20777-39-3

Basic information

• Product Name: (-)-DIHYDROCARVYL ACETATE
• Synonyms: 4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)-, acetate, (R)-;5-methyl-2-(1-methylethenyl)-,acetate,(theta)-4-hexen-1-o;5-methyl-2-(1-methylethenyl)-4-hexen-1-oacetate;5-methyl-2-(1-methylethenyl)-4-hexen-1-olacetate;Lavendulyl acetate;L-DIHYDROCARVYL ACETATE;DIHYDROCARVEYL ACETATE;(-)-DIHYDROCARVYL ACETATE
• CAS NO: 20777-39-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 244-029-9
• Mol File: 20777-39-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 232-234 °C(lit.)
• Flash Point: 194 °F
• Appearance: /
• Density: 0.947 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.459(lit.)
• CAS DataBase Reference: (-)-DIHYDROCARVYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-DIHYDROCARVYL ACETATE(20777-39-3)
• EPA Substance Registry System: (-)-DIHYDROCARVYL ACETATE(20777-39-3)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 2
• RTECS: OT0210000
• Hazardous Substances Data: 20777-39-3(Hazardous Substances Data)

Usage

General Description

(-)-Dihydrocarvyl acetate is a chemical compound that belongs to the class of organic compounds known as menthane monoterpenoids. It is a colorless liquid with a pleasant peppermint-like odor. (-)-Dihydrocarvyl acetate is commonly used as a flavoring agent in the food and beverage industry due to its minty, cooling sensation. It is also used in the formulation of perfumes and cosmetics. In addition to its fragrance properties, (-)-dihydrocarvyl acetate has been found to exhibit antimicrobial and antioxidant activities, making it valuable in various industrial and pharmaceutical applications.

InChI:InChI=1/C12H20O2/c1-9(2)6-7-12(10(3)4)8-14-11(5)13/h6,12H,3,7-8H2,1-2,4-5H3/t12-/m0/s1

Synthetic route

(R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (498-16-8) + acetic anhydride (108-24-7) → (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃;	88%

vinyl acetate (108-05-4) + (+/-)-lavandulol (58461-27-1) → (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (498-16-8) + (-)-(R)-lavanduyl acetate (20777-39-3) + (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enyl acetate (144831-70-9)

Conditions	Yield
With Porcine Pancreas Lipase In hexane at 20℃; for 3h; Enzymatic reaction; Title compound not separated from byproducts;	A 971 mg B n/a C n/a

lavandulyl acetate (25905-14-0) → (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (498-16-8) + (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (50373-53-0) + (-)-(R)-lavanduyl acetate (20777-39-3) + (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enyl acetate (144831-70-9)

Conditions	Yield
With Porcine Pancreas Lipase; sodium phosphate buffer at 20℃; for 0.5h; pH=7; Enzymatic reaction; Title compound not separated from byproducts;

(R)-2-isopropenyl-5-methyl-hexane-1,5-diol (1327155-02-1) → C12H20O2 (1327155-04-3) + (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 16 h / 8 °C 2: thionyl chloride; triethylamine / 3 h / 25 °C View Scheme

C12H22O3 (1345866-27-4) → C12H20O2 (1327155-04-3) + (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
With thionyl chloride; triethylamine at 25℃; for 3h;

(5S)-5-isopropenyl-2-methyl-octane-2,7-diol (1327155-05-4) → C12H20O2 (1327155-04-3) + (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridinium chlorochromate / dichloromethane 2: Acremonium roseum AM346 / water; acetone / 264 h / Enzymatic reaction 3: pyridine / 16 h / 8 °C 4: thionyl chloride; triethylamine / 3 h / 25 °C View Scheme

C12H22O2 (1327155-06-5) → C12H20O2 (1327155-04-3) + (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: Acremonium roseum AM346 / water; acetone / 264 h / Enzymatic reaction 2: pyridine / 16 h / 8 °C 3: thionyl chloride; triethylamine / 3 h / 25 °C View Scheme

(3S)-4-methyl-3-(3-oxobutyl)pent-4-enal (7086-79-5, 85031-77-2, 136521-14-7, 127288-10-2) → C12H20O2 (1327155-04-3) + (-)-(R)-lavanduyl acetate (20777-39-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 30 °C 2: pyridinium chlorochromate / dichloromethane 3: Acremonium roseum AM346 / water; acetone / 264 h / Enzymatic reaction 4: pyridine / 16 h / 8 °C 5: thionyl chloride; triethylamine / 3 h / 25 °C View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (R)-5-methyl-2-(prop-1-en-2-yl)hexyl Acetate (1195619-81-8)

Conditions	Yield
Stage #1: (-)-(R)-lavanduyl acetate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 25℃; for 2.5h; Inert atmosphere; Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 760.051 Torr; Inert atmosphere; Stage #3: With 2-methyl-2-nitrosopropane dimer In tetrahydrofuran for 0.75h; regioselective reaction;	60%

crocetindial (502-70-5) + methyl 4-diethylphosphono-3-methyl-2-butenoate (19945-56-3) + (-)-(R)-lavanduyl acetate (20777-39-3) → (2R,3E,2'R,3'E)-2,2'-bis-(3-methyl-butyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-ψ,ψ-carotene (60252-71-3)

Conditions	Yield
Multistep reaction;

(-)-(R)-lavanduyl acetate (20777-39-3) → (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (498-16-8)

Conditions	Yield
With potassium hydroxide
(saponification);
With potassium hydroxide In methanol

(-)-(R)-lavanduyl acetate (20777-39-3) → Acetic acid (E)-(R)-5-hydroxy-2-isopropenyl-5-methyl-hex-3-enyl ester

Conditions	Yield
(i) O2, (irradiation), (ii) (reduction); Multistep reaction;

