80-26-2

Basic information

• Product Name: Terpinyl acetate
• Synonyms: MENTHEN-1-YL-8-PROPIONATE;FEMA 3047;(+/-)-2-(4-METHYL-3-CYCLOHEXENYL)ISOPROPYL ACETATE;3-CYCLOHEXENE-1-METHANOL, ALPHA, ALPHA, 4-TRIMETHYL:ACETATE;ACETIC ACID TERPINYL ESTER;(+/-)-ALPHA-TERPINYL ACETATE;ALPHA-TERPINYL ACETATE;TERPINYL ACETATE
• CAS NO: 80-26-2
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 201-265-7
• Mol File: 80-26-2.mol

Chemical Properties

• Melting Point: 112-113.5 °C
• Boiling Point: 220 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear liquid
• Density: 0.953 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.515Pa at 23℃
• Refractive Index: n20/D 1.465(lit.)
• Water Solubility: 23mg/L at 23℃
• BRN: 3198769
• CAS DataBase Reference: Terpinyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Terpinyl acetate(80-26-2)
• EPA Substance Registry System: Terpinyl acetate(80-26-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: OT0200000
• TSCA: Yes
• Hazardous Substances Data: 80-26-2(Hazardous Substances Data)

Usage

Chemical Properties

The enantiomers and the racemate occur in many essential oils (e.g., Siberian pine-needle oil and cypress oil), but generally not as the main component. Pure Terpinyl acetate are colorless liquids with a fresh bergamot–lavender odor. Commercially available terpinyl acetate consists mainly of alpha-terpinyl acetate, but also contains a number of other isomeric compounds such as beta-terpinyl acetate. It can be prepared by acetylating the terpineol mixture obtained from terpin hydrate, using a customary procedure for tertiary alcohols. Because of its odor properties, stability, and low price, large quantities of terpinyl acetate are used in perfumery for lavender and bergamot types, as well as in essential oil reconstitutions.

Physical properties

Terpinyl acetate is a p-menthane monoterpenoid that naturally found in melanoleuca, elettaria cardamomum. It is a colorless liquid with a bergamot, bergamot odor. Soluble in five or more volumes of 70% alcohol; slightly soluble in water and glycerol. Combustible.

Occurrence

Reported in over 40 essential oils, including cypress, Malabar cardamom, cajeput niaouli, Siberian pine needles, pine, Melaleuca trichostachya, Melaleuca pauciflora and others; also identified in the essential oils of bitter orange (Fenarolfs Handbook of Flavor Ingredients, 1971 ; Gildemeister & Hoffman, 1966). Terpinyl Acetate is found in Pine oil, Cajeput oil, Pine needle oil, Cardamom oil and other essential oils.

Uses

Perfumes, flavoring agent.

Preparation

Terpinyl acetate was successfully synthesized from (x-terpineol and acetic anhydride in supercritical carbon dioxide (SC-C02) by enzymatic catalysis.By acetylation of a-terpineol or mixed isomeric terpineols (Bedoukian, 1967).

Synthesis Reference(s)

Tetrahedron, 38, p. 1843, 1982 DOI: 10.1016/0040-4020(82)80261-5

General Description

Α-Terpinyl acetate, a monoterpene ester, is a commercially important fragrance molecule. It can be prepared from α-pinene in the presence of H-beta zeolite catalysts. The essential oils obtained from Stachys setifera ssp. iranica, Chamaecyparis obtuse leaves and Thymus willkomii contain Α-terpinyl acetate as one of the main components.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H20O2/c1-9(2)12(14-11(4)13)7-5-10(3)6-8-12/h5,7,9-10H,6,8H2,1-4H3

Upstream product

• 470-82-6 1,8-Cineole 
• 108-24-7 acetic anhydride 
• 98-55-5 terpineol 
• 127-09-3 sodium acetate 
• 18172-67-3 beta-pinene 
• 64-19-7 acetic acid 
• 6921-34-2 benzylmagnesium chloride 
• 64708-29-8 2,2,5-Trimethyl-4-cyclohepten-1-yl-mesylat 
• 64735-91-7 2,2,5-Trimethyl-4-cyclohepten-1-yltosylat 
• 2436-90-0 (+)-β-citronellene 
• 80-56-8 Pinene 
• 546-67-8 lead(IV) tetraacetate 
• 5813-49-0 nitrosyl acetate 
• 13293-47-5 2αH-pinan-3α-ylamine 

