mm Hg(lit.)
• Flash Point: 121 °F
• Appearance: colorless liquid
• Density: 0.917 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.99mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: H2O: insoluble
• Water Solubility: 4.3g/L at 20℃
• CAS DataBase Reference: Prenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Prenyl acetate(1191-16-8)
• EPA Substance Registry System: Prenyl acetate(1191-16-8)

Safety Data

• Statements: 10
• Safety Statements: 16-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: EM9473700
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1191-16-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1191-16-8 differently. You can refer to the following data:
1. Colorless to pale yellow liquid
2. Colorless liquid; natural green apple, banana aroma.

Occurrence

Reported found in ylang ylang oil (0.33%), ylang ylang oil I, Cananga odorata Hook.f. and Thomas. (0.89%), ylang ylang oil II, Cananga odorata Hook. f. and Thomas. (0.08%), ylang ylang oil III (0.02%)

Aroma threshold values

Medium strength odor, fruity type; recommend smelling in a 1% solution or less.

Taste threshold values

Sweet banana, fruity, ripe, floral, green at 30 ppm in water.

Synthesis Reference(s)

Synthetic Communications, 25, p. 2253, 1995 DOI: 10.1080/00397919508011780Tetrahedron Letters, 25, p. 541, 1984 DOI: 10.1016/S0040-4039(00)99932-5

Flammability and Explosibility

Flammable

Safety Profile

Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C7H12O2/c1-6(2)4-5-9-7(3)8/h4H,5H2,1-3H3

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 2190-48-9 3-chloro-3-methyl-1-butene 
• 563-63-3 silver(I) acetate 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 78-79-5 isoprene 
• 766-15-4 4,4-dimethyl-1,3-dioxane 
• 141-78-6 ethyl acetate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 25260-60-0 cis-1,4-bis(acetyloxy)but-2-ene 
• 115-11-7 isobutene 
• 78-39-7 Triethyl orthoacetate 
• 127-08-2 potassium acetate 

Downstream Products

• 25905-14-0 lavandulyl acetate 
• 69343-72-2 2,6-Dimethyl-3-acetoxymethyl-5-hepten-2-ol 
• 27934-33-4 isolavandulyl acetate 
• 94836-09-6 Acetic acid 2-chloro-3-methyl-3-phenylsulfanyl-butyl ester 
• 70473-34-6 Acetic acid 3-chloro-3-methyl-2-phenylsulfanyl-butyl ester 
• 25532-79-0 (E)‐α‐bisabolene 
• 256343-71-2 4-methyl-4-(3-methyl-2-butenyl)-2-phenyl-2-oxazolin-5-one 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 57152-93-9 (E)-4-hydroxy-3-methylbut-2-en-1-yl acetate 
• 36971-12-7 1-(1,1-dimethylprop-2-en-1-yl)cyclohexan-1-ol 
• 63972-14-5 1-(dimethylphenylsilyl)-3-methyl-2-butene 
• 10276-04-7 3-methyl-1-phenylsulfanylbut-2-ene 
• 64-19-7 acetic acid 
• 39491-73-1 (E)-(4-methylpenta-1,3-dien-1-yl)benzene 

Relevant articles and documents

Isoprene related esters, significant components of Pandanus tectorius

Isopentenyl and dimethylallyl acetates and cinnamates have been found in large amounts in an essential oil obtained from the ripe fruit of Pandanus tectorius, their identification has been confirmed by synthesis. This is the first time that these esters, apart from one, have been found in the plant kingdom and, generally speaking, that monoterpene precursors predominate in an essential oil.

A NEW PATHWAY FOR THE SYNTHESIS OF 2,2-DIMETHYL-3,3-DICHLOROCYCLOPROPANECARBOXYLIC ACID

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Paterno-Buechi reactions of allylic alcohols and acetates with aldehydes: Hydrogen-bond interaction in the excited singlet and triplet states? [2]

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Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

Preparation method of 4-acetoxy-2-methyl-2-butenal

The invention provides a preparation method of a vitamin A intermediate, namely 4-acetoxy-2-methyl-2-butenal. The method comprises the following steps: (1) carrying out ring opening on 3-methyl-1,2-epoxybutane under the action of alkaline acetate to generate 2-hydroxyl-3-butyl methyl acetate; (2) dehydrating 2-hydroxyl-3-butyl methyl acetate to obtain 3-methyl-2-butene acetate; and (3) carrying out one step selective oxidation on 3-methyl-2-butenyl acetate to obtain 4-acetoxy-2-methyl-2-butenal. According to the method, 3-methyl-1,2-epoxybutane is used as an initial raw material, the reactionsynthesis route is short, the atom economy is high, the operation is simple, and the method is an industrially optimized synthesis route.

Method for preparing 4-acetoxy-2-methyl-2-butenal

The invention provides a method for preparing 4-acetoxy-2-methyl-2-butenal. The method comprises the following steps: esterifying isopentenol to generate isopentenol acetate; and carrying out illumination oxidation on the isopentenol acetate in the presence of a photosensitizer to generate 4-acetoxy-2-methyl-2-butenal. The method has the advantages of cheap and easily available starting raw material isopentenol, high atom economy of the process route, no use of precious metals, less three wastes, and economic and effective synthesis route.