(-)-(R)-lavanduyl acetate (20777-39-3) → Acetic acid (R)-4-hydroxy-2-isopropenyl-5-methyl-hex-5-enyl ester

Conditions	Yield
(i) O2, (irradiation), (ii) (reduction); Multistep reaction;

(-)-(R)-lavanduyl acetate (20777-39-3) → (R)-lavandulyl senecioate

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / methanol 2: pyridine / diethyl ether / cooling View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → Acetic acid (R)-2-isopropenyl-5-methyl-4-oxo-hex-5-enyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) O2, (irradiation), (ii) (reduction) 2: (oxidation) View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → Acetic acid (R)-2-isopropenyl-5-methyl-4-oxo-hexyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) O2, (irradiation), (ii) (reduction) 2: (i) (oxidation), (ii) (hydrogenation) View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (R)-(+)-Tetrahydrolavandulol (41884-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH 2: H2 / PtO2 / acetic acid View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (2R,3E,2'R,3'E)-2,2'-bis-(3-methyl-butyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-ψ,ψ-carotene (60252-71-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: H2 / PtO2 / acetic acid 3: CrO3*2Py View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (R)-2-isopropyl-5-methyl-hexanal (60244-48-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH 2: H2 / PtO2 / acetic acid 3: CrO3*2Py View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (2E,4E,6S)-6-isopropenyl-3,9-dimethyl-deca-2,4,8-trien-1-ol (60244-51-1, 73365-73-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH 2: CrO3*2Py 3: (i) NaH, Et2O, (ii) /BRN= 5802052/, (iii) LiAlH4 View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (2Ξ,4Ξ,6R)-6-isopropyl-3,9-dimethyl-deca-2,4-dien-1-ol (73365-70-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: H2 / PtO2 / acetic acid 3: CrO3*2Py 4: (i) NaH, Et2O, (ii) /BRN= 5789989/, (iii) LiAlH4 View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (2S,3E,3'E)-2,2'-bis-(3-methyl-but-2-enyl)-1,3,4,16,3',4'-hexadehydro-1,2-dihydro-ψ,ψ-carotene (73365-74-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: CrO3*2Py 3: (i) NaH, Et2O, (ii) /BRN= 5802052/, (iii) LiAlH4 4: (i) Ph3P*HBr, CH2Cl2, (ii) /BRN= 1713035/, NaOEt View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → (2S,3E,2'S,3'E)-2,2'-bis-(3-methyl-but-2-enyl)-1,3,4,16,1',3',4',16'-octadehydro-1,2,1',2'-tetrahydro-ψ,ψ-carotene (30627-86-2, 60269-04-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: CrO3*2Py 3: (i) NaH, Et2O, (ii) /BRN= 5802052/, (iii) LiAlH4 4: (i) Ph3P*HBr, CH2Cl2, (ii) /BRN= 1713035/, NaOEt View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → ((2E,4E)-(R)-6-Isopropyl-3,9-dimethyl-deca-2,4-dienyl)-triphenyl-phosphonium; bromide (73365-71-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: H2 / PtO2 / acetic acid 3: CrO3*2Py View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → ((2E,4E)-(S)-6-Isopropenyl-3,9-dimethyl-deca-2,4,8-trienyl)-triphenyl-phosphonium; bromide (60244-53-3, 73366-50-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH 2: CrO3*2Py 3: (i) NaH, Et2O, (ii) /BRN= 5802052/, (iii) LiAlH4 4: CH2Cl2 View Scheme

(-)-(R)-lavanduyl acetate (20777-39-3) → lavandulal (6544-40-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH 2: CrO3*2Py View Scheme
Multi-step reaction with 2 steps 1: (saponification) 2: K2Cr2O7, aq. H2SO4 View Scheme

Upstream product

• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 108-24-7 acetic anhydride 
• 7086-79-5 (3S)-4-methyl-3-(3-oxobutyl)pent-4-enal 
• 1327155-06-5 C₁₂H₂₂O₂ 
• 1327155-05-4 (5S)-5-isopropenyl-2-methyl-octane-2,7-diol 
• 1345866-27-4 C₁₂H₂₂O₃ 
• 1327155-02-1 (R)-2-isopropenyl-5-methyl-hexane-1,5-diol 
• 25905-14-0 lavandulyl acetate 
• 108-05-4 vinyl acetate 
• 58461-27-1 (+/-)-lavandulol 

Downstream Products

• 6544-40-7 lavandulal 
• 60244-53-3 ((2E,4E)-(S)-6-Isopropenyl-3,9-dimethyl-deca-2,4,8-trienyl)-triphenyl-phosphonium; bromide 
• 73365-71-6 ((2E,4E)-(R)-6-Isopropyl-3,9-dimethyl-deca-2,4-dienyl)-triphenyl-phosphonium; bromide 
• 41884-28-0 (R)-(+)-Tetrahydrolavandulol 
• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 

Relevant articles and documents

Identification of the sex pheromone of the mealybug Dysmicoccus grassii Leonardi

Studies about the sex pheromone of the mealybug Dysmicoccus grassii, a main pest of Canary Islands banana cultivars, showed strong evidence that (-)-(R)-lavandulyl propionate and acetate in a 6:1 ratio are principal components of it. Volatile collection and GC-MS analysis from aeration of virgin females allowed the structural elucidation of the compounds. The activity and stereochemistry of both substances were established by means of relative attraction of mealybug males to synthetic standards in competitive Petri dish bioassays. (R)-Lavandulyl propionate induced a stronger attractive effect when compared to (R)-lavandulyl acetate. The attractiveness of the mixture of the two compounds at the original source ratio showed no statistically significant difference from that of the sum of each of the single compounds alone, suggesting that both components are not synergistic but additive.

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.