25905-14-0

Basic information

• Product Name: ACETIC ACID LAVANDULYL ESTER
• Synonyms: ACETIC ACID LAVANDULYL ESTER;LAVANDULYL ACETATE;4-Hexen-1-ol,5-methyl-2-(1-methylethenyl)-,acetate;2-isopropenyl-5-methylhex-4-enyl acetate;(+/-)-LAVANDULOL ACETATE, TERPENE STANDA RD;2-Isopropenyl-5-methylhex-4-enylacetat;Acetic acid 2-isopropenyl-5-methyl-4-hexen-1-yl ester
• CAS NO: 25905-14-0
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 247-327-7
• Mol File: 25905-14-0.mol

Chemical Properties

• Boiling Point: 228.7 °C at 760 mmHg
• Flash Point: 103 °C
• Appearance: /
• Density: 0.907 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.454
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: ACETIC ACID LAVANDULYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ACETIC ACID LAVANDULYL ESTER(25905-14-0)
• EPA Substance Registry System: ACETIC ACID LAVANDULYL ESTER(25905-14-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 25905-14-0(Hazardous Substances Data)

Usage

Uses

(±)-Lavandulyl Acetate is a component of lavender oil.

Upstream product

• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 75-36-5 acetyl chloride 
• 70473-51-7 1-acetoxy-2-(phenylthio)-3-methyl-3-butene 
• 870-63-3 prenyl bromide 
• 122346-11-6 Acetic acid 3-methyl-2-(naphthalen-1-ylsulfanyl)-but-3-enyl ester 
• 122346-12-7 Acetic acid 3-methyl-2-(2,4,5-trichloro-phenylsulfanyl)-but-3-enyl ester 
• 122346-10-5 Acetic acid 3-methyl-2-(2,4,6-triisopropyl-phenylsulfanyl)-but-3-enyl ester 
• 115-18-4 2-methyl-3-buten-2-ol 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 69343-72-2 2,6-Dimethyl-3-acetoxymethyl-5-hepten-2-ol 
• 24529-80-4 (E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol 
• 35189-96-9 3-methyl-2-butenylmagnesium chloride 
• 76-05-1 trifluoroacetic acid 
• 58461-27-1 (+/-)-lavandulol 

Downstream Products

• 131392-06-8 2-isopropenyl-5-methyl-4-phenylsulfenyl-5-hexen-1-ol acetate 
• 40853-55-2 2-isopropyl-5-methylhexyl acetate 
• 74912-37-1 dihydrolavandulyl acetate 
• 58461-27-1 (+/-)-lavandulol 
• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 50373-53-0 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 20777-39-3 (-)-(R)-lavanduyl acetate 
• 144831-70-9 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enyl acetate 
• 75697-98-2 2,6-dimethyl-3-formyl-1,5-heptadiene-lavandulal 

Relevant articles and documents

PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF

The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).

Enzymatic transesterification of racemic lavandulol: Preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate

(R) and (S)-lavandulol are important compounds in the cosmetics industry and in pheromone research. The senecioyl ester of (S)-lavandulyl has recently been identified as the sex pheromone of the vine mealybug, a significant pest in vineyards. We herein report the preparation of the two enantiomers of lavandulol and lavandulyl senecioate, starting from racemic lavandulol. The preparation is based on a two-cycle enzymatic transesterification of racemic lavandulol with vinyl acetate using Porcine pancreas lipase. High enantioselectivity was achieved while the preparation yielded (R)-lavandulol with 96.7% ee and (S)-lavandulol with 92.6% ee.

A new synthesis of lavandulol via indium/palladium-mediated umpolung of vinyloxirane

A short synthesis of lavandulol is achieved by the In/Pd-mediated reaction of isopropenyloxirane with 3-methylbut-2-enal.

Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10

Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.

Selective 1,5-Diene Synthesis. A Radical Approach

A new synthetic route to 1,5-dienes is described.Irradiation of a mixture of allyl bromides and allyl sulfides in the presence of hexamethylditin gives the cross-coupled products selectively.

PRENYLATION OF OLEFINS IN NITROMETHANE

The prenylation of isopentenyl and 3,3-dimethylallyl derivatives could be achieved efficiently with dimethyl vinyl carbinol and a variety of acids in nitromethane.Geraniol and isopentenylacetate led to farnesyl derivatives.

Model Studies of Terpene Biosynthesis. Intermolecular 1'-2 Electrophilic Condensation of 3-Methyl-2-butenyl Acetate

The stereochemistry of the carbon-carbon bond-forming step in the electrophilic intermolecular 1'-2 condensation of 3-methyl-2-butenyl acetate (1-OAc) to yield lavandulyl acetate (2-OAc) was studied.Treatment of (1S)-3-methyl-2-butenyl acetate ((1S)-1-OAc) with aluminum trichloride in ethyl acetate gave labeled lavandulyl acetate (2-OAc) (30percent) and isoprene (65percent) as the major products.The configurations at C(1), C(2), and C(3) and the relative abundances of the diastereomers of 1-OAc were determined by converting the mixture to 3-(2'-propyl)-butyrolactone (3).The intensities of 1H resonances characteristic of each diastereomer were measured with the aid of Pirkle's chiral shift reagent, (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol.The analysis showed that equal amounts of the (1S,2S,3R), (1S,2R,3R), (1S,2S,3S), and (1S,2R,3S) diastereomers of 2-OAc were obtained, signifying that the 1'-2 condensation was stereorandom at C(1) of the electrophilic isoprene unit.