Downstream Products

• 586-62-9 Terpinolene 
• 99-87-6 4-methylisopropylbenzene 
• 32226-54-3 trans-sobrerol 
• 5718-75-2 endo-4-methyl-7,7-dimethyl-6-thiabicyclo<3.2.1>octane 
• 87578-93-6 (+/-) 4-(1'-acetoxymethylethyl)-1-methylcyclohex-1-en-6-one (8-acetoxyvotanacetone) 
• 98-55-5 terpineol 
• 5502-74-9 7-hydroxy-α-terpineol 
• 83921-01-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-ol 1-monoacetate 
• 83921-01-1 8-acetoxy-c-4-p-menth-1-en-r-6-ol 
• 87578-92-5 8-acetoxy-t-4-p-menth-1-en-7-ol 
• 212832-31-0 4-(1-acetoxy-1-methylethyl)-1-methyl-cyclohexane-1,2-diol 
• 454-77-3 5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 25580-62-5 1,8-dichloro-trans-p-menthane 
• 4436-81-1 homoterpenylmethylketone 

Relevant articles and documents

Pd(OAc)2/M(NO3)n (M = Cu(II), Fe(III); n = 2, 3): Kinetic investigations of an alternative Wacker system for the oxidation of natural olefins

Pd-catalyzed oxidative coupling of camphene by dioxygen afforded mainly a diene, which subsequently underwent oxidation to a ring-expanded β,γ-unsaturated ketone with LiNO3 as reoxidant. However, the instability of LiNO3 results to t

Synthesis of Terpineol from Alpha-Pinene Catalyzed by α-Hydroxy Acids

We report the use of five alpha-hydroxy acids (citric, tartaric, mandelic, lactic and glycolic acids) as catalysts in the synthesis of terpineol from alpha-pinene. The study found that the hydration rate of pinene was slow when only catalyzed by alpha-hydroxyl acids. Ternary composite catalysts, composed of AHAs, phosphoric acid, and acetic acid, had a good catalytic performance. The reaction step was hydrolysis of the intermediate terpinyl acetate, which yielded terpineol. The optimal reaction conditions were as follows: alpha-pinene, acetic acid, water, citric acid, and phosphoric acid, at a mass ratio of 1:2.5:1:(0.1–0.05):0.05, a reaction temperature of 70? C, and a reaction time of 12–15 h. The conversion of alpha-pinene was 96%, the content of alpha-terpineol was 46.9%, and the selectivity of alpha-terpineol was 48.1%. In addition, the catalytic performance of monolayer graphene oxide and its composite catalyst with citric acid was studied, with acetic acid used as an additive.

Preparation of α-terpineol and perillyl alcohol using zeolites beta

The preparation of α-terpineol by direct hydration of limonene catalyzed by zeolites beta was studied. The same catalyst was used to prepare perillyl alcohol by isomerization of β-pinene oxide in the presence of water. The aim was to optimize the reaction conditions to achieve high conversions of starting material and high selectivity to the desired products. In the case of limonene, it was found that the highest selectivity to α-terpineol was 88% with conversion of 36% under the conditions: 50?wt% of catalyst beta 25, 10% aqueous acetic acid (10?mL) (volume ratio limonene:H2O = 1:4.5), temperature 50?°C, after 24?h. In the case of β-pinene oxide, it was found that the highest selectivity to perillyl alcohol, which was 36% at total conversion, was obtained in the reaction under the following conditions: dimethyl?sulfoxide as solvent (volume ratio β-pinene oxide:DMSO = 1:5), catalyst beta 25 without calcination (15?wt%), demineralized water (molar ratio β-pinene oxide:H2O = 1:8), temperature 70?°C, 3?h. The present study shows that the studied reactions are suitable for the selective preparation of chosen compounds.

Heterogeneous zeolite-based catalyst for esterification of α-pinene to α-terpinyl acetate

The purpose of this study is to determine the most effective type of heterogeneous catalyst such as natural zeolite (ZA), Zr-natural zeolite (Zr/ZA) and zeolite Y (H/ZY) in esterification of α-pinene. α-terpinyl acetate was successfully synthesized from α-pinene and acetic anhydride by their heterogeneous catalysts. The esterification reaction was carried out with reaction time, temperature and zeolite catalysts. The most effective catalysts used in the synthesis of α-terpinyl acetate is catalyst H/ZY with the yield is 52.83% at 40oC for the time 4 h with a selectivity of 61.38%. The results showed that the effective separation of catalyst could contribute to developing a new strategy for the synthesis of α-terpinyl acetate.

Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation

A series of novel α-terpineol derivatives were designed and synthesized through structural derivatization of the tertiary hydroxyl moiety or reduction of the double bond. Of the resulting compounds, eight compounds enhanced relaxation of airway smooth muscle (ASM) compared to the α-terpineol precursor, and four compounds (4a, 4d, 4e, and 4i)were superior or comparable to aminophylline at a concentration of 0.75 mmol/L. Assays for 3′-5′-Cyclic adenosine monophpsphate (cAMP) activation revealed that some representative α-terpineol derivatives in this series were capable of upregulating the level of cAMP in ASM cells. Further in vivo investigation using the asthmatic rat model, illustrated that treatment with the compounds 4a and 4e resulted in significantly lowered lung resistance (RL) and enhanced dynamic lung compliance (Cldyn), two important parameters for lung fuction. Moreover, treatment with 4e downregulated the levels of both IL-4 and IL-17. Due to its several favorable physiological functions, including ASM relaxation activity, cAMP activation capability, and in vivo anti-asthmatic efficacy, 4e is a promising remedy for bronchial asthma, meriting extensive development.

M -C2B10H11HgCl/AgOTf-Catalyzed Reaction for Reductive Deoxygenation

A m -C2B10H11HgCl/AgOTf-catalyzed reaction of allyl silyl ethers with N -Boc- N ′-tosylhydrazine has been developed. Under mild conditions, the resulting allyl hydrazine products were transformed into naked alkenes in good yield. Furthermore, the used m -C2B10H11HgCl could be recovered quantitatively.

Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies

The tail-to-head terpene cyclization is arguably one of the most complex reactions found in nature. The hydrogen-bond-based resorcinarene capsule represents the first man-made enzyme-like catalyst that is capable of catalyzing this reaction. Based on noncovalent interactions between the capsule and the substrate, the product selectivity can be tuned by using different leaving groups. A detailed mechanistic investigation was performed to elucidate the reaction mechanism. For the cyclization of geranyl acetate, it was found that the cleavage of the leaving group is the rate-determining step. Furthermore, the studies revealed that trace amounts of acid are required as cocatalyst. A series of control experiments demonstrate that a synergistic interplay between the supramolecular capsule and the acid traces is required for catalytic activity.

Proton-gradient-transfer acid complexes and their catalytic performance for the synthesis of geranyl acetate

Special proton-gradient-transfer acid complexes (PGTACs) in which the bonded protons are not equivalent and have gradients in transfer ability, acidity, and reactivity were reported. The acidity gradient of the protons gave the PGTACs excellent catalytic activity and selectivity in the esterification of terpenols. These PGTACs are “reaction-induced self-separation catalysts” and can be easily reused. The kinetics with PGTACs as catalyst in the esterification of geraniol were also studied for use in engineering design.

Α-terpineol fatty acid ester derivatives and use

The invention belongs to the technical field of medicine and discloses alpha-terpineol aliphatic ester and a preparation with the compound. The alpha-terpineol aliphatic ester is formed by alpha-terpineol and fatty acid after esterification reaction. According to a method, first, fatty acid and thionyl chloride react to prepare acyl chloride, and then acyl chloride and alpha-terpineol react to prepare the alpha-terpineol aliphatic ester. The alpha-terpineol ester can be used as penetration enhancers to be used for external preparations of patching agents, Cataplasm, ointment agents, gel agents and the like, accordingly, the percutaneous absorptive amount of medicine is improved, and the alpha-terpineol aliphatic ester is good percutaneous absorptive penetration enhancers and has wide application prospect.

Α- [...] enol derivative and its preparation method and application

The invention discloses alpha-terpineol derivatives, the structure of which is shown as the formula (II), wherein R or H is C1-C5 alkyl. The alpha-terpineol derivatives can be obtained by performing esterification reaction on a raw material alpha-terpineol with acid or acid anhydride at the temperature of 18-30DEG C under the action of 4-methylbenzenesulfonyl chloride. The invention further discloses applications of the alpha-terpineol derivatives in preparing antiasthmatic drugs, carboxylic ester prodrug formed by introducing carboxylic ester on the hydroxyl of the alpha-terpineol derivatives can be slowly hydrolyzed in a human body to release parent drug and further prolong the curative effect and the acting time, in addition the bioavailability can be improved, and the antiasthma activity can be further enhanced.